Regrets Of The Living And Regrets Of The Dying

On regrets
Thomas Kelley

In six months I’ll be 50 but I already know what I’ll regret.

This is the cliche answer. “If anything had been different I wouldn’t be who I am today.”

If I wanted to, I could put an “!” at the end of that sentence. Like what I am today is so great I’d never want to change it.


I wish I could’ve done some things differently in the past and still be the person I am today.

Life is pretty hard and complex. And our brains aren’t smart enough to figure it all out. Even the best baseball player in the world bats only 30%. And I’m mediocre at best.


I wish I had spent more time with my kids. Sure, I spend quality time with them now.

But I worked really hard and, I admit, I probably avoided them when they were really young and difficult to wake up and get ready for school when they were younger.


I wish for 15 years or so I wasn’t so focused on money. I only realized in the past few years that there’s two feelings in the body

– CHEST. When I do things I love, I feel it in my chest and I forget the rest of the world. If all I did was do the things that feel good in my chest, I’d be a happy person, nothing else would matter.

– GUT. This is where my anxiety and stress seem to live. For 20 years I lived in a world of all stress.

Now I wake up every morning a little bit nauseous. After all these years of just doing things that hurt in the gut.

I probably should see a doctor. Everyone tells me I should. But I haven’t gone to a doctor in 31 years so why should I now?


I began my career in my 20s doing things that were really creative that I loved.

I was trying to write a novel. I was trying to do a TV show. I was always around people I loved so much. And I spent time with them because I loved them and not because I wanted anything else.

I wish I had stuck with that. I got sidetracked by starting an Internet business. I made money doing that but I wasn’t cut out for that life and I was miserable.

I was starting to get good at creative things. Now, in my 40s, I’m trying to catch up.

It’s never too late, of course. But this isn’t about “too late”. It’s about “regret”.


When I first made some money I became a bit arrogant. “A bit” is an understatement.

I started investing in all of these horrible companies and real estate and having horrible friends and horrible horrible. It’s the double-horrible that finally kills you.

If I were humble and just went back to what I loved, I bet I’d be happier.

I would have said, “I’m too stupid for this” and just got back to the things I loved.


I couldn’t say “no” to people. I still have a hard time with that. I wish when someone does something that I don’t like or agree with that I would say “no” a bit more often.

There would be a few days of confrontation and then life would move on. I’ve gotten into a lot of bad situations because I didn’t say “no”.

Here’s two cases where I should have said “no” more often:

— When someone treats me bad.
— When I don’t want to do something but I feel bad about hurting someone.
— And sure, I’ll add a third: when it’s not a “hell, yeah!” I should say “no”. I’m better at doing this now.


If I had a time machine would I go back in time? I’m not sure. It’s ok to feel regret sometimes.

I thumb through it like I would a deck of cards with pretty pictures.

I would have held my daughter’s hand when she came home from school.

And I would have taken her for a walk around town. And she would’ve told me about her day. And I would ask her lots of questions.

I’d listen while she talked and talked. She would tell me everything.

And we’d walk for a really long time, until the sun went down and I’d try to tell her the names of all the stars above us. Even if I had to make it up. Thought Catalog Logo Mark

About the author

James Altucher

James Altucher is the author of the bestselling book Choose Yourself, editor at The Altucher Report and host of the popular podcast, The James Altucher Show, which takes you beyond business and entrepreneurship by exploring what it means to be human and achieve well-being in a world that is increasingly complicated.

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