Courtney’s Good Life as an Entrepreneur

Written By Courtney Hartman

To kick off Season Two: Finding The Good Life, we dive into the personal story behind The Glass Advisory and go deep with Courtney about her journey into entrepreneurship. This is a conversation about what it actually feels like to build something from the ground up - the quiet pressures, the unexpected hurdles, and the honest search for what it means to live "the good life."

The Invisible Scripts We Carry

The journey didn't start the day the business was incorporated; it started much earlier. Courtney opens up about how our childhood roles - whether you were the "high achiever," the "reliable eldest," or the "kind one" - create the scripts we follow in our professional lives. For Courtney, the drive that made her successful in her early career also brought a heavy internal pressure to "know it all."

We talk about the transition from the structure of a corporate role to the wide-open space of entrepreneurship. It’s a shift from executing someone else’s vision to carrying the full weight of every decision yourself. We explore the reality that while entrepreneurship offers agency, it also requires a new kind of resilience to sit with the uncertainty of being the one who makes the final call.

Defining the "Good Life"

We learn about what the Good Life means to Courtney, and how flexibility, freedom and the ability to control and continually redefine success are at the core of it.

  • Moving Beyond the Highlights: We discuss how the most rewarding moments aren’t always the big wins, but the messy process of building a life that finally feels like yours.

  • The Beginner’s Mindset: As we get more senior, we often stop giving ourselves permission to be beginners. Courtney shares how reclaiming that "newness,” and the discomfort that comes with it is where the most significant growth happens.

  • Success vs. Significance: We reflect on the importance of values as a compass. When you’re no longer chasing a title or a specific ladder, you have to ask yourself: What actually gives me energy? What kind of impact do I want to have when no one is watching?

Actionable Tips & Takeaways

While the "good life" looks different for everyone, Courtney’s story offers several ways to start auditing your own path:

  • Audit your childhood "script": Take a moment to reflect on the role you played growing up (e.g., the high achiever, the caretaker). Ask yourself: Is this role still serving my career, or is it creating unnecessary pressure?

  • Embrace the "beginner" discomfort: If you are starting something new - a business, a role, or a project - don't fight the feeling of being a beginner. Remind yourself that growth is naturally uncomfortable and that you don't need to have all the answers on day one.

  • Prioritize agency over logistics: When evaluating a career move, look beyond the salary or the hours. Ask: Does this role give me more agency over my work and life? Does it allow me to act in alignment with my core values?

  • Build a "worth" support system: Surround yourself with people who value you for who you are, not just your professional output. This is the ultimate buffer against the loneliness and self-doubt that can come with high-pressure roles.

Tips For Managers

Leadership isn't about having all the answers; it’s about the courage to be seen while you’re still figuring it out.

  • Normalize the transition: When you’re honest with your team about your own career pivots and the pressures you feel, you give them permission to be human, too.

  • Model growth over perfection: By showing that growth is a lifelong, often uncomfortable process, you create a culture where people feel safe to take their own risks and find their own version of alignment.

  • Connect work to values: Help your team members identify what "the good life" looks like for them and look for ways to align their current responsibilities with those personal drivers.

Links & Resources:

Courtney Hartman
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Putting Your Performance Review Into Action (Part 2)