Planning isn’t primarily an analytical tool. It’s a psychological one. Maybe a political one too.
The spreadsheets, the roadmaps, the phase-gate reviews — they exist as much to manage anxiety as to manage the future. Leaders have a profound intolerance of ambiguity, so they produce documents that feel like a form of control. The document becomes the thing. The process disappears.
That’s uncomfortable to sit with when you’ve spent years thinking of yourself as someone who plans rigorously. I have.
There’s a compounding problem underneath this. The deeper you go into your own project’s details — what behavioral economists call the inside view — the more delusionally optimistic your forecasts become. More data, worse accuracy. You stop seeing the outside world entirely. Kahneman knew this better than almost anyone alive, and still couldn’t escape it. That’s not a story about stupidity. It’s a story about how seductive the inside view is once you’re in it.
And yet — here’s where I get stuck — the optimistic bias that causes all of this is also the only reason anyone attempts anything genuinely difficult. Perfect statistical awareness of your own odds of failure would empty the field entirely. No companies started, no wars fought, no infrastructure built. The planning fallacy isn’t a bug in human cognition that smarter processes will eventually fix. It might be the engine.
Which leaves the hardest question. The “stay flexible, iterate, adapt” playbook works beautifully for startups, software teams, and military units operating in fast feedback loops. It has no answer for organizations building nuclear plants, pharmaceutical pipelines, or national rail networks. Decades of irreversible capital before a single assumption can be tested.
My best guess — and it is a guess — is that leaders who navigate this successfully hold two things simultaneously: a twenty-year ambition large enough to be genuinely disorienting, and a three-year plan focused ruthlessly on what matters right now. The flight path will be ninety percent off. The destination might still arrive.
That’s not the plan working. That’s the planning.