The Cost of Regret

When you see regret in a person’s eyes, it’s painful. I mean that. I’ve sat across from people who are 80, 90 years old, and I’ve watched what it looks like when someone runs out of time to fix something. It’s not sadness. It’s something heavier than that.

You should go volunteer at a retirement home. One time. That’s all it takes. Go sit with people who are at the end of the runway and just listen. It will make you want to do something with every single minute you have left, because when you’re 90, and you’re not mobile, and you’re tired, and it’s over, you can’t do it anymore. You can’t build the company. You can’t spend the time with your kid you kept meaning to spend. All that’s left is regret.

I’ve said this a hundred, maybe a thousand, different ways over the years, but it always comes back to the same idea. The biggest poison in us is regret, not failure, not rejection, not the business that didn’t work or the person who said no.

Regret.

Pretty much everyone reading this already has two or three things they can think of that they regret. You’ve got a lot of life left, so it still feels manageable. It still feels like there’s time to go fix it or go do it. But spend real time with people in their 80s and 90s and you’ll learn fast that regret doesn’t get any lighter with age. It gets heavier.

Go talk to a 90-year-old. Ask them what they’d change. The opening line is almost always some version of “I wish.” I wish I’d started that business. I wish I’d told her how I felt. I wish I’d taken the trip. I wish I’d spent more time with my dad before he passed. That’s the sentence you hear over and over. Once you hear it enough times, it changes you. It will pierce something in you that you didn’t know could be touched, because these are people who are standing at the place where time has run out. There’s no more at-bats left for them. There’s only the accounting of what they did and didn’t do.

Business is my vehicle for pushing this message. Not meditation, not wellness, not some non-profit mission statement. Business. I can’t help it, it’s what I love. I love building, I love competing, I love trying to beat you at the game. But beyond all of that competitiveness, what I’m pushing through that vehicle is an awareness of how good life really is, and how little of that awareness people carry around with them.

You can tell me all day why you can’t. Why the timing’s wrong, why you don’t have the resources, why your situation is different. I hear it and I don’t buy it, because if anybody’s ever done the thing you’re trying to do, that means you can do it, too. Stop making excuses. Stop complaining. Nobody’s listening, not really, anyway. People might nod along, but the market doesn’t care about your excuses, and neither does time.

What you need to do is make one person happy first: you. Get yourself right, and everything else you want to give the world gets easier. It won’t be perfect. But things will get a little easier. I like making people happy because I’m already happy myself. That’s the order it has to go in. You can’t run on empty and expect to build something that lasts, and you definitely can’t pour into other people from a place of resentment about your life.

When you’re 60 and your parents are pushing 80 or 90, if they’re still alive, and you spent your whole life doing what they wanted instead of what you wanted, it gets ugly fast. That’s resentment, and resentment is a different animal than regret. It’s arguably scarier, because now it’s not just about you. Now there’s another person on the other end of it, someone you love, and you’re carrying this anger toward them for a life you created around their expectations instead of your own.

That’s the biggest reason I push people so hard to go do what they want instead of what their parents want for them. Please, please, I urge you: squeeze the shit out of this one life you’ve been given, and pursue the things you truly want. Please.

I would rather you fight for five or six years chasing the thing you love, and land in one of two places, because both of them are wins. Maybe you find out you really are the amazing fashion designer, or chef, or whatever it is, not the engineer everyone assumed you’d be, and you build something legit, and eventually your parents end up proud anyway. Or maybe you find out you’re not great at it and it doesn’t work out. That’s still a win, because now you get to live the rest of your life without ever asking yourself “what if.” You don’t carry that question around for the next forty years. You already answered it.

You win both ways. The only way you lose is by never finding out, by never taking that chance.

Here’s the trade people don’t want to make. The instant sting of going for something and getting rejected is nothing compared to the slow burn of regret that follows you around for decades. Think about something as small and dumb as not asking someone out in high school. That stuff lingers. It’s not the things you did that end up bothering you most. It’s the things you didn’t do. So if you’re sitting on an idea, a business, a conversation you’ve been meaning to have, I’m asking you to make the move now, because the window closes. It always closes.

I don’t want anyone looking back in twenty years, wavering on a moment that was right there in front of them, available and free, and just letting it pass because it felt safer to wait.

You’re going to hear this message from me eventually one way or another. Either you hear it now, while you’ve still got time to act on it, or you hear it later, looking back, wishing someone had grabbed you by the shoulders sooner. The sooner you understand that you have to attack life instead of letting life just happen to you, the sooner you get to enjoy the ride instead of burning years on stress and anxiety and worry.

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Now, I want to be open and sincere here, because I talk a lot about having no regrets, and people take that the wrong way. I don’t walk around in agony about my past. But if you ask me directly, I’ve got what I’d call micro-regrets. Little ones. I should have gone to a couple more parties in high school. I shouldn’t have come home every single weekend in college to work instead of living a little. I should have taken more vacations with my friends in my twenties. I should have had a bit more fun.

None of those keep me up at night. They’re not the kind of regret that sits in your body like a heavy weight. But they’re legit, and I think it’s important for people to hear that even someone (me) who talks about being at peace still has a list of regrets. The difference is where you let regret be. The kind of regret that hurts, that really stngs, only shows up in one place for me: the people I love. Did I spend enough time with them? That’s it. That’s the whole test.

I’ve put in the work on the family side of my life. I mean that. And because I did, I get to say no to certain things now, because the deposits were already made years ago. But even with all that work, I’ve got a brewing regret with my best friend, someone I’ve known since the first day of high school, someone I built a business with. Lately I haven’t given him enough one-on-one time as we get older, and that’s something I want to go fix, not just talk about.

That’s the difference between a regret you let calcify and one you catch in time. You can’t undo the ones from thirty years ago. But the ones happening right now, in real time, those are still yours to change.

If you’re in your 20s or 30s and you think you missed your window, you didn’t. Fifty years is a long time to make your mark. This life, this opportunity, isn’t just for the young. It’s for anyone willing to take a swing. You have more time than you think, and right now might be the best time you’ll ever have to start the thing you’ve been putting off.

Stop being crippled by every mistake you’ve made or every dollar you’ve lost. I make mistakes every single day. I passed on an investment early on that would be worth hundreds of millions today. That’s real. But dwelling on it doesn’t create a single dollar or a single extra hour with the people I love. The only thing dwelling does is steal time from what’s next.

I don’t want you to be the person at 72 saying “I wish, I wish, I wish.” About the money, or the family, or the shot you never took. Everyone’s chasing something different, and that’s fine. You don’t need to want what I want, but find what you truly want, and stop making excuses for why you haven’t gone after it yet.

Go talk to five people in their 90s. Really listen. The only thing you’ll hear, if you listen closely enough, is regret. Let that be the spark instead of the warning you ignore. Let it light something in you that keeps burning for the next forty years. The opportunity is right in front of you, right now. Use it. Stop the self-pity. Get to work. One life, my friends. One time. Remember that.

Leaving you with one more thing. How you make your money is more important than how much you make. Create your life and career in a way you won’t regret, and you’ll never have to sit in that retirement home wishing you’d done it differently.