A few days ago, I asked a coaching client a simple question: When was the last time you really felt the sting of rejection?

He thought for a moment and told me about a neighbor who had decided not to list their apartment with him.

“But did they sell it?” I asked (I knew that they had wanted to shop it themselves within the building).

“No.”

“Then that doesn’t count. The story isn’t over yet.”

He laughed.

“Give me another one.”

He sat quietly for a long time. Long enough that the silence started to become the answer. Eventually, he looked up and said, “Wow.”

I didn’t say anything. Sometimes coaching is just holding up a mirror.

After another moment, he said, “I think the reason I can’t come up with anything is because I’m not really putting myself out there.”

There it was.

It struck me because most of us assume the absence of rejection is evidence that we’re doing something right. Maybe. But sometimes it’s evidence that we’re only pursuing opportunities where the answer is already mostly yes.

The older I get, the more I think rejection is an interesting metric. Not because we should seek it out for its own sake, but because a complete absence of rejection can be a sign that we’re playing a smaller game than we realize.

Years ago, before real estate and coaching, I spent several years auditioning as an actress. One of the first lessons you learn in that world is that you should never appear to want the part too much. Desperation is detectable. The casting director can smell it.

So I developed a strategy. Before auditions, I would tell myself that the role wasn’t that interesting anyway. The project probably wasn’t that great. The opportunity wasn’t that important. If I didn’t get it, no big deal.

Looking back, acting taught me something useful and something dangerous. The useful lesson was that rejection is survivable. The dangerous lesson was that the best way to protect yourself from rejection is not to want anything too much.

Somewhere along the way, I realized that the strategy I had developed as an actress was quietly limiting me as a business owner. I had become very good at protecting myself from disappointment. The problem was that I was also protecting myself from possibility.

In acting, your job is to audition. In business, your job is to ask. Ask for the meeting. Ask for the referral. Ask for the introduction. Ask for the opportunity. Ask for the listing.

And the people who ask most often tend to hear no most often.

That’s the trade.

If you want a life with more possibility in it, you have to be willing to collect more no’s.

This is where I think many high achievers get stuck. We spend years believing that if we work hard enough, prepare well enough, and perform well enough, we should get the outcome. When we don’t, it feels like a violation of the bargain.

But there was never a bargain.

We control our effort. We do not control the outcome

Coaching Corner

The people I know who accomplish the most are not detached from their goals. They care deeply. Often more deeply than everyone else around them. What makes them different is that they are able to separate desire from attachment. They can walk into a room genuinely wanting the business and still be okay if they don’t get it. They can lose a client, a listing, a deal, or an opportunity without turning it into a story about their worth. They understand that one outcome is not their entire future.

I’ve come to believe that one of the most useful skills in business is the ability to hold two thoughts at the same time: I really want this, and I’ll be completely fine if I don’t get it.

The first creates energy. The second creates freedom.

Barbara Corcoran has a rule that after a big loss you’re allowed one day to lick your wounds. I’ve always liked that. Not because disappointment is weakness. Quite the opposite. If you cared enough to pursue something meaningful, disappointment is part of the deal.

A lost listing should sting. A missed opportunity should sting. Rejection should sting.

The goal isn’t to avoid feeling bad. The goal is not to renew the lease.

Feel disappointed. Complain to your spouse. Take the long walk. Replay the conversation. Eat the ice cream. Then move on.

Because the opposite of attachment isn’t indifference. It’s trust. Trust that there will be another opportunity. Trust that one rejection isn’t a verdict. Trust that your future is bigger than this one outcome.

As an actress, I learned how to protect myself from rejection by pretending I didn’t care. As a business owner, I’ve had to learn something much harder. How to care deeply. How to ask boldly. How to put myself out there. How to genuinely want the thing. And then somehow let it go.

Because ambition isn’t the problem.

Attachment is.