Risky Conversations with Jamie Lee
by Jamie Lee
BusinessE · Explicit
Latest episode
What I Gained from Being Pushed Out of a Job by a Former Friend/Mentor
What I Gained from Being Pushed Out of a Job by a Former Friend/Mentor
About this podcast
Everything that's rewarding is on the other side of a Risky Conversation.
In this podcast for professional women, we have honest talks about topics often considered taboo or "too risky" at work -- salary negotiation, mental and reproductive health, office politics, social injustices, and unconventional ways smart women navigate their path forward despite a flawed and sexist society.
Join me as we dive deeper into these risky yet rewarding conversations, embracing the growth they bring.
Episodes
The newest 20 of 151 episodes
- What I Gained from Being Pushed Out of a Job by a Former Friend/Mentor · 9 min · Episode 149In spring 2013, I realized I was being pushed out of a sales job at a startup founded by a friend and mentor I had admired for years. I quit, went home, and cried my eyes out…
- Gracefully Assertive (Part 2 of 2): Boundaries, Control, and When to Drop the Grace with Jamie Lee and Sade Curry · 25 min · Episode 148When I was a teenager and a member of a church youth group, someone crossed a physical line with me, and when they saw how angry I was, they asked me to lead the group prayer, as…
- Gracefully Assertive (Part 1 of 2): Avoiding the Traps of People Who Liked the Old You · 28 min · Episode 147Once upon a time, when I was the only woman working at a nearly all-male equities trading desk, I was told I was too quiet, like it was a problem to be fixed. Some time later, I…
- Leadership Lessons from Brazilian Zouk and Getting the Exact Job and Salary You Want with Kimberly Lai and Jamie Lee · 36 min · Episode 146What if leadership is really about following? I sat down with my friend Kimberly Lai, coach, leadership facilitator, and Brazilian Zouk dancer whose infectious joy for the dance…
- New Manager, Team Not Doing What's Needed? Here's the Agency Shift That Changes Everything · 19 min · Episode 145If you just stepped into a leadership role and your team keeps avoiding the one task that actually moves the needle, there's something simple and concrete you can do to start…
- How to Build a Queer Third Space from Scratch After Illness, Addiction and Burnout with Jeff Vicente and Jamie Lee · 44 min · Episode 144In 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…
- How Engineers Can Turn Setbacks and Layoffs into Growth and Opportunity with Poornima Vijayashanker and Jamie Lee · 43 min · Episode 143In 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…
- The Coverage Trap: Why Overfunctioning Women Get Passed Over for Promotion And What to Do About It · 13 min · Episode 142In 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…
- How to Raise Money and Get Paid Well Without Betraying Your Values with Alexis Morin and Jamie Lee · 1 h 0 min · Episode 141In 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…
- Possibility Thinking: Creating Options When You Feel Stuck with Executive Coach Irina F. Cozma, PhD and Executive Coach Jamie Lee · 38 min · Episode 140Ever 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…
- Clarity Becomes Currency: Rewriting Loyalty Pacts with Founder Debbie Heiser and Executive Coach Jamie Lee · 30 min · Episode 139In 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…
- How to Be Gracefully Assertive · 16 min · Episode 138Gracefully 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…
- Postpartum Dads, First-Gen Pressure, and Leaving Corporate to be a Healer with Psychotherapist Steve Alexander Jr. and Executive Coach Jamie Lee · 44 min · Episode 136Know 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…
- We’re All Going to Die: Money, Love, and the Treasure Map with Allie Irwin and Jamie Lee · 53 min · Episode 135Beneficiary 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…
- Anti-Networking: The Surprising Power of Not Asking for Anything At All · 16 min · Episode 134The 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…
- Diverse Books and Risky Career Pivots with Literary Agent Kat Kerr and Executive Coach Jamie Lee · 50 min · Episode 133In 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…
- Building Bridges Across Cultures: Redefining Leadership with Ai Asakura of TOMODACHI Initiative and Executive Coach Jamie Lee · 50 min · Episode 132What 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…
- How to Exit Toxic Jobs and Make More Money Without Burning Bridges: Two Client Case Studies · 21 min · Episode 131Just 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…
- How to Pivot in Your Career, Claim Your Value, and Negotiate Higher Pay: A Case Study · 23 min · Episode 130Women 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…
- De-Risking Pay Negotiation for Women Professionals: Three Core Skills to Implement Right Away · 23 min · Episode 129Ever 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…
