Stuck on the Runway (How perfectionist planning keeps you from taking off)


I once worked with a founder who spent three weeks designing the perfect morning routine.

He built spreadsheets. Drew diagrams. Color coded his journal.
He got stoked about the latest productivity tool, onboarded himself for half a day.
His planning was thorough. Every detail accounted for.

Except doing the routine.

He was not lazy. He was caught in analysis paralysis. Planning felt safe. Starting felt dangerous.

Here is the problem. Preparation looks productive. It gives you the feeling of progress. But it keeps you on the runway while the work never takes off.

Here are three ways to break this loop:

  • The 5-minute contract. Commit to only five minutes. Starting is harder than continuing.
  • The messy draft. Make a bad version on purpose. Once something exists, it is easier to improve.
  • The body lead. Take one small action. Write a sentence. Send one message. Begin moving.

When you’re stuck on the runway, getting off the ground is the first step. Mapping the terrain beyond is next. Momentum matters more than clarity.

And the founder who kept planning the perfect routine instead of living it? That was me.

The Pocket

A newsletter for ambitious minds learning to live with more intention. Each week, you’ll get grounded reflections and practical tools to quiet your inner critic, realign with your values, and build a life that feels sustainable — not squeezed.

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