Have you ever bailed on a “seat at the table” moment because imposter syndrome convinced you you didn’t belong?
This episode is basically a reality check for that spiral. If you’ve ever walked into a room of bigger titles, bigger experience, bigger confidence—and immediately started listing all the reasons you’re “not enough,” Megan Reilly’s story will feel uncomfortably familiar (in the best way). She breaks down what imposter syndrome costs you, how to stop self-eliminating, and how to stay in the game long enough to actually grow—whether you’re building a company, scaling a team, or just trying to lead without burning yourself out.
What you’ll walk away with
- A simple way to quiet imposter syndrome when you feel outmatched—so you stay in the room and find your value instead of fleeing.
- A scrappy growth mindset you can copy (no perfect plan required): how momentum, feedback, and “green lights” can guide your next move.
- A healthier approach to scaling in real life by recognizing seasons—so you can build something meaningful without feeling like you’re failing at everything else.
Press play and borrow Megan’s mindset reset for imposter syndrome—so the next time you get the opportunity, you take the seat and don’t look back.
Imposter Syndrome, Opportunity, and Owning Your Seat
02:00 – Jim sets the stage for a non-linear entrepreneurial story, teeing up why real CEO paths rarely look clean or predictable.
07:00 – Megan shares how walking onto a D1 basketball program taught her an early, painful lesson about imposter syndrome and self-elimination.
11:00 – The moment Megan quit the team, and how imposter syndrome made her overlook the real value she brought as a teammate, not just a scorer.
16:00 – The reframe that changed everything. When you’re invited into the room, you belong there even if you don’t understand why yet.
21:00 – Megan explains how learning to stay seated at the table helped her later navigate intimidating business rooms without letting imposter syndrome win.
From Scrappy Beginnings to Scaled Growth
~27:00 – Turning dance classes at daycares into a profitable business by leaning into natural strengths instead of forcing a “serious” career path.
~33:00 – Why was there no formal business plan? How paying attention to momentum, customer feedback, and green lights mattered more.
~39:00 – The unexpected pivot to franchising after a major setback, and why curiosity (not confidence) fueled the next phase of growth.
~46:00 – Managing a fast-growing franchise while raising kids, and how recognizing seasons of life helps neutralize imposter syndrome around “doing it all.”
~55:00 – Exiting the business, redefining success, and choosing work that fits the next chapter. Even when it means letting go of the entrepreneur label.
About Megan Reilly
Megan Reilly started as an entrepreneur at age 19 and over the last two decades has built an international franchise, received multiple offers on Shark Tank, started a top 12 podcast, and ignited crowds all around the country as a keynote speaker.
Megan is the creator and host of one of the Top 12 Parenting Podcasts on Apple Podcasts, Who Is Your Momma Podcast, where she speaks to the mothers of some of the world’s most successful CEOs, athletes, and entertainers. Megan speaks to organizations all across the country, sharing the lessons she has learned from more than 20 years as a thriving entrepreneur.