Risky Conversations with Jamie Lee

In 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.

Thirteen years later, I'm sharing what that day gave me: relief from a job that was never going to fit, and the first glimmer of the coaching work I do now.

I also tell the stories of three clients who each felt grief, doubt, or panic with a spark of "what if" right beside it, and what they built from it.

If your heart is breaking today, this episode is for you.

When you're ready for 1:1 support, you can book a free consultation with me at http://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. 

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• 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 [email protected] 

When 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 if that would pacify me. 

I said no, because that was not the moment for grace, and that story is exactly why Sade Curry and I spent Part 2 of our open discussion stress-testing the framework. 

If gracefully assertive only ever meant staying polite, it would be one more way of telling women to behave, so we dug into where a boundary ends and control begins, what to do about people who genuinely push their way through your door, and when the most effective move is to drop the grace and be blunt, messy, or angry. 

Whether you're asking for a raise from a boss who keeps ignoring your emails or dealing with a bully looking for a target, you'll leave with a clearer sense of which tool to reach for and when.

In this episode, we tackle:

• You are not your job: how does individuation show up at work, and why is managing other people's disappointment not your business?
• When does setting a boundary turn into controlling someone?
• Is asking your boss to find out the maximum raise manipulation, or just a smart request?
• What if some people genuinely are too much, and how can a woman know she's right?
• What can you do when you keep asking for things and keep getting the same result?
• When is it right to drop the grace and be blunt, messy, or angry?

More on this: 

• Watch the full video replay of this episode on YouTube: https://www.youtube.com/watch?v=Eun63CwmgOY
• Learn about Sade Curry: https://sadecurry.com/
• Learn about Jamie Lee: 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 [email protected] 

Once 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 was told I was too loud, with a "will you please pipe down" tone.

Here's what I noticed: "too much" in other people's estimation can just mean "different from the version they were used to."

In this first part of my open discussion with divorce coach Sade Curry, we dig into the traps that open up when you've evolved and the people around you still hold you to an outdated set of expectations, from the ex who still expects your automatic yes to the employer who bristles when you finally ask for what you want.

We brought dating, work, and co-parenting into one dialogue because the same pull to shrink and accommodate follows you into every room, and the same skill of reading the room with grace lets you stay assertive without losing your spine or your warmth.

If the people who liked the old you are making your growth feel like a problem, this one is for you.

In this episode, we tackle:

• Who gets to decide whether a woman is "too much"?
• What happens when people liked you better when you were accommodating?
• What is individuation, and how does it help you stop managing another adult's thoughts, feelings, and reactions?
• Can being direct kill the spark in dating, and what's really happening when you attract the wrong people?
• Can asking for what you want backfire at work, and what can you do instead of making one-sided demands?
• Is "graceful" just one more thing women have to get right?

More on this: 

• Watch the full video replay of this episode on YouTube: https://www.youtube.com/watch?v=Eun63CwmgOY
• Learn about Sade Curry: https://sadecurry.com/
• Learn about Jamie Lee: 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 [email protected] 

What 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 got me into dance classes for a whole year. 

In this episode, she shares how Zouk taught her to embody leadership in a new way, and how she landed the exact job and salary she wanted after everyone told her that it would be "impossible." 

What You'll Learn

• What partner dancing teaches you about trust, control, and leading people at work
• How Kimberly got her dream job at her exact salary by getting crystal clear and telling everyone
• Why asking "How do I want to feel?" beats searching for the perfect script
• How to move through fear by giving equal time to what could go right
• How your body holds intelligence the mind chatter misses, from felt sense and interoception to nonverbal connection, and how they connect to leadership presence 

Follow us: 

• Kimberly Lai on LinkedIn: https://www.linkedin.com/in/kimberly-h-lai/
• Kimberly Lai (dancing) on Instagram: https://www.instagram.com/kimberlaidancing
• Jamie Lee on LinkedIn: https://www.linkedin.com/in/leejieunjamie/
• Jamie Lee 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 [email protected] 

If 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 motivating people the right way. 

In this episode, I walk through the exact reframe I taught a sales manager client to get her team motivated without micromanaging, making ultimatums, or losing her own voice in the process.

You'll walk away with the one sentence that turned dreaded work into shared ambition, and the mindset shift behind it you can use in your very next team meeting.

What You'll Learn in This Episode

• Why a system that wasn't built for you can make you feel like the problem, when you're over-performing yet under-earning 
• How to reframe the work your team dreads so they run toward it instead of away from it
• Why moving people toward a win beats moving them away from pain, and how to discern what precisely to say as a manager
• What happened in one coaching consultation that made my client say, "That just blew my mind. I'd never seen it that way!"
• How to book your free 1:1 consultation for executive coaching with me here: 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 [email protected] 

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 reflect on friendship, identity, and what it really takes to create spaces where unconventional, magical misfits can finally feel at home.

Key takeaways: 

• What it looks like to turn a non-linear career path—and even your lowest moments—into a uniquely powerful business and community.
• How building systems (not controlling people) helps leaders avoid burnout and create sustainable, values-driven organizations.
• Why queer third spaces and creative hubs like Iron Feather matter for belonging, resilience, and cultural change.

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 [email protected] 

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 of accountability and honest, risky conversations. If you’ve ever wondered how to stay relevant in an AI-driven world while staying true to your values, this episode is for you.

