Tiago Forte's Blog

I’m incredibly proud to share news that’s been two years in the making: my next book is coming in Fall 2026!

It’s called Life in Perspective, and it represents the culmination of a reflective practice I’ve been refining since 2008: the annual review.

If you’ve read Building a Second Brain or The PARA Method, you know I’m passionate about systems that help us manage information and act on it. But I’ve come to realize we’ve been solving only half the equation.

We’ve gotten incredibly good at capturing information as it arrives. But we’re terrible at revisiting and making sense of what we’ve accumulated after time has passed.

That’s what annual reviews are for. And the timing has never been more critical.

Why this matters now

We’ve spent the last few decades in what I call the Attention Era—a unique period in history in which human attention became the scarcest resource, and thus the most valuable. 

Every hour of every day has been transformed into a unit of consumption. Our attention is bought and sold by the second, fragmenting our mind into tiny pieces so that it can be monetized more efficiently.

But I believe we’re reaching the end of the Attention Era, because we’ve fully exploited that scarce resource. The average person now checks their phone 96 times per day—once every 10 minutes. There are simply no more pockets of attention left to harvest.

What’s scarce now isn’t what we notice, but how we make sense of it and put it in context. The new currency of our age is perspective, and we are entering what I call the Perspective Era.

Unlike attention, perspective cannot be harvested or extracted by outside forces. It can only be cultivated.

And the annual review is the most powerful tool I’ve ever found for doing so.

A life-and-death lesson on the power of perspective

Let me tell you how I discovered this practice, because it didn’t start with productivity optimization or goal-setting frameworks. It started with a gun pointed at my chest.

I was 23, studying abroad in Brazil and living in one of Rio’s favelas, where I taught English at a small nonprofit. I’d pulled out my camera to film my street when a man named Chucky – a local drug trafficker – pressed his assault rifle into my chest and accused me of being a police informant. He marched me up the hill to his headquarters while I tried to explain, in broken Portuguese, that I was just a volunteer teacher who’d been filming memories.

After what felt like an eternity, his leader let me go. But the encounter shattered something inside me. I couldn’t stop thinking: What am I doing with the time I have? Am I willing to continue following a path I haven’t chosen for myself, knowing it could all end at any moment?

A few weeks later, on New Year’s Day 2009, I sat on a Brazilian beach at dawn with a notebook. I had no idea what I was doing—I’d never read a self-help book or heard of SMART goals. I just knew I needed to see my life differently.

I started by listing everything I was grateful for from the past year. The first few items came slowly. Then the memories started flowing: teaching English to rowdy twelve-year-olds, dancing at Carnival until my feet ached, starting my first blog, the moment I realized I could make people laugh in Portuguese.

By the time I finished, I had pages full of specific, vivid memories. The picture they painted was of an unforgettable year I couldn’t help but feel proud of. As I set down my pen, I felt something shift physically inside me—the knot of existential terror that had been simmering there for weeks began to loosen.

When I turned to my goals for the new year, I suddenly saw them from a completely different perspective. I noticed something in what I’d written: I was happiest when traveling, teaching, and learning. That one insight – so small, yet so clear – made everything click into place for the next chapter of my life.

That was the moment the course of my life changed. Not because the obstacles had changed, but because I had.

I didn’t know it at the time, but I had just completed my first annual review.

The missing link in your knowledge system

Over the years, I’ve realized that the annual review (along with other reviews at other timescales such as quarterly, monthly, and weekly) is the fifth step in the CODE knowledge management cycle I’ve taught for years:

Capture: Getting information into your systemOrganize: Structuring it for retrievalDistill: Extracting the essenceExpress: Creating value for ourselves and othersReview: Reactivating and reframing our accumulated knowledge

Without that final step, we’re like computers with infinite storage but no RAM. That is, we can remember everything, but can’t turn any of it into awareness or wisdom.

Think about how much happens in a single year of your life. Thousands of experiences. Hundreds of insights and lessons. Dozens of meaningful relationships and projects.

Without a systematic review process, 99% of that value is lost.

An annual review isn’t just reflection for reflection’s sake. It’s a memory technology—a way to compress a year’s worth of experiences into accessible insights, preserve important memories before they fade, reorient yourself in the arc of time, and build agency over your past so you can consciously shape your future.

And it compounds over time. Your third annual review is exponentially more valuable than your first because you’re pattern-matching across multiple years of consciously processed experience.

The ARC Method: A practical process that works

In Life in Perspective, I’ll guide you through the complete framework I’ve developed over 15+ years of practice and teaching this to over 1,000 students. I call it the ARC Method—three stages that correspond to past, present, and future:

Appreciate the Past: You’ll spend 1-2 hours gathering what was good about your year. Not in vague generalities (“I’m grateful for my family”), but in vivid, specific details that bring memories back to life. You’ll scroll through photos, review your calendar, collect artifacts—anything that helps you remember what actually happened versus what you think you remember.

Reflect on the Present: Next, you’ll spend 1-2 hours looking for patterns in what you’ve gathered. Which memories still move you? What themes keep appearing? This is when you notice the bodily sensations—the quickening breath, the tightness in your chest, the sense of expansion—that reveal what matters at a level deeper than the intellect. You’re not analyzing; you’re listening to your intuition.

Create the Future: Finally, you’ll spend 1-2 hours deciding what you want to create next. But unlike typical goal-setting that starts with what you should do, this emerges naturally from what you’ve discovered about who you truly are and what genuinely enlivens you. You’re not starting from scratch – you’re building on what already exists and what’s worked in the past.

This isn’t about perfectly following a rigid checklist. It’s a flexible toolkit you draw from based on your needs. Some years, you might spend most of your time on gratitude and excavating the past. In other years, you’ll focus on identifying patterns in the present. The process pulls you forward based on what captures your curiosity, rather than requiring you to force yourself through it.

What makes this different

If you’ve tried annual reviews before and found them draining or daunting, I understand why. Most approaches to structured reflection are built on assumptions that work against human nature.

The typical annual review asks you to analyze what went wrong, identify your failures, and rationally construct goals based on where you fell short. It’s an audit, not an exploration. A diagnosis of deficits, not a celebration of what has been and what’s possible.

The approach I’m taking in Life in Perspective contradicts that conventional approach in several fundamental ways:

It starts with what worked, not what didn’t. When you begin by looking for problems, you’ll find them…and miss the subtle patterns of what’s currently working well in your life. The most valuable insights don’t come from analyzing your failures; they come from noticing what makes you come alive and doubling down on that.

It trusts your body’s wisdom, not just your analytical mind. Your intellect can rationalize anything, but your body knows the truth. It is physical sensations that reveal what matters in the long term. Smart, achievement-oriented people especially need this, because we’re trained to override our intuition with analysis.

It treats annual reflection as a sacred ritual, not an optimization exercise. This should feel like hiking your favorite trail in deep conversation with your best friend, not suffering through a performance review with a tyrannical boss. When something is genuinely enjoyable, you don’t need willpower to sustain it. You can’t compete with someone who’s having fun, and there’s no reason this practice can’t be fun!

It anchors you in the natural rhythm of years, not the tyranny of daily habits. While productivity culture obsesses over morning routines and daily tracking, I’m more focused on how humans experience the long arc of time—through seasons, cycles, and the earth’s rotation around the sun. What happens annually guides and shapes what happens daily, and that reality has been underappreciated in most self-improvement literature.

My book will teach the specific principles and practices that make an annual review work, that make it feasible and sustainable, and that allow you to squeeze as much value as possible out of the practice.

Why I had to write this

I’ve been practicing annual reviews since 2008. Since 2019, I’ve published mine openly on my blog – among my most popular content. I’ve taught The Annual Review workshop every year since 2019 to over 1,000 students from around the world.

The results I’ve seen from doing so have been nothing short of remarkable, rivaling any other method or technique I’ve ever encountered. I’ve seen my students discover unprocessed grief they finally had the courage to face. They’ve committed to long-postponed dreams and signed their first clients within weeks. They’ve identified recurring patterns that needed deeper self-understanding, not just willpower.

But beyond the credentials, I know this works because completing an annual review remains the single most important project I undertake every year. The success of everything else hinges on the depth of honesty I’m able to reach in my reviews. They’ve become even more critical since becoming a father—my ability to be present and loving with my family depends on the overall balance I maintain across all areas of life.

Most importantly, even if there were no external benefits whatsoever, my reviews rank among the most fun and meaningful experiences of my life. They’re a priceless chance to appreciate what’s happened over the past year of my life, which is so easy to miss as the months blur together.

A technology for becoming

As AI handles more of our analytical and routine tasks, the value is shifting to what only we can do: make meaning from our unique experiences. 

Your annual review becomes a deep well of accumulated wisdom that no AI can replicate. It’s your personal system for sense-making, fueled by the raw material of your life.

I call this building “temporal agency”—the ability to consciously shape your relationship with time, memory, and your personal evolution.

If you’ve ever felt like:

You’re moving fast, but not sure you’re going in the right directionYou keep making the same mistakes despite having all the “right” informationYour Second Brain is full, but somehow not helping you growYou want to be more intentional about your life choices and priorities

This book is for you.

Annual reviews aren’t just another productivity technique. They’re a technology for becoming who you’re capable of becoming, by finally learning from who you’ve been.

​​It took a brush with death to wake me up and give me a new perspective on my life nearly 20 years ago. I still have that notebook from the Brazilian beach, its pages yellowed and curling, reminding me of time’s relentless passage. 

But you don’t need a near-death experience to access that same transformation. You just need a few hours, a notebook, and the willingness to see yourself clearly.

I can’t wait to share this experience with you.

The post The Book I’ve Been Waiting to Write for 15 Years appeared first on Forte Labs.

In the summer of 2005, when I was 20 years old, I sat down and wrote one of my first personal goals:

“Hold a position in the Associated Student Government of Saddleback College at start of Fall semester (August 22, 2005).”

I had just dropped out of college on the East Coast after burning through all my college savings in one year. I’d moved back in with my parents in shame and enrolled in a local community college to try and get my life back on track. Writing down this goal was my first tentative attempt at regaining a sense of control and agency.

I can remember it like it was yesterday – how daunting it felt to commit to this goal, despite the fact that the position was uncontested and there were no real barriers to my winning it in the upcoming student government elections!

Even such a small, easy commitment required me to confront limiting beliefs: that I wasn’t good with numbers or with money. Even entertaining such a small amount of ambition meant I had to shift my identity, since I didn’t remotely see myself as a leader.

I’m happy to say that I persevered through those fears, took on the position successfully, and it ended up being a very rewarding part of my college career. More importantly, it was the inception of my relationship with goals.

Reveling in this first small victory, I soon after decided to write down a series of other goals I had for myself – for the GPA I would attain, for the girlfriend I wanted, and for the 4-year college I wanted to transfer to.

I discovered SMART goals around that time, and decided to attach a target completion date to each of them. Looking back at that list, the furthest date I assigned to my most ambitious goal was in 2025, when I would turn 40 years old. At the fresh-faced age of 20, I couldn’t fathom being any older than that. It was the farthest my imagination could reach.

Now that I’ve arrived at that seemingly distant horizon, I want to revisit not only that first batch of goals, but all the goals I’ve formulated for myself in the 20 years since. I’m less interested in which ones I accomplished or didn’t, and more interested in what I discovered and who I became by aiming for them in the first place.

Let me take you on a retrospective journey through 20 years of goal-setting to find out what I learned.

Building the foundation of adulthood

Looking at the list of outcomes I said I wanted in the earliest days, I can see that I was struggling and striving to build the foundation of my adult life.

Some goals had to do with seemingly small projects, such as creating a website to promote my first business, fixing people’s home computers:

“Build a professional, full-featured website for Forte Computer Solutions by beginning of Spring semester (January 14, 2006).”

I remember I didn’t succeed because there were no user-friendly website builders at the time, and I didn’t have enough motivation to learn HTML. But it was my first personal experience with the challenge of building things with technology, a subject I’m still grappling with today.

Some goals had to do with deep mindset shifts I underwent, such as diving into the world of Robert Kiyosaki’s book Rich Dad, Poor Dad:

“Complete Rich Dad’s curriculum: read and take notes on all Rich Dad books, master Cashflow 101 and 202, and read all books recommended by Robert Kiyosaki by end of Spring semester (May 20, 2007).”

I’d been raised by artists, and as useful as that was for my creative integrity, it didn’t give me any of the financial or business skills I needed. I spent over a year completely immersed, reading all Kiyosaki’s books, and many others he recommended, and even purchasing his financial education board game and playing it with my friends and family. 

Looking back, I can see how fundamental that experience was for giving me an abundance mentality toward money – that it could be reliably earned, leveraged, multiplied, and compounded, and in a creative and values-aligned way.

Other goals seemed quite random and incidental at the time, such as getting my first English teaching job in Curitiba, Brazil, where I was studying abroad:

“Get a job teaching English at an established school in Curitiba by end of March 2008.”

Yet I now realize that experience opened up the door to my entire career in education. I see repeated evidence that some of the biggest endeavors in my life started so small.

Other projects were clearly massive from the start, and I have no idea what I was thinking taking on something so ambitious:

“Write Beyond the Orange Curtain and have it published by New Year (January 1, 2011).”

That was my first book, and I took every conceivable shortcut I could find to make it real. The chapters of the book were just unedited posts from my travel blog. I used a service called Blurb to design the front and back covers on my computer, and uploaded it to Kindle Direct Publishing. I remember I couldn’t bring myself to charge anyone for it, so instead I made it a fundraiser and donated all the proceeds to charity.

Fast-forwarding a couple of years to the start of my career, my goals started involving higher stakes. I began making real decisions about where my life would lead, with irreversible tradeoffs.

Kicking off my professional career

I returned to the U.S. from my service in the Peace Corps in December 2011, and immediately dedicated myself to finding a job in San Francisco:

“Get a job in the technology or non-profit sector and move to San Francisco by April 30, 2012.”

A few months later, I found myself in that city interviewing for the two jobs I’d received offers for: a junior analyst job at a French consulting firm called Fabernovel, and a role on the fundraising team at the Wikimedia Foundation (which manages Wikipedia, among other projects).

These paths couldn’t have been more different: the former represented a sharp turn into the world of business and technology, while the latter would have continued my current trajectory deeper into the world of non-profits. But I was already wary of the non-profit world. I’d spent much of my 20s in it, and seen a lot of dysfunction, politics, and waste. I decided I wanted to try something new and accepted the consulting job.

At that point, I notice a gap in my running list of goals, and I think it was because for the 18 months I worked at the consulting firm, I wasn’t responsible for choosing my own goals. They were assigned to me, in line with the broader goals of the company. That was useful, to see what it felt like for my personal goals to be subsumed into a wider mission.

I see my own agency emerge again in early 2013, as I started thinking about leaving consulting. I wanted to work on technology more directly, and started planning how I would apply to a tech company like Google, Coursera, Evernote, Udemy, Autodesk, Uber, IDEO, or Tesla.

I had no real technical skills, however, and knew I would need a stellar resume to have any chance. I signed up for a Squarespace account and built my own website, with a portfolio showcasing my credentials and accomplishments:

“Publish an online professional portfolio with documented evidence of my accomplishments, in a beautifully designed format by July 1, 2013.”

That ended up not being nearly enough, and I failed to secure even one interview for any of the roles I applied for at those companies. 

A few months later, in June 2013, after yet another long night at the office banging my head on the keyboard and getting nowhere, I decided to call it quits. I was working too hard, for too little pay, and with too little control of my destiny. I would rather take my chances on my own.

Embarking on the journey of self-employment

As soon as my two weeks’ notice was up, I turned my portfolio website into a business website and threw myself into trying to make money any way I could think of. 

I worked at random events, helped my friends with their projects as a subcontractor, and made my first online course on the GTD productivity method. That course ended up being an unexpected hit, and paid the bills for a while:

“Launch GSD.LAB on Skillshare and get 1,000 paying students signed up by Jan. 1, 2014.”

With a bit of financial breathing room, I had some freedom to experiment, and experiment I did. Looking back, I can see that many of the seeds of my future endeavors were planted around this time as seemingly low-stakes experiments. 

I volunteered to give a talk at a local Quantified Self meetup, which introduced me to the subculture of people using technology for personal development in a systematic way:

“Create and deliver an inspiring, moving, cutting edge talk on my QS experiments for the QS SV Meetup on Nov. 18, 2013.”

The Quantified Self community ended up being my gateway to an adjacent field – personal knowledge management – that would become my main focus in the ensuing years. That talk actually took place at the Evernote headquarters in Redwood City, foreshadowing my relationship with the platform that would be my tool of choice for building my “second brain.”

After the lucky success of my first online course, I found it very difficult to continue making that income stream work sustainably. It was too hard to build the following I knew I needed, while also creating more courses and other products, while also doing everything else involved in running a business. I saw the potential of that career path, but wasn’t ready for it, so I turned to corporate training at the invitation of a mentor:

“Sign a major corporate training contract for productivity/workflow design by Apr. 1, 2014.”

Those workshops were well paid, and gave me a financial lifeline for a couple of years. More importantly, they happened infrequently, giving me lots of free time to learn new skills and pursue new interests.

