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Winter break sounds relaxing — until it actually begins.

In this episode of The Carpool Guys, Asher, Dave, and Jon dive into the realities of winter break and family vacations, exploring the excitement, stress, anxiety, and unexpected joy that come with extended time off and traveling together. Through relatable stories and plenty of humor, they unpack why winter break often feels like anything but a break.

The conversation touches on the pressure to create the “perfect” family vacation, the stress of travel and logistics, and the temptation to compare your holiday experience to everyone else’s highlight reel. Asher, Dave, and Jon make the case for prioritizing authentic experiences over perfect photos, embracing the chaos when things go wrong, and recognizing that the most meaningful holiday memories are often unplanned.

They also share practical, real-life advice on planning family vacations that actually fit your family’s needs, avoiding empty parenting threats while traveling, making intentional time for your spouse during school breaks, and using humor as a powerful tool to navigate family challenges.

Whether you’re packing bags, already on the road, or just trying to survive winter break at home, this episode offers laughter, perspective, and reassurance that you’re not doing it wrong — you’re just living real life.

• 00:00:00 Introduction to Winter Break
• 00:03:00 Family Vacation Anxieties
• 00:06:00 The Importance of Authentic Experiences
• 00:09:00 Navigating Family Dynamics
• 00:12:00 Creating Lasting Memories

Please rate and review The Carpool Guys!

You can email us at carpoolguyspod@gmail.com

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Send us a question, a comment, birthday wish, shoutout, or anything else fun and positive, and maybe we'll feature your addition on the next episode of The Carpool Guys Podcast!

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What day is it? Honestly… does it even matter anymore?

The guys kick things off by trying to figure out the day of the week, debating “real feel” time, and reacting to feedback from the last episode (yes, we read the comments... keep them coming).

From there, the conversation turns more real as Asher, Dave, and Jon dive back into Aliyah anxiety — that very familiar emotional tug-of-war between loving life in the U.S. while feeling deeply connected to Israel. Listener messages spark honest reflections, meaningful laughs, and a reminder that this tension is something a lot of people quietly carry.

Then the episode takes a powerful and inspiring turn with a very special guest: Eli Rosenberg. Eli shares his incredible story of donating a kidney through Renewal, walking us through the process, the support of the community, and what it’s really like to make a life-changing decision that impacts another human being forever. It’s moving, eye-opening, and deeply humbling, and somehow still fits perfectly into a Carpool Guys conversation.

This episode has it all: laughs, big questions, real emotions, and a reminder of how much good one person — and one community — can do.

Buckle up.

Chapters -

00:00:00 Introduction and Banter

00:02:00 Aliyah Anxiety and Listener Feedback

00:27:16 Eli Rosenberg's Kidney Donation Story

00:47:55 Community Support and Impact

01:12:02 Question of the Week

Please rate and review The Carpool Guys!

You can email us at carpoolguyspod@gmail.com

Follow us on Instagram @carpoolguyspod

Send us a question, a comment, birthday wish, shoutout, or anything else fun and positive, and maybe we'll feature your addition on the next episode of The Carpool Guys Podcast!

Send us a text

What starts with a painfully awkward synagogue moment (you know the one, that late guy who somehow blocks everyone’s view) quickly turns into a much bigger conversation.

This week, Asher, Dave, and Jon dive into the very real and increasingly common phenomenon of Aliyah Anxiety, the emotional tension between loving Israel, feeling spiritually connected to Jewish life in Israel, and also being genuinely happy, rooted, and fulfilled living in the United States.

The guys unpack the emotional, mental, and practical challenges of making Aliyah, including identity, family considerations, community pressure, Jewish values, and the fear of making the “wrong” life decision. Along the way, they mix thoughtful reflection with humor, stories, and classic Carpool Guys travel mishaps.

This episode touches on Jewish identity, Jewish community, modern Orthodox life, moving to Israel, work-life balance, parenting, and the emotional complexity of big life choices - all while keeping things honest, relatable, and funny.

If you’ve ever felt pulled in two directions - Israel and America, idealism and reality, dreams and day-to-day life - this one’s for you.

Please rate and review The Carpool Guys!

You can email us at carpoolguyspod@gmail.com

Follow us on Instagram @carpoolguyspod

Send us a question, a comment, birthday wish, shoutout, or anything else fun and positive, and maybe we'll feature your addition on the next episode of The Carpool Guys Podcast!