I Asked 75,000 People About Their Biggest Regrets. These 6 Patterns Changed How I Think.

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Regrets blossom in darkness. When we lack information, and we keep regrets to ourselves, they feel big and embarrassing, as if we should have known better. But the more we share them with others, the more we recognize how common they are — and how small they are by comparison.

So the author had an idea: What if we all shared our regrets with each other? What if we compared notes, saw patterns, and appreciated our shared experience?  That’s why he asked his 75,000 newsletter subscribers: What missed opportunity do you still regret? 

The authro got a flood of responses, which he has divided into six common themes. Now he is sharing them with you, along with his thoughts. It’s time to feel less alone together — and move into 2026, unburdened from whatever came before.

Theme 1: Giving up on a winning idea.  We probably heard many versions of this story: I had an idea, but someone else succeeded with it.  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.  Alexander Graham Bell and Elisha Gray filed patents for the telephone on the same day in 1876.  Examples could 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. 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.

Theme 2: The grass is always greener.  If you regret something you did or didn’t do, it’s safe to assume there are many people out there who regret having made the exact opposite decision.   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.

Theme 3: The missing money.  There were so many regrets about money.  According to the author when he regrets something, he tries holding himy 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.  There is 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.

Theme 4: The ‘What if…’ stories.  I heard so many Sliding Doors moments, when life could have taken a different turn.  Psychologists have a fancier term for it: counterfactual thinking. It’s what happens when you imagine different outcomes for past events.   But here’s the thing to remember: You genuinely are imagining those outcomes. You don’t really know how things would have turned out, and they might have turned out much worse. That’s why, to combat the trap of counterfactual thinking, we must add more counterfactual thinking. Consider all the other ways that things could have turned out.

Theme 5: Wasted time.  Your time hasn’t passed. Your time is now.  According to the author, this is how he has chosen to live today, crafting the life he wants without exceptions. He travels a ton. He optimizes for experience. He is on a constant quest to meet new people. In his wife, I found someone equally down for great adventures.  The past has served its purpose perfectly,” someone said.  “But most people are cherry-pickers: Well, I wish that would’ve changed, or I wish this were [different]. No. The purpose of the past…there’s only one purpose: to bring you and me right here and now.”

Theme 6: ‘I never followed up’.  Here was a common scenario: Someone received a great offer, but they didn’t follow up.  It’s so relatable. We’ve all been burned before. Someone said, “We should do this again,” but never called. Colleagues said “I’m happy to help,” then ignored you when you asked. Politeness can masquerade as genuine interest, and this has taught us not to trust offers of help.  But still: Even if they’re lying, what’s the worst that can happen by following up?

Consider the math. If 10 people make you an offer, let’s say nine of them are “just being nice.” One of them could change your life.  If you don’t follow up with them, then you avoid nine embarrassing interactions and you miss something huge. And if you do follow up, you get ignored nine times and then make the connection that changes everything. 

We need to stop believing that we’re not worth other people’s time. Let’s start with a different assumption instead: People are genuinely interested in us. And that’s because we are genuinely interesting. We are worth their time, and their attention, and their partnership.

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 here’s the best we can do: We can carry forward with gusto, making the most of our time, building the things that matter, pursuing what matters most to us, and living as if there’s nothing to regret.

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