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F'ing Up

F'ing Up

Hosted by Deanne Rhynard

Episodes

49

Latest episode

Jul 2026

Language

EN-US

About the show

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.

Listen to episodes

49 recent
July 15, 2026Episode 51 hr 0 min

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

Send a private message to Host, Deanne RhynardSylvia 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/newsletterSupport the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

July 1, 2026Episode 450 min

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 RhynardAtul 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 pathsWhy “success on paper” can mask deeper misalignmentThe pressure and identity trap of startups and high-growth rolesExperiencing total life collapse at 38—and what it takes to rebuildNavigating mental health challenges, including a bipolar diagnosisThe impact of honesty and vulnerability in pivotal career momentsLetting go of identity tied to work and redefining personal successWhy external outcomes don’t always reflect effort, talent, or capabilityFinding peace, autonomy, and fulfillment later in lifeThis 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/newsletterSupport the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

June 17, 2026Episode 31 hr 9 min

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

Send a private message to Host, Deanne RhynardKatie 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 growthBuilding confidence after being told you’re not enoughNavigating career setbacks and self-doubtPersonal growth through adversityRedefining success and identity at workThis 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/newsletterSupport the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

June 3, 2026Episode 245 min

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 RhynardJosh 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 uncertaintyLetting go of identity and redefining purposeRebuilding your life after everything changesMental resilience and perspective through adversityFinding meaning beyond achievement and performanceThis 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/newsletterSupport the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

May 20, 2026Episode 11 hr 11 min

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

Send a private message to Host, Deanne RhynardStephanie 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 validationThis 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/newsletterSupport the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

May 14, 20260 min

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

Send a private message to Host, Deanne RhynardEpisode 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/newsletterSupport the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

February 19, 2025Episode 1453 min

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

Send a private message to Host, Deanne RhynardPhilip 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 EILPhilip 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 showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

February 5, 2025Episode 1354 min

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 RhynardIn 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 KhanMishae 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 showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

January 22, 2025Episode 1230 min

I Was Told I Wasn’t Good Enough [Lyle Adams - S3 Ep12]

Send a private message to Host, Deanne RhynardDescription:This episode is a raw and unfiltered look at what happens when careers come to abrupt ends, rejection feels relentless, and self-doubt begins to creep in. From the business of professional sports to the emotional toll of career pivots, Lyle shares that resilience isn't about never falling—it's about getting back up, again and again.Episode Takeaways:Coping with Rejection: Why hearing “no” is inevitable—and how to move forward when it feels like no one is saying “yes.”Navigating Career Transitions: The emotional challenges of leaving one dream behind and figuring out what’s next.The Struggle of Starting Over: Whether it’s pounding the pavement for a new job or launching a business from scratch, starting over isn’t glamorous.Facing Self-Doubt: How comparison, rejection, and setbacks fuel doubt.About Lyle Adams:Lyle Adams is the CEO of Spry, a software solution designed specifically for athletic organizations. Before founding  Spry, he worked at Uber and LivingSocial. He completed his undergraduate degree from Wake Forest University and his graduate degree from Columbia University. In his spare time, Lyle loves to solve the Rubik's Cube.Support the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

January 8, 2025Episode 1142 min

Imposter Syndrome Made Me Feel Behind [Ashley Chang - S3 Ep11]

Send a private message to Host, Deanne RhynardDuring this episode with Ashley Chang, we dive deep into the  reality of work, growth, and the constant pressure to prove yourself. From job searches filled with self-doubt to leadership roles that come with unforeseen challenges, this episode unpacks the highs, lows, and everything in between.Episode Takeaways:The Comparison Trap: How measuring yourself against others—especially polished success stories—can hold you back.Leadership Challenges: Managing through layoffs and navigating the emotional toll of tough decisions.Starting Over: What it really takes to build something from scratch and why it’s never as simple as it seems.The Weight of Expectations: Why success doesn’t always feel like you thought it would and facing not realizing the feelings of success.About Ashley:Ashley Chang is the co-founder and CEO of Sundays, an executive assistant service for working parents. She’s on a mission to accelerate parents in their careers while creating more quality time for family. Before starting Sundays, she worked in the technology industry across all stages of companies – she was the first employee at developer tool company ReadMe and helped scale Carta’s Venture Capital business from 10 to $100M+.Support the showThe views, thoughts, and opinions expressed are the speakers’ own and do not represent theviews, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.

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