Bearing It All: Resilience, Reinvention, and Comedy with Jason Dudey

Learn how resilience, reinvention, and comedy can shape a life and career in the conversation during Bearing It All with Kate Ginsberg and Jason Dudey.

In the third episode of Bearing It All, host Kate Ginsberg, founder and CEO of Queen of To Do, chats with comedian and event producer Jason Dudey. Jason Dudey has spent over fifteen years in stand-up comedy, performing across the U.S, and has shared the stage with several other legendary comics. After years on the road, he faced a turning point, realizing the life he built no longer served him the way he needed. In this episode, Jason opens up about making the difficult decision to walk away from stand-up and the pivot into event production, and how he found a new sense of purpose at C3 Presents.

 Episode 3: Resilience, Reinvention, and Comedy with Jason Dudey

Key themes discussed:

• The beauty but unpredictability of life and career transitions.

• Knowing when it's time to walk away from something. Even when it’s your passion.

• The power of humor in overcoming adversities.

• Finding fulfillment and content in unexpected ways.

• Why building relationships and authenticity are key to lasting success.

What happens when you realize the life you built no longer serves you? What do you do? How do you reinvent yourself after a major setback? Do you manage to find humor in resilience and challenges?

 

A recent divorcee and cancer survivor, Jason’s perspective on life is sharper (and funnier) than ever:

“The people who are wildly successful with their friends all have one thing in common—they care about the other person. It’s not about keeping score; it’s about nurturing real, heartfelt connections.”

Life hasn’t gotten him down yet—and it never will!

Jason’s Story: From Stand-Up to C3 Presents

Kate (00:45): Tell us about your journey from New York’s stand-up scene to where you are now.

Jason: Oh, there’s a lot on that road. I moved to NYC with just $150 in my pocket. No real plan, just a gut feeling that I should be there.

From open mic nights to paid gigs, Jason built a solid career in comedy. But the grind of life on the road wore thin. In 2014, while performing at a club in Indiana, he had a revelation: he was done. 

Jason (02:24): I called my manager the next day and said, 'Cancel the rest of the tour.' She said, 'That’s not a great idea.' I said, 'I didn’t say it was a great idea. I just said I’m done.'

Jason’s pivot into event production was unexpected. While performing at the Moon Tower Comedy Festival in ATX, he networked his way into a job at C3 Presents (02:51), where he now works as the Director of Experience. His role blends creativity with logistics, overseeing decor, signage, and art installations at major music festivals.

Jason (04:00): I don’t know all the bands, but I know what their dressing room furniture looks like!

Surviving Cancer and Redefining Life

Jason’s journey took an even more dramatic turn in 2020 when he underwent a stem cell transplant. As if fighting cancer wasn’t challenging enough, he faced it in the middle of a global pandemic.

Jason (24:00): My family could visit until March 15. Then, a nurse walked in dressed like an astronaut. I was like, 'What is happening?' She goes, 'Did you hear what happened in China?' I was like, 'No, I’ve been in the hospital!'

The experience changed everything—his perspective, his priorities, and even his DNA (literally). His donor, someone with vastly different political and social beliefs, became an unlikely yet powerful connection in his life. Another unforseen.

Jason (32:16): I wouldn’t have chosen this man to put his DNA in me. And he wouldn’t have chosen to save a gay man’s life. But here we are. And now we’re friends. Life is weird.

Lessons in Reinvention and Trust

Throughout the conversation, Jason emphasized the importance of trust—in the people around you and in yourself. Whether it’s trusting a new career path, a medical team, or a network of friends and colleagues, resilience isn’t about pushing through alone or pushing through the burnout; it’s about knowing when to lean on the support others.

Kate (16:54): I start with the assumption that I’m going to succeed. The journey may not look like what I think it will, but I know I’ll make it.

One of the biggest lessons we've learned? Even if you have a plan, you can never truly predict where life will take you. You can't choose every path you go on. But you can choose to approach change with an open-mind, curiosity, and humor. Eventually, you'll land where you're meant to. 

Key Takeaways

1. Reinvention is part of life – The career or identity you start with isn’t necessarily the one you’ll end up with. And that's ok! You're allowed to have more than one dream.

2. Humor can be a survival tool – Laughter doesn’t erase hardship, but it can certainly make it more bearable. Have you ever tried fake laughing? It may sound strange, but give it a shot. Keep fake laughing until you really laugh. 

3. Trusting others can open doors – In business, health, or personal life, knowing and growing with the right people make all the difference.

4. Walking away is sometimes the right choice – Sticking with something or someone just because it’s comfortable doesn’t mean it’s right. Be bold. Be radical. Make the crazy decision. Make the move.

5. Unexpected connections matter – Life has a way of bringing people together in ways you never expect. Be open and know that you deserve whatever connection or opportunity come your way.

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