Career Reinvention - Choose, Don’t Chase, Your Career with Shannon Flanagan

Shannon Flanagan on choosing your career instead of chasing it – the break, the pause, and the rewrite.

Shannon Flanagan has run more than 80 Power of We Wednesday interviews at Retail Women in Tech. Not one of those women had a linear career path. All of them hunting for jobs inside a system that only rewards one.

Shannon spent two decades inside Fortune 500 retailers and hypergrowth startups developing teams, leading change management, and supporting people through reinvention. In early 2025 the unexpected happened. A layoff, and suddenly she found herself pausing, reflecting, and looking to reinvent her own career. Two things she'd planned to do at retirement showed up 15 years early. Her fiancé told her to go all in on the nonprofit she wanted to start, Retail Women in Tech (RWIT). Then a friend called to say she wanted to write a book about with her and tell the stories of the women in RWIT. Shannon said yes to both, with three teenagers at home, a mortgage in one of the most expensive areas in the country, and no paycheck coming.

Shannon’s new book, Choose - don't chase - Your Career, is built in three parts: the break, the pause, and the rewrite. Shannon walks Ricardo and Casey through all three, starting with the layoff that opens chapter one and the bottle of champagne she opened on her deck by noon that same day. It's the most personal career reinvention story we've ever had on the show.

This one goes deep. Casey admits that the last real pause she took was the summer she was 17, and that she spent years chasing goals she set at 12. Shannon names money as the hardest thing she had to let go of, then gives the line from her financial advisor that she still repeats every week.

What You'll Learn in This Episode

Why the corporate ladder still gets rewarded even though 80 out of 80 careers zigzag.What the break, the pause, and the rewrite look like week to week.The three months it takes to unwind, and why almost everyone quits at week two.How Shannon answered the mortgage question when she walked away from a paycheck.The reframe that beats the stereotypical deathbed question: what would you tell your niece or nephew to do?The through line she found across all the stories in the book, and why your old journals are the place to find yours.Why Shannon built Retail Women in Tech with no paywall.

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