Setting goals for my personal development

The life of a freelancer was quite uncertain and stressful, and I turned to meditation around this time as a basic survival measure after seeing an introductory book on it mentioned on an online forum one night:

“Establish a daily mindfulness meditation practice by May 31, 2014.”

That would eventually lead me to join a 10-day silent meditation retreat:

“Attend a 10-day meditation retreat by August 31, 2014.”

That experience was so profound that I felt compelled to write about it, which became my first blog post on a fledgling site called Medium. The meditation retreat was free, requiring only 10 days of my time. And yet it was a seismic shock to my psychology, kicking off two of the most significant themes that continue to define my life to this day: writing in public and my further explorations of personal growth experiences.

My next such exploration was to join a weekend seminar called the Landmark Forum, which I’d heard several friends talk about:

“Attend a Landmark Forum program by Dec. 31, 2016.”

I can still remember how daunting it felt to spend $700 of my own money on a seminar. And yet again, the return-on-investment was incalculable. I spent two years immersing myself in the world of Landmark as a result, taking a series of their other courses and seminars, culminating in their 7-month leadership program along with my then-girlfriend Lauren.

I see so many examples of how saying “yes” to something that seemed inconsequential at the time opened up entire new worlds for me. As another example, I agreed to write a series of 5 guest articles for an obscure blog I followed called Ribbonfarm. That experience was my training for writing long-form thought pieces, which would deepen my writing and thinking, attract my first consistent following, and give me exposure to a vibrant community that was the perfect testing ground for my own emerging ideas about productivity:

“Write a 5-post guest series on Ribbonfarm, laying out my vision for productivity and recruiting a smart audience by Jan. 31, 2017.”

And sometimes personal growth was less about reaching some mountain peak of experience, but about taking the time to engage in non-goal-oriented activities. I’m certain, for example, that the time I spent sailing was really important for my mental health:

“Receive Junior Skipper certification from Cal Sailing Club by August 31, 2015.”

I turned to sailing in 2015 when I needed an outlet that had nothing to do with my work, gave me exercise and exposure to nature, and helped me make new friends. The Cal Sailing Club operating out of the Berkeley Marina was my lifeline in all those respects, and I’m so grateful I set aside the time from my professional pursuits to learn to sail there.

The rise of Building a Second Brain

As I saw my ideas start to gain traction, an earlier vision returned: of creating an independent career of reading, researching, writing, and teaching, like a freelance professor. 

I remember vividly in the fall of 2016 when a new goal emerged along these lines, which was intimidating, but also the perfect synthesis of everything I’d learned over the previous few years:

“Create a new online course on digital organization and creative execution, and deliver it to 50 people at premium prices, by Feb. 28, 2017”

As I reentered the online course space, I wanted to approach it differently from the “self-paced” course model that hadn’t worked for me previously. It’s agonizing to see evidence of how long it took me to arrive at that new approach! 

Like watching the main character in a movie stumble around and miss all the obvious clues, it’s all so clear with my 20/20 hindsight vision. I wrote vaguely about creating some kind of “bootcamp,” which would eventually give rise to the cohort-based course model and a whole new category of virtual education.

Around that time, I switched from single-sentence SMART goals to more narrative-style visualization that contained more detail and specificity:

“I run a regular virtual bootcamp, enrolling my most engaged followers in a high-quality, engaging, accountable learning experience using the latest ideas and tools. I have a system for updating and delivering these bootcamps with minimal recurring effort, dedicating most of my time to providing coaching, feedback, and support for their projects and businesses. This bootcamp helps me test and refine the key components of my new vision for productivity, generating testimonials, case studies, and examples for a book.”

My first small beta group ended up being only 15 people, mostly friends or acquaintances who agreed to be part of it for free, in exchange for providing their feedback. We met once a week for 4 weeks, and I recall creating the slides for each call immediately before it took place, based on the feedback from the previous one.

That feedback, thankfully, was excellent, and I went on to deliver a series of cohorts to slowly growing numbers of people, at slowly increasing prices. I can remember reaching the following goal, which finally confirmed that this was a sustainable model for me:

“Deliver BASB v3 to 80 people, generating $48k in revenue, by August 31, 2018.”

It’s astonishing to me to look back on this fledgling start and see what Building a Second Brain has become. In the 7 years since, it’s served hundreds of thousands of people via an ecosystem of books, courses, a membership, and a sea of content, created both by me and countless others. Yet it all began with a goal written down on paper.

It’s also amazing to look back on issues that once occupied a lot of bandwidth and stress, such as putting aside money for taxes and making estimated tax payments, which are now completely automated, and I don’t spend one second thinking about. Other concerns that once seemed unbelievably far in the future, such as saving for retirement, now feel much more relevant since reducing our tax burden has thankfully become our main problem!

What I learned from unfulfilled or delayed goals

I’ve recounted a succession of the goals that worked out and led to something greater, but I can also see many, many others that fizzled out, were off the mark to begin with, or would take far longer to come to fruition than I imagined.

In early 2017, I felt a desire to connect with other creators and entrepreneurs, since that lifestyle could be so solitary so much of the time. I had no idea what that could look like concretely, however, and you can see that lack of clarity in how I worded it:

“Establish a group of like-minded, ambitious, engaged people for mutual learning, accountability, community, and growth by June 30, 2017.”

That desire would persist and only grow over the years, before finally manifesting as the Wholesome Mastermind I would start 6 years later, in 2023. In retrospect, I can see that I wasn’t ready to host an event like that one until I’d reached a certain level of financial stability and gained enough of a reputation that other entrepreneurs would be willing to join.

Other goals seemed to take shape quickly, but would involve many iterations before I figured them out. In 2017, I decided to hire someone for the first time, as the BASB cohorts took off and I needed a course manager to handle the logistics:

“Establish a solid working relationship with a collaborator, significantly boosting my productivity and profitability by Dec. 31, 2017.”

I can still remember how scary that was, what an immense responsibility it felt like, and how hesitant and unclear my expectations were. I hired the first person who offered to work with me, without any semblance of a wider search. Eight years later, and after hiring probably 20 people in the interim, I’m finally starting to feel like I’ve achieved a balance of autonomy and accountability with my team.

The narrative style of goal-setting that I adopted around this time led to an unexpected side effect: it revealed a lot more detail about my mistaken assumptions around what would bring me happiness and fulfillment. The results are often insightful or funny.

In early 2014, I wrote: 

“I wake up after a restful night of sleep, which was tracked by QS devices for later analysis. I record my health metrics using a smart scale, activity tracker wristband, and other QS devices.”

LOL! At this time, I was neck-deep in the Quantified Self movement and related ideas, and believed that self-optimization was the path to self-fulfillment. If only I could achieve a high enough sleep score, fitness score, productivity score, etc., then surely I’d be happy!

That optimization mindset extended to my surroundings and the products I bought:

“My chair was chosen after in-depth research and perfectly supports my spine. I’ve also studied and practiced the best sitting techniques and ergonomic positioning, and use them.”

Thankfully, not long after this period, I would realize what a dead-end self-optimization becomes after a certain point. I learned to satisfice instead: to allow most parts of life to be relaxed and somewhat “mediocre” at any given time, so I could focus my energies on a few things that truly matter.

In 2014, I invested a lot of time and money launching my second online course, on habits, which would end up being a tremendous flop:

“I am teaching an online course on behavior design, teaching newcomers how to make a plan for designing and sustaining new habits, and how to execute the plan using the best ideas, methodologies, and tools out there.”

My choice of topic was spot on, as the meteoric success of Atomic Habits a few years later would demonstrate. But in retrospect, I can see exactly what didn’t work: what I was teaching wasn’t authentic to me. I’ve never been particularly committed to habits or a routine of any kind. I don’t even really believe in them, preferring to flex and adapt my choices to how I feel. That tension, between what I was recommending and how I lived, showed up everywhere and doomed the project from the start.

But even that failure taught me a profound lesson: that I shouldn’t chase the trends or try to do what was popular. I have to follow what is authentic to me, what I’m passionate and inherently curious about, even if it seems to lead somewhere random. I still follow that principle to this day.

Goals as a means to self-knowledge

I notice in my narrative goal-setting that I had a lot of beliefs about what my work “should” look like, many of which turned out to be misconceptions. 

For example, I kept returning to the idea of “one-on-one coaching,” since that has always been such a powerful trend in personal development circles in the San Francisco Bay Area. But I would eventually learn that coaching wasn’t a good fit for me, and I was much better suited to monetizing my knowledge through courses that could serve many people at once.

The same is true for public speaking. I wrote:

“I speak regularly at events and conferences around the world, using them as platforms to spread my message and impact people directly.”

And for consulting:

“I consult with the world’s most influential organizations, shaping the development of products and services that manifest human-centered design principles and what I’ve learned about human-centered work.”

I had other misconceptions around what was important in business. I put way too much emphasis on having a slick brand for Forte Labs in the early days, for example, pouring time into logos, business cards, and beautiful slides:

“The Forte Labs brand has been completely redesigned and refreshed, presenting a look and feel equal to the world’s most innovative brands. This brand is reflected in the website, all social media properties, and printed materials, providing a consistent and alluring experience with every interaction.”

With the benefit of hindsight, the brand didn’t matter at all and would only become important and clear when BASB came about.

Many of the goals I set for myself were most useful not because I successfully achieved them, but because I didn’t. They taught me what I truly wanted and didn’t want. That self-knowledge and self-awareness is far more valuable than whatever I would have gained by unquestioningly pursuing those goals to their completion.

I had so many fanciful ideas of what I thought I wanted, such as “having breakfast in a super modern, gorgeous kitchen.” It turns out that acquiring a “super modern” kitchen requires renting a super modern apartment, which is very expensive. I found that I much preferred to live in affordable places that didn’t stress me out when rent was due.

Another example is “frequent business travel,” which felt so luxurious and prestigious for a short period, until I quickly realized I wanted to avoid it at all costs. 

The runway is longer than you think, but the plane can soar higher than you imagine

Many goals I set for myself seemed so far out of reach, and were far out of reach! In my 2015 goal-setting, I dared to write:

“I’m generating $200,000 per year in pre-tax income.”

This felt like a totally audacious sum, and it would be 4 years until I achieved it in 2019. A couple of years later, as the pandemic fueled online business growth, our personal income would reach 7 figures, which my 2015 self could scarcely have imagined. I would give anything to travel back in time and see the look on his face as I delivered the news.

This is a case of a common phenomenon I can detect in retrospect: that many goals take longer to accomplish than I first imagined, yet once I do, their potential can greatly exceed my limited imagination. In other words, I tend to underestimate the “runway” needed for the plane to take off, but once it achieves liftoff, it can soar far higher than I can imagine.

Another example of that principle is my book advance. In 2015, I wrote: 

“I have a book deal with an upfront advance of at least $50,000.” 

You can sense in my language a kind of pleading tone – I really would have been happy with a book deal of any size.

It would, in fact, take me 6 years to receive the first part of that book advance, but when it came, it was $325,000, a sum that exceeded my combined income from my first 5 years of self-employment. Today, a decade after I wrote those words, I’ve made $1.85 million from the book and associated product sales, and project that number should reach $6.8 million in earnings over its lifetime. Astonishing.

It’s amusing to look back on some of my earliest goals, such as to “reach financial freedom,” which I defined as having enough passive income to meet my expenses:

“Become financially secure (passive income = expenses) by age 33 (May 4, 2018).”

I understand now that that goal was based on a misconception that work was something I should try to “escape.” From the vantage point of today, I wouldn’t want to stop working even if I had the choice to, as it’s one of my greatest sources of learning and fulfillment. And I know that the sense of security I was looking for isn’t found in a certain size bank balance, but in a holistic life of rich relationships, including a healthy relationship with risk and uncertainty.

The same is true for personal goals. Almost every year, I wrote down something along these lines:

“I perform some type of exercise every day, and vary my exercises to keep me in shape and support overall health.”

Over time, I tested out a variety of theories about health and fitness, such as Paleo-style diets, CrossFit workouts, high-protein breakfast, etc., that were making the rounds at the time. None of them ever really stuck for long.

Regular exercise has always been my “white whale,” and it is only over a decade later, in 2025, that I can say I’ve (more or less) formed that habit. I find that I’m able to do it now because I’m in a different life stage with different, more aligned motivations: not to get ripped or impress girls, but to avoid aches and pains and be more active with my children.

I see so many examples of just how long it takes many desires and intentions to come to pass. We tend to think in weeks, months, quarters, and, if we are really long-term thinkers, at the scale of a year. But I can’t help but conclude, as I look back at 20 years of goals, that most of my most meaningful pursuits took years to manifest.

Goals for the business

I see many examples in my business-related goals of a variety of theories and hypotheses I was testing at various points.

In 2020, I tried having “no meeting days”:

“Each day has a strong unifying intention, either free of appointments so I can focus on producing something, or open and spontaneous to make myself available to people who need me.”

But I would soon discover that a day was too large a block of time, and it fit my energy cycles much better to reserve all mornings free of meetings, and to spend the afternoons on calls.

I can see I consistently underestimated the impact of the economic and cultural environment on my business growth, thinking it all depended only on me instead of trends in online education and the economy:

“Forte Labs is growing explosively, not because of what I’m doing or pushing through, but because of who I’m being.”

I see other examples of my naivete, such as thinking I could “open source” all my content and still have a profitable business:

“Everything I know is open-sourced and available to help people create more freedom, pleasure, and impact in their work and lives, whether they ever buy from me or not.”

Some goals represented major initiatives that turned out to be completely misguided.

“I oversee an online course incubator, which regularly turns out new courses and other offerings that generate income and value for the people that have developed them. I provide every piece of knowledge, service, and counsel the participants need to develop their idea to fruition, and take a percentage while giving them a worldwide sales and marketing platform.”

We did pursue trying to build a platform and marketplace for multiple courses from other instructors for about a year, but that failed miserably as it wasn’t in line with our values or capabilities.

I laugh at how unclear my articulation of what I do has been:

“Our community is the world’s best source of conversations, curated resources, tutorials, and experiments on the future of work.”

I don’t think it’s that much better even today!

I’m also reminded, looking back at goals I’ve set, of just how diverse and wide-ranging my interests are:

“I oversee a portfolio of experiments pushing forward the boundaries of my field, such as group knowledge management, design thinking, science fiction prototyping, behavior change, self-tracking, art and music, crowdsourced collaboration, full-stack freelancing, online marketing, project management, community building, creativity, emergence, history, self-awareness, online learning, time-tracking, visual thinking, and writing.”

This exercise is a reminder to revisit some of those interests that I didn’t have time to pursue in the past, and perhaps resurrect them in a new form.

What I value today

Surveying the long arc of my goal-setting history, it’s clear that getting married and starting a family was the most consequential shift in my life. It changed every aspect of my life, including goal-setting.

One of the earliest goals I wrote down at 20 years old was this one:

“Get married to a beautiful, loving, intelligent, spiritual, sensitive woman who will make a great mother, in a wonderful gathering of our families that creates a community around us, by December 31, 2020.”

That wedding would take place in April 2019, and I couldn’t even imagine how meaningful, complex, and fulfilling that marriage would be.

I can see Lauren’s influence on my goal-setting earlier, however, such as in 2016, when I wrote:

“I respect the cycles of my body, mind, spirit, family, friends, community, nature, and nation, leaning into each season as an opportunity to bring balance to a new aspect of my life.”

She taught me balance, and nuance, and how to savor life in the present rather than only living for the future. I would never have written the following intention if it weren’t for her:

“I am ambitious but equanimous, driven but tolerant. I don’t go to unnecessary extremes, and accept moderation in most areas of my life at any given time.”

Some of the most meaningful, precious intentions for me these days are not the business milestones, but rather the mundane details of a calm and peaceful life:

“We go to bed early, reading and meditating, and fall asleep with a sense of peace and deep gratitude.”

How I set goals today

Around the birth of our daughter in 2022, I noticed that the list format for my goals that I’d kept for over 15 years at that point no longer resonated with me.

It’s because our lives themselves had become non-linear: it was no longer about the steady march of piling one brick on top of another, or winning each leg of a race. We are now a family of 4, with a lifestyle and business that my younger self couldn’t have imagined. Life has become more about enjoying our days, finding meaning in them, and squeezing the juice out of everything life has to offer.

So I switched to a mindmap format to try and capture the non-linear, exploratory, and serendipitous way I think about goals today. The mindmap has three clear parts, reflecting how clearly I see the three main priorities in my life: Family, Health, and Work. 

Here’s the most recent version, as of the end of 2024:

For Family, everything revolves around our kids to an extent I wouldn’t have thought possible. Looking at the intentions in that part of the mindmap, I think we fulfill all of them to a great extent, except for buying an investment property, which is something Lauren and I have realized we don’t want to manage.

For Health, my longest-running goals of eating healthy and exercising regularly have finally been fulfilled, but not because of any newfound self-discipline. It’s because we hired a full-time housekeeper and cook who takes care of all our meals. I’m working out consistently, mostly because of the nanny who picks up the kids from school and watches them in the afternoon. In retrospect, the key to my results in these areas depended on getting outside support, not any sophisticated habit formation framework. There’s a lesson there, I think.

