Deanne Rhynard
F'ing Up
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....
Be sure to visit the podcast's website and support the creator: iamfingup.com
Where to listen?
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Episodes
I Kept Running From Leadership Until It Caught Me [4.10 Steve Worthy] 21.10.2026 51:58
Send a private message to Host, Deanne Rhynard Steve Worthy shares the story behind his leadership journey — from serving in the Air Force to building a decades-long career with companies including Caribou Coffee, Barnes & Noble, Target, Dollar General, and Walmart, before finally betting on himself and building Worthy Retail Global. In this episode of The F’ing Up Podcast, we explore what hap...
I Kept Chasing Success - Until My Body Said No [4.9 Krista Casey] 30.09.2026 1:08:05
Send a private message to Host, Deanne Rhynard Krista Casey shares what it was like to spend years building an impressive career—only to realize that the very success she had worked so hard to achieve was leading to her burning out. In this episode of The F’ing Up Podcast, we explore the hidden cost of high achievement, the pressure to constantly prove yourself, and how understanding one simple tr...
I Was a Thoroughbred—But They Only Saw a Workhorse [4.8 Casey Floyd] 16.09.2026 54:06
Send a private message to Host, Deanne Rhynard Casey Floyd shares the story behind her career — including the moments she realized that being the hardest worker in the room wasn't always enough. In this episode of The F’ing Up Podcast, we explore what it feels like to consistently deliver exceptional results while being overlooked, undervalued, and expected to carry more than your share. Case...
I Got Laid Off During Maternity Leave—and Felt Relieved [4.7 Tomide Awe] 02.09.2026 1:00:47
Send a private message to Host, Deanne Rhynard Tomide Awe shares the story behind her career journey — including graduating from Wharton without a job, spending nine months unemployed and depressed, burning out in Big Tech, and ultimately getting laid off during maternity leave while navigating postpartum depression. In this episode of The F’ing Up Podcast, we explore what happens when you spend y...
I Spoke Up About Discrimination — And It Cost Me [4.6 Heather Wallander] 19.08.2026 59:49
Send a private message to Host, Deanne Rhynard Heather Wallander shares what it feels like to work relentlessly toward a dream career only to realize the system you trusted may never have been designed to protect you. In this episode of The F’ing Up Podcast, we explore the reality behind building a career through sheer determination, reinvention, and resilience…and what happens when success collid...
I Turned Down a CIO Role Because I Was Afraid [4.5 Sylvia Kwan] 15.07.2026 1:00:02
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 opportun...
My Life Looked Fine, It Wasn't, And Then It Completely Fell Apart at 38 [4.4 Atul Sood] 01.07.2026 50:52
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...
I Created Something Special—Then Had to Walk Away [4.3 Katie Svilich] 17.06.2026 1:09:04
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 tra...
I Wasn’t Driven by What I Wanted, But By What I Might Lose [4.2 Josh Perry] 03.06.2026 45:35
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...
I Became a Fortune 500 CMO While My Life Was Falling Apart [4.1 Stephanie McCarty] 20.05.2026 1:11:39
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...
Season 4 Trailer: Successful People. Messy Careers. Real Stories. 14.05.2026 0:35
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 th...
I Was Miserable During My “Best” Years [Philip Eil - S3 Ep14] 19.02.2025 53:05
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...
The Year I Got My Dream Job at Google—and Then I Fell Apart [Mishae Khan - S3 Ep13] 05.02.2025 54:47
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, t...
I Was Told I Wasn’t Good Enough [Lyle Adams - S3 Ep12] 22.01.2025 30:25
Send a private message to Host, Deanne Rhynard Description: 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 ag...
Imposter Syndrome Made Me Feel Behind [Ashley Chang - S3 Ep11] 08.01.2025 42:43
Send a private message to Host, Deanne Rhynard During 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 you...
I Lost My Mom… and Then I Lost My Job [Alexandre Seiler - S3 Ep10] 18.12.2024 53:06
Send a private message to Host, Deanne Rhynard Description: 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,...
I Stayed Too Long in a Job That Wouldn’t Let Me Grow [Aimee Gindin - S3 Ep9] 04.12.2024 1:03:58
Send a private message to Host, Deanne Rhynard Description: 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 t...
I Could Survive Anything—Except Normal Life [Tyler Schmoker - S3 Ep8] 13.11.2024 1:01:35
Send a private message to Host, Deanne Rhynard Tyler 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 t...
I had no choice - I had to shut it down [Charlie Gray - S3 Ep7] 23.10.2024 54:53
Send a private message to Host, Deanne Rhynard Charlie Gray has held some remarkable titles for some of the most well known tech companies. He’s been doused with great success. However, what you don’t see, by just looking at his LinkedIn or resume, are all the stops and starts. Charlie has many tales of being hired to grow a company only to turn around and shrink it, often forced to RIF himself. ...
Laid Off on Maternity Leave With Four Kids [Julia Arpag - S3 Ep6] 11.09.2024 39:42
Send a private message to Host, Deanne Rhynard In this episode of F'ing Up, Deanne Rhynard speaks with Julia Arpag , co-founder and CEO of Aligned Recruitment. Julia shares her journey from being laid off during maternity leave and navigating challenging work environments, to ultimately founding her own successful tech recruitment firm. She reflects on growing up as the oldest of seven childr...
My CoFounder Became My Abuser [Natalie Ferguson - S3 Ep5] 28.08.2024 46:13
Send a private message to Host, Deanne Rhynard Natalie Ferguson is a serial entrepreneur, having founded multiple successful companies, enabling her to find “success” quickly. Her journey wasn’t without strife. Early on she navigated an abusive relationship, which started in the workplace. It took a toll on her emotionally, mentally, and financially. It took years for her to get beyond the grips o...
I Got Arrested—and Still Built a Career [Dan Griffin - S3 Ep4] 14.08.2024 43:04
Send a private message to Host, Deanne Rhynard Dan Griffin spent a year jobless. After a successful tech trajectory, Dan was laid off by Microsoft. He battled a brutal job market and had to reshape life in many ways to ensure care for his family. Shame, lack of income, and terminated health benefits were a few of the effects he had to navigate. Dan shares his unvarnished truth in his episode of F’...
Building a Startup While Battling Severe Postpartum Depression [Sara Mauskopf - S3 Ep3] 31.07.2024 58:53
Send a private message to Host, Deanne Rhynard Sara Mauskopf is an intelligent woman, successful especially in the realm of Tech. She’s worked for companies like Google, Twitter and has gone on to found her own company. Though she had a fantastic trajectory, it has come with extreme challenges, particularly in her personal life. She struggled with finding her footing and identity as a mother and s...
I Looked Successful—but Felt Unworthy [Jane Boulware - S3 Ep2] 17.07.2024 48:04
Send a private message to Host, Deanne Rhynard Jane Boulware came from nothing. As one of five children, she was forced to grow up quickly and learn the importance of caring for herself. Not understanding what attending college really meant, she attended, setting the stage for her future. She rose quickly, creating a name for herself as a powerful leader in business. Eventually courted by Microsof...
Golden Handcuffs, Rock Bottom, and the Decision to Live [Austin Moore - S3 Ep1] 03.07.2024 1:12:14
Send a private message to Host, Deanne Rhynard Austin Moore is a sales and recruiting rockstar, having helped countless people find work. He built his own business and witnessed his net worth climb at a rapid rate. Though he experienced highs in the working world, he’s had no absence of struggle - managing through challenges such as getting fired, addiction, conflicts with a co-founder, and choosi...
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