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