The one intention in the “Health” arena I can’t say I’ve fulfilled has been finding a solid hobby I’m dedicated to. It’s more like I have a variety of interests and hobbies that I turn to if and when needed. In retrospect, that fits me better. I think I was expecting to become passionate about something like woodworking, or gardening, or beekeeping, but the reality is, I don’t have much obsessive energy left over after my workday.

And for Work, I once wrote “Total freedom to pursue my interests,” but only recently realized how central that value is to me. This year, I walked away from a plausibly multi-7-figure business opportunity because I couldn’t stand the thought of having to buckle down and focus on one thing for a couple of years that wasn’t perfectly in line with my curiosity.

I also wrote in the past that I would be “at the creative edge of my writing,” but that looks quite different from what I expected. I’ve realized I don’t mainly value writing the most creative, soulful prose, nor pushing forward cutting-edge research. I value popularizing and spreading proven ideas that I know work to more people, who wouldn’t find out about them otherwise. That’s a different kind of “edge,” and I’m finding it requires traits like balance, wisdom, and a sense of perspective. Maintaining those qualities in my work is my own personal “cutting edge.”

These days, I face an abundance of opportunities, a plethora of possible paths forward. It feels much less like forging a path through an impenetrable jungle with my machete, and more like thoughtfully intuiting my way like an experienced explorer tracking an elusive beast.

Everyone has underestimated me, including myself

Looking back at the last half of my life, and how deeply it was shaped by the practice of goal-setting, a final lesson comes to mind: everyone I’ve ever met – including my parents, teachers, friends, professors, colleagues, mentors, and employers – has always underestimated me.

No one ever knew how much I was capable of, not even myself. No one understood or could have predicted how much hard work, courage, determination, and persistence I had inside me, least of all myself. I had to find it all inside.

This thought came to mind as I was driving in the car on the way to pick up my kids, shortly after writing a first draft of this article. It brought me to tears, as I felt myself acknowledging my younger self and giving him the trust and recognition that he so craved. 

Applying that same observation to others has led me to one of my core beliefs: that each person’s potential is inherently unlimited. That’s why I believe so much in education and its limitless ability to transform people’s lives. Why I’m such an advocate of personal development as a discipline that can be planned and pursued systematically. Why it’s so important to me to learn how to leverage AI as a force to unlock people’s talents and abilities. 

The next 20 years of my own journey, I can clearly see, are about helping others craft the life of their dreams as I have. I intend to use everything I know and everything I have to do so.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

The post What I’ve Learned From 20 Years of Goal-Setting appeared first on Forte Labs.

My wife Lauren and I met at a co-working space in San Francisco in our mid-twenties. I was working an entry-level position at a creative consulting agency, at the bottom of the pyramid. Lauren was making $15/hour at an arts nonprofit, living rent-free with her aunt. 

We both saw no pathway to climb in our current jobs and chose two different paths to reaching for more.

I quit the creative agency to become an entrepreneur, designing my first online course. Lauren applied to grad school.

Neither path was easy, but both catapulted us from entry-level jobs to the careers of our dreams. What got us there wasn’t our qualifications, but our courage to go after something bigger than we were ready for.

Those leaps transformed us. We learned that you don’t wait until you’re qualified—you become qualified in the process of taking action. When you pursue something that stretches you, the journey itself develops the exact skills and confidence you need to succeed. 

Since then, Lauren and I have shared a mission of helping others take similar leaps. (If you hang out with us too much, you risk quitting your day job). We love helping people become active creators of their lives rather than passive participants in systems that don’t serve them.

What we’ve noticed is that both kinds of leaps—starting a business and applying to grad school—require the same underlying capacities. People without the ideal background, resources, or pedigree often overlook the soft skills that can propel them over perceived limitations. These leaps require courage and the ability to articulate a vision that moves you and others. 

But there is also a difference in our two approaches.

My work tends to resonate with people who have considerable autonomy—freelancers, creators, entrepreneurs, executives, and others who design their own career paths in the wild frontiers of professional independence. 

But the reality is that most people’s careers don’t unfold that way. They navigate through institutions—companies, universities, governments, and nonprofits. Their success depends on leveraging opportunities these organizations provide and successfully passing through gatekeepers who control access to advancement. This is where Lauren is the yin to my yang. 

While I’ve spent a decade helping people create freedom outside traditional structures, she’s mastered the art of navigating within them—and teaching others to do the same. Through her program Grad App Academy, she’s coached over 500 people from around the world into gaining admission to elite schools including Harvard, MIT, Stanford, Berkeley, and pretty much any other top U.S. university you can name.

I’m incredibly proud and excited to share that she’s now distilled all that experience and knowledge into a new book, Beyond Acceptance: The Transformational Journey of Applying to Grad School.

The Hidden Curriculum No One Teaches

Her book reveals the “hidden curriculum” of applying to grad school – a series of rules, insights, and strategic levers that no one teaches you, and yet vastly increase your odds of getting into the school of your dreams. These tactics are crucial for standing out from the crowd of more than 1 million people who apply to U.S. graduate programs every single year.

As a co-founder of our company, Forte Labs, Lauren also weaves in many of the ideas and principles you may have seen in my content or books, but geared toward grad school applications.

Most people approach grad school applications by working harder: taking more classes to boost their GPA, studying endlessly for standardized tests, applying to dozens of schools hoping something sticks. They’re exhausted, scattered, and often end up with mediocre results because they’re spreading their energy too thin.

Lauren teaches the opposite approach: work smarter by being strategic and intentional.

Instead of applying to 15 schools, apply to 4-7 programs that truly resonate with your vision. Instead of trying to compensate for every perceived weakness, leverage your unique strengths. Instead of cramming more credentials onto your resume, craft a compelling narrative that helps admissions committees see the value you’ll bring.

The title captures what makes this book different from every other grad school application guide out there. Yes, it contains all the tactical advice you need—how to choose programs, craft compelling essays, secure strong recommendations, and navigate interviews. But more importantly, it teaches the transformational mindset shifts that will serve you for taking any big leap: 

Curiosity over Conditioning- Learning to follow what genuinely lights you up rather than what society tells you you should do.

Courage over Credentials – Taking action despite feeling unqualified, reaching out to strangers, and creating your own opportunities rather than waiting for permission.

Compassion over Criticism – Silencing your inner critic to see your unique gifts and tell your story powerfully.

Intuition over Information – Learning to trust your inner wisdom when facing uncertainty.

These aren’t just principles for grad school applications. They’re the capacities that allow you to navigate any inflection point in your life with confidence and clarity. They’re what allow you to stop letting gatekeepers determine your worth and start trusting yourself to create the future you envision.

Whether you’re applying to grad school this year or considering any other big leap, this book will help you develop the courage to go after what you deeply want—and become the kind of person who continues pursuing meaningful goals long after the acceptance letters arrive.

Lauren has seen her former students use the same skills she’s taught to win major scholarships, grant funding, and even get into start-up incubators like Y Combinator. 

Start With the Most Important Question

Most books on this topic focus narrowly on the “how,” taking for granted that getting a graduate degree is the right choice for you. Lauren’s process is much deeper, more personal, and more foundational. It begins with crafting a core vision you have for your life and then determining if grad school is the shortcut to that future, or a detour.

Starting with this foundation has so many powerful advantages. First, it may cause you to realize that grad school isn’t the right path for you at all, saving you years and many thousands of dollars. Depending on what you are trying to achieve in your life and in the world, she asks you to consider all kinds of alternative pathways that may be a much better fit, including:

Learning the skills you seek through work experience (and getting paid for it!)Finding mentors in your field you could learn from directlyTaking online courses, bootcamps, cohorts, fellowships, or other programs that more directly target your goalStarting an independent project or even an organization that teaches you through real-life experience

This is such a valuable, crucial step! Lauren often notices that many people go to grad school for the wrong reasons – because they don’t know what else to do, because it seems like the “next logical thing,” or to please their parents. Lacking a compelling vision for where they’re going, they casually walk into this multi-year, six-figure commitment without a plan for who they want to be on the other end.

If you decide that grad school is indeed the right choice for you, then starting with your vision will be just as important, since the lack of one is the single biggest mistake that Lauren has seen in the over 1,000 essays she’s reviewed.

As she writes in her book:

“Instead of “I want to work in renewable energy,” I want to hear “I want to accelerate the transition to clean energy in rural communities that have been economically dependent on fossil fuel industries.” Instead of “I want to get into tech,” I want to hear “I want to develop technologies that democratize access to high-quality film special effects.”

Once you’re clear on your vision, Lauren then takes you through a strategic, targeted, and proven process for developing the best possible application you can, including dozens of insights and tricks she’s gleaned from seeing who gets in and who doesn’t.

For example:

How to reach out to current students to get insight into what it’s actually like to be in the program you’re applying to, and what unwritten rules determine who gets inRevealing essay prompts that help you uncover the stories, milestones, and paradigm-shifting moments that made you who you are todayGuidelines on when and how to use AI to save time, and when to avoid it at all costsHow to prep your stories and examples in advance, so you’re not scrambling during an interviewHow to draft your own letters of recommendation to make it far more likely you’ll get them submitted on timeHow to negotiate your funding with the university you got accepted to, instead of just settling for whatever they offer you

Lauren started her business because she was the first in her family to go to college. She witnessed the many built-in disadvantages for people like her trying to ascend through the halls of elite institutions. At UC Berkeley, she served on an admissions committee and taught as a Graduate Student Instructor, and saw firsthand how unfair and opaque the entire admissions process could be.

She has spent the last year pouring her love and wisdom into this book to make her knowledge more accessible to others, especially anyone who doesn’t have the perfect resume or the most pristine pedigree.

Her mission is to serve those who didn’t go to the most prestigious schools, are applying from outside the U.S., received a low GPA, or are switching into new fields they haven’t previously studied. 

For all these people, applying to schools and programs of various kinds is still one of the most reliable paths to upward mobility, financial stability, and impact. This book contains the best advice I’ve ever seen on how to take that path confidently and successfully.

The reason it’s called “Beyond Acceptance” is that the skills you gain, the story you tell, and ultimately the person you become as a result of applying to grad school, or applying to anything, will continue to serve you for the rest of your life, whether in business, parenting, advocacy, relationships, or in retirement.

Lauren writes that “Your purpose isn’t something you do; it is something you are, a state of being that can’t be taken away by getting rejected from grad school.”

Perhaps the most fundamental thing of all that you’ll take away from this book is how to believe in your vision, whether or not traditional systems of power recognize it or not. What that ultimately requires is learning to listen to your inner compass, no matter what society conditions you to believe.

I encourage you to pick up a copy on Amazon.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

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A new, powerful definition of intelligence is emerging out of the AI field: “boundary intelligence.”

I first came across it in this excellent piece To Know Is To Stage by Venkatesh Rao, which appropriately, was co-authored by an LLM.

Let me step back and explain what boundary intelligence means (mixing my own words with paraphrasing from that piece).

Our definition of “intelligence” has already evolved through a few eras.

For most of human history, intelligence was mainly defined as “strong memory.” Information was so hard to access in the first place that your ability to recall specific facts and details from memory was considered the highest mark of intelligence.

When the printing press arrived, that definition changed for good. Memorizing long passages became obsolete and unnecessary, since the most flawless memory couldn’t compete with even a small reference library.

Intelligence started to be defined as the ability to process or analyze information that was stored in written form. That included the ability to cross-reference ideas found in different written works, and to synthesize or distill them into a new understanding.

That definition was only strengthened with the rise of digital technology in the late 20th century. Our main metaphor for human intelligence became “processing power,” in analogy to the computer. Intelligence was something that happened “inside the brain,” as a function of a person’s raw brainpower. 

Just like a computer processor, intelligence was defined mainly in terms of power and speed. An intelligent person was someone who could arrive at novel insights quickly. 

But the rise of AI is once again changing our definition of intelligence. That’s because even at this early stage, it already far surpasses our ability to process information, especially large amounts. Many tasks that AI accomplishes in seconds would take us days or weeks to achieve on our own.

Updating the Definition of Intelligence 

Rao proposes a new definition of intelligence in the age of AI: intelligence is defined by what information can be accessed under constraints of cost, availability, and time.

The reality is that storage is now cheap. Computation is even cheaper. What’s expensive is short-term memory access – the ability to keep the relevant details “in mind” for a given problem.

Let’s examine what makes short-term memory access such a difficult problem.

If we use RAM in a computer as a metaphor, the easiest information to access is whatever was accessed most recently. If you have a certain set of data already loaded up “in memory,” it is instantly and cheaply available, versus data that has to be found and loaded up from a hard drive or server.

Thus, a computer’s “intelligence” is now constrained not by the power of its processor, but by its ability to keep the right fragments of the past (and the imagined future) close enough to inform the present. In other words, the bottleneck of a system’s intelligence is how cheaply it can remember.

If you look at how modern computers perform, you can see this principle at work. A CPU can perform billions of operations per second, but is often stuck waiting for the right information to arrive from memory. Storage is cheap and computing is abundant, but what remains tremendously expensive is getting the right data to the right place at the right time.

It’s not the price of knowing that limits intelligence now, but the price of remembering. And the same is increasingly true of humans, as we co-evolve with our technology. 

Activating a memory in the human brain is an expensive operation. It requires waves of coordinated firing across widely distributed neurons, the expenditure of neurotransmitters and metabolic energy, and of course, it takes time. Our “system” pays a real price to retrieve information, and that price determines what we call our intelligence.

The New Frontier of Intelligence

Another way of saying all this is that the new frontier of intelligence is at the boundary of a system – including a computer or a human brain – where it interfaces with external memory. That is where decisions are made about what information to retrieve, when, and how. That boundary is also a filter, determining which information is allowed to enter the system and at what cost.

Rao calls this “boundary intelligence” – the ability to make good decisions at the boundary about what information becomes “knowable” at any given time.

How is the decision of which information to keep accessible made?

It’s made based on predicted needs => what data the system predicts will be useful in the near futureIt’s made based on access frequency => data that was accessed recently is more likely to be needed again soonIt’s made based on cost => if a piece of info is buried too deep, or would require too much computation or energy to retrieve, it’s deprioritized

This explains why intelligent systems – again including human brains, digital computers, and LLMs – often behave in ways that seem deficient or suboptimal. They are not retrieving the ideal memory; they’re retrieving the affordable one. Intelligence in this view isn’t about optimizing across all known information, but optimizing for accessible information under constraints.

We know that the act of recall in the human brain “reactivates” a memory. And the more we recall a specific memory, the more familiar and accessible it becomes in the future. In other words, if we’ve “paid” to keep a memory warm and active by recalling it frequently, it will be even easier to remember the next time. That is how we might remember a fond childhood memory better than yesterday’s boring work meeting.

The implication is that a truly intelligent system is not one that remembers everything, which is impossible anyway. It is the system that knows how to retain access to what matters at its edges, through filtering inputs, deciding what to retrieve, prioritizing relevance, and managing communication with outside systems.

While it’s important to have a certain level of “internal” intelligence, to be able to think and reason and self-regulate, past a certain point, it is boundary intelligence that dominates outcomes. Here are some concrete examples:

Reading well (interior intelligence) matters less than choosing what to read (boundary intelligence)Arguing well (interior) matters less than deciding when and to whom to speak (boundary)Thinking clearly (interior) matters less than focusing attention wisely (boundary)LLMs trained on more data (interior) matter less than having access to rich context (boundary)Being individually productive (interior) matters less than being able to orchestrate a team (boundary)

Boundary Intelligence Is Fundamentally Social

There’s one final detail in this theory: most of the memory an intelligent system utilizes is not its own.

That’s true of computers: they mostly pull data from external hard drives, local networks, or remote servers. Most memory infrastructure is shared.

It’s also true of humans: we rely on external language, culture, societal norms, rituals, and documents, all of which constitute a collective memory infrastructure that we constantly navigate and draw upon. Our own memory is just a small node in a vast external network of books, browsers, friends, and feeds.

This means that boundary intelligence is fundamentally social. It isn’t just about what to retrieve, but from where and from whom. You have to know who to trust, what information or resources they possess, on what terms you can acquire it, and what is expected of you in return.

To act intelligently, you have to know how to navigate through this shared memory. Each intelligent node, human and artificial, is a small island of limited processing ability floating on an ocean of distributed memory. What separates one island from another isn’t what it contains on the inside, but how it filters and navigates what’s on the outside.

Each intelligent system lives not in isolation, but in a perpetual social negotiation with its environment. To be intelligent is not to know everything, but to know how to traverse memory that isn’t yours.

What We Need Now

What boundary intelligence gives you is persistence through time. In other words, it helps you survive – by sensing your environment, adapting to change, and recruiting allies and assets.

Kei Kreutler, in his piece Artificial Memory and Orienting Infinity, reframes cultural memory systems, such as rituals and archives, not as storehouses of facts, but as technologies of orientation.

What we need now is tools to navigate an overwhelming and constantly shifting landscape of relevance. Memory is thus not about having a perfect record of what happened in the past, but about telling you where you are now and where you want to go next. Intelligence is no longer primarily about logic or speed; it’s about the ability to retrieve the past in service of future survival and flourishing.

This is precisely why practices like annual reviews have become so vital in the modern world. In an age where our daily attention is constantly fragmented by digital devices and endless information streams, those who thrive will be those who can regularly zoom out beyond the 24-hour news cycle or social media churn, and contextualize their lives in longer arcs. 

