Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to be more successful and satisfied — and build a career or company you love.
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Last week, I asked you all a question:
What big opportunity did you miss, that you now regret?
And wow. You sent a lot of great answers.
Today, I’ll share some of them — with a very specific purpose: I want you to feel better about whatever you regret.
It’s part of a tactic I shared last week. So, quick recap on that:
Regret is isolating. It makes us feel uniquely foolish and short-sighted. But when we tell someone our regret, we discover that we’re not alone — because everyone feels behind in some way.
So that’s today’s project. To share and feel less alone.
I’ve divided the regrets into five themes. I’ll share each below, along with my thoughts.
I heard many versions of this story: I had an idea, but someone else succeeded with it.
Here are two examples…
Jayson says: “I had an idea for an outdoor product. I started developing it, but didn’t get far. A couple years passed and I was watching Shark Tank, and I saw my same concept being pitched to the Sharks! I couldn’t believe it. Now that product is sold on Amazon. I regret not developing it sooner or getting it to market. I feel like I missed out on millions.”
Patrice says: “Years ago, I started a restaurant review site as a hobby. It got tons of visits. But I had no idea I could make a living off it. My day job was busy, so I stopped reviewing restaurants. Fast forward, and another company launched the same concept and was acquired for millions. I still die a little inside any time someone brings it up.”
My take:
I have my own version of this. When I was in high school, I came up with a story about a man who discovers that everything around him is a TV show. I never did anything with it. Then the Truman Show came out.
If you have a similar regret, then here’s what to know: This is insanely common!
There’s even a term for it: multiple discovery. Across time, multiple independent people tend to develop world-changing ideas at roughly the same time.
- Both Isaac Newton and Gottfried Wilhelm Leibniz independently developed the principles of calculus in the late 1600s.
- Alexander Graham Bell and Elisha Gray filed patents for the telephone on the same day in 1876.
- Charles Darwin and Alfred Russel Wallace independently conceived of natural selection in the 1850s.
Examples go on forever.
Ideas are great, but they’re not unique. Even the law recognizes this: It’s why you can’t patent an idea; you can only protect your unique execution of that idea. So do not beat yourself up for this. Even if you pursued your idea, that doesn’t mean you’d have been the winner. Many others likely had it too. All this means is that you’re a smart thinker — and that will continue to serve you well!
These two people regret the exact opposite things. Take a look:
Justyn says: “I graduated college in 2023 with no debt and an opportunity to work full-time at a mid-size New York firm. However, the firm’s industry did not align with my career goals. So I took a risk to attend NYU for my Masters, taking out a loan to cover my tuition. I have graduated now, but have yet to secure a job in my desired field. Meanwhile, everyone from my undergrad is enjoying the start of their professional careers. I feel behind.”
Chris says: “I was an under-educated, socially isolated child, and attending college was my first ‘real school’ experience. I thrived there, and some professors encouraged me to go on to grad school. I even met with the chair of the department I wanted to be part of. Then I opted to stay at my job and not go to grad school. I’ve regretted it ever since. Now I’m not even in that job any longer. Oof.”
My take:
So: Justyn regrets going to grad school. Chris regrets not going to grad school.
But let’s be realistic about what happened here.
Justyn could have declined grad school, took that unsatisfying job, and today might be employed but miserable. Chris could have attended grad school, but would now be saddled with debt and no job.
The lesson: Whatever you regret doing, someone else regrets not doing it.
No decision is obvious. No path is predictively correct. You simply couldn’t have known what was right — and in the future, the “wrong” decision might turn out to be the right one.
There were so many regrets about money. Here’s a sampling:
CC says: “I was CEO of a startup and had the opportunity to make a strategic investment into a company with three employees. It is now worth $22B.”
Natalie says: “I passed up on Apple stock in 2004 because I thought a dollar a share was too much.”
Ben: “I could have bought a 3-bedroom, 1500-sq-ft. flat in Chelsea NYC for $800k. I passed because the area was a little beaten down. Would have sold that ten years later for $2.5M.”
My take:
When I regret something, I try holding myself to this standard:
Did I make a rational decision, based on the information I had at the time?
If the answer is yes, then I can’t fault myself. In the examples above, every decision was rational. There was no way to predict success.
Should you sometimes take risks? Should you sometimes do the irrational thing? Yes, and yes. But you can’t do it all the time, or you’ll invest in nonsense and run out of money.
All life is a form of gambling. We can’t regret having played and lost.
