Kunal Gupta's Blog

The car rolled up to the gates, and I already knew the drill. It had been a year and a half since the last time, but the memory felt close. The warmth of the air, the smiles on each face that greeted us, the quiet dignity in their movements. A small ritual welcomed us, along with a clipboard and a pen. Within minutes, we were led to our room, and handed our first instruction: to put on our white pajamas.

No explanation. No options. Just a reminder of what we had signed up for. This would be our uniform, day and night, for the next three weeks.

There’s something disarming about being told what to wear. Especially when the choice is removed so completely. The color, the shape, the fabric. All decided.

It felt oddly comforting.

Maybe it was because so much else would be decided too. What we’d eat. When we’d eat. How often we’d see the doctor. When to rest, when to stretch, when to move. It’s a rare thing, to enter a space where autonomy becomes unnecessary. Even rarer still to feel at peace with that.

This was an Ayurvedic detox program, called Panchakarma. Ayurveda, literally translated to the ‘science of life’, is a 5,000-year-old ancient form of Indian medicine that sees illness not as a disruption to be zapped away with quick fixes, but as something to understand, to gradually unwind.

Less than twenty guests are taken in at a time at the hospital my partner and I went to. It’s not a holiday. It’s not even really a retreat. It’s a hospital. A gentle, comfortable and luxurious one.

Where the primary prescription is silence, warm herbal oils massaged into your body twice a day, and meals made uniquely for your body’s state, determined each morning by the doctor’s assessment. We met with the doctor twice daily. And over time, I began to look forward not just to what he’d say, but to not needing to figure it out on my own.

We didn’t leave the grounds. Not once for three weeks. There was nothing to buy, nowhere to go. No packages arriving, no errands to attend to. Devices are only permitted only inside the bedroom. Music, reading, talking are all not allowed during meals. Eating was intentional, focused and peaceful. Each guest at their own small table. Just food and focus.

At first, all of this control felt strange. Mechanical. But soon, something shifted. The routine didn’t feel like restriction. It felt like rhythm.

We drank only warm water. Ginger-infused. Sometimes plain. The taste, initially flat, began to warm me from the inside. After a few days, I noticed I wasn’t missing cold drinks, or coffee, or dessert. I wasn’t missing anything, really.

The food was always prepared within the hour of being served. Fresh, simple, warm. No microwaves. No leftovers. Every meal nourishing in a way I hadn’t experienced before. Not indulgent, not sparse, just clean. I began to feel that in my joints, in my energy, in my sleep. Not because I slept more, but because I finally became aware of what it felt like to feel rested, instead of exhausted and crashing into unconsciousness each night.

My partner and I shared a room. We’d made the decision to come together, and it added a dimension I hadn’t expected. The vulnerability of sharing everything, including bodily discomforts, emotional waves, fears, and fatigue, brought us closer than many conversations ever could. Small acts emerged from that closeness without needing to be asked. Those gestures became part of our language for the three weeks.

There were moments when discomfort rose quickly. The treatments can be intense. They involve purging, not just metaphorically. Liquids going in and and coming out of most holes in our body. I didn’t need to react. I just needed to be still.

Something about being cared for so completely, without needing to solve, manage, or even understand everything, was deeply emotional. There was a tenderness I didn’t realize I had been craving: someone asking the right questions, placing their hands with trust, making food not to impress or entertain, but simply to help me feel whole.

After a few days, I stopped thinking about what day it was. Not in a relieved, vacation kind of way, but in a different way altogether. A slow dissolving of my sense of urgency. I began to use energy only when it was needed. And saved the rest for detoxing and healing.

The transformation wasn’t dramatic. It was gradual. Physical signs came first. A leaner body, lighter limbs, clearer skin, less tension in my shoulders. But the deeper shifts continued unfolding afterwards. A quieter mind. A softer heart. A feeling of being safe, of being held. Not by any one person, but by myself.

Last year, after my first time, I was so inspired by the experience that I wrote a short book detailing each day. I shared a draft with my parents, and they were curious enough to go later in the year. They still feel the benefits more than one year later to this day.

Not everyone will find their feet arriving at a place like this. The time, the cost, the logistics, are not always accessible. This is also why I wrote a book as I believe that many of the practices and philosophies, despite being ancient, are as applicable to this day and even more needed in a modern lifestyle.

The idea that silence can be healing. That food can be slow. That surrender is not abandoning ourselves but coming closer to who we really are beneath the choices and habits and preferences that usually define us.

Wearing white pajamas was required. But over time, it began to feel like a gift. A way to disappear and unearth oneself in the same breath.

And that is how I learned to white pajamas.

White Pajamas: 17 Days at an Ayurveda Luxury Wellness Retreat is available on Amazon in paperback and Kindle.

Most days, it's easy to focus on the surface. The task in front of me, the commitment in my calendar, the decision needing to be made. And so I go ahead. I move, I speak, I act. But lately, I’ve been pausing more often to consider what I’m actually bringing to those actions. What sits underneath them, influencing the action.

