Never Close a Sale
When I first moved to San Francisco, I worked as a personal trainer in gyms. Gyms are intense sales environments. The folks at the front desk are trying to close new members and personal trainers prowl the gym in search of new clients and the “packages” they’re hoping to sell.
I got a job working at World's Gym, a bodybuilder's gym in the Potrero Neighborhood. Every Saturday morning professional bodybuilders would oil up and flex in front of the mirrors. I taught step aerobics. Those 5 AM classes were the only part of the job I got paid for. The rest was “eat what you kill.”
After about two weeks, the manager of the gym got angry with me because I didn’t have any clients. He gave me an ultimatum: close a client today, or don’t come back.
It was already a sales-heavy environment; this pressure made it insurmountable. I didn’t sell any new clients and was fired the following day.
I left World’s Gym and without quotas hanging over me, something shifted. The first client I ever landed came not from a sales script, but from walking out of a contact improvisation dance jam onto the street and noticing a woman holding her knee in pain. As a runner, I was intimately familiar with knee pain. I walked over – not as a salesperson, not even consciously as a trainer – but as someone who had been where she was.
“Hey, I’ve had a bunch of knee pain,” I said. “I’m a personal trainer. Would you like me to give you a free session and see if I might be able to help?”
She said yes. The next day she came to my house, and that free session turned into a working relationship that lasted six years, three days a week. I earned tens of thousands of dollars in lifetime value from a single moment of noticing someone else’s need and offering help.
My second client arrived just as strangely. I was driving my parents’ Toyota pickup down Valencia Street in the Mission when I saw a man hunched over on the sidewalk, holding his lower back. Without thinking, I stopped the truck in the middle of the road, jumped out, and approached him, “You look like you’re in pain. I’m a personal trainer. I might be able to help. Do you want to talk more?”
We ended up working together for three years. I didn’t give him a pitch. I didn’t have a package prepared. I wasn’t even trying to land a client. I was responding to someone in pain, and I had a possible solution.
Those stories sound bold in hindsight; dramatic, even. Who jumps out of a truck in traffic to approach a stranger on the street? They sound like courageous examples of proactive outreach. Or what Internet marketers would call “lead generation.” But I wasn’t approaching strangers out of a desire to do business or to fill a quota, but because I sincerely wanted to help.
At World’s Gym, when I was told I had to close clients or be fired, I froze. But with that pressure removed, I was able to ask people if they wanted help that I was prepared to offer.
In last week’s “How to Sell Yourself” workshop, I shared that I’ve never been good at “closing” – at trying to pressure or persuade a prospective client into buying anything. I avoid closing in favor of asking “Would you like what I have to offer” and making it easy for them to say “yes.” Those early experiences as a personal trainer showed me that the most transformative opportunities don’t begin with a close, but with an invitation.
Homework: Approach a Stranger
This week’s homework is about practicing connection without pressure – strengthening the muscle that makes asking possible.
Approach a stranger. Not from a place of asking for anything, and especially not in an attempt to close. Leave off your agenda. Don’t try to sell. Instead, just say hello to someone. Maybe ask their name. If you’re feeling bold, compliment them – their clothing, eyes, or hair.
So much of getting comfortable asking someone for something comes from a place of authentic human connection. The pressure to get your way is antithetical to simple human connection.
Focus on the connection, not the close.
3 Things I’ve Loved This Week
Podcast I’m Listening To
The DealBook Summit from the New York Times
Andrew Ross Sorkin’s DealBook Summit happened last week in New York. I admire any event producer who can sit down for ten 45-minute fireside chats in two days, and Andrew does so with some of the most influential, powerful, and famous people in the world.
Interviews from the DealBook Summit are released as podcasts and make for great listening. I enjoyed Andrew’s conversations with Gavin Newsom about politics, Jimmy Donaldson (aka MrBeast) about the attention economy, and a roundtable discussion about the future of journalism.
Clip I’ve Loved
Star basketball player Giannis Antetokounmpo on failure
Antetokounmpo, after being asked if he considered the past season a failure:
Do you get a promotion every year at your job? No, right? So every year, your work is a failure?
No. Every year, you work towards something, which is a goal: It's to get a promotion, to be able to take care of your family, provide a house for them, or take care of your parents. It's not a failure, it's steps to success. There's always steps to it. Michael Jordan played for 15 years and won 6 championships. The other 9 years were a failure? That's what you're telling me.
There's no failure in sports. There's good days, bad days, some days you are able to be successful, some days you're not, some days it's your turn, some days it's not your turn. That's what sport's about. You don't always win, some other people are gonna win. And this year, someone else is gonna win. Simple as that.
So 50 years from 1971-2021 that we didn't win a championship, it was 50 years of failure? No it was not, there were steps to it, and we were able to win one, hopefully we can win another one.
Book I’m Re-Reading
Breathe: The New Science of a Lost Art by James Nestor
I read this book in 2020, but picked it up again after listening to a great conversation between James and Tim Ferriss. I’m a big fan of breathwork of all kinds, having tried some throughout my professional athletic life and more since. I learned Tummo breathing from Wim Hof, practice box breathing when I’m stressed, and lately have been jogging with a nose strip to train myself not to mouth breathe on runs.
James Nestor is a scientific investigative journalist, and shares his own experiences, plus countless scientific studies, on the unexpected benefits of better breathing.
If you only take one thing away from the book (or today’s newsletter), it would be “learn to breathe through your nose.”
Want more?
The next How to Sell Yourself workshop series begins January 2026. This is a different approach to selling for people who aren't quite comfortable selling themselves - yet!
The Snafu Conference is an immersive 1-day experience about authentic selling in a chaotic world. The summit will take place on March 5, 2026 at the Oakland Museum of California. Ticket prices go up on December 15, so get yours now!
Responsive Conference is coming back in 2026! Our theme is "attention & work." We'll be looking at how our attention shapes our work – and our lives. Ticket prices go up December 15, so don't wait!
Until next week,
Robin
