Mickey Drexler built the Gap into a $15 billion empire, created Old Navy, helped redefine J.Crew, and shaped American retail culture. And then? He was fired. No warning. No thank you. Just a card, a sentence, and a door. In this episode of The Messy Parts, Maryam sits down with Mickey to talk about what actually happens when you do everything “right” and still get pushed out. They go deep on instinct vs. pedigree, why big companies break good people, how to recover from a public exit, and the price of loyalty in a system that doesn’t always return it. This conversation is for anyone who’s ever felt underestimated, overlooked, or like they were building something real while everyone else chased politics. If you’ve ever asked yourself, “What do I do now?” — you’re in the right place.

Key Moments

From $400 Million to $15 Billion
How Mickey Drexler scaled Gap into a global powerhouse — and why he still hates the word “turnaround.” 📈

“Adversity Is the Advantage”
Growing up in the Bronx, losing his mother young, and how hardship shaped his drive. 💔➡️🔥

Why Mickey Trusts People With Hard Stories
Why he’s drawn to people who’ve struggled — and what today’s work culture gets wrong. 🧠❤️

“Business School Is a Waste of Time”
Mickey explains why he thinks degrees, grades, and pedigrees don’t equal instinct or success. 🎓🚫

The Shy Kid Who Became a CEO
Mickey opens up about insecurity, introversion, and growing into leadership later in life. 😶➡️👔

The $500 Salary Moment That Changed Everything
The quiet injustice early in his career that taught him how systems really work. ⚖️💸

“You Feel It Before It Happens”
Mickey describes the instinctual moment he knew he was about to be fired. ⚠️🧭

Fired After 18 Years… With a Card
How Mickey Drexler was let go from Gap — no warning, no thanks, just a sentence. 🧾💥

“It Was a Gut Punch”
Processing rage, humiliation, and self-worth after a public corporate exit. 🥊😞

Is There a Right Way to Fire Someone?
Mickey explains how leaders should handle endings — and why most fail. 🪑🤝

Betting on People: Why Jenna Lyons Mattered
How choosing the right creative partner helped rebuild J.Crew — and what talent really looks like. 🎨✨

Advice for Anyone Starting Out Today
“Hire your boss. Trust your instinct. If it doesn’t feel right — walk.” 🚪➡️🌱

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At what point does a side hustle stop being a hobby? On this episode of The Messy Parts, Marla Aaron tells Maryam the exact moment she realized she could no longer hedge her ambition. What began as a creative outlet eventually became a full-fledged business, but not without years of doubt, rejection, and financial anxiety. In this episode, Marla and Maryam explore the tension between security and risk, why waiting to feel “ready” is a trap, and how fear can coexist with clarity. They also talk about loneliness, creativity, social media as an unexpected unlock, and what it really takes to start over later than planned.

Key Moments

“So Happy. Not Scared at All.” 😮
Marla describes the emotional moment she finally quit her corporate job and why relief outweighed fear.

Becoming Comfortable With Discomfort 🌍
Marla connects her childhood independence and studying abroad at 17 to her lifelong willingness to take risks.

Graduating Into a “Bad Job Market” 📉
Why Marla believes focusing on opportunity matters more than economic doom narratives for young professionals.

“I’m Scared of Everything.” 😬
A candid conversation about fear, impostor syndrome, and doing hard things anyway.

Choosing Money Over Passion (At First) 💼
Marla explains walking away from journalism due to low pay and financial anxiety.

Fired, Divorced, and a Single Mom 💥
The emotional and financial rock bottom that forced Marla to keep moving forward.

The Boring Job That Funded Creativity 🔄
How working a job she didn’t love gave her space to build her dream at night.

A Hobby With a Dream 💭
How Marla quietly built her jewelry business at night while working full-time and raising a child.

“Everyone Told Me I Was Insane.” 🔥
The Cannes turning point: burnout, injury, rage, and the final decision to quit.

“This Is Not a Hobby.” 🚨
The pivotal boardroom moment when a CEO unknowingly pushed Marla to fully commit.

Instagram Unlocks the Business
How learning social media from her kids helped Marla grow a global direct-to-consumer brand.

The Loneliness of Building Something Alone 🧍‍♀️
Marla opens up about the isolation that comes with entrepreneurship and leadership.

Send us a text

Email us: hello@themessypartspodcast.com

To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.

If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.

Thank you for listening.

Is it possible to be successful, exhausted, uncertain, and stuck — all at the same time? In this episode of The Messy Parts, former Pfizer communications chief Sally Susman joins Maryam on the blue couch to get real about fear, ambition, burnout, and what it really takes to grow. From being told she’d never have a career after coming out, to leading Pfizer during COVID, to leaving corporate life behind, Sally shares the messy, human moments that shaped her leadership. She talks about the risks of playing it too safe, losing identity when a job ends, and why breakthrough moments rarely arrive when you feel “ready.” This isn’t a highlight reel — it’s a real conversation about pressure, reinvention, and learning to trust yourself through change. If your career looks good on paper but feels heavy inside, this episode will help you feel less alone.

Key Moments

“Be Ready — You Don’t Know When It’s Coming” ⏳
Sally reflects on COVID and shares her core career philosophy about preparation and unexpected breakthrough moments.

Growing Up With Privilege AND Pressure 🎭
Sally explains what it was like being raised in an ambitious, high-expectation household.

“You’ll Never Have a Career” 💔
Sally shares the moment she came out to her parents — and the sentence that reshaped her entire life trajectory.

“Nothing Scared Me After That” 🔥
How that painful family moment became the foundation of her courage and leadership confidence.

Leaving Government for Corporate America 🏛️➡️🏢
Why Sally walked away from politics — and what frustrated her most about “doing good” in government.

“My Heart Was in My Throat” 😰➡️💪
Sally explains why fear is her signal for growth — and how discomfort became her career compass.

Walking Into Pfizer’s Reputation Wall 🧱
The moment Sally realized just how deep public distrust of Big Pharma really ran.

COVID Changed Everything 🌍
Inside Pfizer’s pandemic pivot — opening labs to media, sharing trial protocols, and racing against time.

Finding Her Voice on the Global Stage 🎙️
How Sally went from behind-the-scenes operator to public-facing leader during the crisis.

Hiring a “Senior Intern” After Watching a Movie 🎬
The unconventional idea inspired by The Intern that became a Fast Company cover story.

Leaving Corporate Life Was Harder Than She Expected 🚪
Sally opens up about identity loss, comfort traps, and preparing for her off-ramp.

“I Was Too Transactional” — Career Feedback That Stung 🪞
The tough 360 review that changed how Sally approached relationships at work.

Advice to 35-Year-Old You: “Worry Less” 🌱
Sally’s direct message to stressed professionals navigating pressure and self-doubt.

Send us a text

Email us: hello@themessypartspodcast.com

To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.

If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.

Thank you for listening.