The Glass Sessions

The Glass Advisory
  • 5.0 (15)
  • CAREERS
  • UPDATED WEEKLY

The Glass Sessions is a light-hearted business podcast hosted by best friends Courtney and Lauren. After meeting in 2012 at their first jobs, they've grown into seasoned leaders and co-founders of The Glass Advisory, helping businesses scale their operations and guiding individuals in shaping meaningful, sustainable careers. Each episode offers honest takes, real stories, and practical insights on leadership, career growth, burnout, and reinvention. It’s the advice you didn’t know you needed from the friends you wish you had at work .

  1. 6D AGO

    Austin Croteau: Raising Four Kids Abroad and She's Not Bankrupt Yet

    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 GreeceNavigating judgment from family and friendsPaying off debt, living off savings, and rethinking 401k tradeoffsHow relationships and community opened unexpected career doorsRaising kids without a traditional blueprintRisk tolerance (“we’re not bankrupt yet”) and redefining wealthAustin 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

    1h 5m

  2. FEB 10

    Erin Sears on Life as a Military Family and Keeping Her Pace

    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 driveTransitioning from writing and advertising into military lifeNavigating deployment, motherhood, and isolation during COVIDThe strength and complexity of military spouse communitiesMaking bold career shifts Choosing work that aligns with your values and sense of purposePracticing 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

    1h 6m

  3. FEB 4

    Peter Dolkas on Making Bold Career Decisions

    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 careerRecognizing when it’s time to make a changeTaking risks without a clear roadmapThe realities of entrepreneurshipAdvice for anyone who feels stuck or restless right nowTimeline: 00:00 Welcome and weekly catch-up12:32 Peter’s life journey and career transitions29:14 Boundaries and mental health36:38 Embracing failure and identity beyond work39:56 The journey to entrepreneurship43:56 Creating a positive work environment46:44 Future goals and personal growth50:03 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

    54 min

  4. JAN 28

    Lauren's Life in Abundance

    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

    43 min

  5. JAN 21

    Courtney's Good Life as an Entrepreneur

    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 youHow early experiences shape our definition of successThe role of freedom and flexibility (and their limits)Why values matter more than titles or timelinesThe importance of relationships in building a good lifeQuestions 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

    40 min

  6. JAN 14

    The Glass Sessions Season 2: Finding the Good Life

    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.

    8 min

  7. JAN 7

    "Is This Okay?" Compilation

    Welcome back to another episode of The Glass Sessions! In this special compilation episode we are revisiting some of our favorite “Is This Okay?” questions from the past year. What is the “Is This Okay?” segment? “Is This Okay?” is a recurring segment on The Glass Sessions where listeners submit real, anonymized situations they’re dealing with at work. They’re often gray-area moments - not clearly right or wrong - involving: Managers and coworkersBoundaries and expectationsFeedback, promotions, and performanceOffice norms that feel…questionableWe break each scenario down by: What may be happening beneath the surfaceWhat’s reasonable vs. what’s normalizedHow to think through your optionsPractical ways to respond or move forwardYou’ll likely hear a scenario (or two) that sounds…very familiar. Links & Resources: ⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

    45 min

  8. 12/31/2025

    Re-Release: Break Free From Imposter Syndrome

    In this re-release episode of The Glass Sessions, we revisit one of our most resonant conversations in the archive - all about imposter syndrome and how it actually shows up at work. We dive deep into imposter syndrome: What it is (and what it definitely isn’t)How it shows up differently for managers and leadersThe common reactions that keep people stuckPractical tools to interrupt the cycle of self-doubtWe share personal experiences navigating imposter syndrome, especially in moments of visibility, growth, and leadership. We explore the role of both internal and external validation, the importance of psychological safety, and why proactive communication can be one of the most effective antidotes to feeling like you don’t belong. This episode is a reminder that imposter syndrome isn’t a personal flaw - it’s often a signal that you’re stretching, growing, and stepping into something new. Timestamps: 00:00 - Side chat and what we've learned 12:30 - Imposter syndrome discussion 45:54 - Is this okay? My team has been asked to volunteer to lead webinars but I don't want to. Is it okay to not raise my hand? Links & Resources: O*Net⁠⁠⁠: Career and Industries database discussed in episode: https://www.onetonline.org Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast/break-free-from-imposter-syndrome ⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

    51 min
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5
out of 5
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About

The Glass Sessions is a light-hearted business podcast hosted by best friends Courtney and Lauren. After meeting in 2012 at their first jobs, they've grown into seasoned leaders and co-founders of The Glass Advisory, helping businesses scale their operations and guiding individuals in shaping meaningful, sustainable careers. Each episode offers honest takes, real stories, and practical insights on leadership, career growth, burnout, and reinvention. It’s the advice you didn’t know you needed from the friends you wish you had at work .

Information

  • Creator
    The Glass Advisory
  • Years Active
    2025 - 2026
  • Episodes
    42
  • Rating
    Clean
  • Copyright
    © The Glass Advisory
  • Show Website
    The Glass Sessions