How To Be Not Sleazy

There’s a conversation I keep having with social entrepreneurs.

It usually starts with some version of: “I don’t want to be a sleazy salesman.“

I nod when I hear it, because I’ve felt the same thing more times than I can count. That tight feeling in my chest when it’s time to name a price. The small voice that wonders if I’m asking too much, or if maybe I should just offer to help for free.

Underneath that discomfort is a belief I’ve carried for a long time. The belief that asking for money is, in some fundamental way, an imposition. That I’m taking something from someone rather than offering something to them.

I’m still working through this, if I’m honest. But I’ve started to notice something that’s helping me see it differently.

When I pay for something that genuinely helps me, something shifts. There’s a kind of commitment that comes with the exchange. I show up differently. I take it more seriously. The money isn’t just a transaction. It’s a way of saying, “Yes, I’m in. I’m choosing this.”

I think about the times I’ve received free advice or free help, and how often I let it sit untouched. Not because it wasn’t valuable, but because I hadn’t invested anything to receive it. There was no weight to the exchange, and so it floated away.

Money creates weight. Not in a burdensome way, but in the way that a promise creates weight. It anchors intention.

I’ve also started to notice how strange it is that I trust this dynamic when I’m the one paying, but doubt it when I’m the one being paid. When someone offers me something valuable and asks for fair compensation, I don’t feel taken from. I feel invited into something. I feel like a participant, not a target.

So why do I assume others feel differently when the roles reverse?

Part of it, I think, is that I’ve conflated asking for money with the worst versions of sales I’ve seen. The pressure tactics. The manipulation. The inflated promises. I’ve let those distortions define what it means to exchange value, and then I’ve avoided the whole territory to stay safe.

But that avoidance has a cost. When I don’t ask for money, I can’t sustain the work. When I can’t sustain the work, the people I’m meant to help don’t get helped. My discomfort becomes their loss.

There’s a quieter truth I’m learning to sit with: receiving is also a gift.

When someone pays me, they’re not just getting something. They’re also giving something. They’re participating in a flow that allows the work to continue. They’re saying, “I want this to exist in the world, and I’m willing to be part of making that happen.”

That reframe has been slow to settle in, but it’s starting to change how I feel when I name a price. I’m not extracting. I’m inviting. I’m offering someone the chance to be part of something that matters to both of us.

I don’t think the discomfort disappears entirely. Maybe it shouldn’t. A little tension can be a good thing. It keeps me honest. It keeps me asking whether the value I’m offering is real.

But the goal isn’t to feel nothing. The goal is to stop letting the discomfort make decisions for me.

The founders I admire most aren’t the ones who’ve eliminated the awkwardness around money. They’re the ones who’ve learned to act anyway. Who ask for what their work is worth, not because it feels easy, but because they trust the exchange.

Business exists to solve problems. When you genuinely care about solving someone’s problem, and you can actually help them, asking for money isn’t extraction. It’s an invitation into something shared.

The tension between impact and income is often a false one. The value you create is a gift. Getting paid for it is what allows you to keep giving.

I’m still finding my footing here. But I’m starting to believe that the discomfort I feel isn’t a sign that something is wrong. It’s a sign that something matters.

And maybe that’s enough to keep going.