What you can’t learn online

On paying attention to the ones who make it look easy

Dance at Bougival by Peirre-Auguste Renoir, 1883

The internet has created a strange kind of authority figure. A lot of the most successful content comes from people who’ve struggled with a core part of being human—dating, self-worth, intimacy, whatever—and worked relentlessly to change it. That’s why they’re such good translators. They’ve been to the depths, taken notes, and come back with a map.

But there’s another kind of person entirely. Someone for whom that thing just isn’t a problem. It comes naturally, like walking or breathing. And they’re not online explaining it all day because... they’re out living. They don’t think of it as a skill or an achievement. It’s just who they are.

I’ve lived somewhere between the two worlds. In some core domains—health, money, purpose, presence—I’ve had to earn every inch of ground through trial, error, and the occasional spectacular faceplant. At best, I’ve become a decent translator of hard lessons. Plenty of people do it better.

But dating and relationships have always come fairly naturally to me. Not always successfully, for sure, but intuitively. Let’s just say your boy never really struggled to get a date. And that vantage point helps me see this particular corner of internet advice a little differently.

When I watch people try to reverse-engineer intimacy, package formulas for “romantic polarity,” offer takes on masculinity, or listen to some clearly brilliant hyper-nerd explain romance, it rarely resonates. Not because they’re necessarily wrong, but because the whole thing can feel over-coded. It’s like trying to write a manual for dancing. You can break it into steps, but if the music isn’t in you, those steps won’t help much.

You might think, well dude, it’s internet advice. Just log off! But we’re well past that. The internet is where we go to find authority now. It’s where people seek guidance on the basics of being human: how to date, how to parent, how to lead, how to be less of a mess. And to be fair, a lot of these folks have earned their credibility. They’ve actually done “the work.” The catch is, the medium itself favors people who can explain themselves best, not necessarily the ones living the most coherent, grounded, or relational lives.

The trouble with the internet is that it collapses two very different forms of transmission into one. In spiritual traditions, there’s the explicit transmission—the words, frameworks, and carefully articulated methods. And there’s the implicit transmission—the felt sense of someone who is free in a certain way. The first you can get from a Substack essay. You can sometimes catch a bit of that second kind through a podcast or video, though it’s never quite the same as being in the room with them.

But online, we tend to confuse eloquence for embodiment and articulation for realization. We end up over-indexing on the most legible people, rather than the ones most worth paying attention to.

The naturals have their blind spots, too. When something has always been easy, you often don’t know how to explain it. You don’t even realize there’s anything to explain, because there’s no process, no sense that what you’re doing is remarkable. Your strength is invisible to you, so you can’t teach it in a way that lands.

And this isn’t just about dating. You see the same pattern in business advice, parenting, politics, and definitely spirituality. The people with the most articulate frameworks tend to rise to the top. But the ones living the most integrated, sane, or beautiful lives often go unnoticed. The most transformative teachers I’ve met have had very little to say, and they rarely post. They teach by doing, how they move through a room, or how they listen. Which means the only way to learn from them is to notice—really notice—what’s right in front of you.

Lately I’ve been paying closer attention to the people around me, not only teachers, who seem to have certain things come naturally. My partner Grace, for example, has this uncanny ability to put people at ease. There’s something in her presence that’s immediately calming. She doesn’t perform empathy, she simply relates, with a kind of effortless humanity. If you asked her how she does it—and believe me, I have—she’d just say she loves people.

But what I’ve come to see, watching her in relationships, friendships, and even passing interactions, is that it’s truly less a technique and more a vibe. A kind of poetic attunement. She meets people in a relaxed, sincere, responsive, unguarded way. I’m often amazed by how much she actually seems to enjoy small talk. She’s not trying or forcing anyone to go deep—but people end up going there anyway, drawn in by her warmth.

