“You have to persuade yourself that you absolutely don’t care what happens. If you don’t care, you’ve won.” — Felix Dennis

I learned this lesson when I had the chance to sell to the same prospect twice. 

The first time, a mutual contact vouched for her as he introduced us. “She is perfect for what you do,” he told me, “and it could be a lucrative deal.” I showed up full of hope. We had a great conversation. At the end, she said, “I can really see us doing business together.” I went home and put the number in my forecast before I created the proposal. I was so sure this deal was happening!

It did not.

I stayed in touch anyway. Almost a year later, I was back in her office. This time I’d spent twelve months watching her hesitate, stall, and twice tell me she wasn’t sure this was worth pursuing. I walked in with nothing booked next to her name. My actual plan was to ask her why we were even meeting — I genuinely wasn’t sure she saw the value.

That meeting closed the deal.

What changed?

The difference wasn’t that I stopped caring the second time. (This is where the quote isn’t quite accurate.) I cared plenty — I still needed the business, I could see the difference our work could make in hers, and it still felt like a solid fit. The difference was that I wasn’t attached to a specific outcome anymore. Attachment and caring aren’t the same thing, and confusing them is what makes so many of us sound needy on sales calls without ever noticing we’re doing it.

Anytime I decide ahead of time that a deal is going to close, I’ve put myself in a spot where the conversation can only go two ways — meet my already-inflated expectations, or disappoint me. There’s no upside left, only downside. So when the prospect raises a normal doubt, I rush to smooth it over. When they ask a question, I answer instantly instead of finding out what’s really behind it. I’ve decided I’m the right answer to whatever they need, before I’ve confirmed they need anything at all.

What actually shifted between those two meetings wasn’t indifference. It was regulation — a steadier, less anxious energy that let me ask real questions instead of performing a confidence that wasn’t real.

What’s reality?

The worst part is, most potential clients don’t act at all. One widely cited study of B2B sales conversations found close to half of buyers who complete a full sales process end up doing nothing. Not choosing a competitor. Nothing. 

When I hold that truth and compare it to my wild optimism, I start to feel truly delusional.

Where in your pipeline are you already counting money that hasn’t arrived? What would that next conversation sound like if you walked in curious instead of certain?

Hit reply and tell me what you notice.