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.