Jaywalking: Life Unfiltered with Jay Yoder

It’s been two months since I left teaching—and turns out, when you remove 20 years of routine, your brain just… floats.
In this episode, I give a brutally honest (and slightly unhinged) update on life after the classroom. We’re talking identity crisis, unexpected freedom, and realizing I no longer measure my life in marking periods.
Also… nobody tells you how weird it is to not need a bathroom pass anymore.

This week on Jaywalking: Life Unfiltered I sit down with Chelsea and Dan Keota from Die Laughing Inc. — and this story is truly full circle.

Chelsea was actually one of my students in year ONE of my teaching career… and 20 years later, life brought us back together when I became her husband Dan’s comedy teacher.

Dan started doing comedy as a way to take his mind off the unimaginable — waiting for a double lung transplant. What began as an outlet turned into a mission. From that experience, he launched a nonprofit that raises money for others through comedy fundraisers and laughter.

This is a story about resilience, love, purpose… and the healing power of humor.

What a beautiful couple. What a powerful journey.

You do NOT want to miss this episode. ❤️🎙️

In this laid-back episode of Jaywalking: Life Unfiltered, Jay sits down with Meredith Leigh for a real, unfiltered catch-up. From where life has taken them since they last connected to the unexpected twists, growth, challenges, and laughs along the way — nothing is off limits.

They talk about navigating adulthood, relationships, career paths, personal evolution, and how the past has a funny way of showing up in the present. It’s honest, nostalgic, funny, and at times surprisingly deep — the kind of conversation that reminds you how important it is to reconnect with people who knew you “back when.”

Whether you’re reflecting on your own journey, missing old friends, or just here for good conversation and real laughs, this episode is a reminder that life doesn’t move in a straight line — and sometimes the best moments happen when you pause long enough to catch up.

Growing up with two moms gave Jay a strong foundation, but during his college years a handful of men stepped into his life in ways he didn’t expect. Professors, mentors, and coaches who modeled integrity, humor, and accountability—sometimes through advice, sometimes through tough love, and sometimes without realizing the impact they were making.

Now as a dad, Jay reflects on how those lessons stuck with him and how they shape the way he tries to show up for his own daughters today.

After a long hiatus, Jaywalking: Life Unfiltered with Jay Yoder is finally back — and a LOT has changed.

In this episode, Jay catches listeners up on everything from family vacations and life on the road to one of the biggest decisions of his life: stepping away from a 21-year teaching career to pursue comedy, speaking, and creative work full time.

You haven't lived until you've taken a 4-hour flight that feels like 40. Meredith Styer returns to Jaywalking as we break down the chaos of family travel and the sheer joy of sneaking away kid-free. Spoiler: one of these requires snacks and the other requires cocktails.

Jay sits down with Philly comedian and longtime pal Steve Bickel for a hilarious episode packed with inside jokes, brutal roasts, and real talk about the grind of comedy and life.

This week on Jaywalking, Jay sits down with comedian and podcaster Dru Montana of Durag & The Deer Tag and Digital Bazooka fame. Together they dive into the creative chaos that shaped their childhoods, the sideways paths that lead to comedy, and the beautiful mischief that fuels Dru’s style on and off stage.

From unfiltered stories to behind-the-scenes laughs, Dru breaks down his recent trip to New Orleans for Skankfest—the wild moments, the unexpected lessons, and the absurdity only he can deliver.

It’s funny, real, and just the right amount of trouble.

Come walk with us

What’s “normal,” anyway? In this episode, we unpack identity, comedy, and how to manage social media with honesty and humor. It’s smart, real, and seriously funny. We had a blast recording it — and we think you’ll laugh right along with us!

In this episode, Jay sits down with comedian and scientist Dana Charitonchick to reminisce about their wild pandemic days performing at Soul Joel’s — from parking lot shows to the birth of post-COVID comedy energy. They dive into Dana’s double life as a stand-up comic by night and scientist by day, exploring how curiosity, data, and humor intersect in the most unexpected ways.

Laugh, learn, and relive the chaos that turned isolation into inspiration.