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

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

Thanks for joining us for another episode of The Glass Sessions!

In this episode, we sit down with Peter Dolkas, interior designer and co-founder of Studio Dorion, for a wide-ranging conversation about risk, intuition, and building a career that evolves with you.

Peter shares his path from Palo Alto to boarding school, studying costume design at Carnegie Mellon, and eventually building a successful interior design studio in New York. Along the way, he reflects on the moments when he knew something wasn’t working, and how learning to listen to that signal led him to make bold changes.

This episode is a reminder that meaningful careers aren’t linear, and that paying attention to what feels off can be the first step toward something better.

What We Cover:

• Peter’s early life and creative education - and how it shaped his career
• Recognizing when it’s time to make a change
• Taking risks without a clear roadmap
• The realities of entrepreneurship
• Advice for anyone who feels stuck or restless right now

Timeline:

00:00 Welcome and weekly catch-up
12:32 Peter’s life journey and career transitions
29:14 Boundaries and mental health
36:38 Embracing failure and identity beyond work
39:56 The journey to entrepreneurship
43:56 Creating a positive work environment
46:44 Future goals and personal growth
50:03 Advice for those feeling stuck

Links & Resources:

Detailed Show Notes⁠⁠⁠:

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

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

Welcome back to another Glass Session!

In this episode we sit down for a reflective conversation about personal fulfillment, professional growth, and what it looks like to live a life rooted in abundance. We highlight Lauren's journey and explore how clarity and self-reflection shaped her career decisions, including why aligning work with the life she wants requires looking beyond titles, compensation, or external validation.

We talk about the role of supportive families and mentors, the importance of intuition (and how to tell it apart from anxiety), and how definitions of success and fulfillment evolve across different seasons of life.

We also discuss the realities of entrepreneurship - the tradeoffs, the freedom, and the responsibility of choosing your own path - and why abundance isn’t about having more, but about making intentional choices that support a meaningful, sustainable life. At the core of this conversation is a shared commitment to helping others find more joy, clarity, and stability in their professional lives through thoughtful, guided decision-making.

This episode is an honest look at how abundance shows up in real life: through intentional choices, shifting priorities, and a willingness to keep redefining what the good life means to Lauren.

Links & Resources:

Detailed Show Notes⁠⁠⁠:

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

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

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

Welcome to Season 2 of The Glass Sessions!

Season 2 of The Glass Sessions is about work, meaning, and the decisions people make to build a life that feels like their version of the Good Life.

This season, we’ll be introducing you to people who find a genuine sense of meaning in their work - and we’ll talk openly about how they got there. The tradeoffs they made. The risks they took. The moments they questioned themselves. And the choices that shaped where they are today.

We’re not delusional about what work actually looks like.

Even people who find deep meaning in what they do still have tough days. They navigate difficult relationships, conflict, burnout, and uncertainty. Most don’t wake up every morning full of joy and anticipation to go to work - and that’s a reality of modern work (and late-stage capitalism) that we’re not interested in glossing over.

What we are interested in is what’s possible.

We hope these stories serve as inspiration and, just as importantly, as real-world models for what it can look like to pursue meaningful work without pretending it’s perfect.

When we’re not talking to guests, we’ll dig into topics connected to pursuing and defining the good life for yourself - from schools of thought that explore meaning and fulfillment, to practical strategies people have used to create more alignment, agency, and satisfaction in their work.

We’re starting the season next week with Courtney’s story.

We can’t wait to go on this journey with you.