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

In this re-release episode, we re-revisit a favorite conversation from season one with Andy Regal, workplace bullying advocate and longtime media executive.

Andy shares how writing his memoir during COVID led him to study workplace incivility and bullying, including conversations with global experts and research from the Workplace Bullying Institute. He breaks down what bullying actually is (and isn’t), why it’s so often overlooked or mishandled, and how power dynamics play a central role in allowing it to persist.

The conversation explores how to recognize the difference between tough feedback and harmful behavior, why reporting often falls short, and what it looks like to protect yourself in environments that aren’t set up to do so.

Andy also shares practical approaches to coping and healing - from restoring psychological and physical safety to finding support, rebuilding confidence, and knowing when it’s time to plan an exit.

In this episode, we cover:

• What workplace bullying actually is (and how to spot it)
• Why power dynamics make bullying hard to address
• The limits of escalation and HR
• How to differentiate between hard moments and harmful patterns
• Approaches to healing and rebuilding after toxic experiences
• When and how to plan an exit

Timestamps:

00:00 Intro and Recommendations

13:26 Meet Andy Regal

14:27 Writing the Book

17:22 What Bullying Is

25:41 Bullying Culture Dynamics

33:59 Unreasonable Boss Red Flags

38:02 Allies and Culture Fixes

42:02 Six Tenets of Healing

46:18 When to Plan an Exit

49:04 Resources and Movement

51:13 Glassy Insights

Links & Resources:

Andy’s personal website: https://andyregal.com/

Navigating Workplace Bullying Facebook Group: https://www.facebook.com/groups/noworkbullies

Andy’s Substack: https://substack.com/@aregalmedia?utm_source=top-search

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

Courtney's Substack: substack.com/@courtneyattheglassadvisory

If you’re enjoying The Glass Sessions, make sure to follow/subscribe and share with someone who’s figuring out their own version of the good life.

Welcome back to The Glass Sessions.

This week, we’re joined by returning guest Joe Gilgoff, founder of CX Joe, who’s building an advisory business on his own terms after years leading customer experience at brands like Daily Harvest, AG1, and SeatGeek.

We get into:

• How early service jobs (shoutout Dunkin’) shaped his obsession with customer happiness
• Getting fired, and using it as the catalyst to build something of his own
• What CX Joe actually is (and how he’s monetizing it)
• Why he turned down a fractional role to stay aligned with his vision
• The pressure of early decisions and how that stress evolves over time
• How he filters advice (and decides what to ignore)
• His “networking hustle” playbook: LinkedIn, dinners, outreach, and showing up consistently
• Why he started his podcast, In the Business of Humans
• The balance between human connection and AI in customer experience
• What freedom and the “good life” look like in this season of his life

Joe is honest about the uncertainty, the momentum, and the discipline it takes to build something from scratch, while still designing a life that actually feels good.

Timestamps:

00:00 Intro and Recommendations

12:11 Joe’s Life Story Segment

23:31 Getting Fired and Reset

33:09 CX Joe Business Model

40:00 Defining Ideal Clients

42:27 Filtering Advice Practically

49:20 Networking Hustle Playbook

56:13 Why Start a Podcast

01:04:09 What Good Life Means

01:06:49 Where to Find Joe

01:07:44 Glassy Insights Takeaways

Links & Resources:

CX Joe's website: https://www.cxjoe.com/

Follow Joe Gilgoff on LinkedIn: https://www.linkedin.com/in/cxjoe/

Listen to In the Business of Humans: https://open.spotify.com/show/1iN4lTZnChMClWdaZWvSgs

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

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

Courtney's Substack: substack.com/@courtneyattheglassadvisory

If you’re enjoying The Glass Sessions, make sure to follow/subscribe and share with someone who’s figuring out their own version of the good life.

Advice is everywhere.

Friends share what worked for them. Managers guide based on company needs. Family weighs in from a place of security - or fear.

But advice isn’t neutral. It reflects someone else’s experiences, incentives, and worldview.

In this episode, we break down how to tell the difference between advice that helps - and advice that pulls you off your path.

We cover:

• Who’s actually worth listening to (and what to look for beyond success)
• Why “do what I did” is often a red flag
• How to spot hidden incentives from employers, family, and others
• The role of people-pleasing in bad decision-making
• The difference between someone giving answers vs. helping you think

At the core: the best advisors don’t tell you what to do. They help you get to your own answer.

Mastering this skill helps you:

• Make fewer reactive decisions
• Navigate career pivots more confidently
• Build stronger judgment

Timestamps:

00:00 Intro and Recommendations

10:02 Episode Topic: Taking Advice

14:18 Advice vs Comfort Boundaries

16:51 Family Advice and Biases

21:38 Bias in Career Advice

25:25 Connector Mentors

27:48 Trust and Challenge Balance

31:12 Red Flags in Advice

36:59 People Pleasing Pitfalls

38:28 The Neutrality of Coaching

Links & Resources:

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

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

Courtney's Substack: substack.com/@courtneyattheglassadvisory

Welcome back to The Glass Sessions!

This week, we’re joined by Garri Rivkin, Founder and Executive Director of City Tutors , an organization that has helped more than 8,000 learners access tutoring, mentorship, and career guidance in New York City.

Garri shares his journey from arriving in Queens as a Jewish refugee from Lithuania in 1996, learning English while working at a young age, and finding support through teachers, mentors, and the CUNY system that helped shape his path.

That experience ultimately inspired him to build the kind of support network he once needed. What began in 2013 as a tutoring program at City College later expanded through the Colin Powell School, became an independent 501(c)(3) in 2020, and during the pandemic evolved into a broader mentoring initiative connecting learners with professionals around the world.

We talk about:

• Growing up as a refugee and navigating a new culture
• The mentors and teachers who opened doors
• Starting City Tutors as a small campus project
• Expanding the program during the pandemic
• Why access to information and mentorship changes lives

We close with a new segment, Glassy Insights, summing up some key takeaways from Garri.

If you care about education, mentorship, or creating opportunities for the next generation, this conversation will inspire you.

Timestamps

00:00 Intro and Recommendations
09:35 Meet City Tutors
12:02 Garri's Origin Story
25:53 Finding Purpose In Service
29:22 Finding Home at CUNY
33:31 City Tutors Origin Story
36:32 Pandemic Pivot to Mentors
42:44 Impact Stories and Belonging
47:08 Writing and Identity
51:54 Garri's Good Life
53:05 How to Get Involved
54:45 Glassy Insights Wrap-Up

Links & Resources:

The City Tutors: https://www.thecitytutors.org

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

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

Courtney's Substack: substack.com/@courtneyattheglassadvisory

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