The Glass Sessions

The Glass Advisory
  • 4.8 (17)
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  • Updated Weekly

The Glass Sessions is a weekly podcast hosted by the two Principal Advisors of The Glass Advisory, Courtney and Lauren. The two met working their first “real” jobs in customer service in 2012 and have been navigating work and life side by side ever since. At the heart of the show is a belief that guides their work: that work can be a powerful activator of a good life. Through guest conversations and episodes with just the two of them, they share stories, insights, and practical ideas to help listeners build careers that support their version of a meaningful, joyful life.

  1. 2d ago

    From Outsider to CEO: Patty Azzarello's Career Story

    Thanks for joining us for another Glass Session! In this episode, we sit down with leadership expert, former Silicon Valley executive, and founder of The Azzarello Group, Patty Azzarello, to discuss her new 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 life as an introvert to leading teams in some of the world's most competitive corporate environments. Along the way, she challenges conventional wisdom about confidence, networking, mentorship, and what it really takes to build a meaningful career. In This Episode: Why Patty wrote her memoirGrowing up bullied and finding her voiceThe surprising power of delegationLeadership without intimidationHow "secret passageways" open when you ask for helpPractical strategies for finding mentors and sponsorsWhy visibility matters Confidence as an outcome, not a starting pointResilience in the face of repeated setbacksAmplifying your voiceFinding meaning, energy, and purpose at workTimestamps: 00:00 Weekly Catch-up and Recommendations 11:04 Meet Patty Azzarello 18:47 Power Without Bullying 23:02 Secret Passageways Explained 30:08 Making Mentorship Feel Natural 35:36 Confidence Is an Outcome 54:11 Finding Meaning Through Leadership 55:14 Patty's Book and Where to Find Her 58:28 Glassy Insights Links & Resources: Patty's website: azzarellogroup.com Patty's Substack: pattyazzarello.substack.com Patty's LinkedIn: linkedin.com/in/pattyazzarello ⁠⁠⁠The Glass Advisory⁠⁠⁠: 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.

    1h 6m

  2. May 27

    Navigating The Meaningful Middle With Kelly Nash

    Welcome back to The Glass Sessions! This week, we sit down with Kelly Nash, a Chicago-based Career Alignment Coach and Workforce Development Consultant, for a conversation about career identity, reinvention, and what she calls “the meaningful middle.” Kelly shares her path from advertising to tech, spending 11 years at Salesforce, launching her blog Lipstick & Ink, and ultimately building a portfolio career rooted in helping people align their work with who they actually are. Together, we discuss: Why the “messy middle” may actually be the meaningful middleKelly’s framework for “career authorship”Identity loss during layoffs and career transitionsWhy relying only on your manager for validation can hold you backThe importance of self-promotion and visibilityHow AI and modern work environments are impacting human connectionWhat a portfolio career can look like in practiceBalancing planning with openness to unexpected opportunitiesThe difference between transactional and transformational coachingKelly also shares details about her upcoming June 3rd workshop: “Who Am I Without the Title?” - a collaborative conversation around layoffs, identity, and rebuilding confidence during career transitions. Details can be found on her website: www.kellynash.co/events Timestamps: 00:00 Weekly Catch-Up and Recommendations 11:52 Meet Career Coach Kelly Nash 17:48 The Meaningful Middle 20:57 Career Authorship Framework 29:03 Portfolio Career Explained 38:08 Transformational Coaching Depth 42:15 Layoff Workshop And Identity 49:33 Glassy Insights Links & Resources: Kelly's website: kellynash.co Kelly's LinkedIn: linkedin.com/in/kellymarienash Kelly's Instagram: instagram.com/kellynash_co ⁠⁠⁠The Glass Advisory⁠⁠⁠: 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.