There’s the action I take. And then there’s the energy behind that action. I've begun to notice just how different the experience can be when the energy shifts, even when the action looks exactly the same.

Going to the gym has been a regular part of my routine for years. But recently, I’ve started to notice the quiet but powerful force that determines whether I leave feeling full or depleted. Some days, the energy is light, even excited. I'm curious to move, curious to see what my body can do, glad to have music in my ears and time to myself. Those days, I exert a lot of energy, yet somehow leave even more energized.

Other days, I show up from a place that feels heavier. The motivation is fear. Fear of what might happen if I don’t go, fear of losing momentum, of not being enough. And while the workout may look the same from the outside, when I leave, I feel drained. Like something was taken, not given. Same action. Different energy.

I’ve started to see this pattern show up in other places.

In conversations, in decisions, in everyday interactions. Whether I’m responding to an email, moving through a crowded airport, or offering support to someone else, there’s always something humming underneath. I didn’t used to pay attention to this. But now I am starting to.

A few weeks ago, I watched a young child being asked to clean up their toys. The parent’s words were kind, but the energy behind them wasn’t. There was stress, frustration, and impatience barely hidden beneath the surface. The child pushed back. Not against the request, but, as I sensed it, against the energy. It reminded me of moments in my own life when I’ve said all the right things but felt none of the alignment. And wondered later why it didn’t land.

Behind every decision is a reason, but behind every reason is a tone. That tone isn’t always logical. It’s emotional, intuitive, wordless. It doesn’t always emerge in a coherent sentence, but it’s always there, like background music I didn’t know was playing until I leave the room.

Lately, I’ve begun asking myself: what is my real intention here? Not the stated reason, or the justification, but the quiet motivation beneath the surface. Am I writing this because I want to share, or because I need to be seen? Am I saying yes from generosity or from fear of missing out? Am I praying out of surrender or out of panic?

Sometimes the answers surprise me. And the simple act of noticing often shifts something. It’s not about correcting or editing the intention, not in a performative sense. It’s more like an unconscious pattern stepping into the light. The intention softens. Clarifies. Comes into alignment on its own.

I used to think an action was enough. That doing the thing carried its own virtue. But now I’m starting to see that action is only part of the experience. The intention shapes the weight of it, its reception, its echo.

There have been moments when I paused long enough to sense that I was about to act from fear. A speaking engagement accepted out of anxiety rather than joy. A message composed from insecurity rather than care. And I’ve found that bringing attention to this intention sometimes changes the action itself. At the very least, it changes how I feel about it.

Even silence can carry intention. Not speaking out of restraint is different than not speaking out of indifference. And I think others feel that, just as I do.

This reflection hasn’t made me perfect or consistent. But it’s made me more aware. And with awareness comes choice. Not a forced choice, but a natural one. When the action aligns with a true intention, it feels quieter. Lighter. Whole.

It’s not about doing better. It’s about being honest. About noticing what I’m truly bringing to each moment. When I don’t, then fear, habit, or ego will decide for me.

And that is how I learned to Action.

It was a simple cue. To fold forward, lengthening the spine. One I’ve followed hundreds, maybe thousands of times before. But this time, my hamstrings resisted. The stretch stopped short of where I remember it landing. And without warning, a wave of frustration rolled in.

Class had only just begun, but already my mind was somewhere else. Comparing, judging, remembering what once was. The awareness came with a slight sting. Not just in the body, but deeper. Something closer to grief.

I’ve practiced yoga for more than ten years. I practically lived at the studio in New York for a season, completed my teacher training, found my people, my rhythm, and for a while, my purpose. It wasn't just a habit, it was home. I remember being able to glide into postures that now feel distant. Back then, showing up to the mat was effortless. Natural.

Over time, things changed. I started going less often. At first, I explained it away. New gym routines, changing goals, shifting interests. There was some truth to that. And still, a deeper truth lingered: that maybe I had been avoiding the practice because in it, I could no longer hide from what had changed. My body, my limits, myself.

It’s far easier to gravitate toward the things that feel good, that feed the parts of identity we’re proud of. Easier to convince myself that I’m still that person from before, somewhere underneath. That I’m simply choosing differently now. But sitting in that yoga class, I began to wonder if some choices have more to do with protection than preference.

Avoidance is clever that way. It can wear the mask of mindfulness. Of strategy. Of maturity even. But sometimes, it's just fear, dressed up and given a name that makes it easier to live with.

That class became a mirror. Not just for my body, but for other areas where I’ve noticed a similar softening. Mental focus that doesn’t stretch quite as far as it used to. A conversation that tires me faster than expected. A book I want to read that sits untouched. Long flights I now hesitate to take. Languages, Portuguese, Hindi, French, that once lived easily in me, now peeking out only in small fragments.

