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.