    56 min

  3. May 13

    How Jessica Noon Built Her Own Path in Work and Leadership

    Thanks for joining us for another Glass Session! This week, we're joined by Jessica Noon, founder of Daybreak Ideas. Jessica works with founders and organizations on culture transformation, org design, leadership strategy, and hiring - helping businesses build workplaces where people can actually thrive. The conversation explores: Why consistent and humane leadership matters more than everCommon hiring mistakes founders make as they scaleHow to identify your “flow zone” at workPractical advice for creating opportunities instead of waiting for themHow to pitch yourself into roles that don’t exist yetNetworking strategies for introverts and relationship-buildersWhy authentic connection is one of the highest ROI career investments you can makeJessica also shares a powerful perspective on building a career and life around “both, not either” - challenging the idea that people have to choose between ambition, fulfillment, stability, creativity, flexibility, or personal priorities. Timestamps: 00:00 Welcome and Recommendations 10:01 Intro to Jessica Noon of Daybreak Ideas 14:56 What Daybreak Ideas Does 18:13 Common Founder Hiring Mistakes 31:51 Creating Your Own Career Opportunities 37:08 An Introvert-Friendly Networking Playbook 56:53 Glassy Insights Links & Resources: Jessica's Website, Daybreak Ideas: https://www.daybreakideas.com/ Jessica's LinkedIn: https://www.linkedin.com/in/jessicahnoon/ Jessica's Instagram: https://www.instagram.com/daybreak_jess/ The Founder Shift Podcast: https://thefoundershift.com ⁠⁠⁠The Glass Advisory⁠⁠⁠: 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.

    1h 2m

  4. Apr 29

    Finding Confidence Through Style With Wardrobe Editor Founder Gab Saper

    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 performanceHow 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 communityWhat holds people back from making a career leap (money, stability, and identity shifts)How to think about scaling as a service-based founderWhat makes a great client (and how to find them)Real client transformations - from overwhelmed to confident and clearRedefining “the good life” as something you don’t need a vacation fromGab’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 youCloset editing to refine what stays, goes, and needs to changePersonal shopping to fill gaps with intentionOutfit building + ongoing support so getting dressed becomes easy and repeatableTimestamps 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.comGab's Instagram: https://www.instagram.com/wardrobeeditorGab's Substack: https://wardrobeeditor.substack.comGab's TikTok: https://www.tiktok.com/@wardrobeeditorGab's Threads: https://www.threads.com/@wardrobeeditorGab's Free Guide To Feeling Hot Again: https://wardrobeeditor.myflodesk.com/hotagain⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.comCourtney's Substack: substack.com/@courtneyattheglassadvisoryIf 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.

    1h 1m

  5. Apr 22

    Building a Personal Brand That Opens Doors with Allie Fisher (Re-Release)

    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 careerHow your values and audience shape your brandThe “Why → How → What” framework and how to apply itHow to audit what you’re already putting into the world (especially on LinkedIn)Simple prompts to clarify your story and communicate your workHow to translate your experience when making a pivotWays to get outside perspective when you feel stuckTimestamps:00:00 Welcome and recommendations11:23 Allie Background and Career13:19 Why Personal Brand Matters19:29 Three Word Brand Exercise22:40 How to Build Your Brand28:10 Authentic Brand Foundations35:21 Auditing Your Voice38:35 Why–How–What Bullseye46:40 Prompts To Find Your Why50:06 Simple Storytelling Prompts56:33 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.

    1h 2m

  6. Apr 15

    Choosing Intuition Over Expectations: Leah Zaccaria on Building a Life (and Business) That Feels Right

    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 businessThe moment success stopped feeling fulfillingHow to find your intuitionLetting go of external expectations and redefining successBuilding Shefa Yoga - including opening a studio in March 2020Why financial literacy still matters in purpose-driven workCreating belonging through community, not just offeringsTimestamps: 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.

    1h 10m

  7. Apr 8

    Is It Time To Make a Career Change?

    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 purposeGrowth and learningCompensation and benefitsManager and team relationshipsWork-life alignmentIf 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.

    34 min

  8. Apr 1

    Navigating Toxic Power Dynamics and Bullying at Work with Andy Regal (Re-Release)

    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 addressThe limits of escalation and HRHow to differentiate between hard moments and harmful patternsApproaches to healing and rebuilding after toxic experiencesWhen and how to plan an exitTimestamps: 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.

    59 min
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About

The Glass Sessions is a weekly podcast hosted by the two Principal Advisors of The Glass Advisory, Courtney and Lauren. The two met working their first “real” jobs in customer service in 2012 and have been navigating work and life side by side ever since. At the heart of the show is a belief that guides their work: that work can be a powerful activator of a good life. Through guest conversations and episodes with just the two of them, they share stories, insights, and practical ideas to help listeners build careers that support their version of a meaningful, joyful life.

Information

  • Creator
    The Glass Advisory
  • Years Active
    2025 - 2026
  • Episodes
    55
  • Rating
    Clean
  • Copyright
    © The Glass Advisory
  • Show Website
    The Glass Sessions