Welcome to the official season two opening episode of The Glass Sessions!

In this episode, we get personal with Courtney. You'll hear how how experience as an entrepreneur contributes to her definition of the “good life” - what she expected going in, what’s been harder than anticipated, and what’s surprised her most along the way. Together, we unpack the trade-offs that come with building something of your own, including freedom, flexibility, uncertainty, and responsibility, and why none of it fits into a neat highlight reel.

We reflect on how childhood experiences, early jobs, and past career chapters shaped their relationship to work, ambition, and success. The conversation blends honest storytelling with practical perspective, offering listeners space to examine their own values, priorities, and assumptions about what meaningful work actually looks like.

This episode sets the tone for Season Two: real stories and thoughtful conversations about building a life that feels good to you - not just one that looks good on paper.

In this episode, we cover:

• What entrepreneurship gives you - and what it asks of you
• How early experiences shape our definition of success
• The role of freedom and flexibility (and their limits)
• Why values matter more than titles or timelines
• The importance of relationships in building a good life
• Questions worth asking as you think about your own next chapter

Whether you’re an entrepreneur, considering a pivot, or simply rethinking your relationship with work, this conversation invites reflection - without pushing a single “right” answer.

Links & Resources:

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast/break-free-from-imposter-syndrome

⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com