Thanks for tuning into this week's Glass Session!

In this solo episode, we explore what it really means to explore your inner "why" and how to uncover your deeper motivations, values and passions.

Grab a pen and paper for this one - we offer prompts for personal reflection.

We talk about:

• The reflection questions we use in career coaching to uncover patterns
• What your spare time, daydreams, and natural strengths reveal
• The difference between resume wins and eulogy values
• Turning standout moments into future direction
• Why synthesizing your answers (often with outside support) is key

We reference examples from past guests like Erin, Peter, and Austin & Matt, pulling out the through-lines that connect joy, resilience, risk tolerance, and values-based decision-making.

If you’ve been successful on paper but feel disconnected underneath - this episode will give you a practical way back to yourself.

Timestamps:

00:00 Catch up and recommendations

12:47 Intro to Finding Your Inner "Why"

16:24 Why we lose sight of our "Why"

31:33 Defining personal wins

43:39 Daydreaming with purpose

47:38 If you couldn't fail

Links & Resources:

Courtney's Substack: substack.com/@courtneyattheglassadvisory

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

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

Welcome back to The Glass Sessions!

In this episode, Austin Croteau joins us from Greece to share how she and her husband Matt sold their house, left traditional careers, and began traveling the world with their four young boys - all in pursuit of a life that felt more aligned.

“This defined American Dream just wasn’t what we wanted anymore.”

We talk about:

• Selling everything and joining Boundless Life in Greece
• Navigating judgment from family and friends
• Paying off debt, living off savings, and rethinking 401k tradeoffs
• How relationships and community opened unexpected career doors
• Raising kids without a traditional blueprint
• Risk tolerance (“we’re not bankrupt yet”) and redefining wealth

Austin shares how meeting other traveling families helped them build community, how Matt ultimately secured a remote role through a connection made abroad, and why “saying yes and talking to everybody” continues to shape their path.

If you’ve ever questioned the default path - this conversation will resonate.

Timestamps:

00:00 Welcome and weekly catch-up

13:08 Meet Austin

27:28 Selling Everything & Moving to Greece

41:25 Rethinking Wealth & the American Dream

47:04 Raising Great Humans

Links & Resources:

Austin's Instagram: @thewingingitfamily

Austin's Resources For Traveling Families: https://stan.store/digitalnomadfamilyworld?utm_source=ig&utm_medium=social&utm_content=link_in_bio

Detailed Show Notes⁠⁠⁠:

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

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

Welcome to another Glass Session!

This week, we have friend of the podcast, Erin Sears. She's a military wife, mother of two, and real estate agent whose career has evolved alongside some of life’s biggest transitions.

Erin shares her journey from being an elite runner growing up to attending Columbia University, where she studied and eventually built a career in marketing, advertising, and magazine writing. Her path shifted when she met her husband just before his deployment, stepping into military life and moving overseas to Germany, where she raised her daughters largely on her own while her husband was deployed during COVID.

Through it all, Erin reflects on the power of intuition, resilience, and community. She opens up about what it meant to receive help when she needed it most, and how that experience shaped her desire to give back. After returning to the U.S., Erin earned her real estate license and built a career rooted in service, gratitude, and a deep respect for the communities that have supported her family.

In this episode, we cover:

• Erin’s early identity as an elite runner and how it shaped her drive
• Transitioning from writing and advertising into military life
• Navigating deployment, motherhood, and isolation during COVID
• The strength and complexity of military spouse communities
• Making bold career shifts
• Choosing work that aligns with your values and sense of purpose
• Practicing gratitude and giving back to the communities that carried you

Timestamps:

00:00 Welcome and weekly catch-up

15:47 Guest introduction: Erin Sears

18:28 Erin’s life story and career journey

31:37 Receiving help and giving back

39:00 Support systems and healthy conflict

48:56 Choosing military life

59:09 Practicing gratitude and building community

Links & Resources:

Detailed Show Notes⁠⁠⁠:

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

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