Welcome back to The Glass Sessions!

This week we’re joined by Jeff Carlson, Head of Education, Strategy, and Advocacy at Clever, whose career has been shaped by a deep commitment to education and the rural communities that raised him.

Jeff grew up in rural Idaho before heading east to attend Georgetown. After graduating, he joined Teach for America and moved to the Bronx to teach middle school, an experience that solidified his commitment to education equity. From there, Jeff spent time working in Washington, DC, including on Capitol Hill, while continuing to deepen his focus on education policy and access.

Over the years, his work has taken him from classrooms to federal policy to graduate programs focused on rural education. Today, Jeff has returned to Idaho with his husband, Ben, and their dogs, continuing to advocate for students and communities through his work at Clever and through local civic engagement.

In this conversation, Jeff reflects on how relationships and networks have shaped his career decisions, why rural identity still plays a defining role in his work, and how everyday people can meaningfully engage in their communities.

We also talk about Jeff’s volunteer work as a guardian ad litem, his involvement in state policy conversations around education and AI, and why maintaining optimism matters when you care deeply about the future.

Jeff’s definition of a good life?

Contributing more than you take, improving the world for the next generation, and allowing space for daily joy, weekly sorrow, and regular self-reflection.

If you’ve ever wondered how your career can connect to something bigger than yourself, this conversation will resonate.

Timestamps:

00:00 Catch up and recommendations

10:37 Intro to Jeff and his story

29:18 Career decisions and networking

35:47 Volunteering and public service

37:28 Getting involved locally

47:14 Everyday community activism

55:40 Defining the good life

Links & Resources:

Jeff Carlson's LinkedIn: https://www.linkedin.com/in/drjeffcarlson

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

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

Courtney's Substack: substack.com/@courtneyattheglassadvisory

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