One of the best things about being 65 is the full set of experiences I have to look back on.

That includes what I regret and what I don’t. I don’t know if these would be the same for you, but they’re at least worth considering.

I regret all the people I treated badly, even those who deserved it. I don’t regret all the people I treated well, even if they were terrible people or my actions didn’t pay off.

I don’t regret any time I stood up for quality, regardless of how many extra hours it took — or even when the result ended up not be worth the effort. Quality is its own reward.

I don’t regret treating every work-related task as an opportunity for problem-solving. But I do regret failing to understand how to work better with my fellow humans.

Everything I was required to learn along the way in my career, I don’t regret. I don’t regret learning to write well, attain influence, become a good public speaker, or manage multiple tasks and people at once. I don’t even regret the painful mistakes I made along the way.

There were cases where being dishonest would have benefited me, and no one would have known. I resisted. I don’t regret those decisions, and if I had made them the other way, I would certainly regret them now.

I know there are people who ended up detesting me, or at least feeling ambivalent about me. I regret the things I did that caused them to feel that way, but I don’t regret that there are so few of them.

I don’t regret leaving any of my jobs, even those from which I was laid off. Every transition was an opportunity for growth.

I don’t regret any of the freelance clients I turned down, even when they could have been quite lucrative. I do regret a few of those I took — just a few — but the nature of most freelance work is that it is over quickly and you can learn from your mistakes.

The people who did unforgivable things, who I forgave anyway: I don’t regret.

I don’t regret leaving academia, even though at the time it was a very difficult decision. It was like escaping from a cult.

I don’t regret any of the romantic relationships that ended, regardless of who dumped whom. I could not have gotten to the right one without all the wrong ones. And hey, I get to keep the memories.

There were moments when I wondered if I should leave my wife. We all have such moments. Staying instead was the smartest thing I ever did — I have not the slightest regret about that.

I regret the things I said in anger to my children. Apparently I did and said enough of the right things that they still get along with me and respect me. That’s a credit to them far more than it is to me.

I regret making precipitous financial decisions when I could have hedged instead. When it comes to finance, always ask, is there a way to split the difference? That attitude reduces gains, but moderates risks as well.

I don’t regret living below my means. I don’t regret failing to buy new cars, new electronics, vacation homes, or anything else others in my income bracket could apparently afford. The result is that I am now debt-free and secure, with a paid off house and children with college degrees but no college debt.

I regret the times that I was driven by a competitive impulse. Winning is short-lived, losing sucks.

I regret that I didn’t spend enough time with true friends. Some of them are gone now, and I can never get them back.

I regret my lifelong love of sweet things. I don’t regret my lack of interest in alcohol, drugs, or caffeine.

I don’t regret blogging every weekday, even if it sometimes feels like a sign of mental illness.

I have made hundreds of thousands of puns. I regret none of them. Even if the people around me may regret a few . . .

Thanks for listening.

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  1. This post is a keeper. It could serve as your ethical will. Thanks for sharing your regrets and nonregrets so candidly.

  2. Hello, Josh. Thank you for imagining this post and sharing the contents so fully.
    Your ‘don’t regret’ and caveats and even the regrets describe a rich and full life, well-lived. I find many resonances in reading your words, including reminding of some things I need to act on. With well wishes for 2024. Marc V