Oct 22, 2026 · 59 min
Heather Monahan turns workplace sabotage into a confidence practice
Why You Keep Doubting Yourself and How to Rebuild Your Confidence | Heather Monahan - EP 836
The conversation shows how damaging environments can distort self-worth—and how preparation, action, and supportive relationships can restore it.
- 1Confidence grows through repeated action, preparation, and difficult conversations rather than arriving as an innate trait.
- 2Leaving environments that diminish self-worth can create room for reinvention, especially when professional relationships provide support.
- 3Public success often rests on unseen fear, uncertainty, and small decisions that build the capacity to perform under pressure.
Don't miss
Heather Monahan explains why she announced her firing publicly on LinkedIn and used her network to begin rebuilding.
The brief
Heather Monahan traces self-doubt from early life through professional success, arguing that environments can quietly reshape how people see their own possibilities.
Her account of workplace sabotage shows how exclusion and unspoken politics can erode confidence, even after years of achievement and increasing responsibility.
After being fired, Monahan announced the setback publicly on LinkedIn, turning a private career rupture into a visible request for support and new opportunities.
The central lesson is behavioral: confidence is built through repeated choices, preparation, difficult conversations, and the willingness to leave places that make worth feel conditional.
John Miles and Monahan also examine the hidden practice behind public composure, including how preparation matters when pressure removes every safety net.
Books & mentions
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