I’ve made some spectacularly bad decisions in business.

Strangely, they’re not the ones I regret most.

The decisions I made gave me something to work with. A result. A lesson. A chance to do better next time.

The decisions I didn’t make left me with only my imagination.

That’s the harder kind of regret. There’s no result to evaluate, only the mind wondering, “What if…”

Briefly feeling regret can be useful. It shows me what matters and what I want to do differently.

But once I’ve learned what I can, replaying the past only makes me feel bad and less confident about the next decision in front of me.

Regret Has One Job

Even as a child I made decisions quickly. When I was eight, I let go of a swing at the highest point, landed flat on my face, and ended up in urgent care.

I never did that again.

Making fast decisions and course-correcting was one of my biggest strengths in business.

Usually.

Hiring was one area where this approach backfired. I hired with urgency, seeing what I wanted to see, ignoring warning signs, and assuming experienced people knew what to do.

When it didn’t work out, I’d regret it at first.

But there was something useful in the temporary regret. It showed me I needed to define the role, use a scorecard, develop a pipeline of candidates, and create a real onboarding process.

That’s regret doing its job.

After that, continuing to feel regret serves no purpose.

Looking Back 

When I look back on most of my “bad” decisions today, the right choice seems obvious.

But it’s not really fair to judge our earlier decisions based upon information we didn’t have at the time. 

Or to judge our former self by who we are now. Even if the decision was made yesterday, we’re not exactly the same person today. 

We may have been tired, afraid, under pressure, or working with fewer resources and less information.

Regret also assumes there was one perfect option and that is very rarely the case. 

There are usually several imperfect choices, each with a cost. And we only see the cost of the option we chose.

Without realizing it, regret can become an excuse not to risk again. 

The mind tells you it’s protecting you from another mistake, so it keeps hesitating, second-guessing, and playing small.

That’s the real cost.

Not trusting people because of a bad hire. Avoiding new investments because an idea failed. Postponing decisions rather than risking regret.

When we focus only on what went wrong, we leave out everything we got from the decision:

Experience. Knowledge. Relationships. Skills. Boundaries. A better understanding of ourselves.

The Road I Didn’t Take

One decision I sometimes wonder about is whether I should have brought a true business partner into my analytics business.

I wasn’t willing to give up control, so I remained the sole owner. I offered options to a few senior people, but that wasn’t the same as having someone beside me who was equally invested in building the company.

My mentor, Loretta DeLuca, had partners who handled parts of the business she didn’t enjoy. She trusted them deeply, and her company grew much faster than mine.

Sometimes I imagine that a partner with similar values might have helped me grow faster too.

Maybe that’s true.

Or maybe we would have disagreed constantly. Maybe the partnership would’ve created a completely different set of problems.

I’ll never know, because I never tested it.

That’s what makes the decisions we don’t make harder to resolve. The path wasn’t taken, so our mind makes it look better than it might have been.

The danger is that we compare the real business we built, with all its problems and tradeoffs, to an imaginary perfect one.

Of course the imaginary version looks better.

That’s what regret does with the road we didn’t take. It compares reality to a fantasy.

The useful question is not, “What would have happened if I’d chosen differently?” It’s, “What did that path represent, and how can I choose some of it now?”

For me, the idea of a business partnership represents trust, shared responsibility, and having someone beside me who’s equally invested.

I can’t go back and make that exact decision over again. 

But I can ask myself where I’m still holding on too tightly, where I’m willing to share responsibility, and what kind of support I’m finally willing to receive.

Use the Information 

For decisions you’ve already made, evaluate the result without putting yourself on trial: 

What went well? 
What didn’t work? 
What will you do differently? 

Then stop ruminating.

For decisions you didn’t make, ask a different question: What did that path represent to you, and how can you choose a version of it now?