Stephanie Tobin joined me to talk about what happens when you walk away from the job, the title, the so-called plan, without a safety net and still find yourself exactly where you’re meant to be.



She talked through what led up to her decision to leave corporate. No backup plan. No certainty. Just a clear sense that staying was going to cost her more than it was worth. That kind of honesty is rare, and it’s what made this conversation feel so real. She ended up starting a Reiki practice, driving Uber to get by, and somehow turning every ride into a conversation that helped someone else wake up. It was wild in the best way.



We also got into what it feels like to get everything you thought you wanted and realize it’s not it. The promotion, the title, the window office. I’ve been there too. It messes with your head when the thing you’ve worked so hard for feels empty.



Stephanie read from her book, When the Soul Begins, and I wasn’t ready for how much it landed. It was grounded. It was clear. It was exactly what I needed that day.



Follow & Support the Podcast:



🎧 Listen to more episodes of The Corporate Hangover on Spotify, YouTube, or Apple Podcasts 📲 Follow us on Instagram & LinkedIn for behind-the-scenes content and episode updates!💬 Join the conversation! Have thoughts on today’s episode? Drop us a message or tag us on social!



Enjoyed this episode? Don’t forget to subscribe, leave a review, and share it with someone who needs to hear it!

In this episode, I talk with Jon Powell, a father of three who spent more than a decade in tech before deciding it wasn’t working for his health, for his family, or for the kind of life he wanted.



After being laid off (more than once), spending a year unemployed, and watching job listings rack up hundreds of qualified applicants, Jon hit pause. He took on a second job managing a local homeless shelter just to make ends meet. But what he didn’t expect was that it would become the most meaningful part of his day.



We talk about that pivot—how it shaped the way he views work, success, and identity. Why he finally walked away from tech and now works in public education procurement. What it means to be a Black father raising mixed-race kids in a California school district. And why showing up for others, in a job that isn’t flashy, has brought him more peace than any tech paycheck ever did.



We also talk about burnout, salary traps, unlimited PTO, working 80 hours a week for free, and how he dislocated his shoulder trying to pick up a turkey at Costco. (That part’s important too.)



This episode is a must-listen.



Connect with Jon Powell:



🎧 Listen to his podcast — Time Pals PodcastAvailable on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts




* Follow on Instagram – @timepalspodcast



* Follow on TikTok – @timepalspodcast



* Watch on YouTube – Time Pals Podcast




Follow & Support the Podcast:



🎧 Listen to more episodes of The Corporate Hangover on Spotify, YouTube, or Apple Podcasts 📲 Follow us on Instagram & LinkedIn for behind-the-scenes content and episode updates!💬 Join the conversation! Have thoughts on today’s episode? Drop us a message or tag us on social!



Enjoyed this episode? Don’t forget to subscribe, leave a review, and share it with someone who needs to hear it!

What happens when leadership is just for show? In this episode of The Corporate Hangover, host Tiffany Kennedy sits down with Jeremy Duffy, an NSA educator turned advocate for workplace change, to discuss the dangers of performative leadership and why employees are often treated as adversaries instead of allies.



Jeremy spent 16 years at the NSA, training federal agencies in operations security and leadership development, only to discover that bureaucracy and inefficiency were deeply ingrained in the system. Now, he’s sharing his experiences and hard-earned lessons in his upcoming book, Are You Listening?, which breaks down the consequences of ignoring employees and how leaders can rebuild trust.



This conversation dives into:




* The illusion of productivity – how leaders focus on appearances instead of real impact



* Why town halls and surveys fail – and what real listening looks like



* The return-to-office debate – is it about business need or executive vanity?



* Workplace toxicity – how treating employees as stakeholders could change everything



* Tech security & online privacy – small steps to protect yourself from unnecessary exposure




Jeremy also shares practical tips for staying safe online, from avoiding fingerprint theft in photos to recognizing how companies mishandle employee data. If you’ve ever felt unheard at work or wondered why leadership struggles with transparency, this episode is a must-listen.



