I built five books in one day to pick which one to ship.
For 2,000 days, I ran a daily founder standup. 44,110 standups in total. I needed to turn it into a closing artifact. The data was rich. Picking the angle was the hard part.
I could’ve picked the one that felt right and committed. Instead, I built five parallel versions. One book per angle:
- First Sale to Full-Time (milestone tracking through the logs)
- The 2,000 Day Arc (my personal journey through my own entries)
- Building Wisdom from 2,000 Standups (distilled principles)
- The Longest Standup (the whole thing as one continuous narrative)
- The Morning Pages of Founders (Julia Cameron framing)
Each got a full outline, a cover concept and a pitch. Enough weight that I could feel what each book would be like if it existed.
Number five won.
Once all five existed on paper, one of them was clearly harder to vary. Each sentence in the Morning Pages framing carried weight. The others had load-bearing slots I couldn’t fill without flinching.
This is simulation thinking: render a working version of each option, then pick the one that holds up when you can compare them.
Most decisions stall because the options are still descriptions. “Book about milestones” sounds good. “Book about wisdom” sounds good. Each description sounds good until you render it.
The fix is to render enough of each option to compare them. Five is usually the right number. Three is the floor. One is what people do by default, which is why decisions feel so stuck.
Before AI, outlining five books took five days. AI can render all five in an hour. Now you can run simulation thinking on any decision that matters.
The counter-instinct is that this feels wasteful. Four books you’ll never write. Hours spent on versions that die. But the alternative is committing to the wrong angle and finding out ten chapters in.
You can’t judge a book by comparing it to four blank slots.
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What stuck decision would unstick if you simulated five futures instead of imagining one?
