Goals help people and teams define objectives, track progress, and focus on what really matters. I can easily list out our company goals and personal, but I don’t know a single goal my cousin has.

Actually, it’s worse than that. I couldn’t tell you what most of my friends are working toward beyond what I see online. I see travels, restaurants they visited, or rants and memes. But what they’re actually working towards? What keeps them up at night? What they’re betting the next five years on?

I have no idea. And that doesn’t sit right with me.

The Drift We Don’t Talk About

Goals aren’t just productivity tools—they’re windows into what drives someone. They reveal priorities and values, explaining the trade-offs people are willing to make. In business, we obsess over goal alignment. We know that shared objectives bring teams together, and that understanding what someone is working toward makes collaboration possible.

So why don’t we do this with the people we care about?

I’ve been reflecting on this lately, especially as I’ve watched old friendships drift. Friends I used to be close with now feel distant, and I keep asking myself: was it me, them, or just a part of life that no one questions?

If I’m honest, I know my part in it. I obsessively focus on work and projects. I tend to not reach out, to not start conversations, to stay in my own head when it comes to how I invest my time. The problem there is that I don’t spend the hours with others the same way I used to. I’m not having the deep conversations or shared experiences that kept those connections alive.

The Focus Problem

Here’s what I’ve noticed: as life tightens, we focus down on what we like. We find our niche, our Discord servers, our communities of people who “get us.” That focus is powerful—it helps us go deep instead of wide. But it comes at a cost.

We drift from the connections we had before.

You feel this in conversations. A topic you’re passionate about comes up, and you light up. You start talking about it for two or three minutes before you notice your friend’s eyes glazing over. They don’t have the same drive or passion for it. If you keep going, they fade. If you stop, the conversation dies.

I’ve been on both sides of this. I’ve been the one rambling about AI and context engineering while my friend nods politely. And I’ve been the one nodding while someone else talks about something I don’t understand.

The easy answer is to retreat. Find people who share your interests. Stick to safe topics. Keep it light.

But that’s how you end up lonely in a room full of people you’ve known for years.

What We Lose When We Stop Asking

I struggle with small talk. I’m better at being silent and thinking to myself. But silence doesn’t build connection. Neither does surface-level conversation about the weather or shared memories from a decade ago.

What does build connection? Curiosity about what drives someone.

When I don’t know what my friends are working toward, I can’t understand the choices they’re making. I can’t support them in meaningful ways. Maybe I can’t help directly, but maybe I know someone who shares a similar goal. Maybe I can make an introduction, be a bridge, open a door.

But only if I ask.

The Epidemic We’re Living In

There’s a reason we talk about the epidemic of loneliness. Since COVID, the time people spend together has been declining. Some say this is just part of adulting—we naturally spend less time with friends as we age. Maybe.

But I think it’s more than that. Social media, remote work, the death of third places—they’ve all accelerated our disconnection. We’re more connected digitally and more isolated physically.

We’ve built tools to find “our people.” Discord servers for every niche interest. Online communities that get us. We can self-select our bubbles now, curate our feeds, avoid friction.

But what if we need the friction? What if being around people with different interests, different goals, different perspectives is exactly what keeps us from drifting into isolation? Steve Jobs famously talked about friction being a good thing.

What I’m Doing About It

I don’t have all the answers. But I do know this: if I want real connection, I need to start asking better questions.

Not “How’s work?” or “What’s new?” Those are autopilot questions that get autopilot answers.

I mean: What are you working toward right now? What matters to you? What’s hard about it? How can I help?

These questions feel awkward at first. They’re more vulnerable than small talk. You can probe into what drives someone, but you can also stumble into what they fear, what causes them stress, what they’re avoiding.

That’s okay. At least you’re trying to understand. With time and practice, you learn how to be empathetic in an actionable way. You learn how to connect.

If someone asked me what my goals are, I’d say this: I want to help people realize that money and status aren’t everything. That if you work hard and play it smart, you can build a life that matters—and help others along the way.

We’re a community, after all. But community requires knowing what the people around you are actually working toward.

The Challenge

This week, I’m asking three people in my life: What are you working toward right now?

Not as a networking move. Not to extract value or make introductions. Just to understand. To be curious. To rebuild the connection that comes from knowing what drives someone.