Robin Waite tells a story about how he ended up on a podcast that generated three thousand inquiries and hundreds of thousands of dollars in business. But the interesting part isn’t the outcome—it’s the chain of small acts that led there, and how easily any of them could have broken.

If I hadn’t have gone to that event, if I hadn’t have just dumped my coat and helped direct people, if I hadn’t offered to help for free, if I hadn’t got to know the team, if I hadn’t, if I’d asked for the wrong thing or too much or too, I don’t know if I’d got the ask wrong, any one of those things could have ended up being like a Sliding Doors moment where I then I go from 3000 leads to just going about my life as a coach.

Notice the texture of what Waite describes. He arrived at an event and saw six hundred people who looked lost. So he dumped his coat, put his bag on the floor, and started directing people—telling them where the cafeteria was, where the auditorium was, where the book signing would happen. He wasn’t staff. He was a guest. But people needed help, so he helped.

That’s when the managing director noticed him. And because Waite had been genuinely useful, the conversation shifted: “We’ve got a pricing query. Would you have five minutes?” From there, he offered to coach their team for free. He got to know the organization. When the opportunity finally came, he asked for something modest and well-timed—not a guaranteed spot, but a place on the bench if someone canceled.

Here’s what makes this counterintuitive: none of it would have worked if Waite had been calculating the return. He names this directly: “The moment I make it about me and make it about my mortgage and putting food on the table for my kids, it just… it’s gone.”

We tend to think of generosity as an investment strategy—give now, receive later. But Waite is describing something different. The generosity had to be genuine. Not generous-with-an-agenda. Not helpful-because-it-might-pay-off. Actually generous. Actually helpful. The calculation couldn’t be running in the background, because people can sense when it is.

This creates an uncomfortable paradox. Generous acts can lead to extraordinary outcomes. But the moment you’re being generous in order to get those outcomes, you’ve poisoned the well. The very thing that makes connection work—the absence of calculation—disappears when you start keeping a ledger.

What if this applies to conversation more broadly? We often approach dialogue with goals in mind: make a good impression, convey our point, persuade, network. These aren’t bad intentions. But they introduce a transaction into the exchange. The other person becomes a means to our end, even if subtly.

Waite’s “Sliding Doors” reflection suggests an alternative. What if the conversations that matter most require something closer to what he did at that event: showing up, seeing what’s needed, offering help without expectation, and letting whatever happens next happen? Not passive—he was actively helpful. But not calculating. The generosity came first; the outcome was a surprise, not a goal.

The uncomfortable implication: you can’t strategize your way to genuine connection. You can only be genuinely generous and see what emerges.

This field note references the Podtalk episode “Momentum with Robin Waite,” published May 5, 2025.