Takeaways:

• What you can do to reclaim agency in your tech career when layoffs, AI, and leadership decisions feel completely out of your control.
• How to identify, articulate, and communicate your unique expertise—especially when your product fails, sunsets, or gets shut down.
• Why communication is now a critical differentiator for technical professionals who want to thrive alongside AI, not be replaced by it.

Connect with us: 

• Femgineer website: https://femgineer.com
• Connect with Poorima on X: https://x.com/poornima
• Jamie Lee Coach website: https://www.jamieleecoach.com
• Connect with Jamie on LinkedIn: https://www.linkedin.com/in/leejieunjamie/

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 [email protected] 

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, no real recognition. Just more of the same.

In this conversation, I break down why this happens, how it quietly sabotages your career growth, and what you can start doing differently right now—without complaining, over-explaining, or becoming someone you’re not.

I’ll walk you through:

• The Tuesday status update scenario where you think you’re proving your readiness for a promotion, but you’re actually signaling “all good, nothing needs to change.”
• The hidden cost of believing “competence should speak for itself” as a woman, minority, or marginalized leader.
• Why the real gap between you and your next promotion is not working harder—it’s translation: turning the value you’re already delivering into language decision makers can act on.
• What you can expect on Friday, September 18th: The Over-functioning Woman's Negotiation Workshop, which you can register to attend for free here: https://us02web.zoom.us/meeting/register/338KqIokT9qGadSyouHnfw#/registration

In this episode, you’ll learn how to:

• Recognize the “coverage trap” and the subtle ways over-functioning keeps you stuck at the status quo
• Shift from quiet competence to clear articulation of your impact, future vision, and specific asks
• Use leadership-focused language that aligns your work with where the organization is headed—and makes it easier for decision makers to say “yes” to your promotion and raise

If you’ve ever watched a less competent but more outspoken colleague get the promotion you wanted, this episode is for you. 

Let’s stop unintentionally sabotaging your own growth by being “too good” at quietly covering—and start translating your value into the recognition, support, and advancement you’ve already earned.

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 [email protected] 

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 “spiritual but not religious” folks, and has been named to the Forbes 30 Under 30 list twice. 

Today, she blends executive coaching, spiritual care, interreligious theology, and community organizing to support nonprofit leaders and people in career transition who feel called to do work that actually aligns with their values.

We talk about:

• What it’s really like to grow a student group into a national nonprofit — and how idealism collides with the brutal realities of inequality and philanthropy
• The moment a Buddhist coach lobbed a “good grenade” into Alexis’s worldview by asking: “What would it feel like if you really believed the universe was benevolent?”
• Why capitalism functions like the dominant religion of our time, and how that shapes our sense of worth, success, and safety
• How fundraising can be a spiritual practice and civic act, not just “begging rich people for money”
• Why grassroots fundraising and small gifts can build more real power than a handful of billionaire checks
• How Alexis now helps nonprofit leaders and changemakers do “soul work”: interrogating their ideas about justice, money, and calling so they can make aligned decisions about leadership, transitions, and career

I also share some of my own story — from being a first-gen, lower-middle-class student navigating elite spaces, to getting seriously ill and having to confront what I am without my income or productivity. We connect this to the paradox that often, letting go of our tight grip on money and status is what finally frees us to ask for more, lead more boldly, and show up more fully.

If you’ve ever wrestled with questions like:

• How do I fundraise or get paid well without betraying my values?
• How do I hold onto hope and agency in a world that feels increasingly unequal and unjust?
• Can spirituality and ambition actually coexist?

…this conversation is for you.

Learn more about Alexis and her work:

• Website: AlexisMorin.me
• Instagram: @alexisrmorin (personal and business all-in-one, delightfully unhinged at times, in the best way)

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 [email protected] 

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 her journey across four different countries shaped her belief that you always have at least one more option available to you — especially when you feel stuck.

We also get honest about the messy, embodied side of being human: physical pain, hormones, fatigue, and those days when you just want to feel sorry for yourself (I have plenty of those myself). Irina shares how possibility thinking still applies on those days—without pretending everything is fine.

What you'll learn:

• Why surviving a micromanaging boss changed how Irina coaches: she now validates how bad it can really be, stops over‑indexing on “you can always fix it,” and helps clients build parallel options instead of staying stuck trying to change someone who doesn’t want to change.
• How possibility thinking works in practice:understanding all your options (including the ones you don’t like), choosing consciously, and then making peace with—and committing to—your choice so you don’t feel like you’re in a psychological jail.
• How your values and strengths become anchors on hard days: Irina shows how clarity on core values like freedom and fairness, and strengths like persistenceand speed, lets you take action even when you’re in pain, exhausted, or full of self‑doubt.
• Irina’s “possibility thinker” framework: inner, relational, and process possibilities—practical tools that help you expand what you see as possible so you never again feel like you’re truly starting from zero.
• How Irina’s international moves (Romania → Spain → Moldova → U.S.) shaped her worldview: why she now sees “country” as just one small variable, and how clarity about what you want can make even “risky” moves feel obvious rather than terrifying.

Featured in this episode: 

• Irina's Possibility Thinkers Assessment: https://irinacozma.com/assessment
• Connect with Irina on LinkedIn: https://www.linkedin.com/in/irinacozma/
• Jamie's 1:1 coaching for smart women who hate office politics: https://www.jamieleecoach.com/apply
• Connect with Jamie on LinkedIn: https://www.linkedin.com/in/leejieunjamie/

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 [email protected]