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.

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.

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."

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.

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.

In this episode of The Glass Sessions, we sit down with Leah Zaccaria, former corporate CPA turned community builder, entrepreneur, and founder of Shefayoga, to talk about what happens when the professional path you've carefully designed no longer fits who you are. Leah shares her journey of spending 15 years in corporate accounting with a Masters in Taxation before undergoing a profound personal transformation that led her to walk away from corporate stability to open her own business.

In this episode, we’re joined by returning guest Joe Gilgoff, founder of CX Joe. After years of leading customer experience for high-growth brands like Daily Harvest, AG1, and SeatGeek, Joe decided to step away from the traditional corporate climb to build an advisory business on his own terms.

In this episode, we sit down with Garri Rivkin, founder of The City Tutors. Garri’s journey from a refugee arriving in the U.S. to the head of a major educational non-profit is a masterclass in resourcefulness and stewardship. We discuss how his personal history informed his mission to provide professional access to students and alumni who are often overlooked, and why building "social capital" is just as important as building a resume.

In this episode of The Glass Sessions, we sit down with Peter Dolkas, Co-Founder of Studio Dorion. Peter shares his journey from a successful career in the fashion industry to launching his own interior design firm. We discuss the realities of starting over, the importance of transferable skills, and how to build the confidence to make a "bold" move when the path forward isn't perfectly paved.

In this episode, we sit down with Co-Founder of The Glass Advisory, Lauren, to walk through her journey of professional growth and personal discovery. We explore how she moved past the external markers of success, like titles and compensation, to find a path that felt sustainable and true to her own intuition. It’s a reflective conversation on what happens when you stop looking for validation from the outside and start building a life from the inside out.

For many professionals, balancing a full-time career with a passionate side hustle is the new normal. But juggling multiple ventures is a constant challenge, and navigating the waters of time, energy, and communication can easily lead to burnout. If you're dreaming about launching a side hustle or are already trying to keep a few plates spinning, we share lessons we’ve learned from building and maintaining multiple side hustles while working demanding full-time jobs.