Leaving Your Job to Be Your Own Boss

Escape and Empower Podcast with David Greenberg and Peter Gilfillan

Leaving Your Job to Be Your Own Boss

In this episode, Pete and Dave break down the real meaning of the “entrepreneurial lifestyle”—not the Instagram version, but the version built through hard work, structure, and ownership. After decades in corporate, they share how business ownership gave them back their time, their health, and their purpose.

They explore how the franchise model helps you bypass the chaos of starting from scratch and instead build a life where you decide what matters—whether it’s Friday freedom, weekday flexibility, or long-term wealth creation.

In this episode, Dave and Pete discuss:

Life Before Freedom: The Reality of Corporate Constraints
Dave shares what life looked like at the peak of his corporate career—constant travel, 7 a.m. meetings, and the pressure that never left. Pete adds how little control they had: no say in location changes, limited personal time, and energy drained by politics and pointless meetings.

Freedom Redefined: What Happens When You’re the Boss
Both hosts explain how being in control of your schedule changes everything. From running errands on Monday to early Friday finishes, they describe the tangible ways business ownership returns time to your life.

Flexibility Isn’t a Perk—It’s the Point
Whether it’s attending a kid’s soccer game or skipping Monday morning dread, Pete and Dave explain how entrepreneurship creates space for life, not just work. It’s not about working less, but about working when and how you want.

Wealth, Reimagined: Why Financial Independence Isn’t Just About Money
They define real wealth as time freedom, strong health, and the ability to choose your future. Pete shares how entrepreneurship let him reinvest in his well-being and plan for a semi-retired future—on his terms.

Designing a Business Around You
Not all owners are the same. Pete and Dave break down different paths: whether you want to work in the business every day or manage from the top, franchising lets you choose how involved you want to be—and that choice is the ultimate luxury.

Key Takeaways:

• The 9-to-5 trap takes more than your time—it can cost your health and purpose
• Owning your business puts you back in charge of your calendar
• A franchise model gives you structure so you can grow with confidence
• Flexibility means being present for life’s best moments—without asking permission
• Wealth is about more than money—it’s about time, health, and control

“I still work as hard as I did in the corporate world—but now, it’s on my terms. That’s the real power of entrepreneurship.” — Pete Gilfillan

CONNECT WITH PETER GILFILLAN

Meet with Pete: https://www.hireyourself.com/gilfillan/
Website: https://www.hireyourself.com/
LinkedIn: https://www.linkedin.com/in/petegilfillan/

CONNECT WITH DAVID GREENBERG

Meet with Dave: https://calendly.com/empoweredfranchisee/virtual-coffee-with-dave-the-empowered-franchiee-web
Website: https://empoweredfranchisee.com/
LinkedIn: https://www.linkedin.com/in/dave-greenberg-entrepreneur/