Why Second-Guessing Doesn't Mean You Chose Wrong

Why Second-Guessing Doesn't Mean You Chose Wrong

Self-Doubt After Making a Decision

Sara Kuburic

Sep 20, 2026

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This weekend I was on stage at the Wellness Oasis in London, talking about self-doubt. The interviewer asked which form of it I’ve struggled with. (

The audacity! Just kidding, great conversation!

)

The answer was immediate: historically I struggled with doubting my decisions. I second-guessed my choices, replayed them again and again and again and again, and pushed back against my own judgment.

Anyone else?

I think this flavor of doubt feels so common, even second nature, because of how life works.

Our task is to create who we want to become through the choices we make.

And there’s no guarantee any of the choices we make are right.

That’s scary.

A few years ago, I turned down a job opportunity that looked great on paper. I didn’t have the “data” to justify it. I had a gut feeling, and I took the risk of trusting myself. And then I spent months second-guessing it anyway. In retrospect it was 100% the right call. Another time, I ended a relationship while I still loved the person. It didn’t feel good. It didn’t feel like relief or clarity. It felt like grief, and I took that grief as proof that maybe I’d made a mistake.

With time I’ve learned that how a decision feels is not the same as whether it was right.

Right choices can hurt. Aligned choices can come without certainty. The doubt is the cost of choosing, not the verdict on what we’d chosen.

So what does choosing “right” even mean? To me, a choice is right when it’s authentic, when it represents who I want to be and my life still feels like my own. Mistakes are inevitable, and wrong turns are a given. But the way to evaluate them is to ask whether I did my best to honor who I am with the information and options I had.

That’s also why hindsight is a trap. Yes, time told me I was right about the job. But I wish I’d trusted myself without needing that proof. If a choice is only good once it works out, we’ll doubt every decision until the results come in.

There is a question I ask myself now: which decisions am I willing to live with? Regardless of how they end, which turns will I be glad I took? Which lessons am I happy to learn?

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Yesterday marked three years since my book

IT’S ON ME

came out. WILD milestone!!

Currently 50% off!

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