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

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