Cruising eastbound on Hana Highway with a Jeep full of boys, one asked, “What’s O-F?” My elder millennial brain quickly scanned known Gen Z slang these eleven- to twelve-year-olds might use. They say things like “cross-map” to describe the other side of Maui, or “spawn-point” when referencing their mom, but O-F? That one escaped me. I sheepishly replied, “O-F?” One of the boys casually answered, “Yeah, as in OnlyFans.” Yikes.

This moment confirmed what research already proves: boys feel safer asking tough questions when they’re shoulder-to-shoulder, not face-to-face. I don’t think they meant it as a test, but it was one—would I be a safe place to be curious without being shut down with unhelpful platitudes or shame? Apparently, I passed because a few years later they’re still hopping in, buckling up, and asking everything from why I drive the speed limit to questions about geopolitics.

Ironically, as much as I’ve poured into creating intentional gatherings to discuss maturing, purpose, and emotional intelligence, the deepest conversations still happen in that Jeep. Nights out at the movies, grabbing dinner, or simply driving to an activity seem ordinary, but they’ve become conduits for connection and conversation. As a bonus, these outings also give parents a much-needed night off—a small way to serve entire families, not just the boys.

The success of EQUIP Boys doesn’t rest on a polished program; it rests on presence. During early adolescence, boys are primarily focused on acceptance. In his book 10 to 25: The Science of Motivating Young People, David Yeager writes, “Status and respect are to a young person what food and sleep are to a baby.” He argues that the idea teens make poor decisions simply because their brains are “underdeveloped” is an incomplete view. Much of what looks like risky behavior is really a search for belonging and significance. What boys need is less of a “sage on the stage,” as Dr. Tim Elmore says, and more of a “guide on the side.”

That’s the heart of EQUIP Boys: to be a guide on the side. A guide to help them navigate modern challenges like easy access to unhealthy websites and apps, the temptation to compare their behind-the-scenes reel to social media highlight reels, and to find acceptance apart from performance. They rarely come out and say it, but most boys are asking, “Do I have what it takes?” Without intentional spaces to be vulnerable and feel a sense of belonging, it’s easy for them to misplace their identity in medals, likes, followers, or risky behaviors—all attempts to feel seen and understood.

And while all that can seem heavy, we actually have a lot of fun together. That’s important! I recently heard it said that boys need to know they’re not only loved but liked. As much as they’re pursing independence from parents and guardians, boys need safe adults who genuinely enjoy being around them and create opportunities for connection. Sure, holding them accountable is sometimes the most loving thing you can do, because it affirms they’re capable of more. But more often, the best thing we can do is simply create shoulder-to-shoulder spaces—riding in a car, helping with homework, or ordering DoorDash for a movie night—where presence outweighs performance.

So, what’s next for EQUIP Boys after our rite-of-passage trips to Oahu? EQUIP 2.0. Check out the updates at cjwetzler.com/ebnext for ideas to help guide the boys in your life as they make sense of manhood. And while EQUIP isn’t technically recruiting, I’m always happy to share best practices, book recommendations, and lessons learned with anyone wanting to start a mentoring group of their own. I believe we all share a responsibility to invest in the next generation—and I’m committed to mentoring boys and equipping others who want to do the same. Shootz.