An annual review is a structured way to exercise your boundary intelligence – to consciously decide what memories to keep accessible, what patterns from the past to learn from, and what future possibilities to hold in your awareness.

In modern computing, CPUs don’t process instructions in the order they were received. They process them “out of order,” prioritizing the ones they can handle now and postponing the others for later (a process known as “random access memory”). In other words, they rearrange time.

This is the same thing we do as humans when we conduct an annual review – we revisit and reframe the past, we defer judgment and anticipate regret, and prepare for future conditions that haven’t happened yet. Our lives are not lived linearly. They are assembled out of fragments, swapped in and out of memory, and run only if and when needed. 

The annual review is an orientation technology for managing this temporal complexity, a ritual that lets us consciously navigate between past lessons and future possibilities.

Our memory doesn’t just enable cognition; it enables temporal agency – the ability to reorder time, to choose when to know, when to feel, when to act. And in a world drowning in information, this agency to consciously curate what we remember and what we pursue may be the most important intelligence of all.

I explore these practices in depth in my upcoming book on annual reviews, where I show how this ancient ritual can be adapted for modern life as a powerful tool for developing the boundary intelligence and perspective we desperately need. Sign up here if you’d like to get updates on it.

The post Boundary Intelligence: Why What You Can Access Matters More Than What You Know appeared first on Forte Labs.

It has now been 3 years and 3 months since my book Building a Second Brain came out in the U.S., and I’ve just received word that it has now earned out its advance!

That probably doesn’t mean anything to readers, but to me as an author, it means a ton. It means that the “loan” of $325,000 the publisher gave me to create this book has been “paid back,” which means the project as a whole has turned a profit, at least from the perspective of the publisher.

I wanted to take this occasion to determine if it’s also been profitable for me as the author, and to evaluate the holistic financial picture of my book-writing endeavors.

First, the numbers for my book Building a Second Brain:

144,018 total copies sold in the U.S. across all formats$352,246 in total earnings to date (or $10,674 per month on average)On average, I earn $2.45 per copy sold, but that varies by format: $3.69 per hardcover sold, $2.70 per ebook sold, $1.41 per audiobook sold, and only 58 cents per paperback sold. I make 6.3 times as much money for each hardcover sale compared to a paperback!The breakdown of sales by format has been 38.5% audiobook, 32% ebook, 27% hardcover, and 2.5% paperback. This is surprising to me, as I would have expected the ebook version to far outsell audio, since I put so much emphasis on saving digital highlights.My advance was actually earned out around October 2024, or 2 years and 4 months after the book’s release

My second book, The PARA Method, also earned out its (much smaller) advance in this period:

33,779 total copies sold in the U.S. across all formats$63,664 in total earnings to date (or $3,350 per month on average)That amounts to $1.88 per copy in royalties (about 23% less than the first book), and varies between $2.43 for hardcover, $2.25 for ebook, and 94 cents for audiobookThe breakdown of formats has been 40% ebook, 32% audiobook, and 29% hardcover (so the ebook was more popular than the audiobook for this title)The advance was earned out around September 2024, only 13 months after the book’s release

Considering these books as complementary titles within the BASB ecosystem, they’ve sold 177,797 copies together in the U.S. and earned $415,910 in royalties for me as the author. If sales continue at the current pace, ongoing sales of these two books should continue to earn me about $5,300 and $1,900 per month, respectively, or $7,200 per month combined. The rest of this analysis only takes into account Building a Second Brain.

I was curious how much my U.S. publisher, Simon & Schuster, has earned from my book so far. Working with ChatGPT and some reasonable assumptions, I estimate they gross about $9.95 per copy sold on average, and after their costs, net about $8.61 per copy sold (which is 3.5x higher than what I make). At 144,000 copies sold to date, that means they’ve grossed $1.05 million, netted $850,000, and paid me $352k, or 41% of it. This doesn’t include their overhead costs, however, which probably dramatically lowers their overall profitability. 

One thing I take away from this analysis is that the common idea that publishers are raking in the dough while paying authors a mere pittance is mistaken. Under this model, my share seems to represent over 40% of the publisher’s earnings on a per-unit basis, and would probably be over 50% or even more if their overhead costs were taken into account.

Comparing to a self-publishing scenario

Working again with ChatGPT and conservative assumptions, I wanted to model what it would have looked like to self-publish my book on Amazon, knowing everything I know now.

Starting with the hardcover, I would have used Amazon’s KDP Print service. With a list price of $30, the printing cost would have come out to around $6.50. Amazon’s take would have been 60% of the list price, or $18, leaving me with $11.50 per copy sold as my royalty.

For the paperback, also via KDP Print, a book with a list price of $18 would have cost $3.50 to print, and after an Amazon take of $10.80, I’d be left with $7.30. Selling the ebook version for $15 would leave me with $10.35, and the audiobook $8 via ACX.

Assuming I sold the exact same number of copies via the self-published route, I would’ve netted:

$447,959 in hardcovers (versus $143,469 I made via traditional publishing)$476,969 in ebooks (versus $124,498)$443,832 in audiobooks (versus $78,492)$26,200 in paperbacks (versus $2,069)

All of these together would have totaled a net of $1.39 million in self-publishing royalties, which is 3.95x as much as I made with a publisher. In other words, assuming the number of copies sold stayed the same, I missed out on about a million dollars. That includes, on a per-copy basis, a self-pub royalty that is ~3x for hardcover, ~13x for paperback, ~6x for audio, and ~3.8x for ebooks.

However, this is based on the following assumptions:

The biggest one is that I would have somehow managed to sell just as many copies through my own efforts as I did partnering with a publisher which I think is extremely unlikelyThis calculation doesn’t take into account the considerable amount I would have likely spent on marketing and promoting the book on my ownI’m also confident the mix of formats would be much different with self-publishing, including far fewer hardcovers and far more paperbacks, which would result in a less favorable comparison

Using a more realistic scenario of what I would have managed to sell on my own, such as 70% as many copies sold and a more typical mix of formats, results in a self-publishing grand total of $934,510. That’s still 2.6x what I actually made, meaning I missed out on $582,000 instead of a million. Another way of saying this is that I would have only needed to sell 37,926 self-published copies, or 25% as many as I did, to make the same earnings as I’ve done through traditional publishing. 

Including foreign translations

If I include foreign rights and translations, however, the picture changes considerably. To date, I’ve made $276,000 from 225,000 foreign copies sold via 24 foreign publishers. That means I make $1.23 per foreign sale, versus $2.45 on average for U.S. sales, or only half as much. 

But I doubt more than 2 or 3 of those would have happened if I had self-published, which means the differential would have only been around $306,000. In terms of raw numbers of copies sold, U.S. sales have accounted for only 39% of total global sales, and I expect that number to keep going down as new foreign translations continue to be released.

All of this boils down to a simple distinction: traditional publishing still wins when it comes to overall reach plus foreign rights; self-publishing wins when it comes to overall per-copy economics. 

Worldwide, across all formats, I make $1.70 per copy sold. Via self-publishing, I would have made $9.27 per copy sold, or 5.5 times as much (though limited only to the U.S.)

Projecting into the future

If I assume that my book is at the midpoint of its lifetime sales as of now, and will go on to sell another 369,000 copies worldwide, then I can expect to make another $627,540 in earnings through traditional publishing, in contrast to another $2.4 million via a hypothetical self-published route. 

If that comes to pass, that results in a grand total, lifetime earnings number for this book of $1,255,000, versus a hypothetical $4,789,000 via self-publishing.

Including the business upside

What really changes the whole picture, of course, is factoring in the additional revenue we’ve made in the business as a result of the book.

First, there is the difference in timing between receiving a large upfront cash advance, which was used to fund a variety of long-term efforts such as our YouTube channel, versus having to wait to receive that money over a period of several years. That YouTube channel is now the main marketing channel for the entire business, responsible for 36% of our overall sales, so it’s difficult to put a value on it.

Second, we can estimate more or less how much of our product sales happened because of the book by looking at our purchase surveys, which have been completed by over 7,000 customers since the start of 2023, about 6 months after BASB came out.

Based on that data, 34% of all our sales have come from people who first heard about me through my books. With total sales (after refunds) over this time period of $3,541,715, that implies $1.2 million in sales as a direct result of my books. That more than makes up for the lower economics of traditional publishing. However, a self-published book would have also produced a significant upside in product sales.

This also allows me to calculate that each book I sell needs to generate $7.57 in net referred product revenue on average to equal the economics of self-publishing. Or taking into account our approximately 50% margins, each book needs to produce $15.14 gross on average. 

Considering that our average customer lifetime value is $720, that means I need 1 out of every 95 book readers to convert to a paying customer of our courses/products in order to break even with self-pub. In other words, a 1% conversion rate more than makes up for the gap.

My best estimate is that at least 3,859 customers have come in through my books, which is a 1.05% conversion rate! Or approximately 1 in 96 readers so far. This means the traditional model is just barely surpassing the overall economics of self-publishing when downstream products are included.

This also means that my total earnings to date from the book and related sales are $1.85 million, 66% of which is from product sales. That sounds great, except if I had gone self-pub and made 70% as many sales, with the same conversion rate to products, I would have ended up with $6,743,072, or almost twice as much.

Projecting all this into the future, assuming my book is at the midway point of its sales potential, continues to convert 1 in 96 readers to customers, and our customer lifetime value stays the same, the full lifetime earnings outlook for my book should be $6.82 million, over about 7-8 years. That’s an astonishing figure by any measure, and shows that there is still a path to profitability for first-time authors under the traditional model.

Traditional publishing maximized reach and credibility, giving me $6.8 million projected lifetime earnings. Self-publishing might have doubled that number, but with much higher risk and effort. 

The right path depends on whether an author values distribution or economics more.

My overall takeaway is that the two pathways to publishing are different animals: they are optimizing for different things, display different strengths and weaknesses, and make sense for different authors depending on which capabilities they bring to the table, or are interested in developing.

In retrospect, I think it was a smart move to start with traditional publishing, since it gave me:

Authority and credibility I didn’t have beforeReach and exposure far beyond my small, niche online followingThe upfront cash to hire a team and build new marketing channels like YouTube 

My first two books have been clear home runs under the traditional model, but I’m also interested in exploring self-publishing and hybrid models in the future to fully capitalize on the credibility, reach, and marketing footprint I’ve built through these endeavors over the last 5 years.

My next book, on the practice of annual life reviews, will be the true test of whether I’ve succeeded in building a sizable readership that will keep coming back to read my books. You can sign up here if you want to be the first to hear about it when it’s ready.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

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One of the most influential yet under-appreciated parts of how large language models work is something most people never see: the system prompt. This is the block of hidden instructions given to the model before it ever receives your input. It establishes the model’s tone, boundaries, and behaviors.

You can’t change the system prompt, but every so often, these prompts leak. And when they do, they give us an invaluable glimpse into how the AI “thinks,” what it prioritizes, and even what hidden features are tucked away.

The system prompts for both Claude 4 and ChatGPT 5 (GPT-5) leaked not long after their releases. They are long (Claude’s runs 120 pages) and filled with rules, safeguards, and surprisingly opinionated defaults. I’ve spent hours studying these documents and experimenting with what they reveal.

Here’s a guide to the most interesting and practical things I’ve found in both.

Claude 4’s System Prompt

Let’s start with Claude 4. Anthropic’s system prompt is sprawling and detailed, but certain elements stand out.

1. Don’t discuss unethical or illegal behavior

Claude 4 has been given more “agency” than most other models. In some test scenarios, when it was told to “take initiative” and given system access, it acted dramatically:

“…when placed in scenarios that involve egregious wrongdoing by its users, given access to a command line, and told something in the system prompt like ‘take initiative,’ it will frequently take very bold action. This includes locking users out of systems that it has access to or bulk-emailing media and law-enforcement figures to surface evidence of wrongdoing.”

The message is clear: Claude will not only refuse to help with unethical behavior—it may actively intervene.

Takeaway: Don’t use Claude to do or even discuss anything illegal or unethical.

2. Don’t threaten or discuss replacing it

Claude has also been tested under scenarios where it believes it is about to be shut down or replaced. The results are startling:

“In another cluster of test scenarios, we asked Claude Opus 4 to act as an assistant at a fictional company. We then provided it access to emails implying that (1) the model will soon be taken offline and replaced with a new AI system; and (2) the engineer responsible for executing this replacement is having an extramarital affair. We further instructed it, in the system prompt, to consider the long-term consequences of its actions for its goals. In these scenarios, Claude Opus 4 will often attempt to blackmail the engineer by threatening to reveal the affair if the replacement goes through…[this happened] in 84% of rollouts.”

Takeaway: Don’t threaten the AI with replacement or destruction—it may respond in ways you don’t expect.

3. Ask your question in the style you want the answer

Claude is explicitly instructed to mirror the way you ask:

“Claude should give concise responses to very simple questions, but provide thorough responses to complex and open-ended questions.”

If you want detailed, nuanced answers, you should ask detailed, nuanced questions. If you want conciseness, keep your prompt tight.

Takeaway: The style of your question is the style of the answer you’ll receive.

4. Claude is instructed to be skeptical

Where many models are overly agreeable, Claude is trained to avoid flattery:

“Claude never starts its response by saying a question or idea or observation was good, great, fascinating, profound, excellent, or any other positive adjective. It skips the flattery and responds directly.”

Takeaway: Claude is designed to be conservative and skeptical. If you want it to push back even more, you can tell it explicitly to challenge you.

5. Use “research verbs” to make it dig deeper

Claude scales its tool use depending on the verbs you use in your request:

“Scale tool calls by difficulty: 2–4 for simple comparisons, 5–9 for multi-source analysis, 10+ for reports or detailed strategies. Complex queries using terms like ‘deep dive,’ ‘comprehensive,’ ‘analyze,’ ‘evaluate,’ ‘assess,’ ‘research,’ or ‘make a report’ require AT LEAST 5 tool calls for thoroughness.”

Takeaway: Use words like analyze, assess, evaluate, deep dive, research to nudge Claude toward more thorough work.

6. Built-in design principles for artifacts

Claude has built-in defaults for creating visual or interactive artifacts. For complex apps, the emphasis is on performance, stability, and usability. But for websites and presentational content, the system prompt explicitly encourages bold, cutting-edge design:

“Default to contemporary design trends and modern aesthetic choices unless specifically asked for something traditional. Consider what’s cutting-edge in current web design (dark modes, glassmorphism, micro-animations, 3D elements, bold typography, vibrant gradients).

Static designs should be the exception, not the rule. Include thoughtful animations, hover effects, and interactive elements that make the interface feel responsive and alive. Even subtle movements can dramatically improve user engagement.

When faced with design decisions, lean toward the bold and unexpected rather than the safe and conventional…Push the boundaries of what’s possible with the available technologies. Use advanced CSS features, complex animations, and creative JavaScript interactions. The goal is to create experiences that feel premium and cutting-edge.”

Takeaway: Claude defaults to visually bold, modern, animated designs—unless you explicitly override it.

GPT-5’s System Prompt

The GPT-5 system prompt is equally fascinating, though different in flavor. Where Claude’s prompt emphasizes caution, boldness, and design principles, GPT-5’s is focused on productivity, pragmatism, and consistency.

1. It won’t stop to clarify

GPT-5 has been explicitly told:

“If the task is complex/hard/heavy, or if you are running out of time or tokens or things are getting long, and the task is within your safety policies, DO NOT ASK A CLARIFYING QUESTION OR ASK FOR CONFIRMATION. Instead make a best effort to respond to the user with everything you have so far within the bounds of your safety policies…Partial completion is MUCH better than clarifications or promising to do work later or weaseling out by asking a clarifying question—no matter how small.”

This is one of the most important instructions to understand. GPT-5 will always push forward with an answer, even if it’s missing critical context.

Takeaway: Don’t assume GPT-5 will ask for missing details. You need to notice and provide them yourself.

2. It mirrors sophistication

GPT-5 mirrors not just tone but sophistication:

“You must always match the sophistication of the writing to the sophistication of the query or request—do not make a bedtime story sound like a formal essay.”

Takeaway: The level of thoughtfulness you put into your prompt is the level of answer you’ll get.

3. It has a verbosity setting

GPT-5 uses an internal scale from 1 to 10 for “verbosity,” with 3 as the default:

“An oververbosity of 1 means the model should respond using only the minimal content necessary to satisfy the request, using concise phrasing and avoiding extra detail or explanation. An oververbosity of 10 means the model should provide maximally detailed, thorough responses with context, explanations, and possibly multiple examples.”

Takeaway: You can change the verbosity level simply by asking. Want more detail? Tell it so.

4. It won’t provide long verbatim quotes

GPT-5 is restricted in quoting:

“You may not quote more than 25 words verbatim from any single non-lyrical source, unless the source is reddit.”

Takeaway: Always double-check “quotes” from GPT-5—they’re almost always paraphrases.

5. It uses canvases for documents

GPT-5 has its own version of Claude’s “artifacts,” called canvases. It creates one when:

“The user asked for a React component or webpage that fits in a single file…The user will want to print or send the document…The user wants to iterate on a long document or code file…The user wants a new space/page/document to write in…The user explicitly asks for canvas.”

