F'ing Up

Hosted by Deanne Rhynard

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Jun 2026

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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.

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46 recent

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.

December 18, 2024Episode 1053 min

I Lost My Mom… and Then I Lost My Job [Alexandre Seiler - S3 Ep10]

Send a private message to Host, Deanne RhynardDescription:In this episode, we explore the raw and unfiltered realities of professional and personal setbacks. From struggling with career uncertainty and mental health challenges to the lingering effects of toxic work cultures, we uncover the lessons learned in the face of adversity. This conversation is a reminder that no one’s journey is perfect, and “figuring it out” is often the most powerful step forward.Episode Takeaways:The Weight of Job Insecurity: How the fear of losing your livelihood can shape your mental and emotional state.Breaking Free from Toxic Environments: The emotional toll of staying in harmful workplaces and the liberation that comes with leaving.Overcoming Career Comparisons: Why success is often a matter of perception versus reality and how to focus on your own path.Facing Uncertainty with Grace: How to navigate moments of feeling lost in your career and find clarity without forcing it.ABOUT ALEXAlex Seiler has 15+ years of global experience in the People/HR space. He has spent time working in various industries and for companies such as Citi, NBCUniversal and WeWork. Alex’s specific expertise has centered on creating, transforming and building out systems that foster an equitable, innovative and inclusive workplace culture. While Alex has served as a Chief People Officer, he is currently focused on fractional clients. He is also a start-up advisor in the HR tech space, having worked or working with companies such as When Insurance, Kindred Minds and ChangeEngine.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.

December 4, 2024Episode 91 hr 3 min

I Stayed Too Long in a Job That Wouldn’t Let Me Grow [Aimee Gindin - S3 Ep9]

Send a private message to Host, Deanne RhynardDescription:In this episode, we unpack the complicated relationship between ambition, identity, and personal fulfillment. From workplace burnout to the challenges of navigating toxic cultures, and from grappling with misaligned goals to the pressures of leadership, this episode dives into the hard truths of career “success” and what it really means to thrive.Episode Takeaways:Burnout and the Cost of Overwork: The early-career grind can feel like a rite of passage, impacting personal life and well-being. Challenges with Acquisitions: The cultural mishaps that can follow after an acquisition. Advocating for Yourself in the Workplace: The risks of speaking up, the label of being “overeager,” and knowing when it’s time to move on. The Lonely Reality of Leadership: experiencing isolation in leadership. About Aimee:Aimee Gindin is a leadership coach, keynote speaker and author of dozens of published business and lifestyle articles. With a background as both a former mental health clinician and a C-Suite executive, she combines her passion for personal growth with her business and leadership experience to create actionable steps for professionals looking to make positive changes in their lives and in their careers.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.

November 13, 2024Episode 81 hr 1 min

I Could Survive Anything—Except Normal Life [Tyler Schmoker - S3 Ep8]

Send a private message to Host, Deanne RhynardTyler Schmoker brings a wealth of experience in operations management and supply chain strategy, having developed his expertise through a progressive career in the military and paramilitary sectors. In this episode, Tyler candidly shares the challenges he's encountered throughout his journey, including navigating corporate landscapes, accepting that he may not always be the most popular figure, and managing the constant uncertainty of potential deployments looming ahead.ABOUT Tyler SchmokerTyler Schmoker is a retired Army Combat Arms Senior Noncommissioned Officer, former Paramilitary Advisor, and Strategic Projects Consultant to Fortune 500 companies. Tyler has worked in Corporate Security, Strategy, Project and Program Management, and Tech. Tyler is an avid Alpine Climber and Endurance Athlete. Tyler is the Founder & Principal at Winsly LLC, a High-Performance Coaching, Consulting, and Advisory Services Firm. When the going gets tough, the tough choose Winsly. 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.