Seeing this changing landscape within myself has been humbling. At one time, any limit was a challenge. Something to work with. Push through. Solve. The drive to overcome was a source of motivation, and, in some ways, identity.

But something has shifted. The instinct to push has grown quieter. In its place, a new kind of response is emerging. Softer. Slower. Less about returning to what was, and more about meeting what is.

Maturity, perhaps, isn't marked by how many limits are overcome, but by how many are recognized and embraced. By the subtle courage it takes to sit with the truth of one's capacity, without recoiling in shame or rushing to fix.

Midway through that yoga class, my internal narrative began to change. The judgment softened. The comparison receded. I was still folding forward, still not reaching where I used to. But something in how I met the moment changed. The resistance wasn’t gone, but it no longer defined the experience.

I began to see the limitation not as a wall, but as a doorway. An invitation into a different kind of relationship with myself. One where the body need not perform to be accepted. One where effort does not need to be proven.

In that practice, a shift: from fighting to holding. Holding the limitation closer, not as a flaw to correct but as a shape to understand. The same body, the same breath, but a different awareness.

Over time, what once felt like a limit becomes something else entirely. Not a boundary, just a shape. Not a failure, just a fact. And in seeing it without resistance, something else opens. Not wider, but deeper.

I used to think growth was about getting stronger, faster, better. Now I wonder if it's about getting quieter, softer, truer. Learningnot to give up, but to give in to what is.

The mat is rolled up. The postures are forgotten. What remains is a presence that wasn't there at the start.

And that is how I learned to stretch.

A friend was reflecting with me after a few weeks of travel that he felt depleted and worn out. I had also been traveling for a few weeks, yet I didn’t feel the same. I didn’t feel drained, I felt energized.

We began tracing the shape of our experiences. Where had he been? Who had he been with? What had his days looked like? His voice softened as he spoke. Beneath the words, a quiet disengagement. It was clear the places hadn’t really felt like his, and the people, though familiar, weren’t those who met him where he was.

Then he asked me the same questions. And as I described the past few weeks, I found myself smiling. I had been in settings that sparked something, new friendships, different perspectives. Even when tired, I wasn’t tired in a hollow way. I was tired in the full way, like after a good workout.

It made me pause. How could two apparently similar circumstances leave us with such different experiences?

We often speak about time. We often think about money. But rarely do we give much attention to energy. And yet, energy seems to quietly guide far more than either of the other two.

Money is easy to measure. Trackable in numbers and statements, visible in balance sheets and budgets. Time can be organized, capacity calculated by blocks in a calendar. But energy, what is that? It doesn’t follow the same rules. It doesn’t sit still long enough to be charted.

And yet, it has been becoming more important. Perhaps that's what begins to change as some of the other questions around money or time become more settled. Energy becomes the third resource. Invisible, unmeasurable, but unmistakably felt.

I notice how much more I reflect on where it comes from and where it leaks. There are no tools for this. Only patterns. Sensations. Recollections. A sense of brightness after a conversation. A subtle exhaustion after another. A sudden alertness when starting a new project. A mysterious fatigue when continuing an old one.

There seem to be three places I look when I try to notice my energy: people, places, projects.

People are often the most unpredictable source. Sometimes, sitting with a friend I’ve known for years feels nourishing, effortless. We don’t even need to say much. Other times, the same connection feels strained, like something between us is misaligned. Often it has less to do with the other and more to do with me. My state, my openness, my capacity to be with whatever shows up. Meeting new people can be thrilling or tiring. It depends not just on who they are, but on who I am when I meet them.

Places hold their own charge as well. Some cities pull something out from within, make a mind race, a spirit stretch. New York did that for me for years. But the same city that once lit me up began to wear me down. Everything required more energy than I realized I was spending. Lisbon, in recent years, offers a different rhythm. A slowness that feels restorative. But even peaceful places can become dull if momentum fades. Sometimes too much calm begins to press into stagnantly.

Projects are perhaps where this exchange becomes most vivid. The joy of starting something new. The spark of excitement when an idea lands and begins to find form. I feel that often these days, particularly exploring things with AI. That current of curiosity that energizes. But projects are not immune to becoming heavy, when they ask for skills I haven’t yet developed, or when the purpose behind them dims. Administrative work, repetitive tasks, uninteresting priorities, all these feel like small but steady leaks of energy.

What makes it more complex is how none of these areas are static. What gives energy today might ask for it tomorrow. The same person, the same city, the same work. Everything shifts in relationship to the season of life I find myself in. The same conversation that yesterday lifted me, today lands differently.

And so I’ve stopped trying to manage my energy. Not because it can’t be done, but because management implies control. And control isn’t what energy seems to need. What I’ve started doing, instead, is listening.

Just noticing. After a day ends, quietly asking: what gave something back? What quietly took something away?

