Weekly Wisdom #331 - Annual review template before the new year

Get Started, Free Annual Review Template, Antifragile & Optionality

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Happy Monday!

I kept telling myself the product wasn’t ready.

It needed one more feature. The onboarding wasn’t smooth enough. The design could be tighter. I’d been building for weeks, convinced I was almost there—just a few more tweaks before I could show anyone.

Then I finally demoed it. People were impressed. They didn’t notice the things I was obsessing over. They saw something useful and wanted to use it. All that waiting, all that polishing—it hadn’t made the product better. It had just delayed the moment I’d have to put it out there.

The things we put off rarely take as long as we think.

This year I noticed a pattern: the tasks I dreaded for days often took an hour or two. The launches I delayed for weeks could have happened a month earlier. The “big” things weren’t actually big—they just felt that way because I kept avoiding them.

As we head into the new year, I’m trying to remember this. The fear of doing something is almost always worse than actually doing it. And the longer you wait, the heavier it gets.

The hardest part isn’t the thing itself. It’s starting.

I hope you're having a great holidays and wish you the best in 2026.

Graham

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📕 Annual Review: The Complete Annual Review Template​

These are all the questions I've gathered through the years that form the basis of my annual review.

It's less of a strict process, and more of an opportunity to reflect on the good things and bad things from that year, to try and improve the next one.

Feel free to make a copy and fill it out yourself. I usually choose the questions that stand out to me, but don't do all of them.

📚 Book Notes: Antifragile: Things That Gain From Disorder - Nassim Nicholas Taleb

An excellent book that has influenced my thinking more than almost any other, and continues to be a reference I go back to.

Taleb puts forward evidence and definitions for fragility, robustness and antifragility, and explains where they apply in life, and why you want to strive for antifragility.

The core idea: some things break under stress, some things resist it, but the best things actually get stronger from volatility and uncertainty. Great for improving contrarian thinking.

📖 Article: The Trouble With Optionality — Mihir Desai

This short read offers a counter to the prevailing logic that one should always optimize for maximum optionality. Sometimes the best move is to commit—to stop preparing and start doing.

I took the plunge and quit my job this year to pursue some personal projects, and my thinking was largely along these lines.

📣 Quote:

"You're only as good as the chances you take." — Al Pacino

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