What you wear isn’t just about how you look - it shapes how you show up.

This week, 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) that actually works for you.

Gab shares her path from corporate roles to launching her styling business full-time after burnout - and what it actually takes to build something on your own.

What we cover

• Why personal style is more than aesthetics - it impacts confidence, behavior, and performance
• How getting dressed can reduce decision fatigue and free up mental “RAM”
• On of the hardest parts of entrepreneurship: making decisions without a boss and building community
• What holds people back from making a career leap (money, stability, and identity shifts)
• How to think about scaling as a service-based founder
• What makes a great client (and how to find them)
• Real client transformations - from overwhelmed to confident and clear
• Redefining “the good life” as something you don’t need a vacation from

Gab’s approach to styling

Gab doesn’t believe in trends for the sake of trends. Her work is about helping clients build a wardrobe that actually works for their real life - saving time, energy, and mental load while making them feel like themselves.

Her services are designed as structured, high-impact styling experiences, typically including:

• Style discovery to define what actually feels like you
• Closet editing to refine what stays, goes, and needs to change
• Personal shopping to fill gaps with intention
• Outfit building + ongoing support so getting dressed becomes easy and repeatable

Timestamps

00:00 Welcome and recommendations

12:12 Intro to Gab Saper, Founder of Wardrobe Editor

16:11 From corporate to styling

28:55 What felt like blockers to taking styling full-time

30:45 Clothes shape behavior

35:48 Styling service breakdown

40:21 Scaling a solo business

43:37 Advice for new stylists

53:47 Glassy Insights

Links & Resources:

• Gab's Website: https://wardrobeeditor.com
• Gab's Instagram: https://www.instagram.com/wardrobeeditor
• Gab's Substack: https://wardrobeeditor.substack.com
• Gab's TikTok: https://www.tiktok.com/@wardrobeeditor
• Gab's Threads: https://www.threads.com/@wardrobeeditor
• Gab's Free Guide To Feeling Hot Again: https://wardrobeeditor.myflodesk.com/hotagain
• ⁠⁠⁠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 re-releasing one of our favorite conversations from season one: how to build a personal brand that actually opens doors.

We’re joined by Allie Fisher, independent creative director and former magazine art director, who breaks down what personal branding really means - and why it matters more than most people think for both job searching and leadership.

This episode is grounded and actionable. We cover how to define your “why,” translate it into how you show up, and make it visible through what you share - whether that’s on LinkedIn or in everyday conversations. We also get into the exact prompts and exercises you can use to clarify your story, your strengths, and your direction.

In this episode, we cover:

• Why personal branding isn’t optional if you want to grow your career
• How your values and audience shape your brand
• The “Why → How → What” framework and how to apply it
• How to audit what you’re already putting into the world (especially on LinkedIn)
• Simple prompts to clarify your story and communicate your work
• How to translate your experience when making a pivot
• Ways to get outside perspective when you feel stuck

Timestamps:
00:00 Welcome and recommendations
11:23 Allie Background and Career
13:19 Why Personal Brand Matters
19:29 Three Word Brand Exercise
22:40 How to Build Your Brand
28:10 Authentic Brand Foundations
35:21 Auditing Your Voice
38:35 Why–How–What Bullseye
46:40 Prompts To Find Your Why
50:06 Simple Storytelling Prompts
56:33 Glassy Insights

Links & Resources:

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

Courtney's Substack: substack.com/@courtneyattheglassadvisory

Allie Fisher's website: www.allie-fisher.com

Allie's Instagram: www.instagram.com/allie_fish

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!

In this episode of The Glass Sessions, we talk with Leah Zaccaria - former CPA turned community builder and founder of Shefa Yoga - to talk about what happens when the life you’ve built no longer feels like your own.

Leah shares her journey from corporate accounting to creating a community-centered yoga business, and the internal work that made that shift possible. What started as a realization that external markers of success weren’t fulfilling turned into a full re-evaluation of how she wanted to live, work, and show up.

This conversation is equal parts grounded and expansive - from knowing your numbers and managing cash flow, to building a business rooted in service and community.

What we cover:

• Transitioning from CPA to building a community-first business
• The moment success stopped feeling fulfilling
• How to find your intuition
• Letting go of external expectations and redefining success
• Building Shefa Yoga - including opening a studio in March 2020
• Why financial literacy still matters in purpose-driven work
• Creating belonging through community, not just offerings

Timestamps:

00:00 Catch up and Recommendations

13:38 Leah’s Story

32:46 Building Community Through Yoga

46:38 Money Mindset + Financial Clarity

56:29 Listening to Intuition

01:02:47 Glassy Insights

Links & Resources:

Leah's personal website: https://leahzaccaria.com

Shefayoga Venice: https://shefayogavenice.com

Leah's memoir, Seen: https://leahzaccaria.com/seen

⁠⁠⁠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.

Most people wait too long to ask this question.

They push through something that feels “off” ... until burnout hits or a layoff forces a decision they didn’t feel ready to make.

In this episode of The Glass Sessions, we walk through how to spot the early signals that it might be time for a change - and what to do about it before you’re in a reactive position.

At the center of the episode is a repeatable career audit - a tool you can use regularly to assess your current role and make more intentional decisions about what comes next.

You’ll learn how to evaluate your role across five key areas:

• Fulfillment and purpose
• Growth and learning
• Compensation and benefits
• Manager and team relationships
• Work-life alignment

If your work feels off but you can’t quite explain why - or you know something needs to change but don’t know where to start - this episode will give you a clear, practical way forward.

Timestamps:

00:00 Catch up and Recommendations

09:56 Episode Topic: Career Change

11:11 Common Reasons Work Feels Off

16:55 Career Audit Worksheet

24:51 Interpreting Scores and Dealbreakers

26:05 Negotiating and Creating Options

32:51 Wrap Up and Free Resources

Links & Resources:

The Glass Advisory's Free Resources to access the Career Audit Worksheet: https://www.theglassadvisory.com/free-resources-for-individuals

⁠⁠⁠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.

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