Not always acting on that noticing. Sometimes there are things that require showing up to regardless of the energy they demand. But in the awareness, I find something subtle recalibrates on its own. No need to optimize or restructure or intervene. Just attention. And attention, I’ve found, opens something far better than a plan.

In the end, it was that conversation with my friend that brought all of this to the surface.

There is no spreadsheet for this. No formula, no metric. Just a quiet question that rides beneath experience: does this give energy, or does it take my energy?

And that is how I learned to listen.

The apartment was quiet when I returned. The suitcase waited untouched by the door, though I was already unpacking in other ways.

Lisbon was exactly as I’d left it, the soft light through the windows, the smell of the summer heat lingering faintly in the air. Familiarity returned quickly. But something inside took longer to arrive. It was still somewhere up in the mountains.

We had been in a small ski village in Canada last week. My partner, my parents, my sister, my brother-in-law, my nephew. A shared birthday with my sister, and a family vacation folded around it. Time together that felt both rare and full.

What surprised me most was not the scenery, although beautiful and inspiring. It was the spaciousness of being together, uninterrupted. Not by time so much, but by patterns.

Usually, when I’m with family, we gather in someone’s home. And in each home, something quiet and near-invisible takes hold. A pattern. Someone becomes the host. Someone becomes the helper. Someone becomes the guest. I often become tech support—fixing wireless printers, troubleshooting websites, rearranging apps.

But this time, we were somewhere that belonged to no one. A rented apartment with unfamiliar linens, an oddly shaped kitchen, and walls that held no memories. For once, the house didn't tell us who to be.

We shared meals differently. One person would start chopping vegetables while another found spices tucked behind mixing bowls. Someone had already done groceries without being asked. Someone else would quietly wash dishes while a game carried on in the next room. There were no plans. There was no one “in charge.” There was just movement. Exchange. Offering. Receiving.

My nephew, just four and a half, seemed especially alive to it. Curious, playful. His habits didn’t settle in because they had nowhere familiar to land. In this in-between place, he didn’t fall into routines he’d learned at his home or at his grandparents’. He created new ones, and they looked like delight.

That was when I began to notice what had really shifted. It wasn’t just our location. It was something subtler. It was the unpatterning.

There is comfort in patterns. I’ve built many of them into my life here in Lisbon—mornings that begin with hikes, evenings that end with friends. Routines that make the ordinary beautiful. Routines that feel alive and chosen.

But there are other patterns too. Ones I don’t always choose. Ones that choose me.

Returning to my parents’ home can feel like stepping into a costume I outgrew. A version of myself shaped by relationships that once made sense, but now feel slightly out of rhythm. Nothing is wrong. Nothing is uncomfortable. But there is less space to move. Less space to reintroduce myself, as I am now.

Environments have a silent authority. They hold memory. They hold expectation. And without realizing it, I often move to meet them.

Some places invite a self I’ve carefully grown into. Other places summon a self long gone, but quietly preserved in the paint, in the couch, in the dishes we always use.

That’s what made this family vacation different. We were together. But we had left the setting behind. And in that space, a different kind of relating became possible. A different kind of being.

Comfort, without history. Presence, without prescription. Belonging, without blueprint.

I began to wonder what it would be like to travel this way more often. Not just physically, but emotionally. To ask quietly before gatherings what space might allow for a new shape of connection? What setting could allow something unexpected to emerge?

It reminded me that experience is always being designed, even when unconsciously. The environment is part of that design. It sets the stage, even before the first word is spoken.

By stepping outside of our usual frame, a small miracle occurred: the frame did not follow us.

And that is how I learned to Unpattern.

For the past few years, I’ve been orbiting the world of AI. I’ve written about it, built around it, and followed it closely enough that its changes feel personal. It’s something I genuinely enjoy, an intersection of curiosity and creation. And like many others, I’ve welcomed small ripples of it into my daily life.

I’ve used chatbots to brainstorm, summarize, rewrite, organize. Each use quietly functional. A little faster here, a little smoother there. But always within the realm of the familiar. AI was helping me do what I already knew how to do. That made sense. That felt safe.

But it also felt… flat.

Faster didn’t necessarily mean better. Just quicker variations of an already known thing. And after a while, I noticed I wasn’t learning much. I was just moving through tasks more efficiently. The shape of the work stayed the same.

Something shifted recently though. Without deciding to, I began using AI in a different way. Not to accelerate what I already understood, but to attempt something unfamiliar. A kind of quiet boundary was crossed. I started using it for things I didn’t know how to do. Things I avoided because I felt unqualified. Or incapable. Or simply unsure.

That openness surprised me.

At first, it was a technical observation. I have access to a tool that knows much more than I do. So why not use it? But the real question became emotional. Why hadn’t I used it this way before?

It wasn’t about function. It was about fear.

There’s a particular discomfort in not knowing how to do something. Not just the not-knowing, but all that surrounds it. Feeling exposed, unqualified, behind. Even when no one is watching, there can be embarrassment. The subtle pull to return to what is known can be strong.

