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June 17, 2020

Podcast #620: How to Deal With Life’s Regrets

We’ve all asked “what if” questions about our life: What if I had majored in art instead of business? What if I had let my best friend know I liked her as more than a friend? What if I had taken the job offer in Colorado? Sometimes contemplating the imagined possibilities of these alternative histories fills us with sharp pangs of regret.

My guest today says that’s not necessarily a bad thing. His name is Neal Roese and he’s a professor of psychology and marketing and the author of If Only: How to Turn Regret Into Opportunity. Neal and I begin our conversation by unpacking how asking “what if” is to engage in something called “counterfactual thinking,” and how you can create a downward counterfactual, in which you imagine how a decision could have turned out worse, or an upward counterfactual, where you imagine how a decision could have turned out better. Neal then explains why living without regret isn’t actually that healthy, and why even though regret is an unpleasant feeling, it can be an important spur towards greater improvement, action, and agency. We then do get into the circumstances in which regret can become a negative force, before turning to what Neal’s research says are the most common regrets people have in life. At the end of our conversation, we pivot to talking about how imagining how your life could have turned out worse, can make you feel happier. 

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Show Highlights

  • What is regret? What is counterfactual thinking?
  • How often are people doing counterfactual thinking 
  • Why are regrets necessary to improving ourselves?
  • When does regret turn in to the negative?
  • How do you re-work those negative thoughts?
  • The negative impacts of doing counter-factual thinking on behalf of other people
  • What do people tend to regret the most? And why is this such a powerful question?
  • Common relationship regrets 
  • Common work and career regrets 
  • Why aren’t money regrets as powerful as other categories?
  • The counterfactual thinking of FOMO 
  • What we can learn from It’s a Wonderful Life

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