What Leaders Most Regret: my View

By | November 4, 2019

[November 4, 2019]  If there is one thing I learned as a leader, it was that it’s not about what I did that I regret, it’s what I didn’t do.  During my travels and meeting folks all over the world, I had the opportunity to discuss what leaders like and dislike.  Often the conversation turns to leader regrets.

“Twenty years from now, you’ll be more disappointed by the things you didn’t do than by the ones you did do,” – Mark Twain, American writer, humorist, entrepreneur

From my experience with leaders from all walks of life, I put together a shortlist of those things I heard most often.  No, this is not a scientific poll.  I didn’t even write them down until now.  At the time, I didn’t think much of it until a few years ago just before I retired.  Maybe my thinking was too future-oriented to be thinking about regrets, but looking back upon my discussions, I now see that many leaders expressed regrets.

Here is my list of 10 things leaders regret the most:

  1. Showing enough moral courage to act at the right time with the right behavior
  2. Spending more time with family (especially the spouse) and friends
  3. Joining the U.S. military or making a career of it for those who did
  4. Being better at mentoring and coaching others
  5. Trusting subordinates and family members more
  6. Staying in better physical health
  7. Joining a church or synagogue and actively living it
  8. Learning more about the history of their nation (particularly true of Americans)
  9. Being true to yourself, being authentic
  10. Being more honest, open, and humble

A middle-aged Iraqi colonel told me one day while we were alone that he regretted that he did not stand up to Saddam Hussein during the dark days of the dictatorship.  “Disgust” was the word he used to describe himself.  He was, in his mind, a coward, and that is not how “men” act when given a choice.  He chose wrong.  Regrets like this were common, and I found those who talked with me about their lives to be very revealing and unexpectedly honest.

Surprisingly, none of the leaders that I spoke to regretted that they would someday die.  I think the reason is that they had lived a life full of responsibility, had succeeded, and therefore had a full life.  There may have been a sense of proper balance in their lives.  That is why my list of ten might not agree with what most folks regret.

Author: Douglas R. Satterfield

Hello. I'm Doug and I provide at least one article every day on some leadership topic. I welcome comments and also guests who would like to write an article. Thanks for reading my blog.

22 thoughts on “What Leaders Most Regret: my View

  1. Darwin Lippe

    We all have regrets and most of them are about what we did NOT do. Thanks to General Satterfield for his articles that make us all think.

  2. Billy Kenningston

    This may sound a little melodramatic, but no matter how happy you are, at my age your regrets are countless.

    1. Jonathan B.

      Romance, children, parents, education, career, finance, parenting, health, friendship, and charity are most often listed. Hmmmm …. Looks like I did okay!

    1. Ronny Fisher

      Good article. Education is the most often mentioned followed by career. Surprisingly, family is ranked pretty low so I guess people made pretty appropriate choices and have less regrets.

  3. José Luis Rodriguez

    Regret on its own is not a bad thing; in fact, it can spur us to action.

  4. JT Patterson

    “Not speaking up when I should have” is a common regret from people both young and old. We all lack moral courage and it doesn’t come easy.

    1. Georgie B.

      So very true. “Leaving college because I didn’t want to do the work.” A decision that haunts many.

  5. Nick Lighthouse

    Good job with this blog post, Gen. Satterfield. I was hoping for something like this today; something that hits home on what we “see” and “regret” in our past. Not doing something illegal, immoral, or unethical but simply something not done.

  6. Eric Coda

    I read up on several articles that listed “regrets” of people – usually over 50 – that listed many of these. One that I didn’t see in these articles were those that said they regretted not being in the military. I wonder why. Perhaps that is buried in “career” issues. ?

    1. Wilson Cox

      Thanks. I agree. Most men, at least those over 30, will in large part wish they had been in the military. Now that doesn’t apply to all nations but to most Western ones. I lived once in Britain and the Brit youths generally want to avoid military service. I don’t understand that with the great traditions the UK has in its army and navy.

      1. Gil Johnson

        Great comment about England. I wonder too about this phenomenon.

  7. Tracey Brockman

    Just got back from a trip to Europe and saw a lot of people and places that I’ve been wanting to see so much for a long time. Friends said they regret not traveling more during their lives (like me). Another regret.

  8. Eva Easterbrook

    I have found that most folks don’t make a single mistake and regret it the rest of their lives but, the fact is, they make a series of mistakes that are similar and they do regret that.

    1. lydia

      Good point, Eva. This is common of those who are failures in life. And those of us who are successful are under no legal obligation to support them. However, a few of us who are well off financially do have a moral obligation to help. I would hope we all help them.

    2. Darryl Sitterly

      “Give a man a fish and he eats for a day, teach him to fish and he eats for a lifetime.” Interesting quote from some Chinese proverb. This is great philosophy and is diametrically opposed to the liberalism that goes today for compassion.

  9. Harry Donner

    Loved you article today. We always seem to get something that adds just a little bit more understanding to leaders. In this case, what were they running away from that motivated them to do certain things. Like fearing failure on some achievement (e.g., education, career, family) that is significant.

  10. Army Captain

    As I expect, another article that hits to the heart of leadership. In this case, we again look into the psyche of the leader (and others too) and what they regret when they look back upon their lives. I’m not sure if these were older leaders but given what Gen. Satterfield has told us, these are more executive-level leaders.

    1. Roger Yellowmule

      Yes, Army Capt, I agree and will add that we all have regrets. Like having an ice cream when we’re on a diet. But that is not what Gen. Satterfield is telling us here. Look at the list again closely. Some of the items are obvious, like staying in better health but others not so expected like joining the US military.


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