• 462: My Biggest Leadership Mistakes + Regrets

  • May 8 2025
  • Length: 20 mins
  • Podcast

462: My Biggest Leadership Mistakes + Regrets

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  • Summary

  • No one talks enough about the hard parts of leadership — the moments you wish you could take back, the decisions that didn’t go as planned, and the lessons that only hindsight can teach. In this episode, Natalie pulls back the curtain on the biggest leadership mistakes she’s made over the years. From hiring too fast to ignoring gut instincts, and losing herself in the business, Natalie shares what she would do differently, what she’s learned the hard way, and how she’s leading now. Whether you’re building your first team or already leading one, this episode will give you the honest insights most people don’t share. Let’s dive in! TIMESTAMPS 00:00 Why we’re talking about leadership mistakes today + why more founders need to 03:05 The hard truth about hiring fast and leading without clarity 07:40 What happened when Natalie didn’t listen to her gut 11:20 The hidden cost of avoiding hard conversations 16:00 How people-pleasing led to a leadership identity crisis 20:45 A breakdown that forced a breakthrough in how she leads 25:10 The biggest regret — and what she’d do differently now 28:50 What “healthy leadership” looks like today inside Bossbabe 31:20 Natalie’s challenge to every founder who wants to grow with integrity RESOURCES + LINKS Join The Société: Our Exclusive Membership To Help You Build A Freedom-Based Business - start today for just $97. Learn how to Start or Scale a Freedom-Based Business with this free training: bossbabe.com/class. Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More. Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).
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