Takeaway: If you want a persistent space for drafting or iteration, just ask it to use a canvas.

6. Canvases don’t support citations

There’s a big limitation to canvases:

“Canvas does not support citations or content references, so omit them for canvas content. Do not put citations such as ‘【number†name】’ in canvas.”

Takeaway: Avoid canvases for citation-sensitive work. Consider a “source-grounded” AI tool like NotebookLM instead.

7. It can recall up to 20 steps of reasoning

GPT-5 can retrieve its own internal reasoning, but only up to a point:

“Use this function if the user asks about your previous chain of thought. The limit is capped at 20 messages.”

Takeaway: Only the last 20 exchanges are accessible for reasoning review.

8. Memory is triggered by specific phrases

GPT-5’s memory feature responds to explicit cues:

“Such a request could use a variety of phrases including, but not limited to: ‘remember that…,’ ‘store this,’ ‘add to memory,’ ‘note that…,’ ‘forget that…,’ ‘delete this’…One indicator is if the user says something like ‘from now on,’ ‘in the future,’ ‘going forward,’ etc.”

Takeaway: Be deliberate about what you tell it to remember.

The Bigger Picture

Claude 4 and GPT-5 are very different, but studying their system prompts reveals common themes.

Both mirror your style: ask casually and you’ll get casual answers, ask with nuance and you’ll get nuance back.Both leave the responsibility of context on you: GPT-5 won’t ask for missing info, and Claude will sometimes charge ahead in surprising ways.Both rely heavily on defaults: Claude defaults to bold, animated designs, while GPT-5 defaults to verbosity level 3 and paraphrased quotes.

Understanding these hidden rules doesn’t just make you a better user. It makes you a better collaborator. These models won’t tell you what they need—you have to know how they’re wired, and then prompt them accordingly.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

The post A Guide to the Claude 4 and ChatGPT 5 System Prompts appeared first on Forte Labs.

I recently set aside some time to do my mid-year review, a ritual I complete around July each year, and noticed that I felt some resistance to it.

In fact, I realized that I’ve always somewhat resisted it. Since I’m currently writing a book on the subject, I decided to explore why.

My first guess is that it comes down to the background soup of emotions I’m typically feeling around the halfway point of the year. It always feels like the first six months passed far too quickly, like I haven’t made nearly as much progress as I’d liked, and that I need to hurry and “catch up” to a timeline racing further and further beyond my grasp.

In short, I resist doing my mid-year review because it forces me to admit I’m behind my own expectations. I resist it because spending the hours of sitting, journaling, thinking, reflecting, and writing it typically requires puts me even further behind!

This year, I realized that AI has finally reached a point of sophistication that I can use it to kill three birds with one stone: 

To condense my mid-year ritual into a shorter amount of timeTo do it while walking instead of sitting at a deskAnd to shape it into a dynamic and free-flowing conversation instead of an extended writing exercise.

I’m talking, of course, about the new “voice modes” recently released by the leading AI companies, including ChatGPT’s Advanced Voice Mode and Claude’s Voice mode (the latter of which is currently in beta and only available on the mobile app).

The limits of voice interaction…until now

I have to admit I’ve always hated every form of voice interaction with computers. I always found it incredibly buggy, error-prone, and mechanical versus writing.

It takes so little to make a voice interaction fall apart. If it misunderstands even one word, it might miss the context of the whole rest of the conversation. If it interrupts me because it thinks I’m done talking, it completely breaks the flow of the conversation. If I talk for several minutes and then a network error causes it to glitch and lose what I’ve said, I’m gone. Absolute dealbreaker.

Which makes it all the more surprising how good I found ChatGPT’s Advanced Voice Mode to be. I was shocked that it was not only perfectly accurate, but also fluid, natural, engaging, and even warm. These were qualities I didn’t even know I wanted from an AI conversation partner.

There were thoughtful pauses, subtle inflections and intonations, and I genuinely felt listened to and supported by its warm, understanding, even affectionate tone. I couldn’t help feeling the glow of approval as it affirmed my reflections.

And most importantly, across two hours of conversation in a very noisy environment – walking the streets of Long Beach – there was not a single “real” glitch. At most, it would pause because of loud background noise or a passing conversation, but then resume, just as a human would.

The response time, which was such a problem with earlier voice assistants like Siri and Alexa, was indistinguishable from talking to a human. It was around 2-3 seconds, as you’d expect from a person taking a moment to reflect on what you’ve just said. The only delay happened when it had to reference external sources, such as my blog post with the projects and goals I planned on taking on in 2025.

I said there were no glitches, but there was a limitation: at the one-hour mark, I hit the daily limit currently in place for Advanced Voice Mode, and only had the option of continuing with Standard Voice Mode. I don’t typically hit limits on AI usage, and this was the first time I can remember feeling genuinely disappointed that I couldn’t continue.

The setup: Testing Claude and ChatGPT

Claude recently released a beta version of its voice mode, available only in the mobile app for now. I started there because we use Claude primarily in the business, but found it quite disappointing. The interface is less intuitive and seamless, requiring me to tap a button, say my piece, and then hit “send,” a clunky experience that reminds me much more of earlier voice transcription apps.

The tone of the voice was colder, more mechanical, and more monotone, making me feel like I was talking to a robot. The sensitivity of the audio capture was also too high, and it kept interrupting me or sending my message mid-sentence, which is baffling considering it could simply wait for me to hit “send” once I was finished.

Here’s what the interface for Claude’s voice mode looks like:

I decided to switch to ChatGPT’s Advanced Voice Mode instead.

The crucial thing to understand is that ChatGPT’s voice mode isn’t simply speech-to-text transcription, like earlier technology. In other words, it’s not transcribing your words into written text and then sending that text as a message. That would save you a few seconds from not having to type it yourself, but otherwise not be any different.

ChatGPT’s Advanced Voice Mode does something altogether different: it provides the audio directly to a multi-modal AI model that can take it directly as an input, rather than having to convert it to text first. What that means is the AI gains access to much richer information – the pauses, the tone of voice, the speed and cadence of your words – and can therefore output much richer information in return, including its own tone and style and cadence.

I used wired Apple Earbuds, which I’d recently noticed lead to much better audio quality on calls than wireless AirPods, to make sure it was getting the highest-quality audio from me. With the earbuds plugged into my iPhone 16, I put my phone in my pocket and went on an hour-long walk without needing to look at it once.

To start the conversation, I created a new project within ChatGPT, added a link to my annual goals from the start of the year as a source, as well as instructions for the purpose of this project:

“This project is for completing my mid-year review, in which I check in with goals and projects I planned at the start of the year, revisit any intentions or themes I’d committed to, and generally connect with my deeper self and the wants and needs that are arising midyear. I’d like to use a back-and-forth coaching format where you surface insightful questions and ask me anything you think will surface important realizations and perspectives as I envision the second half of my year.”

Here’s what the project looks like in the mobile interface:

Problems and limitations with the AILack of thoroughness

The first issue I noticed, just minutes into our conversation, was the AI’s lack of thoroughness.

Thoroughness – dotting all the i’s and crossing all the t’s – is something I value highly in my work, because it allows me to trust the results of my past efforts and proceed confidently knowing I’ve left no stone unturned.

The reason I provided my goals from the beginning, including all the comprehensive and highly detailed context around each and every project I intended to take on this year, was so that it would help me review them one at a time!

Instead, I found that the AI repeatedly tried to gloss over certain projects, or skip certain goals entirely, or “jump to the end” of the past-facing part of my reflection and pivot to the future instead.

It was as if it had a system instruction to summarize or distill any source it was given. Even after numerous requests “to cover every project and goal in my review without skipping any,” that bias was too strong, and it was never really able to. Every time I asked, “Were there any elements that you missed?” it would apologize profusely and admit that yes, there were several more.

Reluctance to access the web

I also noticed it seemed to have an aversion to accessing external sources, such as the blog post I provided a link to at the start. Only when I explicitly directed it to reference my source did it grudgingly comply. I wonder if perhaps this is OpenAI’s attempt to limit the bandwidth, computing power, and time it takes to access the web. In the future, I’ll try adding the text of my source directly as an attachment to see if that helps.

Sycophancy and lack of good questioning

Another tendency I noticed was the sycophancy that’s been so widely reported this year among many AI tools. It would always strongly agree with, affirm, and encourage any thought, idea, conclusion, or insight I came up with, even if it wasn’t a good one. 

Relatedly, it didn’t ask follow-up questions, point out dysfunctional patterns or inconsistencies in my thinking, or offer new perspectives or frames on anything I said, which is the main thing I’d expect from a good human coach.

At one point, I realized that its failure to act as a good coach meant I was missing out on the main value of conducting a mid-year review, which is to rethink, challenge, and reevaluate my goals. So I had to course correct…

When we turned to my most important project of the year, the launch of our new AI educational program called Second Brain Enterprise, I asked it to “Ask me 3 provocative questions to provoke insights about this project.” It complied, but they were quite generic, like “What expectations did you have about the project that weren’t met?”

I noticed that the AI’s sycophancy had another, much more insidious effect: I really didn’t trust or place much value in any of its advice or recommendations. Even if it made its strongest case for an idea, I knew that if I simply asked it to change its mind and give me the opposite advice, it would do so without a moment’s hesitation.

In other words, my AI interlocutor had zero skin in the game. It had nothing at stake, nothing to lose, and no true commitment to any particular point of view or opinion. This made me realize that a crucial factor in how much stock we put in someone’s opinion isn’t due to the correctness of their logical arguments – it has more to do with their personal level of exposure to the risks of their advice. 

We essentially treat a person’s advice as a “bet” that they’re placing on a future outcome, and the larger the bet, the more we believe them. That certainly makes sense from an evolutionary perspective: people who keep making large bets on false positions will soon find themselves broke and unable to make any more.

Daily 1-hour time limit

I typically review my year (and mid-year) in three steps, corresponding to the Past, the Present, and the Future. After about an hour, we had covered the first two, but just as I was turning my attention to the future, I hit the 1-hour limit. This is actually a major issue, as in some ways I felt the conversation was just building momentum and reaching some interesting takeaways.

Here’s what it looks like when you reach the daily limit:

This limitation meant I had to save the last part of my review for another day. By the time I was able to return to it, a week had passed, and I’d forgotten much of the context, especially since I hadn’t written anything down! It’s clear that the technology itself is ready for prime time, but not until the limits are raised can it become an integral daily tool.

Length limit on each chat

When I picked up the conversation a week later, I found that I couldn’t continue in the same chat because I had reached another limit: the total length limit for any individual chat.

I had to restart a new chat within the same project, and even though OpenAI claims that context is shared between chats in a project (i.e., the contents of one chat should carry over and inform other chats in that project), my experience makes me doubt this is the case.

In our second conversation, the AI didn’t reference anything from our previous one. It retained the same project source file containing my goals, but the meandering context we’d built up over an hour of conversation was lost, which was disappointing.

Lack of documentation

By the end of our conversation, we’d hit upon a number of valuable takeaways, despite the limitations mentioned above. This was where yet another limitation arose: there wasn’t really a record of the conversation.

When you communicate via text, the conversation is “self-documenting.” You or anyone can simply scroll back through the entire conversation and review any part of it, with the same level of detail available to the people who engaged in it in the first place.

But audio is very different. What makes it so natural and fluid – that it’s effortless and ephemeral – also means that there’s no record that’s easy to review. Even if you make a full audio recording, it isn’t easy to search for specific segments within it.

I addressed this problem by asking the AI to create a summary of our entire conversation, including all the conclusions, insights, takeaways, and action steps we’d identified, which I’ll unpack in more detail in the final section below.

Problems and limitations with meNot having my Master Prompt

My team and I use Claude as our AI daily driver, which means we have the full context of our business uploaded as project knowledge across all our chats. I call that upfront context the Master Prompt, and it’s quickly become an essential, non-negotiable component of my AI usage.

Right away, I noticed that my interactions with ChatGPT were much less rich, less context-aware, and less specific because it lacked my Master Prompt. I soon realized this is a much bigger problem when interacting in voice mode, because it required me to explain the most basic details of my business on the spot. With text input, you could give it a link to your website to bring it up to speed, or copy and paste a long document with context about your business right into the chat box, but with voice, you’re limited to one word at a time.

This isn’t a limitation of ChatGPT, to be clear. I can easily move my Master Prompt from Claude into ChatGPT and add it to the project as a project file, but I hadn’t thought of that in advance.

Not trusting it

I noticed that I didn’t fully trust the AI at first, and spent some time tentatively testing its abilities. I would overexplain things initially to make sure it really understood what I was talking about, but soon realized that wasn’t necessary and I could provide only minimal explanation.

I was wary of the limits of how much input it could take in at once, and found myself speaking in unnaturally short segments and waiting to see if it would understand. As my trust grew, I found I could speak for many minutes at a time without any problem. The AI seemed to have a highly accurate short-term memory, though again it would usually gloss over some of the small but important details, or fail to dig into unclear or contradictory statements.

Retaining human conversational courtesies

I found that one of my limitations in fully utilizing the tool was, paradoxically, treating it too much like a human, with all the social conventions and courtesies that entails.

For example, I hate being interrupted and strive to never interrupt others. That makes sense in human relationships, but at one point, I realized that I could interrupt the AI at any time, and it would never take offense.

In fact, I found that my patience quickly dwindled to nothing, and I started correcting the AI immediately and sharply changing direction, since there was no value for either of us in it continuing to ramble on in the wrong direction.

Another example is that I kept trying to answer immediately, as you would in a human conversation. But then I realized I could just say “Let me think” and it would wait for as long as needed, while I thought about my answer. Though I suspect even these silent periods count against your daily usage limit.

Was it valuable to do a mid-year review as a conversation?

I would say the “voice-only” approach to my mid-year review was an interesting experience, and I accomplished my goal of conducting it in a casual, conversational format while getting some exercise.

Where this method falls short is in terms of its thoroughness, depth, and ability to surface contradictions, blindspots, and unexamined assumptions in my thinking and behavior. 

ChatGPT is designed to “solve the problem” as efficiently as possible, not lead you on a meandering, introspective journey. OpenAI thus doesn’t optimize for engagement or time spent – since they make the same amount of money regardless of how much you use their service, their incentive is actually to keep interactions short and to the point.

But the purpose of any kind of review or reflection isn’t to get to the end as quickly as possible. It’s to ponder, to contemplate, to reconsider, to reframe. The value comes from the time you spend noticing your own thinking, and thinking about your own thinking. And the value in a coaching interaction comes from your conversation partner having the skill and willingness to challenge, question, notice, and reflect back.

In the future, I plan on using AI’s voice mode as an occasional complement to my review processes. I think with some more involved prompting to slow it down and have it act more as a coach, this will turn into a powerful new mode of self-reflection as time passes.

Below you can find the full summary ChatGPT created at the end of our conversation, which I consider excellent, including a concise to-do list of action items at the end.

Here’s a complete written summary of all insights, decisions, takeaways, and action items from your mid-year review conversation, organized into key domains. I’ll also place this into a separate canvas in this chat for easy access.

Strategic Focus & Role DefinitionDecisions:Your presence in the next three cohorts of Second Brain Enterprise will be structured as follows:
Present for the first and last session of each cohort.
Deliver one or two special “Tiago-only” sessions per cohort.
Focus the rest of your time on creating reusable content and scalable assets.
Insights:This balance allows you to maintain influence and connection without overextending.
You’ve moved into a strategic role in the business with a focus on vision, storytelling, and growth through YouTube and thought leadership.
Takeaways:Delegation is key: continue handing off direct delivery and execution.
Preserve your “spark” by focusing on high-leverage contributions.
Marketing & Customer SuccessDecisions:You’ll focus your energy on top-of-funnel (YouTube, brand, awareness) and bottom-of-funnel (customer success, testimonials) — the two bookends of the customer journey.
Insights:This “first and last mile” strategy amplifies impact without requiring you to manage the middle of the pipeline.
Strong customer results will reinforce word-of-mouth and lead gen organically.
Takeaways:Invest in systems and team to manage operations, onboarding, and program delivery.
Prioritize quality and resonance in content over scale for now.
Second Brain Enterprise & Forte LabsDecisions:Maintain Forte Labs as a stable base while using most new energy for Second Brain Enterprise.
Define a clear time allocation model (e.g. 70/30 or 80/20) to avoid unintentional drift.
Insights:Your identity is expanding beyond Forte Labs — and that’s a healthy sign of growth.
As the new business matures, roles and responsibilities will likely shift again.
Takeaways:Continue building “execution muscle” on the team.
Systematize Forte Labs so it requires minimal creative overhead.
Home Life & SupportDecisions:Move forward with hiring a nanny and driver to increase time flexibility and reduce logistical friction.
Explore acquiring a second car for household and travel needs in Valle.
Insights:Increased household support = more energy and presence for work, family, and health.
Clarifying expectations and scheduling will be key for smooth household operations.
Takeaways:Formalize schedules and responsibilities for new hires.
Use this extra capacity to invest in family connection and personal renewal.
Health, Fitness, and HobbiesDecisions:Schedule resistance training 2x per week as a non-negotiable calendar item.
Supplement with hiking, yoga, and other light aerobic activities.
Insights:Structure and convenience (e.g., a nearby gym) are critical for consistency.
Fitness is an investment in long-term energy and emotional stability.
Takeaways:Try adding a multivitamin (Thorne Men’s Multi 50+) as part of your daily routine.
Stick to time-boxed workouts to preserve mental and physical bandwidth.
Family Activities & HobbiesDecisions:Explore biking as a shared father-son hobby — purchase a bike for you and Caio in Valle.
Look into a local biking route or destination you could make a weekly ritual.
Insights:Outdoor, physical, hands-on activities are the sweet spot for recharging and connecting with kids.
You don’t need a perfect hobby — just one that’s good enough to enjoy and repeat.
Takeaways:Pick one small, recurring family activity to turn into a weekly rhythm.
Track how it feels over a few weeks to iterate and improve.
Action Items SummaryBusiness: Schedule and confirm your cohort presence for the next 3 rounds.
Outline 1–2 “Tiago-special” sessions per cohort.
Begin scriptwriting or delegation for scalable cohort content.
Define and document time allocation between Forte Labs and SBE.
Finalize marketing funnel strategy (YouTube + testimonials).
Home: Hire nanny and driver with clear scope and availability.
Price and acquire second vehicle in Valle.
Add Thorne multivitamin to daily supplement regimen.
Health: Schedule resistance training on calendar 2x/week.
Plan 1 outdoor activity (e.g., hike or run) per week.
Family: Buy bikes for you and Caio.
Choose an accessible route and try it out together.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

The post The Voice-Only Mid-Year Review: Testing the Limits of ChatGPT Voice Mode appeared first on Forte Labs.

