The Small Habit Behind Every Opportunity I've Had

Prospecting Has a Branding Problem

Most people hear “prospecting” and think of cold calls, lead lists, or someone trying to sell them something they didn’t ask for.

I think that definition is too small.

To me, prospecting is simply the willingness to go first. Start the conversation. Ask the question. Walk into the room you weren’t sure you belonged in.

It’s a habit, not just a sales technique. And I think it applies to a lot more than sales.

Some of the most valuable opportunities in my life have started the same way: I was willing to initiate something without knowing exactly where it would lead.

The Habit Nobody Puts on a Calendar

Here’s what makes this habit easy to overlook: it rarely feels like a big moment. It’s a short conversation at an event. A follow-up message you didn’t have to send. A question you ask instead of letting the silence sit. None of it looks like progress in the moment.

The people I’ve met who seem to have the most options in their careers, investments, and relationships have one thing in common: they keep initiating.

What It Looks Like Outside of Sales

I spent time working at a private country club, and I used to notice something: people golfing on a Tuesday afternoon. They weren’t retired. They were people who had clearly built careers, businesses, or investments that gave them that kind of freedom.

I got curious instead of just impressed. What do you do? How did you build this? Those conversations gave me a perspective on business and money that I never would have gotten by simply observing from a distance. None of them would have happened if I hadn't been willing to ask.

That's the part people miss. Prospecting isn't only about finding customers. It's about finding information, mentors, ideas, and opportunities you didn't know existed, simply because you were willing to put yourself in front of them and ask.

The Trade You're Actually Making

The reason this habit is hard isn’t that it’s complicated. It’s that it asks you to risk a small, repeated discomfort in exchange for a return you can’t predict.

Most people would rather avoid the discomfort. They wait for the opportunity to come find them: the right job posting, the right introduction, the right moment where reaching out would feel natural instead of forced.

Sometimes that works. More often, it means waiting on something that was never going to arrive on its own.

I’d rather take the small, repeated risk.

A conversation that goes nowhere costs me very little. But the right conversation can open doors I didn't even know existed.

Why It Compounds

A single conversation rarely changes anything by itself. What changes things is the habit of having a lot of them.

Every person you meet knows people you don’t. Every room you walk into has information you don’t have yet. Every question you ask gives you a chance to learn something, understand someone differently, or uncover an opportunity you wouldn’t have known existed.

None of that shows up in a single interaction. It shows up over time.

That’s why I think of prospecting as something that compounds. You rarely know which conversation will matter—you just create more chances for one of them to.

What I Actually Do With It

I try to treat every new environment—a networking event, a gym, a new city—as an opportunity to engage rather than simply observe. Sometimes that leads to a business opportunity. Other times it leads to a friendship, a new interest, an investment idea, or simply a different way of looking at something.

I stay in touch with people I might otherwise lose touch with. I ask people how they built what they built, even when it has nothing to do with my own work, because some of the most valuable perspectives I’ve gained have come from conversations I never expected to have.

None of this requires a script or a job title. It requires being willing to go first, over and over, until eventually it becomes part of how you move through the world.

Prospecting doesn’t promise a specific outcome. Most conversations won’t change your life.

But every time you’re willing to go first, you give something unexpected a chance to happen.

And I’d rather create more chances than wait for the right one to find me.