Free Time with Jenny Blake

112: My 3 Biggest Business Regrets


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As tough as it is to stomach sometimes, regret can be a helpful catalyst. As Daniel Pink shares in his latest book, The Power of Regret: How Looking Backward Moves Us Forward, regret is better understood less as a thing and more as a process; one that doesn’t just make us human, it makes us better. 

“By making us feel worse today, regret helps us do better tomorrow,” he says. “Understanding its effects hones our decisions, boosts our performance, and bestows a deeper sense of meaning.” Today I’m sharing three big regrets, or strategic errors, in 11+ years of running my business.

Special shout out: Thank you MoneySmartMom from Canada for the glowing review!

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🌟 3 Key Takeaways from Daniel Pink’s book:

  • Foundation regrets sound like this: If only I’d done the work.
  • Boldness regrets sound like this: If only I’d taken that risk.
  • Moral regrets sound like this: If only I’d done the right thing.

  • 📝 Permission: Forgive yourself and drop the guilt about what you coulda, shoulda, woulda done in your business (thank you SATC for that episode title!). Today is a new day, and you probably had valid reasons at the time for making the decisions you did. Celebrate the wins, too!


    Do (or Delegate) This Next: What are your biggest business regrets? Leave me a voice memo and let me know at http://itsfreetime.com/ask.


    📘Books Mentioned:

    • Free Time: Lose The Busywork, Love Your Business 
    • Pivot: Lose the Busywork, Love Your Business 
    • The Power of Regret: How Looking Backward Moves Us Forward

    • 🔗Resources Mentioned: Jenny’s private BFF community


      🎧Related Podcast Episodes:

      • 058: Look for Measurable Loops
      • Pivot: 021: Reinvent Yourself With James Altucher
      • The James Altucher Show: Pivot: The Difference Between Making Millions and Failure…Episode #183

      • 💻 Access Free Time episode transcripts on Podscribe » 

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        Free Time with Jenny BlakeBy Jenny Blake

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