No more second guessing yourself

Over the past two years, I've second guessed my decisions more than any other time in my life.

I have a few theories about why.

The first theory is related to Coach’s funding--it’s the first startup I've raised money for, and as a result, I feel a lot pressure to deliver to my investors and team. That added pressure makes me feel as if I need to get every decision right and that I can't make a mistake because there's more on the line than my previous bootstrapped businesses.

The second theory is that I'm very fortunate to have a perfectly intact 3 for 3 record in startups--I sold Uncover last year, which I actually haven't written about yet, but will--and I don't want the track record to end there. I don’t want to go backward in my career, and I don’t want to fail.

These two theories have made me sweat and agonize over every major decision I've made over the past two years. I so desperately want to get every decision right now more than ever before.

For example, I’ve lately found myself sometimes taking several months to make a decision and then regretting that I didn't make it sooner.

This certainly isn't the case of everyday decisions, I'm fast and confident with those. What I'm talking about are the bigger, more costly decisions: doubling down on what's working, removing what's not working, exploring big product changes, or any number of things.

Instead of making a quick decision on tough calls, I've been playing out the various scenarios in my head for weeks (and sometimes months) before feeling confident enough to pull the trigger.

Nine times out of ten, if I had just gone with my gut in the first place and not second guessed myself, I would have come to the same decision a lot earlier and saved weeks or months in the process.

Starting today, this is a public pledge to stop second guessing myself.

I have to let my experience, and the experience of my team, guide me to making bigger, more consequential decisions faster.

If I’m wrong, I can always take a step back, and go from there.

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