24 Things I Wish I Had Done Sooner (or my biggest regrets)

Of all the things in life we don’t control, the past is the clearest. It already happened. It’s done. It’s set in stone. 

Perhaps we could have controlled and changed it, but the fact is, we didn’t. And now it is what it is, forever a was. 

For this reason, the Stoics were not big on regret. Neither am I. There’s no reason to whip yourself or be paralyzed by the “What Ifs” of life. Still, we can learn and grow, and in fact, we must. 

I once interviewed the peerless Dr. Edith Eger, Holocaust survivor and the author of one of my favorite books, The Choice. At the beginning of the podcast (you can listen here), I ask her about something I regretted, a relationship I had messed up. She looked at me and said she could give me a gift that would solve that guilt right now. “I give you a sentence,” she said, “One sentence—if I knew then what I know now, I would have done things differently.” That’s the end of that, she said. “Guilt is in the past, and the one thing you cannot change is the past.” 

So below are some things that, while I try not to regret, I do wish I had done differently or sooner or better. I think you might benefit from doing them sooner too…

-I look back at stuff I was so worked up about, things I fretted about, fought about, took personally, held onto, and now think, WHAT? If I had to go back and give a younger version of myself one word of advice it would be: “Relax.”

-This line from Bruce Springsteen captures, in retrospect, almost every argument or grudge I’ve held onto: We fought hard over nothin’ / We fought till nothin’ remained / I’ve carried that nothin’ for a long time. There are very few arguments I’ve had with my wife that I care that much about anymore.

-Writing Trust Me I’m Lying, I was 90% conscious about what other people might think and 10% following what was in my heart as an artist. The book I am most proud of is my book Conspiracy. The only parts of it I wish I could do differently are the few instances which, in retrospect, I was too conscious of what other people might think (particularly journalists). I’ve flipped the ratio by this point, but I wish I had gotten to that happier place sooner.

-I also should have fought harder on the title of my first book (I wanted to call it Confessions of a Media Manipulator, not Trust Me, I’m Lying), and I should have stuck to my guns about the prologue of Ego is the Enemy (I didn’t want to be in it, they wanted me in it). In creative disputes, the publisher/studio/investors/etc are not always wrong, but often they are. And even when they’re not, you have to remember, that whatever the decision, you have to live with it in a way they do not. I’ve regretted anytime I did not go with what was in my heart as an artist.

-As far as saving and investing money goes, there are so many different automatic transfers I should have set up earlier. I don’t know what my block was, but I stuck with doing things by hand for too long. Meanwhile, every account I have and did eventually set up scheduled transfers for–for my retirement, for my kids college, rainy day fund etc–constantly surprises me with how large the balances have been. Set it and forget it…the sooner you do it, the more you’ll have. You won’t regret compound interest. 

-Man, I ate like garbage for so long. When you’re young you can get away with it. Mostly, I just didn’t know any better. But when I started cutting stuff out? Soda, lots of carbs, most sugar, etc etc, I just felt incredible. I look at pictures of myself in my early twenties and even though I was a runner, I was just doughy. But mostly I think about how crappy I must have felt and not even knowing that I was feeling crappy or why I was feeling crappy. 

-There are many books I regret powering through, far fewer that I regret quitting. Life is too short to put up with bad writing—bad anything really. If the food sucks, don’t finish it. If the speaker is boring, get up and leave. If the party is no fun, go home. Stop powering through crap.

-Maybe it’s because I’m a 90s kid, but there’s a part of me that is instinctually a little bit skeptical of stuff that’s popular. If a book really pops or I hear a bunch of people tell me it’s a classic, part of me goes: “Well, I’m not going to read that!” Yet almost every time I have pushed through that, I’m more than pleasantly surprised: David McCollough’s biography of Truman is as good as everyone said it was. Malcolm Gladwell has sold millions of books for a reason. Erik Larson too

-People are waiting longer and longer to have kids. I wish we’d have done it earlier. Having kids at 29 has changed my life for the better in almost every single way…I’m glad I didn’t do it at 19. But there were a couple years there where I was ready, I was just telling myself I wasn’t. 

-I should have taken care of my skin more when I was younger. I should have worn sunscreen more. So should you. 

