F'ing Up

Deanne Rhynard
  • 5.0 (20)
  • Careers
  • Updated Biweekly

F’ing Up is a podcast that peels back the highlight reel of success. Hosted by Deanne Rhynard, each episode features accomplished guests who share the messy, real, and often uncomfortable parts of their journeys—the moments that shaped their eventual success. In a world where social media sells the illusion of overnight success, F’ing Up reminds listeners (especially those early in their careers or considering a major pivot) that growth is never linear. Deanne invites guests to drop the polished narrative, explore their stumbles, and reflect on what those experiences taught them in real time. Because the truth is: what we often label as failure is usually just part of the climb. After all, we’re all F’ing Up. ABOUT THE HOST Deanne Rhynard is a Success Mentor and the Host of The F’ing Up Podcast, where she translates failure into clarity, confidence, and momentum. Known for her grounded honesty and sharp emotional intelligence, she helps people cut through noise, confront blind spots, and define success on their own terms. Before launching F’ing Up, Deanne spent nearly two decades as a Chief People Officer and startup advisor, helping companies navigate the messy, high-pressure stages of growth and scale. She shaped culture and leadership at organizations including Performio and Olo—the restaurant-tech pioneer where she scaled the team more than 30x, led the company through an IPO and two acquisitions, and built a remote-first culture well before the rest of the world caught up. Her background spans people operations, corporate relations, and management roles at the UVA Darden School of Business, KKR, Marriott, and several early-stage startups. This breadth gives her an uncommon ability to read people quickly and understand what unlocks their potential—whether they’re early in their career or leading from the C-suite. Deanne holds a Bachelor of Arts in Business from Walla Walla University and lives in Washington State with her husband and three children.

  1. Jul 15

    I Turned Down a CIO Role Because I Was Afraid [4.5 Sylvia Kwan]

    Send a private message to Host, Deanne Rhynard Sylvia Kwan shares what it looks like to build a successful career without a clear plan—and the moments along the way that force you to question everything you thought success would be. In this episode of The F’ing Up Podcast, we explore the reality behind a nonlinear career—from following the rules and staying invisible, to navigating missed opportunities, fear-driven decisions, and roles that didn’t turn out the way she expected. If you’ve ever felt unsure of your path, struggled to advocate for yourself, turned something down out of fear, or realized too late that a role wasn’t right for you, this conversation will resonate deeply. Topics include: - Growing up with the belief that hard work should speak for itself—and realizing it doesn’t - Building a career by following curiosity and optionality, not a defined plan - Walking away from paths that looked “right” but didn’t feel right - The reality of being underpaid and not advocating for yourself - Learning that visibility—not just performance—is required to grow - Turning down a career-defining opportunity out of fear—and the regret that followed  - Finally taking the leap… into a role she knew on day one was wrong  - Navigating a toxic environment and choosing to walk away to protect her mental health  This is the real side of success most people don’t talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

    I Turned Down a CIO Role Because I Was Afraid [4.5 Sylvia Kwan]

  2. Jul 1

    My Life Looked Fine, It Wasn't, And Then It Completely Fell Apart at 38 [4.4 Atul Sood]

    Send a private message to Host, Deanne Rhynard Atul Sood shares what it looks like to build, lose, rebuild—and ultimately redefine success on his own terms. In this episode of The F’ing Up Podcast, we explore the reality behind entrepreneurial highs and devastating lows—from leading and scaling companies to losing everything in the span of a month, including his career, identity, and mental health. If you’ve ever tied your worth to your work, questioned your path after a major setback, or found yourself starting over when life didn’t go according to plan, this conversation will resonate deeply. Topics include: Building a career through relationships, not traditional paths Why “success on paper” can mask deeper misalignment The pressure and identity trap of startups and high-growth roles Experiencing total life collapse at 38—and what it takes to rebuild Navigating mental health challenges, including a bipolar diagnosis The impact of honesty and vulnerability in pivotal career moments Letting go of identity tied to work and redefining personal success Why external outcomes don’t always reflect effort, talent, or capability Finding peace, autonomy, and fulfillment later in life This is the real side of success most people don’t talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

    My Life Looked Fine, It Wasn't, And Then It Completely Fell Apart at 38 [4.4 Atul Sood]

  3. Jun 17

    I Created Something Special—Then Had to Walk Away [4.3 Katie Svilich]