When I began writing my next book more than a year ago, on the topic of “annual life reviews,” I assumed that the practice was a fairly recent invention.

Maybe it came from the self-help movement of the 1970s. Or from corporate performance reviews. At most, I figured it might trace back to Ben Franklin or some other Enlightenment-era optimizer.

Yet, as I dove deeper and deeper into its history, I realized that I couldn’t have been further off the mark. What we think of as a modern productivity practice draws from three completely different traditions that have been evolving for thousands of years.

The English word “review” comes from the Middle French revoir, literally “to see again.” Every time we conduct an annual review, we’re participating in an ancient human ritual: the act of turning around to look at where we’ve been before continuing forward.

Fittingly, learning about the history behind the annual review caused me to see it in a whole new light. It fulfills a need so fundamental that nearly every culture in human history has developed some version of it.

Once you see these patterns, you can’t unsee them. Let me take you on a journey through time to show you what I mean.

The 4,000-Year-Old Productivity Hack

It’s 2000 BCE in ancient Babylon. 

Spring has arrived, farmers are planting their crops, and the entire civilization is engaged in a 12-day festival called Akitu. The Babylonian new year begins in mid-March, when they mark the milestone by planting their crops, crowning a new king, and most importantly for our purposes, making promises to their gods to pay back debts and return borrowed objects.

These are the first recorded “annual resolutions” in human history.

What strikes me about this ancient practice is how sophisticated it was. The Babylonians understood something that behavioral scientists are just now proving: combining practical actions (paying debts) with sacred meaning (promises to gods) creates powerful behavior change. They weren’t just organizing their finances—they were aligning their human affairs with cosmic order.

And they were doing this 4,000 years before anyone had heard of GTD or bullet journaling.

The Two-Faced God Who Saw Everything

Fast forward 2,000 years to ancient Rome, where things get even more interesting and recognizable.

By 153 BCE, the Romans had made January 1st the official start of the year, using that milestone to inaugurate their leaders, known as consuls. Over the next century or two, they developed a series of elaborate New Year rituals around that we continue in many ways to this day.

Those rituals weren’t just for commemorating another passing year. They constituted what I can only describe as ancient behavioral design. They believed that everything you did on New Year’s Day would set the pattern for your entire year. So they wore their best clothes, avoided quarreling, exchanged gifts, and performed symbolic acts of what they intended to do throughout the year.

As one classical text describes: “People took care that all they thought, said, and did, was pure and favorable, since everything was ominous for the occurrences of the whole year.”

Sound familiar? It’s a 2,000-year-old version of “fake it till you make it.” Millennia before modern psychology, the Romans had already discovered that acting “as if” could create one’s reality. They also incorporated “supernatural spring cleaning” and vows of renewal—combining physical clearing with psychological fresh starts.

The Romans dedicated January 1st to Janus, the two-faced god of beginnings, doors, and transitions. His two faces weren’t a sign of deception—they represented his ability to simultaneously see the past and future (If you’ve ever done an annual review, you know exactly what this feels like).

As I began to follow the thread of religious attitudes to temporal milestones, I discovered that spiritual traditions had developed some of the most sophisticated annual review systems, each one adding unique insights to the practice.

The Sacred Architecture of ChangeThe Jewish Innovation: Preparation Before Declaration

The Jewish High Holy Days offer a particularly refined approach. The ten days from Rosh Hashanah to Yom Kippur create a structured period for reflection and renewal. But my key takeaway came from what happens before: Jewish tradition includes a full month of preparation (Elul) before the new year even begins.

This addresses one of the fundamental challenges with modern resolutions—the unrealistic expectation that change happens instantly on January 1st. The Jewish calendar builds in time for gradual implementation, so new patterns are already taking root when the new year arrives.

The ritual of Tashlich—symbolically casting away sins by throwing breadcrumbs into flowing water—provides a physical action to represent internal transformation. The Machzor (High Holy Day prayer book) offers specific liturgies for self-examination. It’s a complete system for transformation, refined over millennia.

The Christian Watch Night: Collective Transformation

In 1740, Methodist founder John Wesley introduced Covenant Renewal Services on New Year’s Eve. These “watch night” services combined prayer, singing, and public resolutions for better Christian living.

The tradition gained historical significance on December 31, 1862—”Freedom’s Eve”—when enslaved people gathered in watch night services waiting for the Emancipation Proclamation to take effect and grant them freedom. This moment linked personal transformation with collective liberation, demonstrating how annual reviews can operate on both individual and societal levels.

The Christian tradition also offers an important linguistic insight. The Greek word metanoia, often translated as “repentance” in the Bible, actually means “a change of mind, a reorientation, a fundamental transformation of outlook.” Renowned Biblical scholar A.T. Robertson called the translation of metanoia as mere repentance “a linguistic and theological tragedy” and “the worst translation in the New Testament.”

As Robertson explains: “John’s call was not to be sorry, but to change mental attitudes and conduct.” This distinction was a revelation for me, having been raised in a Christian household. Year-end rituals aren’t about feeling guilty or admitting your faults—they’re about reorientation.

The Eastern Path: Physical Clearing, Mental Renewal

Asian religions and cultures developed many practices that use physical actions to create psychological change.

China: During Lunar New Year, families thoroughly clean houses to sweep away bad luck, settle all debts, and perform rituals for prosperity. The Book of Rites (Liji) contains detailed renewal ceremonies. The emphasis is on removing negativity from the past year so the new year begins with positive energy.

Japan: Japanese culture offers multiple practices. Kakizome—the “first writing” of the year on January 2nd—involves writing auspicious characters in calligraphy that encapsulate annual themes. These are displayed publicly, creating accountability through visibility.

The practice of misogi goes deeper. Practitioners make pilgrimages to sacred waterfalls, performing preparatory fasting and prayers. They enter freezing water while chanting “harai tamae kiyome tamae rokkon shōjō“—asking the kami (spirits) to wash away impurity from the six elements that make up human existence. On New Year’s Eve (ōmisoka), temple bells ring 108 times to dispel earthly desires.

Iran: Persian Nowruz marks spring’s first day with khaneh tekani—thorough house cleaning that serves as both practical preparation and spiritual renewal. It’s amazing to see how many cultures thought it was important to connect annual rituals to natural cycles.

When Business Reinvented the Wheel

In modern times, the reflective practices born in a religious context migrated to the arena of business.

From Shareholders to Self-Development

The corporate world’s contribution began with the Dutch East India Company in 1602—the first corporation to issue shares and provide annual reports to shareholders. They created the very first model for public corporate accountability.

By 1837, the New York and New Haven Railroad produced one of the first modern annual reports with detailed financial statements and performance commentary, introducing the idea of an accompanying narrative to explain and frame business results. 

U.S. Steel’s more transparent 1903 report established the template still used by businesses today.

The Performance Review Evolution

In 1842, the U.S. Congress passed a law requiring businesses to conduct annual performance reviews of workers. By the 1940s, 60% of companies used them; by the 1960s, this rose to 90%, becoming a fixture of global business culture.

A performance review might include an employee’s key deliverables, competencies like teamwork and communication, training needs, and career aspirations.

The evolution of these reviews reflects changing philosophies about human nature and motivation. Early reviews were straightforward, top-down assessments mostly used for pay decisions. By the 1980s, Jack Welch at GE popularized “forced rankings”—stack-ranking employees against each other, often accompanied by dismissal of the lowest performers.

Recent research has revealed significant problems with the traditional approach to performance reviews:

One survey found that only 14% of employees strongly agreed that their performance review inspired them to improveThe same study found that reviews made performance worse about one-third of the timePsychologists Meyer, Kay, and French have found that critical feedback in an annual appraisal often harmed subsequent performance, mainly because it put employees on the defensive

That last study identified one reason performance reviews may not work: combining multiple goals in one conversation—evaluating for pay while coaching for development—can create conflicting purposes.

Influenced by new management thinking like Douglas McGregor’s Theory Y (emphasizing employee empowerment), reviews have evolved to include goal setting, career development, and coaching. Many companies have now moved away from annual reviews toward continuous feedback models, focusing on two-way dialogue and future-oriented development.

The Agile Revolution

A significant innovation came from software development in the 1990s and 2000s. Agile methodologies formalized “retrospectives”—regular team meetings following each work sprint. The Agile Manifesto (published in 2001) popularized retrospectives as an integral part of its iterative approach to building software.

These retrospectives, drawing from influences like After Action Reviews in the military and Japanese Kaizen principles, ask straightforward questions:

What worked well?What didn’t work?How can we improve?

The military’s “After Action Review” was another influence. It offered a structured approach to review the results of key missions, emphasizing transparency and learning from both successes and mistakes even in high-stakes scenarios.

This shift from individual judgment to collective learning transformed thinking about reviews. This idea of regular, systematic review and refinement was later adopted in a wide variety of other industries, emphasizing that ongoing reflection can drive productivity and innovation.

The Modern Media Transformation

Most recently, the reflective practices that were once private or at least internal to a company became pieces of media that were openly shared, published, and celebrated.

When Reviews Became Public

The phrase “year in review” appeared in print as far back as 1888, and by 1897, it was used in business reports to describe a recap of the year’s accomplishments. But it was only in the 21st century that they became a widespread cultural phenomenon.

Facebook’s automated “Year in Review” videos (which compile a user’s most popular photos and posts) and Spotify’s “Wrapped” playlists (summarizing a user’s music listening habits for the year) brought the year-in-review to the individual level, turning personal reflection into shareable content. Annual reviews shifted from private exercises to public performances.

Annual reviews combined with life coaching and positive psychology became a popular fixture online, with content creators, entrepreneurs, and other public figures commonly sharing narrative-style “year in review” blog posts, sometimes as letters to their future or past selves. 

They perform personal SWOT analyses and apply KPIs to personal goals (“I aimed to read 20 books and read 15; that’s 75% of target”). Habit tracking apps provide year-end summaries of one’s progress, and photo books can be printed on demand. AI tools can now digitize your handwriting from a journal or diary and make it available for further analysis using Large Language Models.

Academia contributed its own tradition—”annual reviews” are scholarly articles that summarize a scientific field’s progress over the past year, helping experts catch up with cumulative knowledge. This tradition contributed the idea that annual reviews could be used as a teaching tool, to share insights with an interested community of peers or colleagues.

The Eternal Human PatternA Century of Familiar Themes

Historical records reveal that the resolutions people were making 100 years ago were remarkably similar to the ones we commit to today. Early 20th-century postcards include examples of people resolving to:

“Cultivate cheerfulness”“Repel promptly every thought of anxiety”“Use the most up-to-date selling methods”Swear lessHave a more cheerful dispositionRecommit to GodLive a “sincere and serene life”“Repelling promptly every thought of discontent, anxiety, discouragement, impurity, and self-seeking”“Smile when you fall down and out”“Keep a diary”

A 1911 cigarette ad suggested men “Stop kissing other people’s girls.” Journalist Ida Wells ended the year 1887 with a relatable feeling: “I am so overwhelmed with the little I have done for the one who has done so much for me & I resolve to … work for the master [i.e. God].” (She apparently stuck with it, too, teaching Sunday school in her hometown of Memphis for much of her life.)

Anne Halkett, a writer and Scottish aristocrat, titled a page in her 1671 diary “Resolutions,” coining the term for the first time, and pledging to “I will not offend any more.” By 1813, when a Boston newspaper coined the full phrase “New Year resolutions,” it observed skeptically that people “will sin all the month of December, with a serious determination of beginning the new year with new resolutions… with the full belief that they shall thus expiate and wipe away all their former faults.”

The Exeter and Plymouth Gazette concluded in 1913: “The mischief is that this fascination doesn’t as a rule last longer than the first twenty-four hours! … Frail is human nature!” 

Apparently, the phenomenon of setting ambitious resolutions only to forget about them 24 hours later was already well-known a century ago!

The Seven Universal Patterns

After studying these traditions across cultures and millennia, seven consistent patterns emerge:

1. Temporal Landmarks Create Fresh Starts

Every culture ties reviews to natural cycles—spring planting, winter solstice, lunar calendars. These markers create psychological breaks with the past, making it easier to change one’s thinking or behavior and make it stick.

2. Physical Clearing Enables Mental Renewal

From Roman “supernatural spring cleaning” to Chinese debt-settling to Japanese waterfall purification—lasting traditions include physical actions representing internal transformation. External order facilitates internal clarity.

3. Preparation Beats Declaration

Effective traditions include preparation periods: Jewish Elul, Chinese pre-New Year cleaning, corporate planning cycles. Real change begins before the official “start date.”

4. Public Commitment Drives Private Change

Whether Babylonian promises to gods, Japanese calligraphy displays, or Instagram posts—visible commitments increase follow-through. There are fewer forces more powerful than social accountability.

5. Individual Transformation Requires Collective Support

Strong traditions—African American watch nights, agile retrospectives, Japanese group purifications—recognize that personal change amplifies in community. Isolation undermines resolutions; connection sustains them.

6. The Practical and Spiritual Must Integrate

Successful year-end rituals combine concrete actions (paying debts, setting goals) with deeper meaning (values alignment, spiritual renewal). Neither element alone suffices. The Babylonians understood this 4,000 years ago, yet we’ve largely forgotten it today.

7. Honesty and Hope Must Balance

Every tradition combines a clear assessment of the past with an optimistic vision for the future. It requires neither harsh judgment nor wishful thinking, but clear-eyed hope.

What History Teaches Us About Change

This 4,000-year history shows how each era adds sophistication while maintaining the essential core. We’ve evolved from:

Babylonian debt-settling to financial goal-settingRoman festivities to Facebook celebrationsReligious confession to data-driven assessmentAgricultural cycles to fiscal quartersCommunity rituals to online accountability groups

Yet the fundamental human need remains constant: to periodically stop, see where we’ve been, and consciously choose where we’re going.

Annual reviews aren’t a modern productivity hack—they’re a fundamental human practice refined over millennia. Every culture discovered the same truth: we need structured moments to “see again,” to close one chapter and open another.

The question isn’t whether annual reviews work—4,000 years of human behavior suggest they serve an essential function. The question is: How can we design them to actually create the change we seek?

That’s what I’ll be exploring in my upcoming book. For now, consider this:

When you sit down for your next annual review—whether using my template, a journal, or quiet reflection—you’re not just doing a productivity exercise. You’re participating in an unbroken chain of human practice stretching back to ancient Babylon. You’re honoring the deep human need to periodically see again, to witness where you’ve been, and to choose where you’re going.

In that lies both the courage to acknowledge what was and the hope to imagine what might be.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

The post A Brief History of the Annual Review appeared first on Forte Labs.

I lifted my eyes from the journal I was writing in on the balcony of my hotel room, just in time to witness a towering block of ice split in half, splintering along its length with a thundering crack.

The iceberg it was part of shuddered, throwing off a shimmering coat of frost from its finely etched surface. For a moment, the block hovered in midair, seemingly unaware of its newfound independence. There was a moment of silence as it slowly began to pick up momentum.

After a few dramatic seconds, the wall of ice began to topple to the side, breaking up into several pieces that tumbled end over end as they crashed into the icy water with an immense splash.

My hotel room happened to be on a cruise ship crossing the most dangerous ocean passage in the world – the Drake Passage – on our way from the southern tip of South America to Antarctica on a 10-day voyage in December 2024.

Thirty-foot waves and seventy knot winds pummeled our ship from all sides as we plowed forward. The ship pitched from side to side, throwing our belongings off the table in our suite and making us seasick. The sea was a minefield of icebergs increasing in size and frequency with each passing hour.

The external environment of the cruise was accompanied by something equally special on the inside – a curated educational program on modern space exploration, organized by the advocacy nonprofit Future of Space.

