This week, I got a speaking inquiry – and quoted an astronomical figure. Normally, when I quote an amount I’m uncomfortable with, I talk to my wife or consult a friend. This time, I rattled off the email and went on with my day.
I began to wonder why I was able to quote a number that, even six months ago, would have felt beyond the pale. I realized it’s because I have been practicing uncomfortable asks almost every week this year.
As I’ve written about recently, I started selling stuff on Marketplace and Craigslist. Most notably, I sold the 15-foot palm tree in my front yard. An arborist would have charged me $1,000 to remove it. Instead, someone paid me $200 to dig it up and haul it away.
One of my quirks is that I always bargain – even just asking for $1 or $10 off – because I’m mildly uncomfortable doing so. My discomfort is the point. At the very end of the transaction, I also ask the other person to leave me a review. It’s such a small thing that I shouldn’t be uncomfortable asking, but I am, because, after having just completed the transaction, I’m asking for one more thing. (Of course, the person always says yes with a smile.)
In asking people on Marketplace for a small discount and to leave a review, I have unknowingly been practicing negotiation. And the small discomfort of negotiating something tiny has resulted in a much larger change than I realized.
We’re Negotiating Constantly
Paul Graham, the founder of Y Combinator, famously said of Sam Altman that you could parachute Sam onto an island full of cannibals and come back 5 years later, and he would be king. Sam’s gift is dealmaking. Most of us aren’t born with it, but we can train it in small moments.
Negotiation Can Be Small
When I think of negotiations, what comes to mind is a tense meeting in front of stakeholders. Actually, though, what it usually looks like is small moments: my wife and I discussing what we’re going to have for dinner, sharing a passing comment with a colleague. Big moments do happen, but you practice negotiation in low-stakes situations.
Don’t Use Force
I had the pleasure of introducing Doug Kirkpatrick on stage at Responsive Conference 2026. Doug was an early employee at the Morning Star Company, a self-managed tomato processor. The company embraces the principles of “don’t use force” and “keep your commitments,” instead of traditional management structures. When it comes to negotiation, this is perhaps the most important principle of all: that we can ask for what we want without force or pressure.
Train Discomfort
I wrote about the Great AI Divide, about how AI can make our lives more comfortable than ever, or help us learn faster, depending on how we use it. Negotiation sits on the difficult side of that divide. As trivial as it seems, negotiating on Facebook Marketplace enabled me to ask for an astronomical figure without a second thought.