    Send a private message to Host, Deanne Rhynard Katie Svilich shares the story behind her career — including the self-doubt, setbacks, and internal battles that shaped her path. In this episode of The F’ing Up Podcast, we explore what it feels like to navigate high-performance environments while questioning your own worth, and how those moments can ultimately redefine your confidence and career trajectory. If you’ve ever struggled with imposter syndrome, workplace confidence, or feeling underestimated at work, this conversation will resonate deeply. Topics include: Imposter syndrome in leadership and career growth Building confidence after being told you’re not enough Navigating career setbacks and self-doubt Personal growth through adversity Redefining success and identity at work This is the side of success most people don’t talk about. -- 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

    I Created Something Special—Then Had to Walk Away [4.3 Katie Svilich]

  4. Jun 3

    I Wasn’t Driven by What I Wanted, But By What I Might Lose [4.2 Josh Perry]

    Send a private message to Host, Deanne Rhynard Josh Perry shares the untold story behind his career — including facing a life-threatening brain tumor, walking away from professional BMX, and rebuilding his identity from the ground up. In this episode of The F’ing Up Podcast, we explore what it means to confront your own mortality, let go of the identity you thought defined you, and find purpose on the other side of uncertainty. If you’ve ever experienced a major life disruption, identity shift, or been forced to start over, this conversation will resonate deeply. Topics include: Facing a life-altering diagnosis and uncertainty Letting go of identity and redefining purpose Rebuilding your life after everything changes Mental resilience and perspective through adversity Finding meaning beyond achievement and performance This is the side of success most people don’t talk about. 🔔 Subscribe for more real conversations about career growth, failure, and success 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

    I Wasn’t Driven by What I Wanted, But By What I Might Lose [4.2 Josh Perry]

  5. May 20

    I Became a Fortune 500 CMO While My Life Was Falling Apart [4.1 Stephanie McCarty]

    Send a private message to Host, Deanne Rhynard Stephanie McCarty shares the story behind her rise to becoming a Fortune 500 CMO — while her personal life was quietly unraveling behind the scenes. In this episode of The F’ing Up Podcast, we explore what it really looks like to achieve massive career success while navigating personal hardship, and how those parallel realities shape who you become as a leader. If you’ve ever felt like you’re holding it all together on the outside while struggling internally, or questioned whether success is worth the cost, this conversation will resonate deeply. Topics include: - Building a high-powered career during personal adversity - What success looks like from the inside vs. the outside - Navigating leadership while your life is falling apart - The emotional toll of ambition and achievement - Redefining success beyond titles and external validation This is the side of success most people don’t talk about. 🔔 Subscribe to the F’ing Up YouTube channel for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

    I Became a Fortune 500 CMO While My Life Was Falling Apart [4.1 Stephanie McCarty]

  6. Season 4 Trailer

    Season 4 Trailer: Successful People. Messy Careers. Real Stories.

    Send a private message to Host, Deanne Rhynard Episode 1️⃣ of Season 4️⃣ drops on May 2️⃣0️⃣!!  Subscribe to the F’ing Up Podcast where ever you watch/listen to podcasts! The F’ing Up Podcast is dedicated to sharing real truths about the career journeys of successful individuals. Host, Deanne Rhynard, interviews these individuals, points out what they’ve achieved and immediately throws that out the window and focuses on the tripping hazards along the way. Society has programmed us, largely by way of social media, to think success happens easily and overnight. Deanne points out the realities and humanizes the experience by asking probing questions and urging guests to be vulnerable. 🔔 Subscribe for more real conversations about career growth, failure, and success: https://www.youtube.com/@finguppodcast?sub_confirmation=1 🎧 Listen on all platforms: https://www.buzzsprout.com/2057719 💬 Work with Deanne: https://www.iamfingup.com/you 📨 Subscribe to The Art of F’ing Up Newsletter: https://www.iamfingup.com/newsletter Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

  7. 02/19/2025

    I Was Miserable During My “Best” Years [Philip Eil - S3 Ep14]

