Losing stinks. Nobody wants to suffer defeat in a game, flunk a test, or get passed over for a promotion. Losses can feel like stinging humiliations, insurmountable setbacks, like the end of the world; they can even push us to quit pursuing something we love. And yet losses can be the most instructive and meaningful parts of our lives, and be central to our ultimate success.

My guest set out to study and explain these underappreciated upsides of getting bested. His name is Sam Weinman, he’s a sportswriter, and he shares what he learned in his book, Win at Losing: How Our Greatest Setbacks Can Lead to Our Greatest Gains, as well as in today’s episode. Sam and I begin our conversation with how losing is typically a lot more interesting than winning, the difference between losing and failing, and how you can lose without failing, as well as fail without losing. Sam then illustrates the lessons in humility, growth, personal responsibility, and resilience that can come from losing by sharing the stories of famous people who dealt with famously big losses, including golfer Greg Norman, soap star Susan Lucci, presidential candidate Michael Dukakis, and speed skater Dan Jansen. We end our conversation with how Sam’s study of how to turn loss into gain has influenced his own children and the way they deal with setbacks.

Good insights here both on how to deal with your own losses as well as how to help your kids deal with theirs.

If reading this in an email, click the title of the post to listen to the show.

Show Highlights

  • Why losing is more interesting than winning
  • The difference between losing and failing
  • How you can lose without failing, and fail without losing 
  • Greg Norman’s magnificent failure at the Masters Tournament  
  • How losing can soften people’s rough edges 
  • Michael Dukakis and the 1988 presidential election 
  • Susan Lucci, the Daytime Emmys, and what she learned from her decades of losses
  • Why Dan Jansen fell on the ice at the Olympics 
  • Process vs. results 
  • What Sara Hess can teach us about finding new mountaintops 
  • The losing Columbia football team of the 80s 

Resources/People/Articles Mentioned in Podcast

win at losing book cover by sam weinman.

Connect With Sam


Sam’s website

Sam on Twitter

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Read the Transcript

Coming soon!

The post Podcast #646: How to Win at Losing appeared first on The Art of Manliness.

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