I used to think I hated salespeople. The pushy, scripted, “let me tell you why you need this” kind. So naturally, I built my whole identity around never becoming one.
Instead, I became a high school math teacher and taught for 15 years in Beverly Hills.
But in full transparency, I secretly dreamed of being the #1 salesperson in the country long before I ever made it happen. A lot of my friends were in sales, and they were making real money, traveling to cool places, winning contests and awards. I wanted that.
But I also thought salespeople were slimy. Manipulative. Gross. And I refused to become “one of them.” On top of that, I had a whole stack of logical, practical reasons: I couldn’t afford to give up my salary. Nobody would hire a teacher who didn’t have sales experience. I didn’t want to give up my summers off. So I never took a single step toward it.
Then one day, completely out of the blue, a friend of mine asked if I’d ever thought about being in sales.
The Sale Nobody Talks About
Notice something? None of those beliefs were facts. They were sales pitches. And I was the one buying them.
That’s the thing nobody tells you: the hardest sale you’ll ever make isn’t to a customer. It’s to yourself. And most of us are closing that sale every single day without even knowing we’re in the room.
I had sold myself the belief that leaving teaching wasn’t possible. I had sold myself the belief that salespeople were bad and wrong. I had sold myself on staying stuck, because at least stuck was familiar.
When my friend asked, I told him the truth. Yes, actually, I had thought about being in sales. I just didn’t think I could get hired without experience.
He told me he thought I’d be really good at it and offered to get me an interview with his sales manager. I took him up on the offer and went on the interview, scared I was going to get called out for not having experience. Lo and behold, that’s exactly what happened. The guy interviewing me said, “You did a great job, but there are 89 internal people who want this position. Your only experience is teaching, and you’ve never sold anything.”
Without even thinking, I said, “I’ve been selling math to teenagers for fifteen years. Nobody wanted to buy that.”
I’d been “selling” those teenagers for fifteen years, except there was no transaction. They weren’t paying me to teach them math. At least not with money. But they were paying me with their time, attention, and trust.
So what was actually happening in that classroom? Connection. Rapport. Trust. If they liked being there, if they trusted me, they showed up and did the work even when they didn’t feel like it.
When I saw it through the lens of what I did as a teacher, that was the moment I realized selling was never about the transaction. It’s about the relationship.
So that’s exactly what I did once I got into sales. I didn’t have fancy scripts. I didn’t have technical sales training. I wasn’t even comfortable asking people for money. What I could do was show up as myself, take care of people, and build enough trust that they wanted to work with me. The contract came when it was right. My job was just to be of service and help make “right” come sooner when I could.
Whoever's Asking The Questions Is Running The Show
There’s a principle EWTS teaches that most people only consider as pointing outward: the person in control of a conversation is the person asking the questions.
Nobody wants an advice monster who just tells them what to do. We gain more trust and influence when we ask questions about the other person and let them feel seen and heard.
So when we apply that same principle to ourselves (the person in control of the conversation is the person asking the questions) we can create very different outcomes for our lives.
Nobody ever tells you the most important conversation you’ll have all day is the one running in your own head. And in that conversation, most of us aren’t asking questions at all. We’re just handing over statements and calling them facts. It’s not possible. I’m not cut out for it. I’ll never pull this off. I’m too old.
Statements shut a conversation down. Questions keep it open.
This is exactly what I coach founders and executives on now: the moment you catch yourself stating a limitation instead of questioning it, you’ve already handed control of your own life over to a belief you never actually chose. Ask a question instead, and you take the wheel back.
So I started asking myself one question every time an old reason showed up: is this actually true, or is it just familiar?
Two years after that interview, I was the #1 salesperson in the country for a Fortune 500 company. Not because I had some natural gift for sales. Because I finally stopped stating my limits and started questioning them.
The 5-Question Belief Check
Next time you catch yourself saying “I can’t” or “that’s not possible for me,” run it through this before you believe it:
1
Catch it. Notice the moment you’re explaining to yourself why something can’t happen. That explanation is a sales pitch, not a verdict.
2
Ask: Is this true, or just familiar? Old beliefs feel like facts because they’re repeated, not because they’re proven.
3
Ask: What would have to be true for this to change? Get specific. Vague limits stay vague on purpose.
4
Ask: What can I choose to believe instead? Pick a belief that actually moves you forward
5
Take one action before you feel ready. Certainty comes after the step, not before it. Waiting to feel ready is just another belief in disguise.
Run through these five questions the next time an old “I can’t” shows up, and notice how much harder it is to believe once you’ve actually gotten curious with it.
You're One Sale Away
Here’s what I want you to sit with: you are selling yourself something right now. Today. Whether you notice it or not.
There is no neutral. You’re either selling yourself the life you want, or you’re selling yourself every reason you can’t have it. And whichever one it is, you’re the one asking the questions, or refusing to.
So, what have you decided isn’t possible for you, simply because you’ve repeated it long enough that it stopped sounding like a belief and started sounding like a fact?
I unpack the rest of this story, the interview and the epiphany that changed how I saw selling forever, in my TEDx talk.
Watch it here.
