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You can “pick your own hours” and still feel like you never stop working. That tension kicks off a candid conversation with executive coach Michelle Davis about the real cost of solopreneur life, from the guilt of taking time off to the constant grind of marketing and business development. If you’ve ever wondered why freedom sometimes feels like pressure, you’ll recognize yourself here.
Michelle shares her career inflection point: moving from external coaching across multiple organizations to an internal role where she leads an internal coaching practice and builds programs that shape the whole system. We talk about what changed, the loneliness of working solo, and the pull toward team affiliation and shared mission. You’ll hear what internal coaching can actually look like day-to-day, including the “best of both worlds” mix of program design and direct coaching, plus the practical feedback loop of piloting, learning, and improving in real time.
We also get tactical about making a pivot: researching the field through ICF resources, talking to people doing the work, and holding a mindset that allows for uncertainty. Along the way we dig into executive coaching, leadership development, imposter syndrome, and the simple truth that confidence often comes after the reps, not before. If you’re weighing entrepreneurship vs corporate or considering an internal coaching program, this conversation gives you grounded questions to ask about risk tolerance, fit, and impact.
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More about Michelle: https://www.linkedin.com/in/michelle-bard-davis/
Connect with Beki on LinkedIn: Linkedin.com/in/BekiFraser
Learn more about her coaching: TheIntrovertedSkeptic.com
Follow Short Story Long's LinkedIn Page: Linkedin.com/showcase/shortstorylongpod
Get her book, C.O.A.C.H. Y.O.U.: The Introverted Skeptic’s Guide to Leadership - Amazon
Short Story Long is produced by Crowned Culture Media LLC
