Why Most Founders Waste December (And How You Won’t)
A simple alignment practice with AI powered prompts to help you enter January already in motion.
TL;DR: Most founders waste December. The ones who scale use it. This letter gives you the exact prompts I use to close the year with clarity, direction, and a January that hits different.
December isn’t the end of the year.
It’s the clearing.
The moment where everything slows just enough for you to finally hear what the past twelve months have been trying to say all along.
Most founders treat December like a victory lap.
I’ve learned it’s really the recalibration window — the place where you step back, listen, and realign before momentum starts pulling you again.
Last week, I was mapping next year’s world tour — cities, partners, stages, the lift required, and the people I want beside me as this thing scales into what I can already see coming. Milestones, activations, the whole ecosystem, I want to build around it.
None of that planning locks me into anything.
It just gives me clarity.
Because the map isn’t the territory.
But without a map, the territory becomes chaos.
And part of that clarity comes from alignment — not just the internal kind, but with the people who matter to the future I’m building.
So over the next two weeks, I’m lining up calls with my key partners. Not catch-up calls. Not holiday greetings. Actual alignment conversations. So when we hit January, there are no warm-up laps. No easing in. Just shared direction and inevitable momentum.
Here’s the simple alignment process I use every December.
It takes about an hour. I run the whole thing inside ChatGPT.
Use it if it serves you.
I start by emptying everything… voice memos, notes, reflections, messy thoughts.
Then I ask questions that help me see the year clearly, not nostalgically.
And if you want the exact prompts I use, here they are.
Copy them. Paste them. Answer them honestly.
ANNUAL DEBRIEF: YOUR INPUT PROMPTS
Wins
What were the big wins this year?
What were the small wins I forgot to celebrate?
What felt easier than expected?
What did I pull off that the “earlier me” wouldn’t believe?
Losses
What didn’t work, even though I tried?
What did I avoid dealing with?
What cost me more energy than it should have?
What am I ready to admit wasn’t aligned?
Pivots
What changed in my direction, intentionally or unintentionally?
Where did I surprise myself?
What shifted in my identity, values, or aspirations?
Patterns
What kept showing up again and again?
What did I learn late that I should’ve learned early?
What am I pretending not to know?
Vision Board Check-In
What on my last vision board came true?
What no longer resonates?
What needs to be added for who I’m becoming next?
This Year’s Data
What did the year reveal about my strengths?
What did it reveal about my limits?
What feedback did I receive that I brushed off?
What’s the story the data is trying to tell me?
Emerging Truths
What feels undeniably true now?
What did this year make impossible to ignore?
What’s calling me forward?
Alignment
What’s aligned with my next chapter?
What needs to be released before January?
What deserves more of my energy?
This cuts through the noise.
It surfaces the patterns I usually rush past.
Then I zoom out… way out.
I sketch the next 12 months as a narrative arc rather than a rigid plan.
I ask:
What future am I actually stepping into?
What would the “obvious” version of next year look like if I stopped resisting it?
What becomes possible if I stop playing small?
What are the milestones that matter, not the ones that impress?
This isn’t forecasting — it’s direction-setting.
A story I can feel.
Once the future arc is clear, I compress it into the first 100 days.
This is where momentum becomes real.
I narrow down to:
2–3 priorities that lift everything else
the people and partners I’ll need to support them
the systems that remove friction
the commitments I’m actually ready to honor
the things I’m finally ready to let go of
This is where January shifts from aspirational to inevitable.
Why am I sharing this?
Because every December, this little ritual gives me something founders rarely talk about: grounded clarity.
The map will change — it always does.
But the act of creating it keeps me moving with purpose instead of panic.
And maybe that’s the real point of all this.
We plan the path, but in the end…
It’s not the destination, it’s the journey.
Gratefully,
Edwin
P.S. I’d love to hear how you plan your new year. What rituals or prompts do you use to get clear? Hit reply — I read every note.
Insightful. December clarity beats December chaos.