How to Be Gracefully Assertive

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#/registrationIn this episode, you’ll learn how to:Recognize the “coverage trap” and the subtle ways over-functioning keeps you stuck at the status quoShift from quiet competence to clear articulation of your impact, future vision, and specific asksUse 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 raiseIf 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 meBook 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 philanthropyThe 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 safetyHow 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 checksHow 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 careerI 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.meInstagram: @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 meBook 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/assessmentConnect 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/applyConnect 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 meBook 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 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/attractionBook a free 1:1 consultation for executive coaching with Jamie Lee: https://www.jamieleecoach.com/applyText 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 meBook 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] 

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 asserted their needs -- in the boardroom or in the bedroom. Watch the replay on YouTube here: https://www.youtube.com/watch?v=Eun63CwmgOYIn 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: Watch the replay of live event recorded on Thursday, August 20th: Gracefully Assertive for Women Who've Been Told They're Too Much: https://www.youtube.com/watch?v=Eun63CwmgOYSelf-Advocacy is an Act of Service (Podcast): https://podcast.jamieleecoach.com/2033808/episodes/11189143-self-advocacy-is-an-act-of-serviceHow 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/applyText 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 meBook 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] 

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 wantFeaturedLearn 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.com⁠Connect with Steve on LinkedIn: https://www.linkedin.com/in/stevealexanderjr/⁠Follow Steve on Instagram: https://www.instagram.com/thenywellnessLearn 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 meBook 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] 

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 loveHow simple planning (like updating beneficiaries and listing accounts) helps you avoid devastating and expensive mistakesHow doing a “Treasure Map” style audit often leads people to literally find money—forgotten retirement accounts, double-charged interest, unused benefitsWhat actually happens in the first week after a death, and why 80+ decisions at 20% brain capacity is a terrible time to start planningHow talking about death surfaces unspoken expectations, invisible labor, and power dynamics in relationships—and can deepen appreciation for your partnerWhat emotional regulation and hypnosis tools (like Havening) can do to help you stay present and grounded in the midst of grief and big conversationsHow contemplating your own mortality can clarify your true priorities and catalyze bold choices in money, work, and lifeFeatured: Learn more about Allie on her website: www.allieirwin.comFollow 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.comFollow Jamie on Instagram: https://www.instagram.com/jamieleecoach/1:1 Executive Coaching with Jamie: https://www.jamieleecoach.com/applyText 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 meBook 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] 

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 outcomesHow 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-groupInterview 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-leeText 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 meBook 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 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 connectionHow advocacy and self-advocacy are learned, practiced skills—and what mindsets make it possible to speak up when it feels riskyHow 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 themselvesHow traditional publishing, self-publishing, and hybrid models are different and how authors can make informed business choices that fit their goals and resourcesHow taking big, values-aligned risks (for your family, identity, and justice) reshape your career and your life, even when success isn’t guaranteedWhy building or joining supportive communities—like We Need Diverse Books or identity-centered indie bookstores—matter so much for writers and readers from marginalized backgroundsFeatured: 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 meBook 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 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 TakeawaysLeadership 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.FeaturedConnect 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/applyText 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 meBook 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]