Connect with Jeremy Duffy:



📖 Website: TheGeekProfessor.com



Follow & Support the Podcast:



🎧 Listen to more episodes of The Corporate Hangover on Spotify, YouTube, or Apple Podcasts 📲 Follow us on Instagram & LinkedIn for behind-the-scenes content and episode updates!💬 Join the conversation! Have thoughts on today’s episode? Drop us a message or tag us on social!



Enjoyed this episode? Don’t forget to subscribe, leave a review, and share it with someone who needs to hear it!

In this episode, host Tiffany Kennedy sits down with Johnny Flores, who gets real about his journey from a long career in the medical field to embracing life as an entrepreneur and podcaster.



Johnny opens up about leaving a toxic work environment, battling self-doubt, and taking that bold leap toward a career that truly excites him.



With the guidance of supportive mentors and a caring community, Johnny discovered that leaning on others can help you unlock your full potential.



His story is a candid look at growth, learning from failures, and the value of genuine connections in both your professional and personal life.



Connect with Johnny:https://florespodcastproductions.com/

In this episode of the Corporate Hangover, host Tiffany Kennedy sits down with Joshua Thompson, a veteran and entrepreneur who shares his journey from military service to establishing his own tax consulting business.



They discuss the importance of planning for taxes, overcoming challenges in entrepreneurship, and the significance of education in financial planning.



Joshua emphasizes the need for a strong foundation in business, dispels common misconceptions about taxes, and shares valuable tips for new entrepreneurs.



The conversation also touches on personal growth, defining success, and the resources that have helped Joshua along his journey.



Connect with Joshua and the Thompson Tax Group:https://thompsontaxgroup.com/https://www.instagram.com/joshuatheadvisor/https://www.youtube.com/channel/UCIAvlb7XWVaQjFIhEih8XQwhttps://www.linkedin.com/company/29319445/admin/dashboard/https://www.facebook.com/ThompsonTaxGroup/

Leaving the structure of corporate life for the uncertainty of entrepreneurship takes guts—and Roxy Ayaz knows this journey firsthand. In this episode of The Corporate Hangover, I sit down with Roxy, a front-end developer turned business owner, who founded Paper in the City Shop, a South Asian greeting card company with bold, expressive designs.

We dive into the challenges of balancing a creative passion with a corporate career, battling imposter syndrome, and taking the leap to build something of your own. Roxy shares hard-earned lessons about rejection, scaling a business, and the reality of being an entrepreneur. We also talk about mindset shifts, manifesting success, and the small wins that make it all worth it.

If you’ve ever felt stuck between chasing your dreams and the comfort of a paycheck, this conversation is for you!

Be honest—how many times have you found yourself sitting in another endless meeting, staring at your inbox, or questioning if this is really what life is supposed to be? You’ve worked hard, followed the rules, and climbed the ladder, but deep down, something still feels… off.



You’re not alone.



I created The Corporate Hangover for people just like you—folks who are tired of the grind and ready to imagine something different. This podcast is all about exploring what happens when you step away from the corporate world and start building a life that feels like your own.



Every week, I’ll sit down with real people who’ve made the leap. These aren’t celebrities or influencers. These are everyday folks who decided enough was enough and took control of their lives. We’ll talk about the fears they faced, the risks they took, and the lessons they’ve learned along the way.



But this isn’t just for those ready to quit. If you’re still in your 9-to-5 and looking for ways to reclaim your time, rediscover your passions, or just survive the chaos, you’ll find plenty of inspiration and practical tips here too.



So, if you’ve ever felt stuck, uninspired, or just plain exhausted by the daily grind, The Corporate Hangover is for you. No fluff, no clichés—just honest conversations about what it really takes to break free and build a life that matters.



Subscribe to the podcast wherever you listen, and let’s figure out what’s next—together.