Risky Conversations with Jamie Lee

Hosted by Jamie Lee

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Episodes

141

Latest episode

Aug 2026

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EN-US

About the show

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.

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60 recent

August 18, 2026Episode 13930 min

Clarity Becomes Currency: Rewriting Loyalty Pacts with Founder Debbie Heiser and Executive Coach Jamie Lee

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 with their nervous systems, embrace play over hustle, and step into an aligned “lit up life” where clarity truly becomes currency. What you'll learn: How risky conversations can lead to deeper, more meaningful relationships, personal freedom, and major professional turning points (e.g., Debbie telling her boss/friend she could no longer afford to stay as CFO, which catalyzed her full‑time coaching business and significant revenue growth). Why subconscious beliefs and “loyalty pacts” matter: Debbie explained concepts like double binds (conflicting desires such as security vs entrepreneurship) and loyalty pacts (feeling disloyal if you “prove someone wrong”), and how early family stories and cultural conditioning shape subconscious beliefs about worth, safety, and what’s possible—often limiting women and people socialized as women. How competence can become a survival strategy (and a trap): We discussed how many high-achieving women over-rely on competence—constant certifications, over-preparation, over-functioning—as a way to feel safe, which masks deeper issues of self-worth and receiving (including receiving money) and keeps them stuck in burnout rather than aligned, confident leadership. How Debbie coaches clients to work with their nervous system and beliefs: Debbie uses tools like nature walks, perspective-taking frameworks (inspired by indigenous medicine wheel concepts), deep exploration of family-of-origin stories, and gratitude practices to help clients slow down, surface subconscious narratives, and then unwind and rewrite those beliefs. Why play and presence are essential antidotes to hustle and burnout: We contrasted “hustle” (pressure, urgency, victim-y to-do lists) with an approach where play, fun, and presence are central. Debbie argued that work is never “done,” especially for entrepreneurs, so tying play to “after the work” guarantees burnout; instead, integrating joy and play into life and business actually attracts more clients, money, and sustainable success. Featured: Join Debbie's free monthly masterclass called The Embodied CEO: https://thelituplife.com/attraction Book a free 1:1 consultation for executive coaching with Jamie Lee: https://www.jamieleecoach.com/apply Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

August 13, 2026Episode 13815 min

How to Be Gracefully Assertive

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 are going 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 asserted their needs -- in the boardroom or in the bedroom. Click here to register for free. In this episode, I share my definition of Gracefully Assertive. Because it's neither a script nor a gender tax you have to pay for having a need and a voice, but a particular way you relate to yourself first and to others second. I unpack why that makes it a powerful way to walk into a risky conversation and state what you need, cleanly and simply. Featured in this episode: Register to join the live event on Thursday, August 20th: Gracefully Assertive for Women Who've Been Told They're Too Much: https://us02web.zoom.us/meeting/register/OjxWC_LhQH2WNfRR91embw#/registration Self-Advocacy is an Act of Service (Podcast): https://podcast.jamieleecoach.com/2033808/episodes/11189143-self-advocacy-is-an-act-of-service How to Get Promoted and Better Paid with a Compelling Ask (Podcast): https://podcast.jamieleecoach.com/2033808/episodes/12320542-how-to-get-promoted-and-better-paid-with-a-compelling-ask Learn more about 1:1 executive coaching with Jamie (Philosophy, Process, Pricing): https://www.jamieleecoach.com/apply Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

August 4, 2026Episode 13643 min

Postpartum Dads, First-Gen Pressure, and Leaving Corporate to be a Healer with Psychotherapist Steve Alexander Jr. and Executive Coach Jamie Lee

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 too complex, too emotional, or too different for the spaces they’re in. We unpack what happens when you’ve tied your identity and self-worth to a job that was never designed with you in mind, and how to reclaim a sense of self that isn’t dependent on a title, paycheck, or corporate hierarchy. We also talk about the very real gap between how walking into spaces feel for the “male and pale” default versus those of us who are marginalized, and why naming that difference is a powerful first step toward healing, agency, and change. What You'll Learn: What it's like to leave a “safe” corporate job when you’re first-gen and carrying family expectations about money, success, and stability. How tying your identity and self-worth to your job—especially in environments not built for you—can fuel depression, burnout, and feeling “not enough.” Why postpartum mental health matters for both mom and dad, and how anger, anxiety, and loss of autonomy can show up differently from the stereotypical picture of depression. How being Black, first-gen, and highly sensitive in predominantly white, male spaces shapes the way you see yourself, your power, and what feels “allowed” for you. What becomes possible when you stop trying to fit into any one box and start building a life, career, and identity that actually reflect your full, complex self. What Steve’s group practice, New York Wellness Counseling Services , offers first-gen, third-culture, and “don’t-fit-in-a-box” clients—through trauma-informed therapy (including EMDR) for people navigating multiple identities in New York and New Jersey. How Jamie’s work as an executive coach for professional women and entrepreneurs helps clients make more money, build confidence, and negotiate for the roles and recognition they want Featured Learn more about Steve Alexander's NY Wellness Counseling Services, a virtual group therapy practice serving clients across New York and New Jersey: https://www.nywellness.com ⁠ Connect with Steve on LinkedIn: https://www.linkedin.com/in/stevealexanderjr/⁠ Follow Steve on Instagram: https://www.instagram.com/thenywellness Learn more about Jamie's 1:1 coaching practice: https://www.jamieleecoach.com/about Connect with Jamie on LinkedIn: https://www.linkedin.com/in/leejieunjamie/ Follow Jamie on Instagram: https://www.instagram.com/jamieleecoach/ Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

