"It Almost Made Me A Millionaire": How A Former Entrepreneur Became Trapped By Regret, and Why You Must Learn to Let Things Go

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As we near the end of 2021, you may be thinking back on what you accomplished this year… and perhaps on what you regret.

I encourage you to do a lot of the former. We shouldn’t take our successes for granted! But I hope you learn from your regrets and then let them go. To show you why, I’d like to tell you a story about someone who spent a very long time regretting something — and why that was such a foolish thing to do.

A few weeks ago, a one-time entrepreneur pitched me his story. He wanted to write about the time he walked away from something that "almost made [him] a millionaire." And he wanted to tell this story as a cautionary tale.

“Follow your gut,” he wanted to advise Entrepreneur's readers. “Block out everyone else’s input and stick with what you believe in.”

That’s romantic, sure, but as I read the email he sent me, I came to a different conclusion: I think he actually saved himself a lot of trouble. He just never realized it, because he’s been so fixated on what could have been.

Here’s the Story

To protect this person’s privacy, I’m going to be vague about the details. But in short, here’s what he told me. I’ll call him Dan.

In 2012, Dan met a guy who was working on something that, at the time, was a new and largely unused technology. Dan and this other guy decided to partner on building this tech together, but “everybody told me it was stupid,” Dan said. So he eventually quit.

Today, the technology is commonplace. This, Dan says, is what would have made him a millionaire.

He regrets his decision deeply, even today.

But after reading his email, I had a question: What became of Dan’s former partner?

Dan admitted that he didn’t know. I told him he needed to find that out — because chances are, the guy never made a dime off of this! Ideas are secondary to execution, and many, many people are often working on the same technology at the same time. There have been many dating apps, for example, but only one Tinder. Many photo-sharing apps, but only one Instagram.

So Dan reached out to the partner and reported back to me: The former partner never made millions either. He's just working a normal job now.

“I guess you're right," Dan wrote me. "I spent all these years thinking that I lost my chance to become a millionaire, to realize that I probably saved myself by getting out of this one.”

He was liberated from his regret. And if you’re clinging to something like Dan was, here’s my advice for letting go of it too.

Look Towards Tomorrow

Had Dan asked me for advice back in 2012, before he walked away from this project, I might have advised him differently. If these two guys had the right vision and the ability to execute, maybe they would have stood a chance of success. Nobody wins without taking risks, after all.

But he made another decision. Now he has to focus on the life he actually lives, without believing in one that may never have happened. Even if Dan and his partner could have made a successful team, we cannot know that now — so spending brain space on it just isn’t useful.

When we regret things, we’re mourning the loss of what could have been. But who’s to say that thing, whatever it is, is what WOULD have happened if we’d made different choices? It’s impossible to know!

Instead of fixating on narrowly missed success, the only thing we can do is work to shape the life we are living, right here and right now. That’s the only scenario we have control over — and our greatest fortune will be to have a lot of life left ahead.

As you reach the end of your 2021, filled with great successes and surely plenty of failure, I implore you to remember: The one missed opportunity in the rear-view mirror doesn’t do much for you, except for allowing you to project your hopes and dreams onto something that’s lost. Doesn’t it feel more promising to direct those hopes and dreams toward things yet to come?

That is what tomorrow — starting with 2022 — is for.

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Cover credit: Getty Images / Francesco Carta fotografo