From Self Employed To Real Entrepreneur, with Jessica Christy
Wed Feb 04 2026
Many entrepreneurs are technically “in business” but still trapped working for a relentless, 24/7 boss: themselves. In this episode, Dan Sullivan and Jessica Christy unpack what it takes to build a true entrepreneurial company instead. Hear how a painful team exodus became Jessica’s biggest growth catalyst and how clear core values, better leadership, and greater control over your life create a company you never want to retire from.
Here’s some of what you’ll learn in this episode:
Jessica’s original “entrepreneurial moment” while she was still working for someone else.How her medical aesthetics company, Beauty Culture, helps clients far beyond surface-level appearance.What makes her company stand out in a crowded, diluted industry.How to build the confidence to step into big, scary opportunities.What Jessica has gained since joining Strategic Coach®.
Show Notes:
Most entrepreneurs aren’t running true companies yet; they’ve simply created a demanding job where they work for themselves.
When you’re self‑employed, your “boss” follows you everywhere—24 hours a day, 365 days a year—and is often tougher than any previous employer.
Being your own boss doesn’t automatically make you a good boss, especially for your team or for your future self.
The Four Freedoms at the heart of entrepreneurial motivation are freedom of time, money, relationship, and purpose, and true entrepreneurial companies are built to expand all four.
If you’ve designed a life and business you truly love, the desire to retire largely disappears because work is an expression of your purpose.
When entrepreneurs get together, the most valuable conversations are about how they transformed failures and crises into breakthroughs, not just about their wins.
The more you learn as an entrepreneur, the more aware you become of how much you don’t know, which keeps you curious, humble, and growth oriented.
People rarely leave “bad jobs” so much as they leave a lack of leadership; team members crave clear vision, accountability, and support from their boss.
Strong core values act as the navigating compass for your entire company, guiding who you hire, fire, promote, and partner with.
Resources:
The 4 Freedoms That Motivate Successful Entrepreneurs
The E-Myth Revisited by Michael E. Gerber
Unique Ability®
More
Many entrepreneurs are technically “in business” but still trapped working for a relentless, 24/7 boss: themselves. In this episode, Dan Sullivan and Jessica Christy unpack what it takes to build a true entrepreneurial company instead. Hear how a painful team exodus became Jessica’s biggest growth catalyst and how clear core values, better leadership, and greater control over your life create a company you never want to retire from. Here’s some of what you’ll learn in this episode: Jessica’s original “entrepreneurial moment” while she was still working for someone else.How her medical aesthetics company, Beauty Culture, helps clients far beyond surface-level appearance.What makes her company stand out in a crowded, diluted industry.How to build the confidence to step into big, scary opportunities.What Jessica has gained since joining Strategic Coach®. Show Notes: Most entrepreneurs aren’t running true companies yet; they’ve simply created a demanding job where they work for themselves. When you’re self‑employed, your “boss” follows you everywhere—24 hours a day, 365 days a year—and is often tougher than any previous employer. Being your own boss doesn’t automatically make you a good boss, especially for your team or for your future self. The Four Freedoms at the heart of entrepreneurial motivation are freedom of time, money, relationship, and purpose, and true entrepreneurial companies are built to expand all four. If you’ve designed a life and business you truly love, the desire to retire largely disappears because work is an expression of your purpose. When entrepreneurs get together, the most valuable conversations are about how they transformed failures and crises into breakthroughs, not just about their wins. The more you learn as an entrepreneur, the more aware you become of how much you don’t know, which keeps you curious, humble, and growth oriented. People rarely leave “bad jobs” so much as they leave a lack of leadership; team members crave clear vision, accountability, and support from their boss. Strong core values act as the navigating compass for your entire company, guiding who you hire, fire, promote, and partner with. Resources: The 4 Freedoms That Motivate Successful Entrepreneurs The E-Myth Revisited by Michael E. Gerber Unique Ability®