The 4 Most Common Regrets and How to Get Past Them

The 4 Most Common Regrets and How to Get Past Them

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So, throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain

Three of my clients are facing major career decisions.  On one side, they could make a choice that is totally inside their wheelhouse – safe, familiar, and not likely to challenge them much.  When they talk about it, their energy is low.  They give me reasons why it ‘makes sense.’

On the other side is something that scares them.  They could give me endless reasons why it doesn’t make sense, but here we are, still talking about it.  And their energy is sparky. Alive. They almost wish they could forget about it.  It would make life easier. 


Best-selling author, Dan Pink’s most recent book, The Power of Regret: How Looking Backward Moves Us Forward, gathered 16,000 regrets from people living in 105 countries.  The amazing result is that everyone had the same 4 regrets.

  1. Foundation regrets.  “I wish I had done more to lay solid foundation.  I should have saved more money, worked harder in school, taken better care of my health.”

  2. Boldness regrets.  “I should have taken the chance – started the business, asked him/her out, spoken up more.”  People regret inaction more than they regret action.  We are more likely to regret what we didn’t do that what we did do (even if that involved a failure). 

  3. Moral regrets.  “If only I’d done the right thing – not bullied, been unfaithful, done something hurtful.”

  4. Connection regrets.  “If only I reached out and not let the relationship fade.”

Pink encourages us to have compassion for ourselves. All of us have regrets. It is part of what makes us human – being able to look back and wish we had done something differently. 

How to Avoid Regret Next Time

Pink offers two great tools to help you the next time you find yourself at a juncture.

1.     Go forward 5 years and look back.  What decision would you want your 2027 self to tell your 2022 self? 

2.     What would you tell your best friend to do? 

“They say, ‘Look before you leap.’ So, look. But do not look for too long. Do not look into the void of uncertainty trying to predict each and every possible outcome, to evaluate every possible mistake, to prevent each possible failure. Look for the opportunity to leap, and leap faster than your fear can grab you. Leap before you talk yourself out of it, before you convince yourself to set up a temporary camp that turns into a permanent delay on your journey into your own heart.” – Vironika Tugaleva

For more information, check out these resources:

Dan Pink’s TED Interview about regret (23 minute video)

Oliver Burkeman’s 4000 Weeks, Time Management for Mortals to get clear about what matters most to us

Starla Sireno is an Executive Coach in New York City. Starla is in the business of transforming executives into better leaders and better humans. Inquire how to work with Starla or her team.

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