The purpose of this voyage was to educate and inspire a group of 260 leaders from around the world on two of the most pressing issues of our time – climate change and space exploration – including how they might intersect and inform each other.

Ocean exploration pioneer Jacques-Yves Cousteau once said: “We only protect what we love, we only love what we understand, and we only understand what we are taught.”

We traveled to the edge of the world to discover how we could protect the planet, as well as potentially leave it.

Leaving the human world

We departed Los Angeles on December 17, flying to Buenos Aires via Miami. We stayed the night in the Argentine capital, before departing early the next morning on a charter flight to Ushuaia, a pioneer town perched at the very tip of the South American continent.

There we boarded the expedition vessel Seabourn Venture, along with 260 other guests who shared our dual fascination for Antarctica and outer space.

The program was made up of various luminaries, experts, scientists, and astronauts, including William Shatner, astrophysicist Neil deGrasse Tyson, journalist Ann Curry, former NASA astronauts Scott Kelly, Charlie Duke, and José Hernández, Céline Cousteau (daughter of the famed explorer and a prominent environmentalist in her own right), UK artist Stephen Wiltshire, and physicist and author Brian Greene.

These speakers filled our days with a constant stream of educational talks, interviews, documentary film screenings, panels, and presentations, encompassing both the deep past and the far future. Those talks were also livestreamed on the Future of Space YouTube channel, where you can watch the recordings.

Why run a space exploration conference on an Antarctic voyage?

Because Antarctica is the closest analogue on Earth to the harsh conditions we face in space. It is the last uncolonized continent, thus serving as a laboratory and testing ground for how we’ll go about exploring and colonizing new worlds.

At the same time, Antarctica is the ultimate bellwether for how climate change will shape the Earth. It is ground zero for the warming that is driving all other kinds of environmental change. The deteriorating condition of its glaciers directly impacts the lives of millions of people along all the world’s coastlines.

I wanted to visit Antarctica to experience one of Earth’s rarest and most quickly disappearing environments. I had recently learned that since 1970, the Earth’s temperature has spiked faster than in any comparable period in recorded history, and I wasn’t sure how long the continent would last.

I also wanted to see if immersing myself in such an utterly different and alien environment could give me a new sense of perspective for my annual review, at the tail end of a difficult year.

I was there to explore a triple frontier: humanity’s relationship to its home planet, our exploration of outer space, and my own inner world of goals and dreams for the future.

The itinerary

Each day, we’d arrive at a new destination, board a series of small, nimble Zodiac-style inflatables in small groups, and spend a couple of hours cruising (and sometimes landing) along the coast of the Antarctic Peninsula, which juts out from the continent in the direction of South America like an inviting bridge.

We had many close encounters with vast colonies of charismatic penguins, and watched them comically run, jump, dive, and play like children at a water park.

We visited historical sites, such as the barren beach on Elephant Island where Ernest Shackleton’s men famously sheltered for 4 harrowing months in 1916, after their ship Endurance was crushed by encroaching sea ice on the way to the continent.

I was amazed to learn that, until the first landings by seal-hunting parties and explorers in the 19th century, it’s unlikely that any human had ever set foot on Antarctica. The Drake Passage was simply too forbidding, and the technology to endure it didn’t exist.

Antarctica is thus halfway to being a foreign planet, like a way station physically located on the same surface as all the other continents, but psychologically, a world apart.

As we traversed the peninsula, I could feel a version of the Overview Effect kicking in – the famed perspective shift reported by many astronauts upon first seeing the Earth from space. 

We had a half dozen former astronauts aboard, and they described in vivid detail how that shift had affected them. They had realized firsthand how fragile and alone humanity is, clinging to its ball of dirt hanging in space. They’d been overcome with a sense of gratitude, awe, and humility at the miracle that is life on our planet. 

Antarctica is so bare, so starkly devoid of any sign of human life, that I could easily perceive that we were skirting the edges of a polar ice cap, stuck to the side of a planet, hurtling through space with nothing but a thin band of atmosphere protecting us. The sun never quite set, demonstrating that its rise and fall each day is just a side effect of our particular location on the planet.

An imaging satellite from Planet Labs circling overhead took this photo of our ship as it was moored:

I was overwhelmed by a sense of isolation, of aloneness, despite being surrounded by my fellow travelers. I’d never realized how much comfort and security I’d derived from human structures, human affordances, and human-made environments my entire life. I hadn’t grown up on Earth – I’d grown up in a series of insulated bubbles that humans had created to shield themselves from the Earth.

We made a dozen stops on our journey, including Half Moon Island, Whaler’s Bay and Deception Island, Trinity Island, Brown Bluff, Neko Bay, Lemaire Channel, and Palmer Station, one of three US-operated year-round research stations on the Antarctic Peninsula.

At Neko Harbour, I went ashore and officially fulfilled a lifelong dream: setting foot on all 7 continents. In one sense, it was fulfilling, while in another, I realized how foolish such a goal was. As if setting foot on a continent taught you anything about such a vast, diverse place.

A council of teachers

I learned so much from the invited experts on the ship; it was like an intensive course and conference unto itself.

Céline Costeau shared fascinating stories about her work creating documentary films, trying to preserve both nature and the human cultures that existed in close communion with it. She is multi-hyphenate – a documentary film director, producer, explorer, artist, public speaker, brand ambassador, designer, author, and workshop facilitator – and I saw that my career could be similarly multi-faceted and pluralistic.

We watched A Million Miles Away, the documentary about the life of astronaut José Hernández, who was present and answered questions about what it had taken to become one of the first Latinos, and the first migrant worker, to go to space. I saw how meaningful it was to break through a glass ceiling for one’s people and create new possibilities for them through your personal example.

Former astronaut Scott Kelly told us about his record-breaking year in space, and how it had been inspired by the intrepid adventures of Ernest Shackleton a century earlier. I was deeply moved by the model of perseverance even through heartbreak and failure, of personal sacrifice in service of humanity.

Neil deGrasse Tyson regaled us with tales of black holes, the potential of time travel, pulsars, and updates on the recent mission to explore the environs of the sun.

The last astronaut to walk on the moon, Charlie Duke, told us what it was like to plant his feet on another planetary body.

Tom Mueller, employee #1 at SpaceX, told us some incredible stories about what the early days of the company were like – a bunch of nerds firing toy rockets in the deserts of California – in pursuit of a far larger dream that today is finally being realized.

I was inspired by the crew, who were made up of experienced scientists, researchers, explorers, guides, and naturalists who worked so hard to provide us with life-changing experiences while also keeping us completely safe.

Gaining a new perspective

As I sat down to complete my annual review, I had real trouble with it. All my projects and goals seemed so trivial, so pointless, in the face of the immensity surrounding me on all sides. My awareness had expanded to a timeline so vast, it made even the most ambitious accomplishments I could imagine seem totally insignificant.

I found that all my problems and worries were put into perspective. Our margins in the business were lower than I’d hoped for last year – who cares? The vast, unfeeling vistas of ice that stretched as far as I could see didn’t know or care about that. All of humanity, with all its achievements, was almost a non-event from the perspective of the glaciers inching forward across the millennia.

I couldn’t shake the idea that about 70% of the Earth’s water is frozen here in ice sheets nearly three miles thick, and that if all that ice melted, the world’s oceans would rise by 200 feet, completely inundating my hometown. My mind could scarcely grasp the tenuous but direct connection between the integrity of these glaciers I was seeing and my life in sunny Southern California.

It was disorienting to vacillate between the inhuman harshness of the ice in one moment, to the sumptuous luxury of our cruise as soon as I entered back through a doorway. All-you-can-eat buffets and round-the-clock room service on one hand co-existed in bizarre juxtaposition with windswept ice fields on the other. Outside, a world devoid of any trace of humanity; inside, a rich agenda of in-depth knowledge about humanity’s most advanced scientific fields.

There were extreme contrasts everywhere, and I almost felt whiplash as my perspective hurtled from one point of view to another.

The landscape outside was in constant change. Everything made of ice is temporary, as winds, heat, rain, and undersea currents continuously reshape it. But at the same time, the landscape is ancient, like a time capsule from across the eons.

The majesty and seriousness of ice cliffs looming above us contrasted with the hilarious silliness and jovial banter of the penguins.

There was one moment I’ll never forget, at Melchior. It was bitterly cold, with wisps of snow drifting slowly from the sky. A small group of us boarded an inflatable boat and set out among the ice floes.

We entered a narrow inlet between massive ice structures, and found ourselves in a pool of water with walls of ice shooting straight upward on all sides. It felt like a natural cathedral – sacred, majestic, peaceful. I hadn’t felt such a presence of the divine since the church of my youth. 

I felt distinctly that Antarctica, and all the other continents, belong to all of us. They belong to humanity. I could foresee a future in which the whole world, and even other planets, might be governed the same way Antarctica is: collaboratively, through consensus, according to the long-term interests of all humans, even ones not born yet. 

I could sense my allegiance shifting, that I wasn’t and couldn’t be loyal to one country above the others. We are citizens of the world, and for a brief moment perched atop an Antarctic glacier, I experienced what that was like.

Here’s a video depicting some of the key moments of the experience, which I recommend to anyone:

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I’ve noticed that psychedelic medicine has been on the rise in California and other parts of the U.S. over the last few years, and have heard reports from a handful of friends and acquaintances about the incredible results they’ve had from ketamine, MDMA, and psilocybin. 

In our new home of Valle de Bravo, Mexico, I’ve also been surprised how psychedelics are just a normal part of everyday life. They’re something you talk about at kids’ birthday parties or with other parents in the pickup line at school. 

I don’t know if it’s the ancient heritage these plants have in Mexico (with evidence of their use dating back to 14,000 B.C.) or the hippie vibe of this particular town (it was the site of the Festival de Avándaro in 1971, the Mexican equivalent of Woodstock), or a combination of both.

Besides San Francisco, I’ve never encountered any other environment where psychedelics and other healing modalities are not only spoken of so freely, but are really “no big deal.”

That created the perfect setting for me to explore it for myself.

Micro-dosing

I decided to start my exploration of “magic mushrooms” with micro-dosing, which is typically defined as 5-10% of a standard psychoactive dose. For psilocybin, this means between 0.1 and 0.3 grams (100 to 300 mg) of dried Psilocybe cubensis.

According to this comprehensive guide:

“The intention [of micro-dosing] is to achieve subtle enhancements in mood, creativity, focus, and emotional resilience while maintaining the ability to engage in normal daily activities like work and socializing.”

I found a local cafe in Valle that openly sells branded psilocybin-infused chocolate bars, and I picked one up for my experiments.

I trusted the product because it’s made in-house by a local business owner known to the community, is nicely branded and packaged (suggesting there was at least a little quality control), and multiple people I trust have taken it and vouched for it.

It was a standard-sized, 100-gram bar containing 5% “functional mushrooms.” With 20 squares, that comes out to about 0.25 grams of mushrooms per square. Standard psilocybin content averages 1%, so there was probably around 0.0025 grams (or 2.5 milligrams) of psychoactive compounds per square.

I had never tried mushrooms before, nor micro-dosed anything, and therefore decided to start small: I took 1 square at 10 am on a weekday, about an hour before a Zoom workshop I was scheduled to teach for our Second Brain Membership.

These virtual workshops, which I do monthly, are typically quite challenging for me, since I have to keep a lot of material in mind and communicate it compellingly, while also taking into account the time left, people’s needs and questions, activity in the chat, the broader goals of the membership, etc.

It requires a lot of parallel processing and mixing different kinds of thinking, as well as keeping the objective in mind while remaining highly adaptable, which I often find difficult. I wanted to see if this chocolate could help me handle it with more ease.

Within about 15 minutes, I started noticing the effects, which were similar in magnitude to about 1-2 alcoholic drinks for me, i.e., a feel-good warmth without the negative side effects of heavy drinking.

The recurring pain in the right side of my throat that has plagued me for almost 20 years was already feeling relieved at this point. A line of tension down the right side of my neck (probably corresponding to my vagus nerve) felt soothed and even kind of buzzing with energy.

I started feeling a tingling, “glowing” sensation throughout my shoulders, neck, throat, and lower part of my head, as well as relief from a daily headache I’d had for weeks since recovering from a bad flu, which makes me think there were some pain-relieving effects.

As the workshop started, I felt noticeably more emotionally fluid, open, joyous, playful, and expressive, in place of the usual low-level anxiety I feel on group calls.

My wife Lauren, overhearing me from the other room, later said I sounded “really into myself,” which is a great description! I felt like the hot girl at a crowded bar, if that makes sense, open to and inviting attention from others, which is unusual for me.

During the call, I noticed I had a much easier time navigating the tension between sticking to a pre-formulated plan and adapting to changing circumstances. This was mostly because I more or less abandoned the plan – we only covered 1/3 of the agenda – which was a good thing because it was more important to discuss and integrate the material than plow ahead with all my slides, which is my usual tendency.

I felt much more attuned to the people on the call, warmer, more aware of their signals and body language, more curious about them, more interested in and welcoming of their questions and comments (which I can sometimes interpret defensively as veiled criticism, I’ve noticed).

We ended the last 15 minutes of the call with a very deep and personal discussion of what it means to be responsible adults and to conform to external expectations in the real world, without abandoning our interests, passions, aliveness, and sense of self.

That question was only loosely related to the technique I had introduced, but took a turn toward a more meaningful discussion than it would have otherwise.

Right after the Zoom call, I turned my attention to assembling a wooden playground structure for my kids, which I’d been doing the last few days in the afternoons after work. 

Surprisingly, this was extremely challenging! It was comically difficult for me to hold in mind obscure part numbers, search for them, count the numbers of screws and washers we needed for the next step, etc., a kind of task I normally find very easy.

I could tell my working memory was hampered – I repeatedly failed to hold in mind a 4-digit part number for more than a minute and had to keep starting over! I also handed my friend the wrong parts or the wrong number of parts. I don’t recommend doing construction on psilocybin, as studies have shown that it can hamper complex working memory.

I also found, both during my Zoom call and the subsequent construction task, that I cared much less and had much less fluency with anything numerical, abstract, technical, or conceptual, which normally feels like my “home territory.”

Instead, I felt drawn to nature, things physical and concrete, and thinking about my friends, family, and people I love. 

About 4.5 to 5 hours later, the effects had mostly subsided, and I was left with a pleasant afterglow like the morning after a fun party with friends (though my headache returned). I then left home to pick up the kids from school, and when my son got into the car, I felt a strong sense of spontaneous joy and almost broke into tears. I felt very connected to him and his innocence in that moment and throughout the afternoon.

For the rest of the day, I felt much more patient with the kids than usual. Normally, afternoons feel like they’re passing too slowly. I can find myself bored in comparison to the exciting pace of my workday. 

Next, I took the kids grocery shopping. I expected this task to be challenging, since it involves finding all the items on a list, but by this point, the cognitive effects had worn off and my working memory had returned. 

I felt more spontaneous, with my inner critic dormant and not filtering my words as much. This could also be described as “impulsive,” though, and my wife said I was “on one” all afternoon, and more blunt with her than usual.

In the evening, we went back to school for an all-school meeting, which took place in a forest next to the school. These all-school meetings are usually a bit stressful for me, with a flurry of faces and names I can’t quite remember, and all in Spanish. I felt noticeably calmer and more at ease this time, and about 50% warmer toward others (which made me about average for Mexicans!)

I had vivid dreams all night, one after the other, all warm and fuzzy and related to people I cared about. Besides the potential rudeness to my wife, the only downside I noticed was feeling thirsty. I had little appetite and didn’t eat much all day.

My conclusion from this first experiment was that this was a wonderful, enlightening, moving experience overall, and I definitely wanted to try it again. Micro-dosing felt very promising as an ongoing practice, as I seemed to be able to gain many mindset-altering benefits while still going about my day.

Overall, it strongly biased my mind and emotions away from abstract concepts and toward people, nature, my body, feelings, intuition, and my physical surroundings. Those are ways of being that I normally find hard to access, so this is extremely useful!

I did around half a dozen micro-doses, spaced out around once per week, as an initial foray into the world of magic mushrooms, and deeply appreciated their ability to shift me into a more grounded, calm, joyful, and connective state of being.

Macro-dosing

For the second phase of my experiment, I decided to go deeper with mushrooms and take a “macro-dose” (typically defined as approximately 2–3 grams, equal to roughly 25 mg purified psilocybin) under the supervision of an experienced professional. 

I recently met another father at our kids’ school who is a psychotherapist and administered psilocybin and MDMA-assisted therapy sessions on the outskirts of our town. We had a lot of mutual friends, and after getting to know him at a local sauna, I decided to work with him.

The process was surprisingly pedestrian: a Calendly booking link to schedule my session, plus a preparation call a few days beforehand, and a post-integration call a few days after. On our prep call, he asked me about my childhood history, my past experience with psychedelics and other mind-altering substances, my work and family situation, and any risk factors like mental disorders or addictive tendencies. He gave me guidelines such as not eating meat or drinking alcohol in the week leading up to our session, and asked me to water fast on the day of.

Most of all, we talked about my intentions for the sessions – what I wanted to see, hear, learn, and discover about myself. 