-Do I regret writing Trust Me I’m Lying? Like I said, regret is a tricky word. I wouldn’t be here if I hadn’t. It was the only first book I could have written. I don’t like all the ways it was received and used, but the main thing I wish is that I had been compelled to write it earlier–or more accurately, I wish I had been aware enough to question my life and my choices and my industry sooner. That might have actually made the book impossible, the stories less interesting, but I would have been a better person. I was just too blind, too caught up at being good at something to figure out it wasn’t a good thing to be good at. 

-I also distinctly remember as I sold that book to my publisher feeling so rushed. Like it had to come out right away, or I would miss the window, that the ideas wouldn’t hold true. Lol. It was a book about ‘fake news’ before that phrase even existed! I wasn’t late, I was early. I have since learned the importance of being patient, that taking your time, getting it right instead of first, is much less likely to be something that leads to regret than the alternative. 

-In the afterword of Courage is Calling, I tell the story about being asked to do something terrible at American Apparel. I didn’t do it, but I also didn’t take much of a stand about it. Why? I didn’t want to get fired. Only much later did it fully occur to me how ridiculous that is: A job where you have to be worried about getting fired for not wanting to do something wrong is not a job worth keeping!

-I’ve made a few very costly mistakes as an entrepreneur/business person. I noticed one trend: My wife was against them all at the time. It took me longer than it should have to notice this very illuminating signal. 

-I should have drawn better boundaries with my parents sooner. 

-It’s clear to me in retrospect that my desire for approval, for being seen, for being a part of something important or newsworthy or exciting, blinded me to the character of certain people I worked for. Of course, this was something those people understood and exploited in me and lots of other more vulnerable victims, but it’s still on me. You have to wake up to the ways that the wounds you experienced as a kid make you a mark, or create patterns in your life. It’s not your fault things happened to you, it is your fault if you don’t learn how to adjust accordingly.

-You know deep down that accomplishing things won’t make you happy, but I think I always fantasized that it would at least feel really good. I was so wrong. Hitting #1 for the first time as an author felt like…nothing. Being a “millionaire”…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake. The mistake to really avoid though is the one that comes after the anti-climatic accomplishment, the one where you go: “Ah, it’s that I need to repeat this success, it’s that I didn’t get enough. More will do it.” You know this but then you act otherwise…

In many interpersonal conflicts over the years I have come to rue acting quickly, responding emotionally or getting personal. I have never regretted taking my time, being firm but still understanding, and trying to give the other person a way out, a way to save face.

-With 36 years of data now, I can confidently say that I have never once lost my temper and afterwards said, “I’m so glad I did that.” 

-When I look back at my old writing, the main thing I regret is usually tone. Certainty does not age well. Life is complicated. Situations are nuanced. My books have gotten longer as I’ve gone on. I don’t think I’m being self-indulgent, I think I am being more fair, more compassionate, more truthful. 

-If you keep having to put down your horses, it’s because you’re riding them too hard. Unfortunately, I have lost a lot of otherwise great talent because I put too much on them. Just as athletes have to think about personal load management, coaches and GMs have to think about it for the whole team (and understand that every person has a different threshold).

-With the exception of the kind of people for whom no contact is a necessary strategy, I have never regretted the impulse to send someone a check-in text or call. And I have twice regretted neglecting the impulse to reply or reach out to my friends Seth and Bret, because I never got another chance, as I detailed here.

-Every repair or improvement I put off doing for my house, when necessity eventually came around and I had to do it anyway, I’ve thought: What did I put this off for? It cost the same and I deprived myself of the enjoyment in the interim. I’m trying to get better at not kicking cans down the road. 

-Most of all, I wish that I had enjoyed my work sooner. A few years ago, I was talking to a retired pro athlete and they were telling me how they regretted not enjoying the game as much when they played, that they hadn’t had more fun while they played. It wasn’t a particularly unique insight. I’ve heard it in a million speeches and interviews, but I was in the middle of a particularly hard writing project at the time and not having much fun. I remember thinking: I’ve made it. I’m a pro at this really cool job…why am I not enjoying myself? 

I’ve made a conscious effort since to consciously appreciate that I get to do this, to not let it turn into a grind or a slog. You don’t know if you’ll actually make it to publishing a book–you could die, the book could die–so why not have fun while you’re doing it? Why not make each day the win, the joy, the experience as opposed to the end result? 

As Marcus Aurelius said, it’s insane to tie your wellbeing to things outside of your control. Success, mastery, sanity, Marcus writes, comes from tying your wellbeing “to your own actions.” If you did your best, if you gave it your all, if you acted with your best judgment—you’ve won.

Written by Ryan Holiday