Risky Conversations with Jamie Lee

10 Episodes
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By: Jamie Lee

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. 

Beyond Promotions and Paychecks: A Blueprint for Deeper Happiness for Ambitious Women Leaders
#94
Yesterday at 6:00 PM

Today, I want to share something I originally wrote as an email to one of my coaching clients. It touches on something that shapes nearly everything we do: the pursuit of happiness.

Here’s the context. One of my clients is an executive at a major tech company. She’s leading a bold new initiative that involves hiring, retaining, and coaching a team of sharp, high-performing people who can deliver results fast.

She’s working hard. She’s making real progress. And in one of our sessions, a powerful question came up:

How do I...


Balancing Ambition and Inner Peace: A Conversation with Buddhist Teacher Billy Seol
#93
04/22/2025

This year, I'm turning Buddhist, meditating with a sangha (a community of Buddhist practitioners), bowing in the morning, and taking lessons from Buddhist teachers. 

This happened because I started reading Billy Seol's Substack (https://substack.com/@julylifecoach), which he writes every single day (impressive!) 

I've come to consider Billy as a kind of spiritual god brother. 

In this deep dive into the intersection of Buddhism, coaching, and personal growth, Billy takes us through his journey of: 

Early experiences with depression Career in tech companies (Apple, Disney) Searching for a comprehensive approach to unders...


Zen and the Art of Dealing with Office Politics (An Excerpt)
#92
04/08/2025

I recently led a group session called Zen and the Art of Dealing with Office Politics, where I helped professionals—especially women and underrepresented folks—navigate the messiness of workplace dynamics with more calm and clarity.

We kicked off with a guided brain exercise to shift out of high-frequency beta brain waves (you know, that anxious, go-go-go energy) and into a slower, more grounded alpha state. It’s a small shift that opens up space for creativity and better problem-solving.

Then I walked folks through three key ideas:

1. Power Differential
We nam...


The Wild Unicorn with Emily Maggiotto: A Journey of Embracing Curiosity and Creativity
#91
03/27/2025

In this captivating episode, Emily Maggiotto shares her inspiring story of navigating pivotal career and life decisions guided by her insatiable curiosity. 

From leaving a stable finance job to pursue a musical adventure, to leading HR teams through challenging times, Emily's journey exemplifies the power of embracing risk, learning continuously, and finding fulfillment on one's own terms. 

This conversation offers invaluable insights for anyone seeking to redefine their career and life path. 

Connect with Emily on LinkedIn HERELearn more about The Wild Unicorn HERE


Text me your thoughts on this epi...


Harmonizing Fitness and the Female Cycle: A Conversation with Lizzy Palmer
#90
03/17/2025

Did you know that a survey of over 4,100 young men from Brazil, Indonesia, the Netherlands, and Uganda revealed that menstruation is still considered taboo around the world? In fact, many associate periods with words like ‘dirty,’ ‘embarrassing,’ and ‘disgusting.’ This deep-seated stigma is something women and girls are taught to internalize, making us feel shame around a natural biological process.

But today, we’re changing that narrative.

Welcome to Risky Conversations. I’m Jamie Lee, a certified integrative hypnotist and executive coach, and I work with women to help them achieve career growth, even when they’re the only...


Sovereign: A Candid Conversation about Relationships, Sex, and God with Michaelann Gardner
#89
03/06/2025

I work with a sex coach, not because I have sex problems, but because the coach and I are on a similar wavelength. My coach, Michaelann Gardner, is a deeply compassionate and fascinating person who has studied hypnosis under Melissa Tiers, just like I have. 

(To give you an idea of what our coaching sessions are like: Michaelann guides me through hypnotic trances where we meditate on death, on the impermanence of life. I emerge from these meditations with a profound appreciation for my earthly existence.) 

Michaelann has written a powerful book called Sovereign, a po...


Overcoming Guilt and Imposter Syndrome in Salary Negotiations
#88
03/03/2025

I'm a coach who helps smart folks who don't like office politics get promoted and better paid. Part of that work is helping professionals negotiate their salary. 

98% of my clients are women, and I often hear this objection when I coach on salary negotiation: "I feel guilty for asking for the money I want." 

In this episode, I share insights on how to shift your mindset, presence, and strategy to approach salary discussions with poise and confidence. 

You'll learn: 

Why focusing on using the "right words" is a losing proposition Why self-advocacy (when...


Replay: 7 Winning Steps for Salary Negotiation
#87
02/18/2025

Since 2011, I've hosted negotiation trainings that can be best described as scrappy, pragmatic, and useful. 

It started with humble Meetups where I got a bunch of the smartest women I know into a room and had them practice asking for what they wanted -- out loud.

When the pandemic hit, I consciously decided to focus primarily on my 1:1 executive coaching, and everything moved to Zoom.

(You can read about my coaching philosophy, process, and pricing right over here on the website)

Since then, I've continued to host free negotiation w...


5 Truths About Salary Negotiation Your Employer Doesn't Want You to Know
#86
02/05/2025

🔥This might get me fired, I say to my clients to preface this truth bomb — 

The game is rigged against employees. 

Learning to negotiate for yourself is an essential part of playing to win the game. 

The system is rigged to benefit the select few at the top and shareholders, not the hard-working manager or multi-talented individual contributor. And if you’re a hard-working woman or a minority, the odds are even worse. 

But all is not lost. You need to learn how to: 

✅ Advocate for yourself 
✅ Negotiate...


No-Nonsense Guidance for Facing Workplace Discrimination for Women and Immigrants with Anne Donnelly Bush
#85
01/23/2025

In this interview, employment lawyer Anne Donne Lee Bush shares practical advice for navigating workplace discrimination. 

Anne draws from her own experience as an immigrant lawyer who reinvented her career in New York to provide no-nonsense guidance on 

building evidence, challenging performance improvement plans, and leveraging mediation to negotiate better severance packages. 

Whether you're facing microaggressions, retaliation, or the threat of layoffs, Anne's honest, empowering approach will equip you to advocate for your rights and find a path forward.

About Anne Donnelly Bush: 

Anne Donnelly Bush is an attorney who specializes in emp...