The Planning Fallacy: Why We Take On Too Much

Hi friend,

This week, I was reading The Art of Thinking Clearly by Rolf Dobelli, one of those books that quietly rewires how you see the world.

One chapter hit me harder than most: “Why You Take On Too Much.”

It describes something we all experience, making ambitious to-do lists, mapping bold project plans, believing this time will be different.

And then… reality intervenes.

Dobelli explains this through the planning fallacy, a term coined by Daniel Kahneman and Amos Tversky.

We consistently underestimate how long tasks will take, even when we’ve made the same mistake hundreds of times before.

Our optimism blinds us.

My favorite example from the book: the Sydney Opera House.

It was supposed to be finished in 1963 at a cost of $7 million.

It finally opened in 1973, at $102 million.

Fourteen years late, fifteen times the original estimate.

It’s a funny example until you realize we do the same thing on a smaller scale every day.

Every time we say, “I’ll just finish this tonight,” or “I can easily take one more project.”

The solution? Dobelli shares psychologist Gary Klein’s idea of the premortem, imagining your plan has already failed, and asking,

By writing that story before you start, you force yourself to see what you’d normally ignore, interruptions, overcommitment, wishful thinking.

So this week, before you add one more thing to your list, try this:

Look at your week as if it already collapsed.

What caused it? What could you remove or simplify now?

Because productivity isn’t about doing more.

It’s about thinking clearly.

💬 Have you noticed the planning fallacy in your own work, maybe a project that took twice as long as expected? (Reply to this email or comment below!)

Thanks for reading!

Selim Uysal

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