What made the difference now?

I think it was a mix of things. Some practical. Some personal. Over lunch recently, a friend reflected something to me I hadn’t fully named. That to do something unfamiliar requires humility. A softening of ego. A willingness to not have all the answers, or any answers. It requires emotional capacity. Not just time, but energy. Space inside.

For me, there was also a kind of remembering. I started a company at 20. I had no idea how to build an organization, raise money, hire people. Everything I did, I was doing for the first time. There was a lot I got wrong. And back then, that felt okay. The pressure to be polished hadn’t taken hold yet. Mistakes were expected. Even welcomed.

I think I had unlearned that along the way with success. Grown accustomed to the illusion and identity of competence. The safety of operating inside a box labeled “things I’m good at.” It’s a soft trap. Comfort masquerading as ease. After all, doing what I’m good at feels good. It’s stable, predictable, efficient. But over time, it can also be numbing.

I’ve noticed how rarely I give myself permission to try something I don’t know how to do. Not because the stakes are high. Often, they’re not. But because the fear of failing, of not being good, tugs quietly at the edges. So I stay inside the frame. Efficient. Capable. Stuck.

But here’s what I’ve been discovering.

When I use AI to try something I don’t know how to do—not to polish, but to explore—I find myself feeling something I didn’t expect: satisfaction. Even when it doesn’t work. Especially when it doesn’t work. Because when it doesn’t work, I try again. I ask a different question. I take a screenshot. I probe. I iterate. I learn.

I don’t see these early failures as failures. They’re just part of the process. Like trying a new piece in a puzzle without knowing where it fits. There’s no shame in getting it wrong. There’s only information.

And because AI doesn’t judge. Because it’s patient, immediate and available, it makes the process easier. Not less challenging, but less personal. I can be clumsy without consequence. That feels rare. And spacious.

None of this is really about AI. It could be a person. A book. A blank page.

It’s about something else. Choosing to try to do something I don’t know how to do. To experiment before expertise. To do before knowing how. To allow myself to be not good and to do it anyway. That’s not a technical capability. That’s emotional permission.

And I’ve realized how deeply satisfying that is.

Not because it’s productive or efficient. Not because it leads to something useful. But simply because it expands something inside. A reminder that I am not fixed. That I can try. That I can learn. That I can grow.

And that is how I learned to AI.

There was a time, not long ago, when booking flights felt like a form of self-care. I would sit with tabs open, measuring layovers like puzzle pieces, lining up departure times with sleep schedules and sunlight. The choices felt precise. Refined. A satisfying kind of order would settle after clicking the final button. The destination was chosen. The plan was made. Some small corner of the future had been neatly put away.

And yet, more and more, I notice how rarely life goes as planned.

It’s not subtle. Looking back on the past few months, three out of every four flights I book, I don’t take. I cancel them. Change them. Move them to a different day, or a different city altogether. The destinations shift. The timelines move. The ideas that once felt so certain become soft around the edges.

At first, it felt like a practical problem. Something to optimize. Better forecasting, clearer communication, more decisive decision-making. But something deeper kept nudging. An unease that this wasn’t about poor planning at all. This was about the need to plan in the first place.

There’s something seductive about having a plan. It gives the illusion of direction, of preparedness, of control. When a flight is booked, there’s less room for doubt. When dates are in calendars and confirmations in my inbox, I can tuck them away. A kind of quiet knowing: I’ve done it. The future is accounted for.

But it never is, really.

I used to believe planning was practical. Economical. That flights were cheaper when booked ahead, that being early meant being smart. It turns out, that’s not always true. Especially in places like Europe, where price protections exist and common routes are well-traveled. Waiting isn’t necessarily more expensive. Sometimes, it’s quite the opposite.

But even when it is more expensive, the trade-off has changed.

There’s a cost to locking my future self in, from the vantage point of today. To deciding where I’ll want to be, what I’ll want to do, before I get there. The emotions I use to justify my plans—the logic of saving money, of protecting my calendar—are often just that: justifications. I find myself talking logic to defend a deeper need for certainty.

And I’ve started to notice how emotional that need really is.

Oliver Burkeman, in “Four Thousand Weeks,” writes that planning is how we try to control the future. I keep returning to that phrase. It makes me smile, partly because of how innocently true it is, partly because of how absurd it becomes once seen clearly. Of course the future cannot be controlled. Not entirely. And more importantly—why would I want to?

What felt like effective travel planning slowly began to feel like something else entirely. A kind of performance. A script that became harder to follow as life’s tempo shifted. I began to wonder if the pattern was pointing to something deeper.

Maybe the canceled flights weren’t mistakes after all. Maybe they pointed to something right.

So much of the inner work I’ve done in the last decade—through meditation, therapy, personal reflection—has been about cultivating awareness. Presence. Closeness to reality. And that decisions made from presence will feel more grounded than decisions made from prediction.