July 29, 2026Episode 13553 min

We’re All Going to Die: Money, Love, and the Treasure Map with Allie Irwin and Jamie Lee

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 week after a loved one dies—when you’re forced to make 80+ decisions at about 20% brain capacity. This is end‑of‑life planning without the euphemisms. Together we unpack why we avoid talking about death, how to turn that avoidance into radical preparedness , and why doing this work now can shift your relationships, your money, and even your career choices . Ultimately, this conversation is a celebration of life , the people we cherish, and living with real authenticity and integrity . What you'll learn: How end-of-life preparedness can actually be an act of care, freedom, and service to the people you love How simple planning (like updating beneficiaries and listing accounts) helps you avoid devastating and expensive mistakes How doing a “Treasure Map” style audit often leads people to literally find money—forgotten retirement accounts, double-charged interest, unused benefits What actually happens in the first week after a death, and why 80+ decisions at 20% brain capacity is a terrible time to start planning How talking about death surfaces unspoken expectations, invisible labor, and power dynamics in relationships—and can deepen appreciation for your partner What emotional regulation and hypnosis tools (like Havening) can do to help you stay present and grounded in the midst of grief and big conversations How contemplating your own mortality can clarify your true priorities and catalyze bold choices in money, work, and life Featured: Learn more about Allie on her website: www.allieirwin.com Follow her on Instagram: https://www.instagram.com/allie.p.irwin/ Treasure Map with Allie Irwin: https://allieirwin.com/treasure-map/ Learn more about Jamie on her website: www.jamieleecoach.com Follow Jamie on Instagram: https://www.instagram.com/jamieleecoach/ 1:1 Executive Coaching with Jamie: https://www.jamieleecoach.com/apply Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

July 21, 2026Episode 13416 min

Anti-Networking: The Surprising Power of Not Asking for Anything At All

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?" I explain it in detail in this episode. What you'll learn: How not asking for anything in preliminary conversations can grow your negotiation leverage for job offer or promotion negotiation Key questions I ask about my client's organization’s promotion cycle, decision-makers, and influencers and why answering those questions matter How curious, no-ask conversations across functions and levels help you better understand the system and negotiate better outcomes How can you use informational interviews to cut through information asymmetry when you’re negotiating a job offer or raise? Case Study 1: How a client used informational interview to secure a $250K base salary as director of finance at an AI startup Case Study 2: How another client used informational interviews to compel her boss to secure the highest pay increase possible as director of marketing What you'll learn and gain from joining Anti-Networking workshop with Sarah-Neel and me on Friday, July 24th Mentioned: Interview with client Grace Anniskett: https://podcast.jamieleecoach.com/2033808/episodes/12125488-from-minimum-wage-to-ceo-with-grace-anniskett-of-anniskett-consulting-group Interview with client Sarah-Neel Smith: https://podcast.jamieleecoach.com/2033808/episodes/19111448-50-raise-self-advocacy-informational-interviews-sarah-neel-smith-phd-with-coach-jamie-lee Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

July 21, 2026Episode 13350 min

Diverse Books and Risky Career Pivots with Literary Agent Kat Kerr and Executive Coach Jamie Lee

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 some of our favorite Asian American authors, why representation in literature matters, the realities of the publishing industry (including agents, querying, and self-publishing), and what it really takes to take bold risks for your career, your values, and your family. You'll learn: Why diverse representation of marginalized voices is not a luxury, but foundational to empathy, identity, and genuine human connection How advocacy and self-advocacy are learned, practiced skills—and what mindsets make it possible to speak up when it feels risky How Kat’s decision to speak up boldly against bigoted remarks in high school created a ripple effect that emboldened other students of color to advocate for themselves How traditional publishing, self-publishing, and hybrid models are different and how authors can make informed business choices that fit their goals and resources How taking big, values-aligned risks (for your family, identity, and justice) reshape your career and your life, even when success isn’t guaranteed Why building or joining supportive communities—like We Need Diverse Books or identity-centered indie bookstores—matter so much for writers and readers from marginalized backgrounds Featured: Kat's agency, Donald Maass Literary Agency: https://maassagency.com/ Yu & Me Bookstore in NYC: https://yuandmebooks.com/ Jamie's coaching practice https://www.JamieLeeCoach.com/ Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

July 14, 2026Episode 13249 min

Building Bridges Across Cultures: Redefining Leadership with Ai Asakura of TOMODACHI Initiative and Executive Coach Jamie Lee

