*Shannon Flanagan* spent 20 years running organizational design and change management inside Fortune 500 retailers and hypergrowth startups, which is career reinvention work done on behalf of other people. In spring 2025 she pointed it at herself: she walked away from the paycheck, founded the nonprofit Retail Women in Tech, and then wrote a book, _Choose, don't chase Your Career,_ 15 years ahead of the plan she'd made for retirement.
Shannon walks *Ricardo Belmar* and *Casey Golden* through the book's three parts (the break, the pause, the rewrite), the layoff she celebrated with champagne on her deck by noon, the money question nobody says out loud, and the mug on her desk that says "I literally do not know what I'm doing."
This is a career reinvention conversation with the receipts attached, and it gets deep and personal. If you're mid-pivot, or thinking about one, this episode of the *Retail Transformers* podcast is for you. Be prepared to look inward and find your own reinvention!
Like and subscribe if career reinvention is the thing you're working on right now, and tell us in the comments which of the three parts you're in.
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*The Retail Razor: Retail Transformers S2:E9*
*Released on August 26, 2026*
*Guest info*
*Shannon Flanagan.* https://www.linkedin.com/in/shannon-e-flanagan/
*Author.* _Choose - don't chase - Your Career._ https://a.co/d/0cXKYT1f
*Founder.* Retail Women in Tech.* https://retailwomenintech.org
Shannon has spent her career inside complex organizations, driving significant paradigm shifts in how teams operate at fortune 500 companies and hyper growth startups. This has given her a rare practitioner's view of what moves people, culture and business forward. At twenty-five, Shannon discovered her why: to create the conditions for people to love what they do every day. That purpose has been the through line of her work ever since. Drawing from her experience in organizational design, leadership development and change management, she has dedicated her career to supporting people and organizations through reinvention. Whether that means launching new businesses, optimizing talent or moving through the seasons of our lives.
Shannon made a life-changing decision in the Spring of 2025. She started a non-profit, Retail Women in Tech, and wrote a book — two things she planned to do when she "retired." When the opportunities to do both manifested in front of her within weeks of each other, fifteen years ahead of schedule, she knew she couldn't turn a blind eye. So, she faced her fears, listened to her gut and pivoted to seeing herself as an asset to invest in, giving up a paycheck and security to actualize her life's work.
She's a business owner, an author, a speaker, a life coach and a mother of three. And she believes that by sharing our stories, we spark the inspiration and change we seek in our own lives and the world around us. Shannon didn't have this figured out before she wrote a book telling other women how to figure it out. She still doesn't. And that's the point.
*Chapters*
00:00 Teaser
00:55 Show Intro
03:29 Introduction & The Mystery Mug
04:28 Why She Wrote the Book Now
07:47 The Mug Story Revealed
09:09 Getting Laid Off
12:21 The Corporate Ladder Myth
18:06 Break, Pause, Rewrite
24:27 Letting Go of Money and Fear
31:56 Facing Fear and Choosing Not Chasing
37:57 Redefining Success
45:43 Final Reflections & Where to Find the Book
53:08 Show Close
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#RicardoBelmar #CaseyGolden #retailpodcast