Field note: January

January is the month where most of the planning energy goes, and most of it is wasted. I know this from experience. I've done the ten-page strategy doc. I've done the OKR cascade. I've done the vision board (once, in 2021, I will not describe it further). None of it survived contact with February.

This year I did something different. I wrote four bets on an index card and taped it to the wall above my desk. Not goals — bets. A goal is something you expect to achieve. A bet is something you expect has a real chance of paying off and a real chance of not. The word "bet" forces honesty about the odds.

The four bets for 2026: ship Sage After Dark publicly, get Trayd to 50 paying customers, write one long-form piece I'm proud of every month, take one real week off. That's it. No supporting objectives, no key results, no scoring rubric. Just four things that matter, in a form I can see every morning without opening a browser.

What I shipped

• The annual review — I wrote a 2025 retrospective for myself. Not published. Twenty pages in a private document. The useful output was a list of ten things I stopped doing that made the year better and six things I started that made it worse. I reread it at the end of January and cut two more things.
• Trayd pricing page rebuild — we had been on the same pricing page since 2024. Rebuilt it around a single tier for small teams and an "enterprise" path that's just a form that reaches me. Conversions went up in the first week.
• The 30-second rollback rule dispatch — the first Sage After Dark piece I was happy with. Wrote it in forty minutes. Sometimes the fast ones are the good ones.

What I read

• Thinking in Bets — Annie Duke · Reading this was the proximate cause of the index card approach to annual planning. The framing of decisions as bets with probabilities is obvious once you see it and changes how you talk to yourself about outcomes.
• Four Thousand Weeks — Oliver Burkeman · Second time reading this. The January reread is now a tradition. The book's central premise — you will never finish your to-do list, so choose what stays undone — is the most useful thing I've read about time management.
• Letters to a Young Poet — Rilke · Not applicable to product work. That is the entire reason I read it in January. Something without a lesson.

What I noticed

The annual planning ritual I've landed on takes one day, not a week. Half a day to look back — the year's wins, losses, surprises, and the things I told myself I'd do but never started. Half a day to look forward — four bets, not forty. The output fits on an index card. If it doesn't fit on an index card, I haven't made the hard choices yet.

January also reminded me that the first two weeks of a new year are a calendar that belongs to everyone else. The decisions I'd been hoping to make in quiet reflection got made in a series of calls, threads, and "quick syncs" that arrived like they always do when you've been off for two weeks. The actual planning happened in week three, when the noise settled.

Writing the bets on a physical card matters. I tried keeping them in a document. I tried a pinned Notion page. The wall works in a way the screen doesn't. The card is always there, it requires no login, and it never has a red notification badge in the corner.

January score: 8/10. The four bets are on the wall. The rollback dispatch shipped. The pricing page is better. I still owe myself a real thinking day in Q1 — the kind where no one can reach me.