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When Success Creates Self-Doubt: How Leaders Move Through "Wonderhell"

The Enlightened Executive · 2026-03-26 · 32 min

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Episode notes

What happens when success does not bring the confidence you expected? In this episode, Susan Drumm sits down with Laura Gassner Otting to explore the tension many leaders feel after reaching a new level of achievement. Instead of clarity, they often experience pressure, self-doubt, and the sense that they now have even more to prove. Together, they unpack Laura's concept of "Wonderhell," the space between recognizing your potential and fully stepping into it. They also discuss why imposter syndrome often shows up at moments of growth, how external success can pull leaders away from intrinsic motivation, and why self-awareness is essential for sustainable leadership. This conversation is especially relevant for executives, founders, and high achievers who are navigating the discomfort that often comes with growth.

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