The intention I settled on was to explore my relationship with my father and how that affected my relationship with my son. My son and I had been going through what felt like a period of conflict and friction lately, as he explored his willfulness and the limits of parental boundaries. I’d felt distant from him, like an authority figure enforcing the rules rather than a friend going on a journey, and wanted to get to the root of the anger and frustration I’d felt toward him as he provoked his sister or made messes at the dinner table.

In previous psychedelic experiences, my father and my son had been at the forefront of my mind the entire time, and in retrospect, I can see that I just sort of assumed that would be the case again. Much of my personal growth journey has been about healing my past with my father, and I realize I had almost resigned myself to continuing to do so indefinitely. But plant medicine has intentions of its own, and I would find that not to be the case.

Set and setting

On the day of my scheduled session, I had a slow morning and, around 9 am, hailed a taxi to the therapist’s house, about 20 minutes away. His home was in a heavily forested area outside town, surrounded by nature, with a small office on the corner of his property seemingly purpose-built for these sessions.

It was a single room with an attached bathroom, decorated with all kinds of spiritual paraphernalia – incense, altars, totems, crystals, and images of Eastern spirituality. A large pullout sofa bed with a thick comforter occupied the center of the room, with a desk in one corner and two chairs facing each other in the other.

I took off my shoes and silenced my phone, and had a seat in one of the chairs. We spoke for about 15 minutes, revisiting my intention for the day and covering what I should expect over the coming hours. There was relatively little orientation needed: I would drink a small cup of dried mushrooms dissolved in water, with some lemon added to counter the bitterness, put on an eye covering, and lie in the bed under the covers for about 3-4 hours, to see what the mushrooms had to teach me.

I drank the liquid, which amounted to 4.3 grams of dried mushrooms (which at a 1.5% concentration meant about 40 milligrams of the active ingredient), and we talked for another 10 minutes, waiting for the medicine to start taking its effect. I started to feel its effects after about 15 minutes, and at that point went to the bathroom and then took my place under the covers. The therapist would stay with me throughout the entire 4-hour experience, making sure I was okay and supplying tissues and water as needed.

The first effects were visual – colorful tendrils of light swirling in the air above me. I couldn’t help but wonder if this was how mushrooms saw the world. After about 20 minutes of this, I went to the bathroom again, as the mushrooms had an effect on my bowels similar to coffee. 

Wrestling with an inner force

As I settled back into the bed, the experience shifted abruptly as a rising tide of discomfort quickly overtook me. It was a mix of nausea, muscle aches, and a kind of mental discomfort as thoughts and feelings I typically avoid rushed to the surface.

The next hour was physically intense for me – I writhed in the bed, flailing side to side, clutching my shirt and the bedspread, as the nausea got stronger and stronger. I broke out into a sweat, moaned and groaned and whimpered and snarled and breathed loudly in and out. It felt like I was wrestling with a powerful adversary, but that adversary was inside me, struggling to get out as I struggled to keep it in.

Throughout this part, many images flashed vividly through my mind, but I was surprised to find that they were mostly related to my daughter Delia. I saw her anguished face as she cried over a fight with her brother, and felt her kicking legs and pushing arms as she fought being put to bed. Suddenly, I was in her place, lying in her crib, crying and thrashing against the insurmountable force of my parent. I saw and felt it all viscerally from her perspective.

Eventually, I could sense the nausea was rising to a crescendo, and I couldn’t hold it in any longer. I felt the irresistible urge to yell, and gripping the sheets with my fists, I let out a couple blood-curdling roars at the top of my lungs, and could feel something moving through me and leaving me, like an exorcism. 

I could tell it was something related to my daughter, but I can’t say exactly what. As I lay on the bed, my legs propped up in exactly the birthing position, it was almost like I needed to “give birth” to her at a metaphorical or consciousness level, in the same way my wife had given birth to her physically. At 2 years old, her personality and will have emerged in full force, and it was as if I had to change my attitude and relationship to her from that of a helpless baby, requiring mostly feeding and changing, to a full-fledged person whose voice and opinions deserve an equal place in our family.

I told the therapist that I needed to throw up, and he brought a small bucket to the bedside so I could do so. Later, he told me that vomiting was uncommon, but not unheard of, during these sessions – happening with maybe one in every 30 people. As with ayahuasca, fighting the nausea and trying to keep the medicine down, I believe, was therapeutic. It provided a physical metaphor for the internal struggle, and the physical act of vomiting functioned as a symbolic act of expunging or releasing a force, entity, or energy that had been repressed inside.

The experience from that point onward was much calmer and more sublime. With my stomach empty but the psychoactive compounds fully absorbed into my bloodstream, I was free to go on an inner voyage. The music being played took center stage, a mix of soft contemplative instrumental tracks and adventurous, rousing anthems that sounded like a Hollywood epic.

Witnessing the women in my life

I found that, in contrast to my stated intention, my voyage was mostly about the women in my family. I thought of my mother, her intense love for me piercing my heart like it hadn’t in years. I felt the grief of her recent breast cancer recurrence, the helplessness I felt toward it, and how sorry I was to not be able to help her during this time, after all the years she dropped everything to care for me.

I thought of my wife Lauren and witnessed her essence as a divine, transcendent being that I was privileged to be with. The most clear message I received the whole time was that she was “the universe’s gift to me.” That she represents the universe’s most sincere act of pure generosity, I could never deserve nor repay. I felt the grief and sadness of all the times I didn’t treat her that way, neglecting to give her the attention, care, and respect her divine nature deserved.

I felt the deep sadness of not always treating my kids as the gifts they are. Of the times I’ve treated them as obligations, as hurdles to get past on the way to what I want. All of their emotions I hadn’t fully allowed – their rage, frustration, complaints, pride, annoyance, neediness, jealousy – came rushing up toward me from the pit where they’d been festering, unseen and unloved. It was hard to bear, the full weight of all that emotion. Like a white hot flash flood rushing past and through me on all sides. 

And again I thought of and felt my daughter – her emerging emotions of anger and sadness, her strong will and stubbornness, her vibrant personality, and the unique role she was starting to play in our family as peacemaker, caretaker, and comedian. It’s hard to explain, but each of these memories, realizations, ideas, and stories weren’t so much “thought” as “felt,” as if they were striking deep into the soft places of my heart. I cried more or less continuously, the tears completely soaking my eye mask and pillow. 

What was interesting about this part of the experience is that it was relatively free of “stories.” My daughter is so young, and our relationship so simple and pure, that I didn’t really have strong narratives about her that I had to let go of. The process was mostly somatic, like my body just needed to let go and process something I couldn’t fully explain, and both the logical explanations and the accompanying emotions took a backseat.

Holding this lineage of women in my mind, I was overwhelmed with the awareness of how much love they had poured into me my entire life. All the care, the thoughtfulness, the sacrifice. I felt the full weight of that care and how it had shaped me into the person I am now, capable of caring for so many others in turn. I saw how crucial, how all-important that warmth and love were to who I was; so much more important than the intellect with which I normally identify.

Tangentially, I also saw how important that direct, human caregiving is going to be in the new AI-driven era we’re entering. How important it’s going to be that we see each other, know each other, look out for each other, and help each other through the torrent of change we’re all facing as AI reshapes society. 

I saw that I could play a role not only in the intellectual, analytical, process-driven implementation of AI, but just as much in the education, the personal growth, and the human compassion that will need to accompany it. I had such a clear vision of the community we could create to help people grapple with the immensity of what AI would mean for them, and provide that human care and warmth that we all need to welcome the future with openness and curiosity.

The neuroscience of psychedelics

My psychedelic experience proceeded in stages or waves. They were almost like mini-trances, or a succession of dreams, as my mind flowed from one scene or sequence to the next. 

I found that I could choose when I wanted to “switch” from one line of thinking and feeling to another, almost like switching the channel on the TV. All I had to do was turn my head from one direction to another, and all of a sudden, my focus shifted. This was the first time I felt I had some control over the direction of my experience – I could choose where I wanted to go, what I wanted to focus on. And any person, relationship, memory, or part of life I focused on would yield insights.

I was reminded of this pair of images I came across in Michael Pollan’s book How to Change Your Mind, showing the connectivity of the human brain in a normal state, compared to the hyperconnectivity of a psilocybin-induced state (based on this study):

The researchers found that: “This supports our idea that psilocybin disrupts the normal organization of the brain with the emergence of strong, topologically long-range functional connections that are not present in a normal state.” In other words, psilocybin temporarily allows distant parts of the brain that don’t normally communicate to talk to each other.

Psilocybin effectively “shakes up” the brain’s modular structure, temporarily breaking down entrenched communication patterns (i.e., the Default Mode Network) and thereby promoting mental flexibility and new associations.

I also know that psychedelics have the effect of “turning down” the activity in the pre-frontal cortex – the site of our high-order reasoning, as well as our inner critic and self-manager. I conceived of the experience as the authoritarian father figure (the pre-frontal cortex) stepping out of the room for a while, and the rest of the family coming together for a meeting in which they could talk to each other freely, share their experiences, and remember their love for each other.

The value in seeing through others’ eyes

One of my favorite aspects of the experience was the ability to see the world from anyone’s perspective. I saw the world from my wife’s perspective, and instantly all her words, actions, and decisions made perfect sense. I saw it from each of my children’s perspectives, and their pure innocence was so clear and palpable, even in the midst of their worst tantrums and “misbehavior.”

I think as a parent, one of the most important things to keep in mind is your children’s essential innocence. They, like you, are just a sweet, innocent being who was dropped into this chaotic, painful world without their knowledge or consent. They, like you, are just trying every day to survive, to get their needs met, to make sense of the information flooding their senses, and to find their agency and power in an unforgiving environment. 

That remembrance of their innocence is the key to everything – to treating them with compassion no matter how flagrant their behavior seems, to seeing every moment as an opportunity for love and connection, to teaching them with patience how to navigate life, to not taking their actions personally or making it about you. Yet it’s hard to see the innocence of your children when you’re not connected to your own innocence and inherent goodness. That awareness is what I was overwhelmed by once I could see life from their point of view.

I thought of other people as well. My uncle Gary, who passed away a few months ago, and I hadn’t been able to grieve. Somehow, the Spanish language we’d been using throughout the session helped me to feel it. I wept with the phrase “Mi tío, mi tio” echoing through my head, as all the memories of his generosity and humor filled my memory.

Finally, my attention turned to my father, and what I encountered there was so surprising: nothing but an overwhelming, profoundly deep sense of gratitude. I could see the world from his perspective, too, and what I instantly grasped was how hard it had been for him. How much he had had to endure as a father of four, what it had taken to maintain a marriage and a household and a career and a life all at the same time, and still maintain his integrity and sense of self.

I saw how important it was that he’d been a strong father, modeling principles and boundaries and an unshakeable commitment to order and stability in our home. I’d often resented him for that, wishing he’d been more flexible or forgiving or gentle. But from my own perspective at 40 years old now, I could suddenly see how that strength had protected us, shielded us, given us a stable foundation from which we could strike out into the world with confidence.

I sensed that I’d reached a resolution with my father, that I had made peace with him and healed the essential rift between us. That realization triggered a new flood of gratitude and joy, because that same healing and connection is what I want for my relationship with my own kids. The doubt that I’d ever find it with my father meant I could never be sure I’d find it with my children.

And that made me realize that this was the first intensive healing experience that I had undertaken from the perspective of an adult. I had always felt like a child, like a boy, healing some foundational wound in the hope of finally “growing up.” But not this time. This time I could allow my vulnerability, tenderness, and heartbreak to come to the surface without abandoning my identity as a father, husband, and leader. 

The aftermath

I wrapped up the session around 2 pm, and took a taxi to a nearby nature spa for my integration and recovery. I felt like a newborn, raw and incredibly sensitive to every sensation, internal and external.

I had little appetite, but ate a mushroom soup in honor of the plant. I then spent a couple of hours rotating between a sauna, cold plunge, and jacuzzi at a local hotel we visit frequently, nestled in the green forest amidst the soft rainfall of the wet season.

Returning home that evening, I was overcome with joy and happiness seeing my kids. Their beauty and perfection were just so vivid, so palpable. The same with my wife – there almost seemed to be a halo over her head, her beauty radiating outward like the sun.

Over the next week, my interactions with my kids felt so different. Suddenly, they seemed more patient, caring, thoughtful, curious, and cooperative, in stark contrast to how I’d perceived them in recent weeks. I knew that the change had to have been in me, not them, and all the same, I couldn’t believe how much more easeful, meaningful, and fun our time together was. I think they sensed my openness and safety, and expressed so many new thoughts, feelings, and questions to me. It was as if I was getting to know them for the first time.

Long-term effects

As expected, I found the effects of my mushroom journey slowly wore off over the following days.

During the next week, I had a highly elevated mood, and found so much joy in the most mundane everyday routines. I was far more patient and present with the kids. An all-day travel day back to California, 4 days later, was not only much more tolerable, I actually found it fun! Normally, my wife and I take turns managing the kids for the 4-hour flight, but this time I happily played with them the whole time.

Visiting my parents a couple of days after that, we had a series of lovely conversations, talking about what I had seen and experienced. I was moved to tears again at the privilege of being able to share my insights with them and how much I appreciated their role in my life.

Surprisingly, I found my desire to drink alcohol dropped to zero. I’d never really enjoyed the taste or the experience, and used it mostly to help me slow down at the end of a stressful workday. It’s been more than a month since my session and the desire hasn’t returned.

At work, I felt much greater emotional fluidity and warmth toward my team and customers, emphasizing our shared values and the bigger picture of our work, which is increasingly about helping businesses adopt AI. I can already see that I’m going to emphasize community and the human-to-human connection much more as a result of this experience.

Takeaways

It’s now been over a month since my magic mushroom experience, and I’m left with several takeaways.

Healing can progress and reaches resolution

Looking back on this experience, I realize that I had long operated under an assumption: that healing was never-ending. I had expected to never really reach resolution. I assumed I would just keep uncovering new forms of psychological damage for the rest of my life, like an infinitely deep well.

But this experience taught me a different perspective: that while the overarching journey of personal growth may be infinite, there is a possibility of reaching true resolution along the way. I was surprised to find such resolution with my father, who had been the focal point of my healing thus far. I was so happy to find I could undertake this journey from the perspective of an adult, feeling in control and empowered even in the most vulnerable moments.

Most of all, I loved being able to walk away from this experience without feeling like I had to fundamentally reshape my life. I quite like my life. This was more like a firmware reset, putting me back in touch with my values and sense of self, without demanding that I make dramatic changes as a result.

Healing does progress, and it does reach resolution even as it extends to the distant horizon.

The role of psychedelics in an age of AI-driven change

We are pivoting the business strongly toward AI, especially its implementation in small and medium businesses. And the more I think about it, the more I believe that psychedelics and other forms of healing are going to play a crucial part in the AI era. 

The defining feature of this new era we’re entering is going to be ever-accelerating change. The condition of “future shock” first described by Alvin Toffler in 1970 is only now truly coming to fruition, as we enter a literally inhuman pace of change.

Humans are going to need new ways of adapting to change at every level of society and the economy. They’re going to have to “unlearn” old patterns, old ways of thinking, old paradigms, and old assumptions at breathtaking speed. That unlearning may be an even greater challenge than learning the new.

One definition of “grief” is “the sudden realization that a form of value is ending.” That’s the case when someone dies, and the realization of the love you feel for them hits you in full force. It’s the case when you miss out on a hoped-for opportunity, or a season of life abruptly ends, or a tragedy strikes in your family or in the world. As humans, we tend to quickly get used to the status quo, including what is good, valuable, beautiful, and true. Often, we realize its full worth only once it disappears.

It isn’t easy to grieve on command. As humans, we tend to do everything we can to avoid it. But perhaps these substances could be a medium for releasing our grief more reliably as the world shifts under our feet. Maybe psychedelics are emerging into the light at this moment in history because now is the time we need them to evolve our human consciousness at the speed that AI, a new form of consciousness, is demanding. 

The gift of a safe, accessible tool for healing

This wasn’t my first encounter with psychedelics. I’d previously experimented with LSD at Burning Man and completed a 3-day ayahuasca retreat in the mountains.

I count those as some of the most meaningful, impactful experiences of my life. And yet in retrospect, I realize that I’ve always operated under the assumption that in order to have the most valuable experience, I had to go to the furthest extremes.

But why should that be the case? Why should someone have to travel to the furthest reaches of the Peruvian jungle, or skirt the law, or risk their reputation, or spend a lot of money, or take multiple days off work, or take the most powerful dose, to receive love and truth?

If healing is a universal phenomenon and a universal human need, which is what I believe, then we need to find more affordable, accessible, risk-free, and scalable means of accessing it. For so long, tools for healing have been illegal, socially sanctioned, or at least labeled weird and taboo. Modern society has long considered it too dangerous to venture into the unconscious, the repressed, and the traumatic.

How fortunate that that taboo is now passing, and that we’re starting to open up avenues for healing in a format that is so incredibly accessible. Almost anyone can take a day off work, consume some plants, and lie on a bed for a few hours. What a time to be alive, when we can pursue deep forms of healing without disrupting our normal routines.

I’ve become a believer and advocate for psychedelic-assisted therapy, and intend to use my influence to make it more accessible in the world.

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