Choosing your career means deciding what fits, fuels, and fulfills you before you decide which title to chase. Shannon Flanagan, founder of Retail Women in Tech, says the difference plays out in three stages to career reinvention - a break, a pause, and a rewrite. Her evidence is 80 interviews with women whose careers never ran in a straight line.
Who is Shannon Flanagan?
Shannon Flanagan spent two decades inside Fortune 500 retailers and hyper-growth startups doing organizational design, leadership development, and change management. In spring 2025 she left the paycheck to found Retail Women in Tech, a nonprofit built on mentorship and community with no paywall, and to write Choose - don't chase - Your Career.
Both were things she'd planned to do at retirement. She did them 15 years early as her career reinvention.
Why does the corporate ladder still get rewarded?
Shannon runs an interview series at Retail Women in Tech called Power of We Wednesday. She's completed more than 80. Not one of those women had a linear career path. Meanwhile hiring managers open by asking for a generalist and then run five to seven rounds screening for deep functional expertise.
Her read on the cost: LeanIn.org and Deloitte find six in ten senior-level women are frequently burned out, because the system was never designed with them in mind.
What are the break, the pause, and the rewrite?
Career reinvention goes through 3 stages:
The break is the layoff, the burnout, or the realization that the work isn't the work you want, and the loss of identity that comes with it.
The pause is the interval almost nobody schedules.
The rewrite is defining success from the inside out and building on it.
Shannon says readers stop most often inside the pause chapters, and several have told her they had to put the book down partway through and reflect on their own career reinvention.
How long does a career pause actually take?
A true career reinvention takes about three months, in Shannon's experience and in what she's watched happen to others. Most people never get there. At week two the networking starts, the to-do list comes back, and the pause quietly ends.
She points to her own first layoff, when the one thing she did differently was refuse to make a to-do list.
How do you afford to choose your career?
Shannon doesn't pretend this part is easy. Money was the hardest thing she had to let go of. She lives in one of the most expensive areas in the country, has three teenagers, and now works 10 to 12 hour days with no paycheck.
The line that moved her came from her financial advisor of 25 years: see yourself as an asset, not a liability, and you'll make money again. Then she asks the counter-question:
Is the McMansion worth being miserable at your job?
Is the $10,000 trip to Hawaii worth the other 48 weeks?
What question should you ask instead of the deathbed question?
Ask what you'd tell your niece or nephew to do: follow the money, or follow the thing that puts a fire in their belly.
Shannon's argument is that the deathbed version is too abstract and too far away to answer honestly, while the niece-and-nephew version gets a real answer in about two seconds. She pairs it with a three-word test: what fits, what fuels, what fulfills.
What is Retail Women in Tech?
Retail Women in Tech (RWIT) is the nonprofit Shannon founded to build bridges across retail's sectors and put a value on transferable skills. It runs on mentorship, community, and the Power of We Wednesday interview series. Membership is free with no paywall at retailwomenintech.org, because Shannon's position is that access shouldn't cost money.
Career reinvention is the outcome the organization exists to produce.
Frequently asked questions.
Who wrote Choose, Don't Chase Your Career?
A: Shannon Flanagan, founder of the nonprofit Retail Women in Tech, wrote it with a co-author after both of them decided to move a retirement-age plan forward by 15 years. It's available on Amazon.
Is a non-linear career path a problem?
A: In the data Shannon has collected, it's the norm. More than 80 women interviewed for Retail Women in Tech's Power of We Wednesday series, and not one had a linear path. The problem is a hiring process that still screens as though linear is the default.
How long does it take to recover from career burnout?
A: Shannon's answer is roughly three months to unwind from a sustained go-go-go period. Most people abandon the pause around week two, when networking and to-do lists reappear.
How do you handle the money side of a career break?
A: Shannon's framing came from her financial advisor: see yourself as an asset, not a liability, because you'll earn again. She also pushes people to price the trade honestly, weighing the house, the car, and the annual trip against 48 weeks of misery.
What is Retail Women in Tech?
A: A nonprofit founded by Shannon Flanagan focused on mentorship, community, and getting more women into the rooms where retail technology decisions get made. Joining is free at retailwomenintech.org.
Hear the whole story.
🎧 The full conversation with Shannon Flanagan is on The Retail Transformers, Season 2 Episode 9.
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ABOUT THE AUTHOR
Ricardo Belmar is a retail tech analyst, top industry influencer and host of the Retail Transformers podcast, part of the Retail Razor Podcast Network, the #1 indie podcast network for retail, where he and Casey Golden interview the leaders shaping retail, consumer brands, and the future of commerce. He writes and speaks on retail technology, AI in retail, retail media, marketing, commerce strategy, and the leadership behind real retail transformation. He has spent his career working with retailers and the technology companies that serve them.
ABOUT THE PODCAST GUEST
Shannan Flanagan 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, Choose - don't chase - Your Career — 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.
