I Spent Three Months at 29 Agonizing Over a Jacket — And It Wasn't About the Jacket

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At 29, I spent nearly three months going back and forth over whether to buy a jacket.

Nothing expensive. Just an ordinary jacket, well within my budget. But I couldn’t press buy. I’d read reviews, compare brands, imagine different outfits, ask friends, then circle back to the reviews again.

The thing is, I wasn’t thinking about a jacket. I realized that much later.

TL;DR

Overthinking is rarely about the decision that’s holding you up. It’s usually a displacement for a bigger, scarier question you’re not ready to face. Seeing this clearly is more useful than any “decision-making efficiency” technique.

The Jacket Was a Proxy Problem

At the time, I was deeply uncertain about my career direction. Change jobs? Leave the city? Go back to school? These questions were too large to approach directly.

So I channeled all my “serious thinking” energy into a jacket. It became a safe container — I could feel like I was thinking hard about something, without having to look at the things that actually frightened me.

This is a very common pattern in overthinking: displacing unbearable anxiety onto a manageable small decision.

Why “Set a Deadline” Advice Usually Doesn’t Work

You’ve probably heard: “Give yourself a deadline and commit when it arrives.”

The problem is that this treats overthinking as a time management issue, when it’s actually an emotional one. If the root cause is anxiety, a deadline just makes you anxious faster — it doesn’t make the anxiety disappear.

What Actually Helps: Ask “What Am I Avoiding?”

When you notice yourself stuck on a decision longer than makes sense, try asking:

“If I stopped thinking about this decision entirely, what would I be forced to face?”

That question usually cuts to the core faster than any decision framework.

For me, the answer was: if I stopped thinking about the jacket, I’d have to sit with my doubts about my job.

How the Story Ended

I eventually bought the jacket. I wear it sometimes. The actual purchase took five minutes.

The decision itself was never hard. What made three months long was using it to avoid something else.

I later changed jobs. That was the decision that actually kept me up at night. But strangely, it took me far less time to make — because by then, I knew the problem was the real problem, and I didn’t need a jacket to stand in for it.