Charlie Gilkey's Blog

The last couple months have been about regrouping, resetting, and replanning our ambitious (sometimes too ambitious) goals for the last quarter of the year into some thing more realistic to the time and capacity we actually have.

And now we’re in December, where that time and capacity amounts to, for most of us, about two workweeks before the year-end holiday festivities claim what’s left.

Plus there’s the year-end push for many companies, trying to hit revenue numbers in the calendar (and fiscal) year, which usually means other projects you had on deck get dropped or delayed to focus on the bottom line.

So rather than trying to “finish everything,” let’s do our best to finish well. Which means things like these (which we’ll be talking about at our next Leadership Strategy Session — call details below):

Ending the year without overstretching

Creating rituals of completion and learning

Setting conditions now that make January less chaotic

Key among those is setting aside time now (yes, even in the shortened, hyper-busy of December) to review and reflect, as the first step to planning a smarter, stronger 2026.

Which is why Charlie and Maghan will be facilitating an Annual Reflection Workshop on December 17 (call details below), to help you with this important step toward finishing 2025 well and starting 2026 stronger.

~Steve

Check out October’s and November’s resources for some...

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🌟 Enjoy a special preview of this month's call replay! We're sharing a short snippet to give our free subscribers a taste of the rich discussions and timely insights we explored together. If you're not already a paid subscriber, consider upgrading to access the full recording and be part of upcoming sessions.

Thank you to everyone who joined our November Monthly Momentum Call!

With the year’s end in sight, this session centered on a powerful question: What can you let go of so you can step into what’s present for you now?

Rather than adding more pressure to “finish strong,” we explored how letting go of outdated stories, unrealistic commitments, and versions of ourselves we’ve outgrown creates space for what truly matters. From strategic project decisions to releasing narratives that no longer serve us, our conversation offered practical ways to move through the final weeks of the year with clarity and grace.

Here are some of the key themes we explored this month:

Making Strategic End-of-Year Decisions: Getting clear on how you want the final weeks of the year to go rather than trying to force everything across the finish line.

Thinking in Seasons, Not Years: Why three-to-five-year “Seasons” (capital S) create healthier context than trying to force transformation within a single calendar year.

Choosing Devotion Over Discipline: Recognizing when it’s time to shift your customer base or business model toward work you’re...

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December arrives with its usual paradox: there’s so much left undone, yet so little time and energy to do it. The default response is often to push through exhaustion to finish everything and end the year on fumes.

But what if December’s real work isn’t finishing everything but instead gaining the perspective to see where you actually are?

When you pause to look back at the year that was, something shifts. You see not just what’s incomplete, but what you’ve navigated, what you’ve learned, and how far you’ve actually come. That perspective creates clarity about what genuinely needs closure now and what needs to be reconsidered with fresh eyes in January.

This month, we’re exploring how to close the year with integrity rather than exhaustion.

On December 3 during our Leadership Strategy Session, we’ll focus on what that looks like when stewarding a team through year-end.

And on December 17, we’re doing something special: we’re dedicating our Monthly Momentum Call to a facilitated Annual Reflection workshop. Instead of our typical Q&A format, we’ll work through the reflection process together — helping you see where you actually are before you jump into planning where you want to go.

We hope to see you in December! (Details below 👇🏽)

For leaders navigating team dynamics, organizational priorities, and the challenge of maintaining sustainable momentum while...

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This month we’re doing something different. Instead of our typical Monthly Momentum Call, we’re offering a 75-minute facilitated workshop to help you reflect on 2025 before you start planning 2026.

Most people jump too quickly into vision-casting for the new year and spend too little time in the reflective space. They can’t see that they’re either closer to where they last cast their vision, or that where they thought they wanted to go is no longer as relevant for them.

In this workshop, we’ll work through the reflection process together, including:

Taking stock of your accomplishments and your challenges

Identifying the key lessons and patterns from the year

Recognizing the members of your success pack who supported your best work and how

Surfacing insights from this year that will shape how you approach the next

This isn’t about making plans. It’s about seeing clearly — processing the year that was so you can step into the year ahead with intention rather than reaction.

Come prepared to: Reflect rather than plan, be honest about what worked and what didn’t, acknowledge what you’ve learned about yourself this year, give yourself permission to let go of what no longer serves you, and identify which insights deserve to inform your next moves.

These monthly calls are part of a paid/premium subscription to Productive Flourishing.

If you’re not a premium subscriber yet, I encourage you to upgrade your subscription and join...

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To be a leader means managing constant complexity. Shifting priorities, team dynamics, capacity challenges, and the pressure to execute while everything keeps changing.

Our Leadership Strategy Sessions are supportive, no-fluff monthly virtual meetings for leaders navigating the real challenges of modern team life.

Each session blends practical guidance, coaching, and peer Q&A. We tackle what’s most timely and relevant, from clarifying team roles and managing capacity to leading through change and building trust.

You don’t need to prep. You just need to show up as you are, with whatever’s on your plate. These sessions are designed to meet you where you are.

By December, the emotional and operational fatigue is real. Some teams coast. Others panic. Many just collapse.

This session is about helping leaders close the year in a way they’re proud of — aligned, spacious, and clear. We’ll explore themes like:

Ending the year without overstretching

Creating rituals of completion and learning

Helping your team (and yourself) arrive at the end of the year, not just survive it

Setting conditions now that make January less chaotic

Leadership in December is less about productivity and more about stewardship. Finish well, and you’ll start stronger.

Bring questions about: Creating meaningful closure without forcing completion, helping your team process what the year taught them, navigating the...

