Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to achieve a breakthrough at work — and build a career or company you love.
This edition is brought to you by the Solo Summit, where I’ll be giving a free virtual keynote for solopreneurs! Details below.
You missed an opportunity, and you can’t stop thinking about it.
Maybe it was big and life-changing, or small and nagging. Whatever it is, you keep wondering: If you’d made the right decision, would you be wealthier by now? Happier? More successful?
This thinking isn’t healthy. So today, I’ll show you the most powerful way to let go.
I call it: Declare it, then deflate it. It’s a way to make your regret feel smaller and less consequential — by comparing it against all the other things that could have been.
But before I explain how it works, I’ll share a decision that’s haunted me for years… and how I just started to feel better about it.
The opportunity that got away
A few years ago, I met a fellow newsletter writer who’d built an impressive audience. We talked about ways to support each other, and he made me a nice offer:
He would add me to his recommendations list — which is to say, whenever someone subscribed to his newsletter, they’d get a pop-up recommendation to subscribe to mine.
But there was a problem: He was on one newsletter platform, and I was another. To make this work, I’d need to switch to his.
That sounded like a hassle. So I thanked him, but passed.
Then his popularity exploded. He’s now one of the most successful newsletter writers, with more than 1 million subscribers. Meanwhile, I have 75,000 — which I’m proud of (and thank YOU for being one of them!), but it’s a fraction of what he could have gotten for me.
This isn’t just about vanity metrics. Newsletters drive significant opportunities, which is why I keep thinking about how much bigger my entire business might be today… if only I’d said yes to that guy.
I hadn’t told anyone about this until…
I’ve kept this story to myself for years, because it seems silly and frivolous. Like, oh woe is me.
But last week, as I texted with a friend who also writes a newsletter, I told him about it.
His response really took me back: “Here’s the worst for me,” he wrote. “A client told me to invest in Bitcoin in 2015.”
Oh no, I said.
“It was about $250 a Bitcoin,” he continued. “Don’t do the math. It’s painful.”
Yes. Painful. Millions and millions of dollars’ worth of painful. And this client was a savvy investor. Very trustworthy. It was worth taking seriously.
When my friend said this, something switched in my brain. I suddenly realized two things:
- I am not the only person to miss a big opportunity.
- Even if I said yes to that newsletter writer, do I really know what would have happened?
That’s when I came up with a helpful framework for countering this regret: Declare it, then deflated it.
Let’s break it down…
Step 1: Declare it
Regret is an isolating experience. It makes us feel uniquely foolish, short-sighted, and unable to see around corners — as if we fell behind while others sprinted ahead.
So we need to counter that. We must tell someone.
When you share your regret with others, you discover that you’re not alone. You didn’t fall behind in the race. Everyone else fell behind too. We are all behind where we wish to be.
In fact, let’s try an experiment right now:
Click here — I created a simple form, where YOU can anonymously share your greatest missed opportunity. Next week, I’ll share some of the results. We’ll all feel better.
But this is just the start. Because the next step is even more important…
Step 2: Deflate it
When we regret something, we often fall into a trap called counterfactual thinking.
It’s what happens when you imagine alternate versions of reality — then beat yourself up for not making them real. For example, you might regret missing an opportunity, and now you imagine how much happier or wealthier you could have been. The imagined “what if” is counterfactual thinking.
I’ve done it. I’m sure you have too. And I wanted to know: How do I get this outta my head!?
That’s why I called social psychologist John Petrocelli at Wake Forest University, who studies this stuff.
“This is going to sound a little funny,” he told me, “but the trick is to consider additional alternatives — to consider other counterfactuals.”
We often imagine how things could have gone perfectly, but of course, there’s no guarantee of that. Outcomes will vary! And many outcomes are neutral or negative.
For example…
- I could have switched to that guy’s newsletter platform. Then he could have recommended me for a month and moved on. It would have been a lot of work for nothing.
- My friend could have invested in Bitcoin at $250 — and then, when Bitcoin doubled in price (to $500!), he could have sold. His earnings would be modest.
Honestly, these outcomes are more realistic.
The thing we regret isn’t real. It’s just one possibility among many — and often not even the most likely outcome. The sure thing isn’t a sure thing.
When you let it out, you let it go
So, here’s what we’ve done so far:
- We had a regret stuck in our head
- We shared it with someone
- We compared it against all other outcomes
In other words, we kept zooming out — out of our head, out past our friends, out into the world.
Now I want to zoom out even further: Imagine all the missed opportunities you don’t even know about.
Did you play the winning lottery numbers, but on the wrong week? Were you on an elevator, a foot away from someone who could change your life, and you didn’t notice? Did you not pursue an idea you’ve long since forgotten about, but that would’ve made you millions?
If this sounds stupid, that’s the idea. We cannot get lost in infinite what-ifs. There’s no point. No limit. It isn’t real or productive.
Our lives are the product of everything that came before, not the victim of it.
So if you’re carrying around a regret, it’s time to let it out. Place it in its rightful place — somewhere in the middle of an endless spectrum of unknowable outcomes, where some are much greater, and some much worse, but none of them should hold you back the decisions you still have the great privilege to make today and tomorrow and for all the days after.
That’s how to do one thing better.
I’m giving a free keynote for solopreneurs!
Ready to grow your solo business in 2026?
I am excited to be a part of the virtual Lettuce Solo Summit, where solopreneurs can access executive-level strategy, tax optimization, and structured annual planning.
If you’re a consultant, coach, creator, fractional, or anyone else who’s going big alone…
Join me on November 6 for my talk — and then stay to learn how to:
- Minimize taxes and maximize wealth
- Scale infrastructure without teams
- Multiply your output with AI
- Break the time-for-money trap
And in my talk, I’ll help you become more adaptable and find new opportunities… because that’s the key to everything.
This isn’t freelancer 101. It’s boardroom-level strategy you can implement yourself.