Maybe all these changed plans are not a failure to commit, but a growing capacity to listen. A willingness to say yes to what is happening right now, rather than what was planned.

There are still moments when planning is necessary. Especially when involving others: family trips, group dinners, business meetings. When more people are involved, more coordination is needed. That’s real. But when it’s just me, or just my partner and I, that need softens.

There’s more room to respond to the present. More room to let the present shape the plan, rather than forcing the plan onto the present.

Sometimes that means booking a flight only a few days before leaving. Sometimes that means not booking at all. And sometimes it means changing something that, from a practical lens, "should" have worked, but from a deeper knowing, no longer does.

It might cost more in fees. That’s okay. It’s a small price to pay for closer alignment to my reality.

The shift, I’ve realized, is from control to freedom. Not freedom as chaos, but as responsiveness. Gentleness. Trust. The trust that life can be met in real time, not always prearranged. That clarity doesn’t always come months in advance. Sometimes it arrives on the morning of departure.

And in those moments, I’d rather be free than prepared.

The map still matters. But the roads that get drawn now are softer lines. They can be erased. Rewritten. Or simply walked, one breath at a time.

I don’t always know exactly when or where I’m going anymore. But I feel closer to wherever I am.

And that is how I learned to Unplan.

My sister and I share our birthdays, born just a day apart. Growing up, we celebrated together every year. She’s younger than me, but it never really felt that way, at least not to others. Maybe it was her confidence. Her ease around people. Everyone mistook her for being older.

I didn’t mind. I was a shy kid, the kind who preferred the corners of the room to the center. I liked being near the action but not in it.

Every summer, our parents would host a little garden party for our birthdays. There would be one birthday cake, and we’d blow out the candles together. Friends and family gathered on the lawn, and I remember it always felt festive without feeling overwhelming. What most people didn’t see was that I was hiding behind my sister. Letting the spotlight fall on someone else. And quietly enjoying that.

Being a summer baby meant that school was out during my birthday. A small blessing, in that it saved me from the classroom song, birthday attention, and the inevitable cookies or cupcakes brought in to share. Our birthday parties had more of her friends than mine, but I didn’t mind. I had a few close friends, not many, but enough. What I remember most is the quiet comfort I felt in not having to perform happiness, or celebration. Not having to be seen.

Later, at university, nothing really changed. Birthdays fell between semesters. A moment of stillness that didn’t ask for much. Conveniently placed for slipping by unnoticed. There was a pattern forming. Each year, I found subtle ways to avoid the weight of that particular kind of attention.

But, eventually, the context shifted. I was in my twenties, living on my own, and surrounded by friends who showed their love a bit more loudly. Birthdays became occasions to celebrate in the way everyone else did. Parties, dinners, dancing, drinking, staying out too late. The kind of nights that live loudly and fade quickly. I enjoyed those moments. They were fun. But something always felt slightly out of sync. Like I was playing a part I hadn’t auditioned for. I still showed up, and I liked the version of myself who did. But something was missing.

It was my thirtieth birthday that changed things.

The day before, my sister asked what I wanted to do. Where I wanted to go. What I wanted to eat. Her enthusiasm was genuine. I normally would've answered quickly, but this time, I paused. Something felt different. Over the past year, I had begun meditating, and had started paying more attention to the feelings that surfaced quietly, without reason. What I noticed was discomfort. A kind of pressure that was hard to name. It wasn’t about turning 30. It was about the unspoken expectation I felt to make something of the day. To make it count.

So I told her the truth. I didn’t want to celebrate.

She was surprised. Maybe a bit confused. So I explained that I wanted a quiet birthday. No invitations. No toasts. No decisions about what to wear, what to eat or where to go.

I turned off my phone the night before and decided to fast for the day. Strangely, that made things easier. Fewer things to coordinate, fewer boxes to check, fewer moments to try and perfect. I meditated in silence for three hours that morning and still remember some of the places I went. Memories that weren’t thoughts. Feelings that weren’t emotions. A kind of presence with myself I hadn’t felt before.

Later that day, I went to see my family. We had cake, quietly. It didn’t feel like a birthday so much as it felt like a still point in time. A moment of returning home, not just to the people I grew up with but to myself. I spent the rest of that evening journaling.

When I turned my phone back on the next day, messages flooded in, surprised friends, missed calls. I began replying, one by one. But I noticed that something had shifted. Connecting back to others now came from a place of deeper connection to myself. The reflection came first, the participation after.

That was also the year I stopped drinking, and I suspect looking back, that also made my birthdays more memorable and more meaningful for me.

That spontaneous birthday practice became a ritual. Each year, I would fast for the number of years I was turning. I would turn off my phone. I would meditate for longer than usual, write for longer than usual, and say less than usual. It became the way I reminded myself how to return within myself. I did that for seven years.

And then, I moved to Portugal.