I heard so many Sliding Doors moments, when life could have taken a different turn. A sample:
Jim says: “A friend of mine, a billionaire, discouraged me from investing further in a business partnership I was in because he didn’t like my partner. He offered to help me start a business of my own. I didn’t accept. My partner later betrayed me and it nearly left our family in ruin.”
S says: “The year I graduated college, my professor offered me a university lecturer gig in my hometown. He was going on a year-long sabbatical and I could fill in. I assumed these opportunities would always come, so I said no — because I wanted to attend art school overseas. My parents were mortified. After four more years of study, I finally entered the workforce and feel stunted compared to my peers.”
Bill says: “As a decent high school basketball player, I was recruited by Coach K to attend West Point. I declined. The next year, he left for Duke. I could have been on his first graduating class and a foundational player as he built that epic program.” [For non-basketball fans: Coach K is legendary college coach, and his Duke program was dominant for decades.]
Copper says: I turned down a fantastic job opportunity that involved moving to Italy for a minimum of 3 years and a HUGE salary increase — because my ex-husband wouldn’t relocate with me. He and I divorced a few years later because he said I outgrew him. I so so so wish I had said yes! Never got over it!
My take:
I get it — how can you not obsess over these paths not taken? But if you have a “what if” story, then please remember this:
Last week, I wrote about “counterfactual thinking.” We regret not taking an action — but that’s because we imagine the perfect outcome of that action. Then we beat ourselves up for not living our dream.
But that’s not realistic. So let’s start imagining other possible outcomes.
Jim’s friend could have funded a new business, so Jim imagines that the business would have succeeded. S could have taken that university gig, so he assumes it would have led to a wonderful career. Bill imagines being on Coach K’s Duke team. And so on.
But Jim’s billionaire friend could have also funded a crappy business, then accused Jim of wasting his money. S could have taken that job, and now feels stuck in their hometown. Bill could have gotten cut from Coach K’s team!
Imagine finishing the sentence “what if…” in a more positive way…
- What if… I dodged that bullet?
- What if… I learned something critical?
- What if… I’m on the right path?
What if, indeed.
This theme resonates with me personally the most. Here are examples:
Linnea says: “I stayed at the same job for 10 years because I thought they would recognize how great my work is and reward me for it.”
Ajay says: “I missed out on so much free learning at my previous job. If I had been just more forward and asked for opportunities and kept an open mind, I would’ve been more experienced now.”
Jane says: “I missed out on being lighthearted and partying when I was the age where you would start with those experiences.”
My take:
Jane, that was me too. I was too insecure in high school. Then I was in a long-term relationship through college and most of my 20s. I never just let loose when everyone else did.
So here’s what I’ve learned for myself, which I hope you’ll all take to heart, no matter your regret:
Your time hasn’t passed. Your time is now.
Remember a few weeks ago, when I wrote about saying “yes” to more things? I suppose, in some way, that’s how I “make up for lost time.” But I don’t see it that way; I just see it as a way to live the life I want now. I travel a ton. I optimize for experience. I’m on a constant quest to meet new people. In my wife, I found someone equally down for great adventures.
“The past has served its purpose perfectly,” someone said on a wonderful recent episode of the podcast Heavyweight. “But most people are cherry pickers: Well, I wish that would’ve changed, or I wish this were different… No. There’s only one purpose to the past, and that’s to bring you and me right here and now.”
True words.
First, thank you to everyone who sent in regrets. I’m so honored you shared them with me. I read and thought about everything.
Here’s the one that stood out to me the most… because it’s the only one with a complete ending. Most regrets hang in the air like an unfinished sentence; we never truly know what could have been.
But this woman knows. Here’s her regret:
KGJ says: I was living with my mom after graduating from college, where I spent 4 years as a varsity softball starter. One day, my mom read in the paper about local auditions for a movie, where they were looking for “girls who could throw a baseball” and suggested that could mean me. Because it was my mom and I was SOOOO busy waiting tables at Applebee’s (and maybe a little fear), I declined to take a shot at being an extra in A League of Their Own. Oh what could have been…
But years later, I told a colleague at work about this, and they had a friend who DID attend those auditions. That person ended up “being Madonna’s bitch for a year” (her words). Did I want that too, or did I dodge a bullet? Who knows, but it makes me laugh and remember how much I love my life. Regrets and all.
My take:
I love this so much, KGJ. You got to see the path your life could have taken. And it was just as complex and unpredictable as the life you actually got to live.
Big moments can mean nothing. Small moments can change our lives. The good can become bad, and the bad can become good, and it’s simply impossible to predict what will actually matter in life.
So the best we can do is this: We can carry forward with gusto, making the most of our time, and living as if there’s nothing to regret.
That’s how to do one thing better.
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