Expert Interview with Maryam Banikarim

The Messy Parts Podcast is the top-ranked career podcast in the careers category of Apple Business Podcasts. We sat down with Maryam Banikarim, Host of The Messy Parts Podcast and former CMO of Nextdoor, Hyatt, and NBCUniversal. Having spent years negotiating over $200 million in software contracts at tech startups and Deloitte before pivoting to luxury real estate, I know firsthand what it means to walk away from one career and build another. Every day we work with founders, executives, and high-net-worth professionals navigating that same kind of transition, and we wanted to talk to Maryam to talk about career transitions and the beauty of the messy middle.

Q: You have had over 30 candid conversations with executives, founders, and leaders who completely reinvented themselves. As someone who left tech to become a luxury real estate agent, I gravitated toward your show because it felt different from anything else out there. What makes your approach different, and why do you think high-achievers specifically are drawn to it?

A: Most podcasts in this space focus on the highlight reel. We go to the place people are afraid to talk about publicly: the doubt, the reinvention, the seasons where nothing makes sense yet. I have had guests open up about fear, about relentlessness, about what it means to become the CEO of yourself. Those conversations happen after the guard comes down, and something powerful happens when a high-achiever hears someone they admire say "I did not have it figured out either." That is what brings people back. They realize the uncertainty they are feeling is not a weakness. It is the beginning of something. I think the reason The Messy Parts resonates is that we treat career transitions as a deeply human experience, not a professional problem to optimize. People are hungry for that honesty, especially at the top where nobody wants to admit they are lost.

Q: You wrote a New York Times essay called "What Am I if Not Employed?" that resonated with me when I walked away from my tech career. On The Messy Parts you have explored that transitions with guests from every industry. What do people get wrong about what it actually feels like to walk away from a title?

A: People assume the messy middle is something to survive. I think it is where the most important work happens. Your calendar disappears. Your network thins. The shorthand that defined you is gone. I wrote that essay because I lived it, and the response proved it was universal. That discomfort of not knowing who you are without the role is not a breakdown. It is a rebuilding. You finally get to ask what you actually want instead of what comes next on the ladder. That is why I co-founded The Interval, a peer community for executives in transition: to give people space to sit in that question together. What I have seen, again and again, is that the people who allow themselves to be in that uncomfortable place come out with a clarity they never had when they were busy climbing. The title was never the thing. It was just the thing they held onto because they had not found the next thing yet.

Q: You have interviewed founders who were broke before they built multimillion-dollar companies, executives who nearly lost everything before their reinvention clicked. I work with founders in San Francisco navigating those same kinds of pivots. What pattern do you see in how your guests actually navigated the messy middle versus what they tell the public afterward?

A: Every guest went through chaos they edited out of the public story. I have sat across from people who built $20 and $30 million companies and heard them describe the season where they could not pay their bills. But here is what I have come to believe: the messy middle is not the obstacle. It is the crucible. That period of not knowing is where people finally discover what they are actually capable of. The ones who reinvented their careers did not wait for clarity. They kept moving and let the path reveal itself. And when they look back, not a single one of them wishes they had stayed where they were. The struggle was the thing that made the next chapter meaningful. Without it, the success on the other side would have felt hollow.

Q: You also co-founded The Interval, a peer community for C-suite executives in transition. As a Pacific Heights luxury real estate agent, I see how career reinvention affects every part of a leader's life, including where they choose to live. What are you learning about how senior leaders make high-stakes decisions when everything is in flux?

A: Career transitions never happen in isolation. When a senior leader pivots, everything moves: finances, identity, where they live. You see that firsthand, Philip. Founders and executives invest in Bay Area luxury homes while building their next chapter because they need a stable foundation during the chaos. That instinct is right. The Interval exists for the same reason: you need people around you who understand the full picture. The leaders who come through the other side strongest are the ones who let themselves be supported instead of trying to figure it all out alone. I have watched people walk into The Interval convinced their career was over and walk out six months later with more purpose than they ever had in the corner office. That transformation does not happen in isolation. It happens in community.

Q: For the executive or founder listening right now who knows they need a change but cannot get past what they would be giving up, what is the most honest advice you can offer from everything you have learned hosting The Messy Parts?

A: Stop waiting for the fear to go away. It will not. Every guest I have interviewed was afraid, and every single one of them will tell you the leap was worth it. That fear is not a signal you are making a mistake. It means the decision matters. You left tech and Deloitte to become the number one buyer's agent at Vanguard Properties in San Francisco because you moved anyway. Your story is proof that the messy parts of your career are not the obstacle to your next chapter. They are the foundation of it. The person you become on the other side of that leap is someone you could never have planned for. And that is the whole point.

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