Why Regret?

by Scott Harper

“Regret is a form of perfectionism.”

Rangan Chatterjee

February 11, 2026

Do you have any regrets?

Do you regret mistakes you’ve made—with family? Friends? Employers? Employees? Even strangers?

I don’t think I’m in the minority for feeling regretful about a lot of things I've done—or haven’t done—in life.

I regret actions, inactions, thoughts, and words. I even regret some things that were out of my control.

There are countless things in my life that I wish I had done differently or avoided altogether . . . i.e., I regret.

Regret can be a useful tool—or a crippling, destructive weapon.

Regret without forgiveness and a clear understanding can be disabling. It can hold you back and make you, or others, believe imperfections are unacceptable.

Regret can improve decisions.

Regret can help you learn from mistakes.

Regret can make you wiser and a more compassionate teacher.

Your inability—or unwillingness—to learn and grow while letting go of regret (your own or someone else’s) could be one of your biggest regrets. 

How you use regret, how you express it, and how long you hold onto it can make all the difference.

SHARPER LEADER:

1.      Do you use regret as a tool or a weapon?

  • Action Step: Write down an action you regret. How often do you mentally punish yourself over it?

 

2.      How can regret make you better?

  • Action Step: Looking at that regret, write down all the specific ways you’ve grown since then.  

 

3.      Does the way you condemn your regrets communicate that you expect perfection—from yourself or others?

  • Action Steps: It’s okay to acknowledge past failures. Practice expressing gratitude for uncomfortable lessons and use them wisely moving forward.  

 

Recommended book: Make Change That Lasts: 9 Simple Ways to Break Free From the Habits that Hold You back by Rangan Chatterjee

 

Before next week’s The Sharper Minute:

  • Make a short list of personal or professional regrets.

  • Recognize all the ways you’ve grown since then.

  • Ask for or offer forgiveness (as appropriate).

  • Seek help to avoid repeating the same mistakes.

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