Another person I learn from all the time, about leadership and charisma, is my dearest friend Conlan. He’s probably the funniest person I know: effortlessly witty, self-deprecating, sharp in a way that engages. We went out for sushi one night with my mom and dad in Chelsea, and somewhere in the middle of dinner, he inserted a raunchy joke—something about anal sex and poop—that could’ve easily flopped, but instead had everyone in stitches. The bit took on a life of its own, and he carried into the night as we wandered the city, eating ice cream and laughing down the sidewalks like kids. It wasn’t crude for shock value, it was just him, being hilarious and loose and totally himself.

He’s taught me something like comedy as a way-of-life, and I try to bring that into the groups I lead and the projects I run.

To be clear, I can’t quite mimic that. A big part of this process, for me, is learning my own limits. I’m funny, I’m playful—but I’m not that funny. Yet being around it does something, leaving a trace. And even when I’m not trying to be funny, if I can just remember it, it opens some silliness in me.

And of course, neither Grace nor Conlan is posting about any of this.

I keep finding myself pulled towards that kind of effortlessness, wanting to see where it leads. Sometimes it’s noticing how my dad plays with my 14-month-old son; stacking toys, building towers just to knock them down again, narrating the whole thing in a voice that keeps him enthralled. I watch them and realize I’m not quite as good at it yet. Maybe I’m still learning (and tired).

Other times, I notice how a friend pulls back, setting boundaries that can feel distant or even cruel. But they hold, and in their own way, they inspire me. I’ve absorbed something there too: I’ll say “no” now, more quickly and with less apology, even with small things. Like the other day, when someone tried to rope me into building a campfire on the beach, and I just didn’t want to. Which, I know, might sound lame—but we were about to leave and I had a baby to tend to.

The hard part, I think, is discernment. We live in a time when so many voices are vying for our attention. Everyone has a take, method, or framework. And the truth is, some of the most visible ones really are worth listening to. That’s what makes it tricky.

My friend Jonny Miller, for example, has taught me a lot about how to build a thriving business in public that actually helps people, while having fun and not losing yourself in the process. He’s also one of the friendliest, most generous people I know. At least once a month, someone reaches out to me saying, “Hey, I’m a friend of Jonny,” because seemingly everyone is a friend of Jonny.

Then there are friends like Anne-Laure Le Cunff, who just wrote a bestselling book on experimental productivity and somehow made it feel like a fun gift rather than a project. And there are plenty of others, too.

These are people who are visible and living well. They are not mega-influencers. And maybe that’s part of the magic. They’re just visible enough, rewarded for their earned insight, but not yet flattened by it. That balance is rare.

What I’m tracking, I think, is ease. The kind that not only shows up in how someone lives, but also in how they share. Some people live so fully they hardly need to say anything. Others post on social media because they’ve walked through pits of hell and come back with language. And then there are a few who share because they simply love to. For this third Goldilocks group, even posting comes naturally. Not performatively, but as a form of contact, and a way of being generous.

While I’m often wary of advice from people who seem to inhabit the internet more than the world, some of them are still worth learning from. When I see that kind of ease, in any of its forms, I pay attention.

The question, then, is what to do with that attention. How do you learn what comes intuitively to someone else? Unfortunately, there’s no formula. The best I’ve gathered: you watch closely, you experiment, and you let yourself look a little foolish in the process. And more than anything, you relax—enough for their way of being to seep in, like a friend’s catchphrase naturally sneaking into your own speech patterns. That’s the slow transmission, the kind that happens without you even trying. Which is why it matters who you spend time around.

Because the digital age still makes it dangerously easy to confuse eloquence with wisdom. And if we’re not careful, we end up shaping our lives around the people best at explaining themselves, rather than the ones best at living well.

My hunch is we still need to pay more attention to the ones who have something deeper to offer, whether or not they’re putting it into words. You can catch it in the way someone pauses before answering, the air between two people who trust each other, the softness in someone’s face. The signal is always there, right in front of us.