Mail Bag – Do You Have Any Regrets?

Tonight, I’m answering one of the most insightful Mail Bag questions I’ve ever received: Do I have any regrets?

Dear Joshua,

You’ve obviously accomplished more than most people do in their lifetime despite being young.  You don’t have to answer to a boss, you spend your day doing whatever you want, you give a lot of money away, you seem to travel several times each year, and you help many people through your writings.  Here’s my question.  Do you have any regrets?  Is there anything along the way you wish you could change?

Harris

It depends entirely upon what you mean by the word “regret”.  Not everyone uses words the same way.

I’ve achieved much of what I desire (God willing, the rest will come with time), I have total freedom over my time, I get to play a role in improving people’s lives by helping them understand the world better, and I am surrounded by friends and family who love me and whom I love to a degree about which most people can only dream.

That doesn’t mean I don’t make mistakes and I haven’t made mistakes along the way.  Far from it!  Just because you win the ballgame doesn’t mean you can’t learn from botched plays.  Both in business and personally, life is a constant learning exercise and mistakes will happen (in fact, I recently did a case study of the single biggest investment mistake I ever made).  There have been personal situations that could have been handled better or things in business that, in retrospect, could have been better handled but I don’t have regrets.

In the big sense, then, no, I don’t have any regrets.  Perhaps saying I have no regrets has to do with my philosophy about decision-making, which is you look at the opportunities available to you (opportunity cost) and make the most rational decision you can consistent with the price you’re willing to pay.  Once you make that decision, don’t look back, don’t second guess yourself, and don’t retroactively apply new data that wasn’t available at the time the decision was made because it will lead to cognition errors.  If your decision turns out to be sub-optimal, learn from it, analyze it, and don’t repeat it.  If you can’t fix it, you have a moral duty to learn from it to improve yourself in the future.

I suspect that much of this has to do with:

• My willingness to settle, very early in life, the list of priorities as to what was most important to me.  That made the big decisions easy, sort of like a blue print to a construction project.  I explain this in Mapping Out Your Main Life Goals and Lesser Life Goals.
• My scorecard is largely internal.  My own sense of self-worth comes from the decisions, accomplishments, and methods I used to live my life and achieve my objectives, not from people, institutions, credentials, or other crutches frequently used by those who need validation.  If I were convinced my actions were right, I’d sleep better at night having everyone hate me than I would being loved and knowing that what I did was wrong.  An enormous portion of humanity is wired just the opposite.  Character is what you do when you’re alone and no one is watching.

It’s very difficult to have regrets when you live your life awake, purposely choose your priorities, and run decisions through a rational framework in relation to those priorities.  So, yeah.  I’ve never lost much sleep over a business deal, a personal decision, a relationship, or anything but much of this is because I’ve trained myself for many years to go through the mental model list before taking major actions.  I factor in emotional considerations, as well, and acknowledge when they are clouding my judgment or causing me to act in a way that may not make intellectual sense but will leave me feeling better.  Be grateful for the good things and, if you make a mistake, recognize it, learn from it, and move on with your life.  To hang on to ghosts of the past is to allow situations or people to live rent-free in your head without adding any value to your life.