The Minutes

Bill Gurley on

regret

11 entries, 12 Feb 2026 to 8 Jul 2026

On the recordsourced and dated, oldest first

    1. spoken

      Gurley's Wharton survey found six in ten people would choose a different career if they could go back.

      “It led to us doing this survey with Wharton where we asked people, if you could go back in life, would you choose a different career? And six in 10 people say yes.”

      12 Feb 2026 · Tetragrammaton with Rick Rubin · 1:09:22 · source · permalink
    2. spoken

      Gurley says regrets of inaction weigh on people's minds increasingly over time, unlike mistakes they forgive themselves for.

      “But the thing we never did, the thing we always thought we should do that we didn't get to, those things weigh on our brain more and more and more as we get older.”

      26 Feb 2026 · On with Kara Swisher · 19:19 · source · permalink
    3. spoken

      Gurley says regrets of inaction weigh on people's minds more heavily over time than mistakes made.

      “the thing we never did, the thing we always thought we should do that we didn't get to, those things weigh on our brain more and more and more as we get older.”

      26 Feb 2026 · On with Kara Swisher · 19:19 · source · permalink
    4. spoken

      Gurley's Wharton survey found six in ten people would choose a different career path if starting over.

      “We hired we hired Wharton to do an official academic review, and that one came out six and ten. There's a book by Daniel Pink about regrets called the power of regrets.”

      5 Mar 2026 · Bloomberg Podcasts · 19:33 · source · permalink
    5. spoken

      Gurley reports survey finding that 60% of people would choose a different career if starting over.

      “we did a survey where we asked people if you could go back in time and start your career over again, would you do something different? And six out of 10 said yes.”

      16 Mar 2026 · Silicon Valley Girl Clips · 2:19 · source · permalink
    6. spoken

      Gurley's survey found six to seven out of 10 college graduates would do their career differently if starting over.

      “if you could start your career over again, would you do it differently? And in our original SurveyMonkey, seven out of 10 said yes. With Wharton, it was six out of 10.”

      17 Mar 2026 · Anthony Scaramucci · 5:44 · source · permalink
    7. spoken

      Gurley cites Daniel Pink finding humans dwell on boldness regrets, inactions they never tried.

      “Daniel Pink in his book, The Power of Regret notes that humans dwell on regrets of inaction. He calls them boldness re regrets.”

      17 Mar 2026 · Anthony Scaramucci · 5:55 · source · permalink
    8. spoken

      Gurley contrasts humans easily forgiving action mistakes but struggling with things never tried.

      “And the older you get, the more they weigh on you. Humans are fabulous at forgiving themselves for mistakes, kind of what you just walked through. Those are action mistakes.”

      17 Mar 2026 · Anthony Scaramucci · 6:05 · source · permalink
    9. spoken

      Gurley explains that regrets of inaction intensify with age more than mistakes made.

      “Daniel has, in his book on regrets, talks a lot about regrets of inaction. He calls them boldness regrets.”

      10 Apr 2026 · Metis Strategy · 17:17 · source · permalink
    10. spoken

      Gurley cites survey data showing 60% of people would choose a different career if they could start over.

      “we did a survey where we asked people if you could go back in time and start your career over again, would you do something different? Six out of 10 said yes.”

      27 Apr 2026 · Silicon Valley Girl Clips · 4:00 · source · permalink
    11. spoken

      Gurley cites Daniel Pink's research showing regrets of inaction are the number one regret people have at end of life.

      “And the number one thing people regret at the end of their lives is what he calls boldness regrets, their regrets of inaction.”

      8 Jul 2026 · Jackson Square Ventures Book Club · 4:55 · source · permalink

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