The Glass Sessions Podcast
The Glass Sessions is a weekly podcast hosted by the two Principal Advisors of The Glass Advisory, Courtney and Lauren. The two met working their first “real” jobs in customer service in 2012 and have been navigating work and life side by side ever since.
At the heart of the show is a belief that guides their work: that work can be a powerful activator of a good life.
Each week, Courtney and Lauren explore how people build careers that support their version of a meaningful, joyful life. Sometimes that means conversations with guests who share the decisions, risks, relationships, and turning points that shaped their path. Other episodes are just the two of them reflecting on their own experiences advising leaders, navigating their careers, and building The Glass Advisory.
Along the way, they share practical ideas, questions, and tools listeners can use in their own lives and careers.
Expect thoughtful conversations, real stories, a few actionable takeaways, and plenty of laughter — all centered around one question: how do you build a career that supports the life you actually want to live?
New episodes are released weekly on Wednesdays. Subscribe on Apple, Spotify or anywhere you listen to podcasts.
Making AI Your Career Advantage With Stephanie Hills
In this episode of The Glass Sessions, we tackle one of the most prominent shifts impacting today's labor force: the rise of Artificial Intelligence (AI). We are joined by tech leader and AI integration expert Stephanie Hills to demystify what AI means for your day-to-day career.
Instead of letting anxiety drive you into "job hugging" or avoiding the topic altogether, we explore how to turn AI into your biggest professional differentiator. We unpack the most common fears holding professionals back, break down how to get over those mental blocks, and share highly practical, everyday ways you can use AI to work smarter, reclaim your time, and gain a massive advantage in your career.
From Outsider to CEO: Patty Azzarello’s Career Story
We had the opportunity to connect with leadership expert, former Silicon Valley executive, and founder of The Azzarello Group, Patty Azzarello. We dive deep into the insights from her memoir, Why Is SHE Still Here? My Ungraceful Journey From the Playground to the Boardroom.
Patty shares the deeply personal story behind her rise to executive leadership - from being bullied as a child and navigating corporate life as an introvert, to becoming the youngest General Manager in HP history.
Navigating The Meaningful Middle With Kelly Nash
Careers don’t always move in a clean, upward line, and hitting a mid-career plateau or transition point can feel deeply destabilizing. This week, we’re joined by Chicago-based Career Alignment Coach and Workforce Development Consultant, Kelly Nash, to talk about how to navigate these shifts and find clarity in what she calls "the meaningful middle."
How Jessica Noon Built Her Own Path in Work and Leadership
People and culture Consultant, Jessica Noon, founder of Daybreak Ideas joins us this week. Jessica works alongside founders and organizations to rethink culture transformation, org design, leadership strategy, and hiring.
In this episode, we dive into what consistent and humane leadership looks like in practice, especially as companies scale. Jessica shares a grounded perspective on building a career around the concept of “both, not either” - challenging the idea that you have to choose between ambition, fulfillment, stability, creativity, or personal priorities.
Finding Confidence Through Style With Wardrobe Editor Founder Gab Saper
We’re joined by Wardrobe Editor founder, Gab Saper, to talk about the real impact of personal style on confidence, decision-making, and building a life (and business) based around a life-long passion she never thought possible.
Gab shares her path from corporate roles to launching her styling business full-time after experiencing burnout. It’s an honest look at what it actually takes to build something on your own, the identity shifts that come with leaving a corporate title behind, and why finding your style is about so much more than aesthetics.
Making The Move to Freelancing Full-Time with Julia Halperin
Julia Halperin, acclaimed arts and culture journalist, joins Lauren and Courtney to talk about how she made the move to freelance after rising to leadership at prominent publications. If you’ve ever considered moving to self-employment, or starting your own business, we talk lots of practical tips and strategies you can employ to help.