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

Ryan Holiday
8 min readJul 27, 2023

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’ll 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.

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Ryan Holiday

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR