The Planning Trap

I spent the first two months of my sabbatical building an elaborate plan to market my book and my author brand.

I had project plans in Notion with dependencies and timelines. I mocked up world maps and built out character sketches. I created social media calendars and content pillars. I waffled between three or four different pen names and researched website hosting options.

You know what I didn’t make progress on? The book.

This is the planning trap, when structure becomes procrastination. The systems we build to help us succeed become the very things preventing us from starting.

I’m basically best friends with this failure mode. We’ve spent a lot of time together in Airtable, among other places. But it surprised me to find myself wasting my own personal time this way outside of work.

Why we fall into the planning trap

It feels productive. Making project plans and organizing research gives you that same dopamine hit as actual progress. You feel busy and accomplished.

It feels safe. Planning has no risk of failure. You can’t write a bad scene if you’re still perfecting your character development spreadsheet.

It gets rewarded. Thorough planning and documentation got me pretty far in my marketing career. I wrote a lot of words, big memos, big proposals, and people said nice things about them.

The planning trap in action

In startups: I’ve seen startups spend months building products, then scramble to find problems they solve. Mock up sleek product images before writing a single line of code.

In marketing: How many onsite strategy sessions fizzle out because brainstorms never translate into action? I’ve seen teams spend weeks debating attribution models instead of running tests to generate actual revenue.

In creative work: Obviously, this isn’t something that my boss is making me do. It’s intrinsic. I don’t think I’m the only aspiring writer getting stuck in the weeds and mechanics instead of fully committing to writing.

The planning trap shows up everywhere, but it’s particularly dangerous in creative work because there’s no external deadline forcing you to ship.

How I tripped the trap (and how you can too)

Finally, I Googled “how many words in a typical romance fantasy novel” and realized I’d made, like, 1% progress. It forced the honest question: If I get to the end of my sabbatical with regrets, wishing I had more time, what would I have done wrong?

I knew the answer right away. If I get to the end of the year with a big pile of notes and nothing written, I will deeply regret it. I know I’m not going to get to do this radical no-work experiment again any time soon.

So I deleted the project plans. Went radio silent on social media. And focused on one simple metric: did I write net-new words today or not?

The result? In one month, I wrote more than I had in the previous two months of “preparation.” Five complete chapters emerged. Characters started asserting opinions and telling jokes. The story found its voice.

The secret to productivity isn’t better plans and systems. It’s doing the thing. When in doubt, ask yourself what will you regret more? Not making progress, or having an imperfect plan?

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