    Send a private message to Host, Deanne Rhynard Philip Eil opens up about anxiety, quiet suffering, and the disorientation of feeling unwell during a season that was supposed to feel joyful and successful. ------------------- In this deeply honest and vulnerable episode, we dive into the personal journey of dealing with anxiety, depression, and the profound effects they've had on both personal and professional life. Philip Eil opens up about the challenges of battling mental health, facing rejection, and pushing through discomfort to pursue his passions. This episode explores the messy realities of self-doubt and rejection. Through all the turmoil, this guest has emerged stronger, finding healing through writing, commitment to therapy, and a sense of purpose in sharing their experiences with the world. Key topics in this episode: The raw emotions behind not following the traditional milestones of adulthood (marriage, homeownership, etc.).The discomfort of being in a job that doesn’t align with your talents and the struggle to find what’s next.Overcoming rejection: how 25 publishers passed on the guest’s book, and the emotional rollercoaster of freelance journalism.A candid discussion about the realities of mental health struggles, including the times it’s knocked them completely out of action.The power of vulnerability and why writing about mental health has become a source of healing and purpose.This episode serves as a reminder that mental health is just as important as physical health and that we are all in this together. If you've ever struggled with your own mental health or faced rejection in your journey, this one is for you. ABOUT PHILIP EIL Philip Eil is an award-winning freelance journalist based in his hometown, Providence, Rhode Island. He is the former news editor of the alt-weekly newspaper, The Providence Phoenix. Since the paper’s close in 2014, he has contributed to The Atlantic, Men’s Health, the Boston Globe, Huffington Post, and the Columbia Journalism Review, among other outlets. He has also taught writing and journalism classes at Brown University, Columbia University’s School of the Arts, and the Rhode Island School of Design. He holds an MFA in Nonfiction Writing from the Columbia University School of the Arts. Prescription for Pain is his first book. Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

    I Was Miserable During My “Best” Years [Philip Eil - S3 Ep14]

  8. 02/05/2025

    The Year I Got My Dream Job at Google—and Then I Fell Apart [Mishae Khan - S3 Ep13]

    Send a private message to Host, Deanne Rhynard In this raw and heartfelt episode, we dive deep into the chaos of life, career, and self-discovery. From navigating societal pressures to figuring out how to rewrite the rules of success, this episode is a battle cry for anyone who feels like they’re “f’ing it up”. Mishae Khan shares her journey of the immense pressures placed on immigrant children, the relentless pursuit of external validation, and the grind of trying to live up to others' expectations—all while discovering the courage to live authentically. This episode highlights the following: The dangers of expecting overnight success and perfection.How societal and family expectations shape our self-worth and career paths.The emotional toll of navigating parental expectations, including stories of retaking the MCAT and finding identity beyond others' approval.The overwhelming pressure of trying to balance humility and confidence in a world obsessed with highlight reels.The toxic cycle of feeling like you’re never doing “enough” and the importance of learning to love and care for yourself. About Mishae Khan Mishae Khan is figuring it out as she goes. She's an investor, soon to be author and founder.  Leaving the world better than she found it is her obsession. Her company Bold&Kind is a jewelry meets affirmations brand focused on changing the self talk of women that are too hard on themselves. She's no stranger to high pressure environments having worked for 10+ years in training and operations at companies like Google and Samsung. Her designs focus on changing women's inner narrative and have been in publications like Vogue, Glamour and Vanity Fair UK. She's most excited about her puppy getting over his teething phase and editing her book.  Support the show The views, thoughts, and opinions expressed are the speakers’ own and do not represent the views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

    The Year I Got My Dream Job at Google—and Then I Fell Apart [Mishae Khan - S3 Ep13]
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Trailers

5
out of 5
20 Ratings

About

F’ing Up is a podcast that peels back the highlight reel of success. Hosted by Deanne Rhynard, each episode features accomplished guests who share the messy, real, and often uncomfortable parts of their journeys—the moments that shaped their eventual success. In a world where social media sells the illusion of overnight success, F’ing Up reminds listeners (especially those early in their careers or considering a major pivot) that growth is never linear. Deanne invites guests to drop the polished narrative, explore their stumbles, and reflect on what those experiences taught them in real time. Because the truth is: what we often label as failure is usually just part of the climb. After all, we’re all F’ing Up. ABOUT THE HOST Deanne Rhynard is a Success Mentor and the Host of The F’ing Up Podcast, where she translates failure into clarity, confidence, and momentum. Known for her grounded honesty and sharp emotional intelligence, she helps people cut through noise, confront blind spots, and define success on their own terms. Before launching F’ing Up, Deanne spent nearly two decades as a Chief People Officer and startup advisor, helping companies navigate the messy, high-pressure stages of growth and scale. She shaped culture and leadership at organizations including Performio and Olo—the restaurant-tech pioneer where she scaled the team more than 30x, led the company through an IPO and two acquisitions, and built a remote-first culture well before the rest of the world caught up. Her background spans people operations, corporate relations, and management roles at the UVA Darden School of Business, KKR, Marriott, and several early-stage startups. This breadth gives her an uncommon ability to read people quickly and understand what unlocks their potential—whether they’re early in their career or leading from the C-suite. Deanne holds a Bachelor of Arts in Business from Walla Walla University and lives in Washington State with her husband and three children.

Information

  • Creator
    Deanne Rhynard
  • Years Active
    2022 - 2026
  • Episodes
    49
  • Rating
    Explicit
  • Copyright
    © 2026 F'ing Up
  • Show Website
    F'ing Up

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