I made new friends. Started a new life. And when my birthday arrived in Lisbon that first year, I felt something I hadn’t in a while. A desire to share. To celebrate, not to be celebrated. To gather people, not to be the center of them. So I rented a boat on the river in Lisbon. Everyone dressed in white. As friends stepped aboard, we collected their phones. We drifted down the river without screens, music playing, food shared, eyes meeting. Laughter. Conversation. Connection.

Somehow I had brought the rituals with me into the gathering. The distraction stayed out, the connection stayed in. The next year, I did it again. More people. More joy. Still no phones.

Last year, my partner surprised me with a trip to the Swiss Alps. It was quieter. Colder too. A summer mountain escape, a few close friends, silent mornings. Again, the outer shape had changed. But I recognized the same feeling on the inside.

This year, I’ve celebrated in different ways, with different people. No single answer to what the birthday was, or was supposed to be. Just a moment, really, to notice how much I’ve changed.

I used to think there needed to be a blueprint, a tradition to hold on to. But maybe that’s what birthdays are best at revealing. The gap between who I was and who I’ve become. A part of me still craves solitude. And another part of me craves connection. And they don’t need to be in conflict, anymore. The celebration with self and the celebration with others can coexist, so long as neither asks for performance.

The places have changed. The people have changed. The feelings, too. But each year, the desire is the same. To return, to reflect, and to notice.

Birthdays have become the mirror I forget about until I’m standing in front of it, wondering what’s changed. They help me remember that change is not something that happens once. It’s something that’s still happening. One quiet, invisible shift at a time.

And that is how I learned to birthday.

Recently, I found myself in a quiet corner of the Portuguese countryside, surrounded by twenty-five of my closest friends.

Some who have known me for decades, others more recently. All of them, in one way or another, had walked by my side through different chapters of life. They came from different cities, Sydney, London, Toronto, and New York, to be with me to celebrate my upcoming birthday.

Some had seen me stumble, some had seen me rise. Many had seen me change.

There was light agenda for the weekend. My partner had taken the lead in organizing it, and somehow, the lack of structure allowed space for something far more meaningful to arrive. People connected easily, as if they had been meant to meet, as if the story of my life had been stitched together into the kind of gathering that needed no explanation.

Lately, I’ve been working with a coach on developing a five-year vision. The intention behind it feels simple but daunting: to develop clarity as I enter a new decade, to deepen alignment between where I place my energy and define what truly matters for me right now. One of the exercises in this process involved writing my own obituary.

At first, I struggled. The very notion felt strange. But surprisingly, what unlocked the exercise was asking ChatGPT to write a first draft based on what it knew about me. Reading what it generated created space for me to respond. Not with edits, but with presence. Soon after, I wrote my own version. I shared it with my coach. We reflected that while it captured my own perspective, it felt incomplete.

Not long ago, my aunt passed away. After the funeral, my parents called me. They spoke not about the sadness, but the beauty of the words shared about her. And then they said something that stayed with me: “Why do we only share these kinds of things after someone is gone? They should hear them while they’re still here.”

Back to the birthday weekend away with my friends now. Halfway through the weekend, I made a spontaneous announcement.

I would host my own funeral. A living one.

My friends were surprised, but after a moment of it sitting in, not surprised to hear that I would want to experiment with something like this.

A friend stepped in to facilitate. He split our group of twenty-five into smaller groups. Each group was handed post-it notes and pens and asked to write a eulogy for me. Not from prepared thoughts, but from spontaneous presence. No time to rehearse, only time to reflect and write.

While they wrote, he and I set up chairs for everyone outside beneath a wide patch of sky, with a beautiful view of rolling hills.

After about thirty minutes, everyone was invited into our makeshift space. Music was playing in the background. My partner and I sat at the front. And then, one by one, each group sent one person forward to read what they had written.

Some were funny. Some were tender. Some wrapped kindness in mischief and others unwrapped truths through tears. They spoke about curiosity, calm, and kindness. About presence over performance. One spoke about patience. Another about wonder. There was much laughter, and shared stories I had long forgotten.

As I sat there, quietly receiving their words spoken in past tense, I felt something unexpected.

I felt seen. Appreciated. Held. And also… surprised.

None of the eulogies focused on the aspects of life I spend the most time on. My work, my health, and my relationship. Areas that occupy much of my conscious living energy were barely mentioned. Instead, what surfaced were subtler qualities. How I show up in a conversation. The way I create space. How I listen. The lightness I bring, even unknowingly.

Afterwards, debriefing with a few close friends, I shared that observation. And they gently offered a reframe. Perhaps those domains of life I focus on so intensely aren’t ends in themselves. Perhaps they are means. Means to a more authentic self. Means to deeper connection. That the work isn't in being remembered for any one thing, but in being present with who I already am.

And perhaps friends are the ones who see that most clearly.

