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.

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 coworkers
• Boundaries and expectations
• Feedback, promotions, and performance
• Office norms that feel…questionable

We break each scenario down by:

• What may be happening beneath the surface
• What’s reasonable vs. what’s normalized
• How to think through your options
• Practical ways to respond or move forward

You’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

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 leaders
• The common reactions that keep people stuck
• Practical tools to interrupt the cycle of self-doubt

We 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

In this re-release episode, we revisit one of our favorite conversations on networking, with friend and former colleague Joe Gilgoff, CX Advisor to Elite Brands.

With the holiday season and new year in full swing, this episode is a timely reminder that networking doesn’t have to feel transactional, awkward, or performative. Joe shares practical, grounded advice on how to build relationships authentically - whether you’re attending holiday parties, navigating career transitions, or simply trying to expand your professional circle with intention.

Together, we unpack:

• Why most people overthink networking (and how to stop)

• How to manage social anxiety in professional settings

• What actually makes someone memorable

• The role curiosity, generosity, and follow-through play in long-term career growth

If networking has ever felt uncomfortable or unclear, this conversation offers a refreshing, human-first approach.

Timestamps:

00:00 - Side chat and what we've learned

14:10 - Networking conversation with Joe

53:33 - Is this okay? How to handle a request for a job referral from someone you don't know and haven't worked with

Links & Resources:

⁠⁠⁠Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠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

Thanks for joining us for part 2 of Putting Your Performance Review Into Action!

In this episode, we build on last week’s conversation by focusing on what comes after you’ve done the reflection work for your performance review - how to actually use it to move your career forward.

We weave together end-of-year reflections, personal stories, and practical guidance on making your growth visible. From updating your LinkedIn profile to sharing your wins more publicly, this episode is all about turning insight into momentum.

In this episode, we cover:

• How to make the work you did for your performance review visible
• Practical ways to update your LinkedIn to reflect your growth
• Why reflection is most powerful when it leads to action
• Lessons learned from a challenging year - and how to apply the learnings moving into next year

This is a thoughtful, actionable listen for anyone heading into the new year wanting to be more intentional about how they show up professionally.

Timestamps:

00:00 - Sidechat and what we've learned

12:38 - Putting your performance review into action discussion

38:22 - Is this okay? A colleague continues to pronounce my name incorrectly and I'm at the point that I want to report him to HR. Am I blowing this out of proportion?

Links & Resources:

⁠⁠⁠Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠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

Welcome back to The Glass Sessions!

In this episode we break down how to turn your performance review into meaningful, achievable progress for the year ahead.

This episode is your step-by-step guide to moving from feedback → clarity → action.

You’ll learn how to:

• Translate review themes into concrete, measurable goals
• Use AI tools to get clearer on strengths, gaps, and blind spots
• Align your goals with your manager’s priorities (and why this matters more than most people realize)
• Identify skill gaps and build a plan for strengthening them
• Create simple systems for tracking wins and momentum throughout the year
• Proactively get support from mentors, peers, and your broader network
• Recalibrate goals as the business shifts — without losing momentum

This is Part 1 of a two-part series designed to help you take ownership of your growth, deepen your self-awareness, and walk into the new year with a clear, grounded plan.

Timestamps:

00:00 - Sidechat and what we've learned

9:03 - Putting your performance review into action discussion

30:23 - Is this okay? A manager from another team asked me for feedback about their direct report but I don't want to get them in trouble.

Links & Resources:

⁠⁠⁠Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠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

Thanks for joining us for another Glass Session!

This week we chat with Nik Kinley, London-based leadership consultant, psychologist, and author of The Power Trap, to explore one of the most important (and misunderstood) topics in leadership: how power actually changes people.

Nik breaks down the six psychological and behavioral shifts that happen as people gain authority, including decreased empathy, increased goal-focus, and the amplification of whatever internal states a leader already brings to the table. We unpack why these changes occur, why they’re often invisible to the leader themselves, and how even well-intentioned people can fall into the “power trap.”

We discuss what leaders can do about it:

• Reducing distance between themselves and their teams
• Creating open channels for information and criticism
• Building habits that keep ego in check
• Staying grounded during rapid career growth

Whether you’re already in a leadership role or preparing for one, this conversation offers a practical roadmap for managing the effects of power.

Timestamps:

00:00 - Sidechat and what we've learned

11:37 - Conversation with Nik Kinley about power

48:05 - Is this okay? I don't know if my manager has given me credit for work we co-created with senior leadership.

Links & Resources:

Nik Kinley's website: https://nikkinley.com

Nik Kinley's Substack: https://substack.com/@nikkinley

Nik Kinley's LinkedIn: https://www.linkedin.com/in/nikkinley/

⁠⁠⁠Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠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