Why Does Imposter Syndrome Hold You Back From Success?

Dec 22, 2025

Megan Reilly, a successful entrepreneur and Shark Tank alumna, shares her journey of overcoming imposter syndrome. She recounts her experience as a D1 basketball walk-on, illustrating how self-doubt led her to quit prematurely. Megan discusses shifting from a side gig to a thriving franchise, emphasizing the importance of momentum over rigid planning. She highlights life’s seasonal challenges in balancing business and family. Packed with mindset tips, her insights inspire listeners to claim their seat at the table and embrace their value.

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ANECDOTE

Walked On Then Walked Away

Megan Reilly walked on to a D1 basketball team, was the only walk-on retained, but quit because she felt she didn't belong.
She later realized she missed a huge opportunity and now refuses to self-eliminate from rooms she earned.

ADVICE

Stay In The Room And Own It

When you sit at a table where you feel outmatched, shut up, sit down, and take the opportunity.
Own whatever value you bring instead of exiting because you feel 'not enough'.

ANECDOTE

From Side Gig To Proven Product

Megan and her sister started teaching dance to daycares as a college side gig and gradually turned it into a profitable business.
They leaned into what was easy, got repeated customer 'green lights', and scaled without a formal plan.

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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.

Check out:

10:00 – The imposter syndrome turning point Megan tells the D1 basketball walk-on story and the moment she quit—then reframes it into her core lesson: why imposter syndrome makes you walk away from rooms you've already earned entry into.
25:00 – From "side gig" to real business The shift from teaching dance as a flexible college job to realizing, "Wait, this actually works," and how trusting momentum (not a formal plan) led to massive growth.
50:00 – Scaling, seasons, and not doing it all at once A candid conversation about building a 70-location franchise while raising kids—and why recognizing life seasons is critical to sustainable leadership and sanity.

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.