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🌟 While we no longer record the Q&A discussions during our Leadership Strategy Sessions, we continue to record the opening teaching. Enjoy a special preview of what I shared about navigating November’s compression. If you want to see the complete teaching and take part in upcoming sessions, consider upgrading to join us live next month.

November compresses everything. Time. Energy. Attention.

The calendar says eight weeks remain in the year, but with the holidays and events the reality is closer to four or five. The temptation is to push harder, do more, optimize every hour. But November isn’t the time for heroics. It’s the time for precision. Strategic choices about what finishes, what ships, and what seeds for next year.

During this month’s session, we explored how you can help your team manage the tension that comes when trying to get everything done before the clock runs out while also enjoying the season.

Re-evaluate your strategic horizon. The year feels like a natural endpoint, but it’s often too short to judge if a strategic initiative is actually working. Treat year-end as a checkpoint, not a finish line.

Give your team permission to release. Just because you committed to something in May doesn’t mean it’s still the highest-impact work. Without explicit permission, teams stay locked onto projects that drifted far from your key results.

Shift from activity to outcomes. Your team’s long list of completed tasks can...

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Since writing about the Centaur approach to AI last year, I’ve done even more deep diving into where AI is especially useful, where it’s over-hyped, and where it’s trash. In that piece, I argued for a centaur model — AI augmenting human capability, not replacing our thinking. I warned about the “siren song of outsourcing our thinking” to AI.

Most people get that AI can’t replace them as planners. But what’s less obvious is how badly it fails as a planning partner — even though that’s exactly how most people try to use it.

Important Note: In this article I’m using the term “planning” in the narrowest sense: making commitments, sequencing projects, resolving priorities, etc. In other words, this is the work of the middle, “Designer” productivity persona from our Momentum Quiz. Some of you may be thinking of ideation, visioning, and brainstorming as part of planning, too. They are part of the planning process in the broadest sense, though in this context I’m considering “Visionary” work like those as important preliminaries to the core work of planning. Those visionary tasks (and some of the action-oriented tasks of the “Creator”) are places where AI can be useful.

When I started testing AI as a planning assistant, I approached it with both optimism and a healthy paranoia that it’d make a good bit of my body of work obsolete. I was genuinely hopeful that AI...

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November is when knowing you’ve got fewer workweeks in the month turns into feeling the reality that (in the US), you have three workweeks in November.

No matter how well you planned, how clearly you prioritized, or how firmly you said no in October, November has a way of surfacing every deferred decision and delayed project. They all seem to need attention right now, right when your team’s capacity is at its thinnest.

What makes November particularly cruel is that everyone’s feeling the same squeeze.

Your clients or bosses want things wrapped up. Your team wants clarity about what’s actually going to happen. You want to end the year strong without burning everyone out.

And somehow you’re supposed to navigate Thanksgiving logistics on top of it all.

Instinct compels you to push harder to get it all done. Wisdom suggests prudent subtraction.

November isn’t when you discover you can fit 30 days of work into 15. It’s when you discover what actually matters when there’s no room left for wishful thinking. The projects that seemed “important” in August reveal themselves as either truly essential or surprisingly droppable.

The resources below won’t give you more time — nothing will. But they can help you use the time you have without depleting the reserves you’ll need to actually enjoy December.

~Charlie

Check out October’s resources for some good ones that still...

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Many of us only think of “projects” as the big, visible work commitments: the big seasonal project, the hiring sprint, the new book draft. We forget that personal projects count, too.

‘Round here, anything that takes time, energy, and attention is a project. There’s nothing inherently different between a personal project and a professional/work project in this regard. The distinction between your personal self and your work self isn’t helpful here: there’s one you, with limited time, energy, and attention.

Projects like moving, renovating, getting your kids back in school or college, figuring out your new health insurance, or moving banks all take time, energy, and attention over time, aren’t going to happen on their own, and will displace other projects. They thus count as one of your Five Projects.

It turns out that being sick is a project, too. I’m writing this in late September, having just navigated my own three-week sick project, which is what prompted me to finally put this framework on paper.

One of the more frustrating aspects is that it’s simultaneously disruptive, not something you can control, and something you probably didn’t plan for. It barges onto your plate and takes up a project slot whether you acknowledge it or not. When you don’t count it as a project, you’re still trying to juggle five other projects plus an invisible one that’s draining your energy, attention, and morale.

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Sometimes you don't need a complete system overhaul — you need focused expertise to solve a specific challenge. Our 90-minute Catalyst Sessions provide targeted guidance to help you break through obstacles, gain clarity, and create momentum on what matters most.

Catalyst Sessions are focused, single-session coaching experiences designed to create breakthrough moments in your work and life. In just 90 minutes, you'll work directly me (Maghan), to tackle a specific challenge, unlock new possibilities, and walk away with actionable next steps.

Unlike ongoing coaching, Catalyst Sessions target one key area where you need immediate progress. They’re perfect for people who are feeling stuck, overwhelmed, or in need of expert guidance to move forward on something important.

Introductory Rate: $300

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You might be someone who:

Wants to stop losing ground on what matters most

Needs to unstick a stalled project

Wants a schedule that honors your capacity and energy

Needs clarity to move forward on an important decision

Wants focused guidance on one pressing challenge without a longer coaching commitment

These sessions are designed to give you expert support on that one thing standing in your way.

Bana Biri, Coach and Founder of Biri Publishing:

It’s a humanistic productivity. As a passionate, lifelong learner, I tend to overcommit only to find myself overwhelmed and out of time. I knew the solution was in the PF system,...

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