Regret is at the core of being human.

It’s also the most common thing founders won’t talk about publicly. The investor conversations they wish they’d handled differently. The hire they should have made faster. The hire they should have fired sooner. The partnership they ignored red flags to enter. The years they spent grinding on the wrong problem. The relationships they let erode while they were building something else.

Most regret talk is about avoiding regret in the first place. “Live with no regrets.” The advice is hollow. You will have regrets. Every operator does. The question isn’t whether — it’s what you do with them when they arrive.

Done right, regret is one of the most useful emotions a founder can develop a working relationship with. It sharpens decisions. It surfaces patterns. It points directly at the parts of yourself you haven’t taken ownership of yet. Done wrong — repressed, dismissed, drowned in productivity — it festers and quietly degrades every decision you make from underneath.

This piece is about the 20 regrets founders most commonly carry, the patterns those regrets reveal, and what to actually do with the emotion when it shows up. Not how to avoid regret — how to use it.

The Four Types Of Regret

Daniel Pink’s research on regret — based on a global survey of more than 26,000 responses across 130 countries — identified four foundational categories that show up in nearly every life:

Foundation regrets. “If only I’d done the work.” Stability regrets — health, finances, education, skills you let slip when the cost of building them was cheap and the future was abstract.

Boldness regrets. “If only I’d taken the chance.” The risks you didn’t take, the opportunities you watched pass, the leaps you wanted to make and didn’t.

Moral regrets. “If only I’d done the right thing.” Ethical lapses, betrayals, integrity compromises that you knew were wrong at the time.

Connection regrets. “If only I’d reached out.” Relationships you let drift, things you didn’t say, people you didn’t show up for.

What Pink’s research showed and what the founder-specific data confirms: the vast majority of regrets are regrets of inaction, not action. Things you didn’t do, not things you did. The risk you didn’t take. The conversation you didn’t have. The truth you didn’t tell. The leap you stayed on the wrong side of.

This is significant because the OS layer of The Mind Model is the source of most inaction. The Software layer rarely talks you out of action — by the time you’re consciously deliberating, the action is on the table. The OS talks you out of action before you ever consciously consider it. Fear patterns, worthiness scripts, threat responses, inherited beliefs about what kind of person you are — all of them run silently in the background, vetoing options before they reach awareness.

Most regrets are not failures of courage in the moment. They’re failures of OS architecture, accumulated over time.

The 20 Regrets Founders Carry

The full list, organized by Pink’s categories. Each one is common enough that if you’ve been operating for any meaningful length of time, you’ll recognize at least half of them in yourself.

Connection Regrets

1. Working at the expense of family and the people who mattered. The most common regret across every founder dataset that exists. You weren’t there. You missed the time you couldn’t reclaim. The business needed you and you went. The business will not pay you back what those years cost.

2. Not being present even when you were physically there. You were at dinner but your mind was on the deal. You attended the school event with one ear on Slack. The presence you sold to the people who needed you was performative — and they could feel it.

3. Settling in relationships because the business was the priority. Marrying or staying with the wrong person because you didn’t have the bandwidth to navigate something better. Choosing convenience over fit because the building was consuming everything.

4. Not saying the thing. The thank-you you didn’t give. The apology you didn’t offer. The hard conversation you avoided. The “I love you” you assumed would be said later.

5. Not forgiving — or not asking forgiveness. The grudges you carried because being right felt safer than being free. The relationships you let calcify around old wounds that didn’t matter anymore.

6. Letting friendships erode while you were busy. The friends who tried to stay close and eventually stopped trying. The network of people you used to know that now feels like a list of strangers.

Boldness Regrets

7. Not starting sooner. Watching someone else build the thing you’d been thinking about for years. The cost of waiting until you felt ready — which turned out to be a feeling that never arrived.

8. Staying in a job, role, or company past the point you knew it was wrong. The years you spent waiting for it to get better. The energy you burned managing a situation that wasn’t going to change.

9. Not raising your prices, your rates, or your standards. The years of undercharging. The clients you kept who depleted you. The deals you took because you didn’t believe you could ask for what you were worth.

10. Caring too much what other people thought. Building a business shaped by the imagined opinions of people who weren’t going to help you build it. Choosing the safe-looking move because you were afraid of how the bold one would land.

11. Not having the conversation that needed to be had. With the co-founder you were starting to lose alignment with. With the investor whose expectations were drifting from yours. With the partner whose patterns were starting to cost you.

12. Not taking the risk when the cost of taking it was lowest. Most founders look back and realize the windows they didn’t walk through were wide open at the time. They didn’t seem that way. They were.

13. Comparing yourself to other founders instead of building your own thing. The years of measuring against people whose context was nothing like yours. The energy spent on metrics that didn’t matter to your actual mission.

Foundation Regrets

14. Not taking care of your physical health while you were building. Sleep you didn’t get. Movement you didn’t do. Food you ate in front of the laptop. The body you’ll inherit at 50 is being built by what you’re doing at 35.

