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Missed the last issue?
I told April Sabral on air that this might be my favorite topic. She then spent 15 minutes making me feel like I should audit my own last three meetings. April wants leaders to end your meeting by asking the team: what did you learn from me today? The question that would tell you the most about your leadership is the one you avoid, and you avoid it for exactly the reason you should be asking it.
The pause you should take, but rarely ever do.
My co-host said something on the podcast recently that I’m still thinking about.
Casey went through Shannon Flanagan’s new book, got to the part about pausing, and asked herself when she last had three months where nothing was scheduled.
Her answer: the summer she was 17.
Seventeen. She went further and said she’d spent years chasing goals she set at 12 or 13, before high school, before her first job, before she knew a single thing about the world she was aiming at. It took her six months of writing to build a new list.
When a founder with that much self-awareness tells you her life plan was written by a seventh grader, the rest of us should probably go check who wrote ours.
That’s the conversation we had with Shannon on The Retail Transformers podcast recently. Shannon founded Retail Women in Tech (RWIT) and just published Choose, Don’t Chase Your Career. She wrote it in the middle of doing the thing the book describes, which is a strange and useful place to write from, but it’s something none of us knew we needed for our own careers.
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The number that stopped me.
At RWIT, Shannon runs an interview series called Power of We Wednesday. More than 80 published. Not one of those women had a linear career path.
And every one of them still walks into a hiring process where the manager says they want a generalist, then runs five to seven rounds screening for functional depth.
It’s easier to defend a hire that looks like the last one.
Fifteen years ahead of schedule.
Shannon had a plan for retirement. Run a nonprofit, write a book. Then in early 2025 both showed up 15 years early after an unexpected layoff, within weeks of each other. Her fiancé told her to go all in on RWIT. A friend called and said she wanted to write a book with her about the women of the community.
Now this is the part people skip when they tell these stories.
Shannon has three teenagers, lives in one of the most expensive areas in the country, and has never struck it rich. She said yes anyway. She now works 10 to 12 hour days plus weekends for no paycheck, and describes herself as the most stressed and the most fulfilled she’s ever been.
Money was the hardest thing she had to let go of. What moved her was one line from her financial advisor, a friend of 25 years:
See yourself as an asset, not a liability. You’ll make money again.
Shannon says she still repeats it to herself most weeks.
Three months, and the week-two trap.
Shannon explains that a real pause is about three months. That’s roughly how long it takes to come down from years of go, go, go. And almost nobody gets there, because week two is when the LinkedIn networking starts, the to-do list reappears, and the pause quietly converts into a job search with better scenery.
She told us about a friend, an EVP at a huge media company, laid off with a serious severance package, who called the next day already networking. She had a plan for yoga and walks in the park, which is what a to-do list looks like in gym clothes. When Shannon suggested she actually stop, the friend said, “I don’t know how to do that. It’s not me.”
Shannon’s answer:
Of course it’s not you. You’ve never done it. That’s how you got here.
The one thing Shannon did differently after her own first layoff was refuse to make a to-do list. That’s it. That’s the whole intervention. She sat where she was. It makes sense when you hear her say it.
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Where I landed.
I went into this recording thinking the pause was a luxury good. Something you can afford at a certain level of severance and not before.
I came out thinking most people in corporate roles have more room than they act like they have, and that the reason we don’t take it has very little to do with the mortgage. Taking three months means telling people you’re taking three months, and there’s no comfortable way to say that at a dinner party. The to-do list is easier. It’s proof you’re still a serious person.
Shannon’s counter-question gets under your skin.
Is the McMansion worth being miserable at your job? Is the car? Is the $10,000 trip to Hawaii worth the other 48 weeks?
And the reframe I’m stealing:
forget the deathbed question, it’s too far away to answer honestly. Ask what you’d tell your niece or nephew to do. Follow the money, or follow the thing that puts a fire in your belly.
Nobody answers that one with the BMW.
Two things I’m leaving in the episode.
Shannon reads the quote she closes the book with at 48:39. I’m not writing it here, because the point is hearing her read it, and Casey nearly cries over it. It’s truly, a very real, honest moment. Go listen to that bit. You’ll thank me later, and you’ll really appreciate why Shannon’s story is one you didn’t know you needed to hear.
Earlier, at 41:12, the story of why she isn’t narrating her own audiobook turns into the most surprising number in the hour. Worth your time as one of the most fun moments in the episode.
Go even deeper.
Season 2, Episode 9 of Retail Transformers: “Choose – don’t chase – your career, with Shannon Flanagan”
Watch or listen to the full conversation. It’s available now in your favorite podcast player and on our YouTube channel.
Shannon’s book, Choose, - Don’t Chase - Your Career, is on Amazon. Retail Women in Tech is free to join with no paywall at retailwomenintech.org.
Your turn.
If this one hit, forward it to the person you know who’s in the middle of a rewrite right now. And if you’re not subscribed yet, that’s the button.
Next time on the Retail Transformers: we talk with Miya Knights about her new book, “The Future of Shopping,” and what retailers must do to stay relevant.
Comment on this newsletter or join the conversation on LinkedIn! Your insights may help shape the topics we explore next.
Until next time! Stay sharp. Be Bold. And Transform Retail!
Sincerely,
Ricardo Belmar
The Retail Razor: Retail Transformers
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Retail Transformers is part of the Retail Razor Podcast Network, alongside The Retail Razor Show, Blade to Greatness, and Data Blades. Find us at RetailRazor on LinkedIn, Bluesky, Threads, and Instagram. For a full transcript of this episode, visit our retailrazor.com website!