Family wasn’t there that weekend. Neither were professional colleagues. My partner didn’t speak. What was reflected back to me came from friendship alone. And there’s a particular honesty in that kind of mirror. It’s where nothing needs to be proven. Where the self can be witnessed without the scaffolding of achievement, responsibility or identity. I felt known in a way that words rarely allow. And what I heard, almost universally, were not just stories, but feelings. Unfiltered, unearned, freely given.

At the end of the ceremony, I stood and gave a brief, impromptu speech. No notes. No idea what I was going to say until I heard myself say it. That I am not just me. I am, in some quiet way, made up of every person here. Every strength, every quirk, every moment of laughter I offer to the world is borrowed or mirrored from someone I’ve loved. I spoke of how each of their reflections helped me see myself more clearly. Not as a static thing, but as a living dynamic being, shaped by others with every passing year.

I’m still integrating what happened that weekend. I’m still listening to what was said. And to what wasn’t. I walked away with a full heart and an open question. What are the things I chase now, that in the end may not matter? And what are the things that matter deeply already, but go unnoticed because they ask nothing in return?

I’ll likely do this again. Not as an event. But perhaps as a practice. A way to pause and ask. A way to make space for reflection not just from within, but through the lives I’ve touched and been touched by. Not to be praised, but to be mirrored.

There are truths about my life I can’t see alone.

And that is how I learned to be remembered.

My birthday is approaching. And this one is an important milestone.

I gave myself the summer to develop a five year vision for my life, as I enter a new decade and chapter. Not a rigid one. Not a plan. Something softer.

For much of my life, I’ve lived with a plan. For fifteen years, I led a company as CEO. I planned in quarters and years. That type of planning was tied to outcomes—concrete, prioritized, trackable. This is different.

The starting point for my five year vision surprised me. It wasn’t a question of what I want to build, achieve, or even who I want to become. It began with qualities. Ways of being. Not in the shape of my accomplishments, but in the shape of my presence. It is about how I move through life, regardless of when or where, or even why.

So I started making a list of qualities that are important to me. It came quite easily. Now I am working with my coach to sift through them to discover which ones are the most important to me right now, and relevant to this next chapter of my life.

In a recent conversation with my coach, we shifted from qualities to something else altogether. A prompt he gave me. A writing experiment I hadn’t expected: to write my own living obituary.

Had it come at any other time, I might have hesitated. But the timing made sense. I’d recently been reminded of the idea by Tuesdays with Morrie, a book that I read many years ago. In it, Morrie, a professor facing a terminal illness, hosts a living funeral. He wanted to hear what people will say about him before he dies. A subtle rebellion against a world that waits too long to speak honestly and lovingly.

And recently, my parents returned from the funeral of my aunt. When they spoke about the experience, they kept returning to one observation: how strange it is that we only seem to say these things after death. Why wait? they asked.

So when the prompt came to write my own obituary, I felt a surge of energy pass through me. I had to do it.

I’ve written every week for this blog for over ten years. I journal several times a week privately. I have written four books. Words are a home for me.

However, when it came to writing my living obituary, my page stayed blank.

It’s easy to write about an experience from within it. It’s harder to zoom out, to see myself from the outside. I didn’t know where to begin. Not because there was nothing to say, but because the exercise required looking at myself differently than I am used to. And maybe that was the point. Looking not out at the world, but across my life. Not forwards in time, but backwards.

After a few attempts, I found myself turning to one of my AI assistants, ChatGPT. I gave it a single line: “As part of a reflection exercise, and knowing what you know of me, I’d like your help writing a living obituary.” I wasn’t sure what, if anything, would emerge.

Six seconds later, a draft appeared.

And I sat back. And I read quietly and slowly about my life.

The words held a mix of familiarity and distance. They were about me, but not by me. There were facts about my life, but what surprised me was how present my hidden desires were embedded throughout. My hopes. My aspirations. My dreams. Not written in the usual future tense where they live in my journal and my mind, but in the past tense. As if they had already happened.

It changed something in me.

Sometimes, speaking about the future feels like building a story we may never enter. But reading that future as if it had already occurred, there was a strange intimacy in that. My ambitions felt less speculative, more lived. They felt, for a moment, like memories.

When I journal, there’s always a sense of reaching, into the unknown, toward something unformed. But here, the past tense created a kind of grounding I didn’t expect. A possibility dressed as remembrance.

Of course, the words weren’t perfect. They weren’t mine. But they gave me something to work with. A clay form. I’ve always enjoyed editing, and this now feels like that. A chance to shape. To soften. To reveal. And in doing so, not just to craft a better piece of writing—but to better understand myself in this moment in time. The prompt pointed not to the end of life, but to the center of it.

It reminded me of how powerful it is to pause and look, not forward or inward, but from the imagined edge, backwards. The things that feel vague become visible. What I’ve value begins to reflect back towards me with more light.

The obituary isn’t finished. And neither am I. But what emerged was clarity.

And that is how I learned to remember.

If you are curious to read it, simply reply to this email and I’ll send it to you.