15. Not building financial discipline early. Not saving, not investing, not setting aside, not knowing your numbers. The freedom that compounding gives you is a function of when you start, not whether.

16. Not learning the skills that compound. Negotiation, communication, finance, systems thinking. The capabilities that pay you back for decades while you’re investing in something more immediately visible.

17. Not building real systems early. Founders pay for this one for years. The dependencies you didn’t document. The processes you ran out of your head. The team you couldn’t grow because nothing was scalable.

Moral Regrets

18. Cutting a corner that came back. The customer you didn’t quite tell the truth to. The investor pitch where you implied something you couldn’t deliver. The team member you treated badly because the pressure was high. Most founders have at least one of these.

19. Staying silent when you should have spoken up. Watching something go wrong at your company and not naming it. Letting a bad pattern continue because confronting it was inconvenient.

Composite Regrets

20. Not enjoying any of it. The years you spent grinding through milestones without celebrating them. The wins you couldn’t feel because you were already onto the next problem. The life you traded away in exchange for a business you weren’t even present enough to enjoy when it succeeded.

What Most Founders Get Wrong About Regret

There are two common ways to handle regret, and both make things worse.

The repress-and-grind approach. “I don’t have time for regret. I just keep moving.” This is the dominant founder mode and it’s catastrophic over time. Repressed regret doesn’t disappear — it migrates. It shows up as low-grade anxiety, decision fatigue, irritability with the people you love, and a steady erosion of the satisfaction that should accompany your wins. You can’t outwork the emotion. You can only outrun it for a while.

The wallow-and-victimize approach. “My biggest regret defines me. I’m broken by what I didn’t do.” This is the opposite failure. Treating regret as identity. Making your unmade choices the centerpiece of your self-concept. This is the version of regret that feeds depression, paralysis, and the slow drift into bitterness.

Neither works. Both are forms of refusing to actually engage with what the regret is showing you.

The Real Function Of Regret

Regret, handled correctly, is OS feedback.

When something you didn’t do — or did do wrong — keeps surfacing as a thought, an ache, a thing you can’t stop reviewing, what’s actually happening is that the OS layer is showing you a pattern. It’s saying: “This is what your priorities actually were. This is what your fear patterns produced. This is what your worthiness scripts cost you. Look at it. Understand what’s running you. Update.”

The regret isn’t there to torture you. It’s there to teach you something specific about your operating system that you haven’t been willing to see.

This is why Daniel Pink’s research shows that regret, properly engaged with, predicts better future decisions. People who can sit with their regrets — not avoid them, not drown in them, but actually examine them — make sharper choices going forward. The regret becomes operational intelligence. The pattern, once named, becomes catchable next time.

What To Actually Do With A Regret When It Shows Up

When a regret surfaces — about a hire, a missed opportunity, a relationship, a strategic decision — try this:

1. Name what’s underneath it. Most regrets are not really about the specific event. They’re about the pattern that produced the event. The hire wasn’t the regret — the worthiness script that wouldn’t let you wait for the right person was. The missed opportunity wasn’t the regret — the fear pattern that activated every time you got close to a real leap was. Get underneath the specific to the structural.

2. Locate the OS pattern. Once you’ve named what’s underneath, ask: Where else does this pattern show up in my life? Almost always, the answer is everywhere. The same fear that cost you the missed opportunity is costing you a similar version of it right now. The same worthiness script that produced the bad hire is producing the underpricing, the over-promising, the apologizing in pitches. The regret is a window into a pattern that’s still active.

3. Take one small action that breaks the pattern, today. Not the dramatic overhaul. Not the “I’ll never make this mistake again.” A specific, small move in the opposite direction of the pattern. If the pattern is avoidance, have one conversation you’ve been avoiding. If the pattern is undercharging, raise one rate. If the pattern is delay, start one thing. The micro-action retrains the OS. The grand intention does not.

4. Forgive yourself for the pattern, not for the outcome. You weren’t fully running your own OS when the original regret was formed. You were running architecture you didn’t choose, defending beliefs you didn’t install. Self-forgiveness isn’t excusing the cost. It’s accurately recognizing that you couldn’t have acted differently with the operator you were at the time. The operator who could act differently is the one this work is building.

Why This Matters For Founders Specifically

Founders accumulate regrets faster than most people. The pace is faster, the decisions are more consequential, the stakes are higher, and the people around you who could have absorbed the cost of a less-perfect operator are now depending on you to be one.

The compounding cost of ignored regret is significant: every founder I know who’s been in the work for more than a decade carries patterns they can name now but couldn’t see at the time. The ones who’ve done well are the ones who built a working relationship with the regret — used it as data, not punishment. The ones who didn’t are the ones still making the same calls today they were making fifteen years ago, just with bigger numbers attached.

You can’t avoid regret. You can decide whether it becomes feedback or weight.

The work is to keep the regret useful. Let it surface. Examine it. Find the pattern. Take the small action. Move forward as a slightly more aware operator than you were before.

That’s the actual job.

This piece is foundational to the deeper work on identity, beliefs, and the long arc of becoming the operator your business actually needs — anchored in The Mind Model.