Risky Conversations with Jamie Lee

In this episode, I sit down with my longtime friend and Iron Feather co-founder Jeff Vicente to explore how he built a hybrid salon, art gallery, and community “third space” in the heart of SoHo. 

From risky career pivots and “successful failures” to surviving cancer and addiction, Jeff shares how his resilience, queerness, and devotion to Madonna have shaped his leadership and vision. 

Together, we ...

In this episode of Risky Conversations, I sit down with Poornima Vijayashanker, founding engineer of Mint.com, former Apple engineering leader, and founder of Femgineer, to talk about why communication is the edge technical professionals can’t afford to ignore. We explore how her “planned exits” from both Mint and Apple shaped her philosophy on career agency, and how a painful startup shutdown taught her the value...

In this episode of Risky Conversations, I reveal a subtle but costly pattern I see over and over again with my highest-achieving clients—something I call “the Coverage Trap.”

You know that feeling: you work nights and weekends, you hold everything together when your teammates are out, you quietly make miracles happen…and your reward is, “Great, keep it up.” 

No promotion, no extra resources, ...

In this episode, I sit down with my friend Alexis Morin, founder and principal of Soul Work Coaching, for a deep, tender, and surprisingly practical conversation about money, justice, spirituality, and leadership.

Alexis co-founded and led a national nonprofit, Students for Education Reform, through her 20s, earned a Master of Divinity from Union Theological Seminary, won the Interreligious Engagement Prize for her thesis on “...

Ever feel stuck or trapped in your work or life?

My guest Irina F. Cozma, PhD is an organizational psychologist and executive coach who has repeatedly generated bold options for herself in moments when most people would have resigned with a defeated “it is what it is.”

In this conversation, we talk about surviving a micromanaging boss, why that experience became one of the biggest gifts of Irina’s career, and how he...

In this episode, I talk with business coach and servant leadership educator Debbie Heiser about why risky conversations are often the doorway to our greatest freedom, fulfillment, and financial growth. We explore how subconscious “loyalty pacts,” double binds, and competence-as-survival strategies keep high-achieving women over-functioning, under-receiving, and burning out. Debbie also shares how she helps clients work ...

Gracefully Assertive -- I first heard this from my peer coach Sade Curry, an expert relationship coach, and I immediately thought, This is so good! I need to share it with every one of my clients.

On Thursday, August 20th, Sade and I went live on a podcast-style conversation where we unpack Gracefully Assertive for women who've been told they're too much (both of us have!) and share real case studies of women who gracefully ...

Know what it’s like to feel like you don’t fit into any box? And silently suffer while second-guessing yourself in a workplace where you're one of the extreme few? 

Yep, me too.

In this episode, I’m talking with psychotherapist Steve Alexander, Jr., a first-gen, Black, sensitive human who left a “safe” corporate job in risk management to become a healer for folks who, like me, feel...

Beneficiary forms...sexy?

In this episode, I’m joined by my friend Allie Irwin—hypnotist, coach, and creator of the Treasure Map, an end‑of‑life planning process—who makes a compelling case that it can be.

You’ll hear why preparedness is an act of care and freedom, how Allie’s clients literally find money (forgotten accounts, double charges, missed benefits), and what really happens in the first ...

The truth is, some of the most powerful career moves happen when you don't ask for anything at all. 

This Friday, July 24th, my client Sarah-Neel Smith and I are going to teach you exactly how to have those career conversations where you don't ask for anything at all and generate power for your negotiation outcomes. All the details here: https://antinetworking.jamieleecoach.com/

If you're going, "Wait, what? How does that happen...

In this episode of Risky Conversations, I interviewed my good friend and literary agent Kat Kerr about her unconventional path from Florida state government to championing marginalized voices in publishing. Kat shares how her childhood love of books, early encounters with racism, and a mid-career pivot led her into advocacy-driven literary agenting and involvement with programs like We Need Diverse Books. Together, we talk about so...

What do you do when you're offered an opportunity that will definitely stretch you but also scares you, and your first instinct is to hand it to someone else, because you feel you're not quite qualified? 

That's the moment we unpack in this interview with Ai Asakura, Alumni Program Manager for the TOMODACHI Initiative at the U.S.-Japan Council, who I met at an expat meetup in Fukuoka this spring — one with that sa...

Just in 2025, nearly half a million women left the workforce. 23% of all new businesses were started by women, and 50% of all solopreneurs are women.

Perhaps a part of you knows you need to leave. Maybe the job is toxic. Maybe you're underpaid. Maybe you're just done. But here's what's keeping you stuck: you don't know how to exit without burning bridges, tanking your finances, or sabotaging your next move.

So how do you leave a bad ...

Women are asking to be paid better and promoted but we’re also getting "no" more often than men. What gives?

The problem isn't that women can't negotiate. The problem is that we're negotiating the wrong way—playing by rules that were never built for us.

So what's the right way? Surprisingly, it starts with an internal orientation rather than an external one.

Today, I'm walking you through the three core negotiation skills,...

Ever felt anxious about negotiating your pay? Wondered why it feels so risky when you already know you’re beyond pulling your weight at work?

Here’s the truth I see as a coach for marginalized leaders who don’t like office politics: We've been taught that asking for what we want is risky. Greedy. Aggressive. Ungracious.

But here's the thing.

Women and minorities aren't bad negotiators. We've just been sold a lie abou...

What happens when the pressures of work intensify AND parenting intensifies at the same time? Senior-level mothers are caught in a two-way trap—and many are quietly burning out, believing it's a personal failure rather than a systemic one.

In this episode, I talk with Shalene Gupta, staff editor at Fast Company, about her groundbreaking investigation into how senior-level women are coping with the impossible. After putting out...

Everything worthwhile is on the other side of a risky conversation—especially when it comes to women’s health, birth, and career.

In this episode, I sit down with professional investor–turned–hypnobirthing educator Maria Lernerman to talk about how hypnosis, birth preparation, and self-advocacy can transform one of life’s most intense experiences into a joyful, empowering memory.

Maria shares ho...

In this episode, I sat down with leadership coach and former HR leader Ashley Paré to pull back the curtain on the "risky conversation" that cost her a corporate role but won her ultimate freedom and self-respect. We dive into how that experience became the catalyst for her mission: helping women navigate the complex systems of corporate power to advocate for their worth—without the burnout.

We discussed:

• [09:20] The "Third...

In this episode of Risky Conversations, I sit down with global storytelling expert Gabrielle Dolan, author of Story Intelligence: The craft of authentic storytelling made smarter with AI.

Gabrielle shares how one risky career conversation led her to leave a secure executive role at a major bank to build a global storytelling practice, eventually training leaders at the Obama Foundation.

Together, we unpack why perso...