462: My Biggest Leadership Mistakes + Regrets
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
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May 22
