Instrument Three — Predict
What happens next?
Not the version you’re hoping for. All of them.
A set of prompts for private reflection — no score, no ranking, no comparison. The honesty is the point, not the answer.

I’ve noticed something about the way I plan, and it isn’t flattering. When I imagine how something will go, I don’t actually run several futures side by side. I run one — the one where it works — and I call that my plan.

It doesn’t feel like optimism when I’m doing it. It feels like planning. The timeline seems reasonable. The risks seem manageable. I’ve accounted for the obvious problems, so I assume I’ve accounted for enough of them.

The Favorable Draft
There is a well-documented pattern in how people forecast their own plans — we systematically underestimate time, cost, and difficulty, while overestimating the best-case outcome. It isn’t a character flaw. It’s a predictable feature of how forecasting works when the forecaster has a stake in the answer.

When I actually force myself to lay out the branches, most of them were sitting there the whole time. I just hadn’t looked.

Drafted The plan works close to as intended. This is the branch I already rehearsed.
Skipped The plan technically works, but produces a side effect I didn’t want and didn’t plan for.
Skipped Someone else responds in a way that changes the situation entirely — a response I could have anticipated if I’d asked what they had at stake.
Skipped It fails outright, for a reason that would look obvious in hindsight.
Before You Commit to a Plan, Ask
  • 1 What would have to be true for this to go badly — and how likely is that, honestly?
  • 2 Am I forecasting from evidence, or from how badly I want this to work?
  • 3 If someone else described this exact timeline to me, would I call it realistic?
  • 4 What does the other party stand to lose here — and have I actually asked how they might respond to that?
The Premortem
Before acting, imagine it’s a year from now and this has failed completely. Write down why. Not vaguely — specifically, as if it already happened. The failures that are easy to imagine in advance are, overwhelmingly, the ones worth planning around.

This isn’t a call to expect failure, or to talk yourself out of acting. It’s a call to actually look at the other branches once, on purpose, before betting everything on the one where nothing goes wrong.

Draws on the planning fallacy (Kahneman & Tversky; Buehler, Griffin & Ross) and the premortem technique (Gary Klein) — Meraki Institute original material.