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 memoir
• Growing up bullied and finding her voice
• The surprising power of delegation
• Leadership without intimidation
• How "secret passageways" open when you ask for help
• Practical strategies for finding mentors and sponsors
• Why visibility matters
• Confidence as an outcome, not a starting point
• Resilience in the face of repeated setbacks
• Amplifying your voice
• Finding meaning, energy, and purpose at work

Timestamps:

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.

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 middle
• Kelly’s framework for “career authorship”
• Identity loss during layoffs and career transitions
• Why relying only on your manager for validation can hold you back
• The importance of self-promotion and visibility
• How AI and modern work environments are impacting human connection
• What a portfolio career can look like in practice
• Balancing planning with openness to unexpected opportunities
• The difference between transactional and transformational coaching

Kelly 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.

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 ever
• Common hiring mistakes founders make as they scale
• How to identify your “flow zone” at work
• Practical advice for creating opportunities instead of waiting for them
• How to pitch yourself into roles that don’t exist yet
• Networking strategies for introverts and relationship-builders
• Why authentic connection is one of the highest ROI career investments you can make

Jessica 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.

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.