Navigating The Meaningful Middle With Kelly Nash

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 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.

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 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.

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 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 [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.

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 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.

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 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.