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 same eclectic, cross-cultural energy as New York City, where you connect peer to peer with people from all walks of life. Ai is bicultural like me, and she's spent her career building bridges — between Japan and the U.S., and between mentees and the mentors who help shape their paths. But it took her some time to recognize being bicultural as her own superpower, and when she did, it empowered her to say yes to an opportunity most people would've handed to someone with a bigger title. Key Takeaways Leadership is not a job title : You can be a leader as a mentor, a community organizer, a parent, or a volunteer—impact and initiative matter more than status. Networking is people-to-people connection, not transaction : Powerful “networking” often looks like simply being curious about others and building genuine human relationships. Bicultural identity is a superpower : Living between cultures, as Ai does between Japan and the U.S., creates unique insight, empathy, and the ability to act as a bridge. Opportunities often arrive through community : Ai’s major career transitions—from hospitality to translation to TOMODACHI—came through relationships and community involvement. Saying yes can be the real “risky conversation” : Accepting the invitation to represent her region as a mentor felt risky to Ai, but turning it down would have meant betraying the message she gives her mentees about stepping up. Operation TOMODACHI to TOMODACHI Initiative : The humanitarian response to the 2011 Great East Japan earthquake evolved into a long-term leadership and exchange program impacting over 10,000 alumni. Exposure to hope changes trajectories : Young people from disaster-affected regions returned from U.S. programs with renewed hope, agency, and a desire to rebuild their communities. Community work can clarify your own identity : Serving Japanese communities in the U.S. helped Ai reconnect to her Japanese roots and recognize her role as a cultural bridge. Curiosity is a core leadership habit : Being genuinely interested in people—their stories, cultures, and experiences—naturally expands your world and your opportunities. There is still hope in the world : Despite global uncertainty, Ai emphasizes that human-to-human connection, especially across cultures, is a powerful source of hope. Featured Connect with Ai Asakura on LinkedIn: https://www.linkedin.com/in/ai-asakura0977/ Learn about the US-Japan Council: https://www.usjapancouncil.org/ Connect with Jamie Lee on LinkedIn: https://www.linkedin.com/in/leejieunjamie/ Learn about 1:1 executive coaching with Jamie Lee here: https://www.jamieleecoach.com/apply Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

July 7, 2026Episode 13120 min

How to Exit Toxic Jobs and Make More Money Without Burning Bridges: Two Client Case Studies

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 situation and actually land on your feet? What strategies, support, and resources do you need to negotiate before you promote yourself to CEO of your life, your career, and your own company? In this episode, I'm showing you exactly that—through two real women, my coaching clients, who exited toxic jobs and made it work. One doubled her income by negotiating her exit strategically. One quadrupled hers. Both knew exactly what to ask for and who to ask it from. Their stories are your roadmap. Let's dig in. Featured: https://podcast.jamieleecoach.com/2033808/episodes/12125488-from-minimum-wage-to-ceo-with-grace-anniskett-of-anniskett-consulting-group Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

June 30, 2026Episode 13022 min

How to Pivot in Your Career, Claim Your Value, and Negotiate Higher Pay: A Case Study

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, which happen to be the ones you're already using every day. And then I'm diving deep into the first step of the sovereign framework: Vote For Yourself . You'll see exactly how this played out for one of my clients, Sarah Neel, who went from burnt out professor to increasing her pay 7% and then again by 50% while successfully pivoting into a new career. I'm also introducing you to something called the "locus of control" – a fancy phrase for addressing this key question: Who's actually in charge here? And once you answer that question honestly, everything changes. [Quick note: This is a recording of a live training we ran earlier this year called “Exit Negotiations: How to Get Better Paid So You Can Become Your Own Boss.” To stay in the loop for the next live training, take the 2-minute Leadership Archetype quiz at http://www.jamieleecoach.com and subscribe to the weekly newsletter.] Featured: https://podcast.jamieleecoach.com/2033808/episodes/19111448-50-raise-self-advocacy-informational-interviews-sarah-neel-smith-phd-with-coach-jamie-lee Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com

June 23, 2026Episode 12922 min

De-Risking Pay Negotiation for Women Professionals: Three Core Skills to Implement Right Away

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 about what negotiation actually is. In this episode, I'm sharing why I walked away from a six-figure tech career to become my own boss and an independent coach. And I'm showing you the one mindset shift that changed everything for me and my clients. We're talking sovereignty, locus of control, and why that metaphorical tiara (as in: recognition and respect) you're waiting for? You have to put it on your own head. Stick around. This one's foundational. [Quick note: This is a recording of a live training we ran earlier this year called “Exit Negotiations: How to Get Better Paid So You Can Become Your Own Boss.” To stay in the loop for the next live training, take the 2-minute Leadership Archetype quiz at www.jamieleecoach.com and subscribe to the weekly newsletter.] Text me your thoughts on this episode! Enjoy the show? Don't miss an episode, listen and subscribe via Apple Podcasts or Spotify . Leave me a review in Apple Podcasts . Connect with me Book a free hour-long consultation with me . You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1. Connect with me on LinkedIn Email me at jamie@jamieleecoach.com