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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.
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.
F'ing Up
I Turned Down a CIO Role Because I Was Afraid [4.5 Sylvia Kwan]
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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
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.
