The question I ask before every decision now

Overthinking isn't protecting you. It's costing you.

I spent three weeks deciding whether to take on a new client last year.

Three weeks of spreadsheets. Pros and cons lists. Asking friends what they’d do. Lying awake at night running scenarios.

You know what happened? By the time I made up my mind, they’d hired someone else.

I didn’t lose the client because I made the wrong decision. I lost them because I couldn’t make any decision at all.

That’s when I realized: overthinking wasn’t protecting me from mistakes. It was the mistake.

So I started asking myself one question before every decision. Everything changed.

Why most decision-making advice is useless

Here’s the advice everyone gives: make a pros and cons list. Trust your gut. Sleep on it. Seek counsel from people you respect.

Cool. Helpful. Except it doesn’t work when you’re paralyzed.

The real problem isn’t that we don’t know how to make decisions. It’s that we treat every decision like it’s permanent.

We agonize over taking a client like we’re signing a lifetime contract. We stress about launching a project like we can’t pivot later. We debate whether to have a difficult conversation like we’ll never get another chance.

Meanwhile, the truly irreversible stuff—who we commit to long-term, whether to have kids, burning bridges with people who matter—we sometimes rush through.

We’ve got it backwards.

Most decisions are reversible. You can leave the job. You can fire the client. You can change direction on the project. But we don’t treat them that way.

We confuse “important” with “irreversible.” And we waste weeks trying to optimize for a perfect choice that doesn’t exist.

The cost isn’t making the wrong decision. It’s making no decision while opportunities slip away.

The question (and why it works)

Here’s what I ask now: “Will I regret not trying this?”

That’s it.

Not “Will this work?” Not “Is this the optimal choice?” Not “What if it fails?”

Just: will I regret not trying?

It cuts through everything. Because it reframes the decision from “What’s the safest bet?” to “What can I live with?”

I can live with trying something and it not working out. I learn something. I get a story. I move forward.

What I can’t live with? Playing it safe and wondering “what if” for the next five years.

Here’s how it works in practice:

That client I was stressing about? I asked myself: will I regret not working with them? The answer was no. They were fine, but nothing special. Decision made. Moved on.

The uncomfortable conversation I’d been avoiding for weeks? Will I regret not having it? Absolutely. Had the conversation the next day. It was awkward for ten minutes. Then it was done.

The side project I kept putting off because I wasn’t sure it would work? Will I regret not building it? Yes. Started it that weekend.

Notice what this question does: it exposes whether you’re avoiding something because it’s actually wrong, or just because it’s uncomfortable.

If you’re avoiding it because it’s wrong - because you genuinely won’t regret passing - great. Easy no. Move on.

But if you’re avoiding it because it’s scary? Because you might fail? Because it’s uncertain? That’s exactly why you should do it.

Regret of action fades fast. You tried. It didn’t work. You learned. Life goes on.

Regret of inaction compounds. The “what ifs” never really go away.

I’ve failed at plenty of things. Started projects that went nowhere. Took opportunities that didn’t pan out. Said yes to things I probably should’ve said no to.

None of those keep me up at night.

You know what does? The opportunity I turned down three years ago because I didn’t feel “ready enough.” The conversation I didn’t have because I was worried about how it would go. The project I didn’t start because I was waiting for the perfect moment.

Those are the ones that stick.

Make the call

Think about the decision you’re sitting on right now.

The one you’ve been overthinking. The thing you keep coming back to but can’t quite pull the trigger on.

Ask yourself: will I regret not trying this?

If the answer is no, you’re done. Move on. Spend your energy elsewhere.

If the answer is yes - or even maybe - you already know what to do.

Stop waiting for certainty. It’s not coming. Stop looking for the perfect choice. It doesn’t exist.

Make the call. Own it. Move forward.

You’ll make mistakes. That’s fine. At least they’ll be your mistakes, not your regrets.

The real cost isn’t making the wrong decision. It’s letting indecision steal months of your life while you spin in circles.

Ask the question. Make the call. Move forward.

That’s how you build a life you can actually live with.

Talk soon,

-Zohvib

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What’s your take on today’s topic? Do you agree, disagree, or is there something I missed?