Don’t Sell Expectations

A trip to Costa Rica, a high school promise, and a better definition of success

We went to Costa Rica for my mom’s 80th birthday.

The five of us saw both two-toed and three-toed sloths. We saw monkeys, toucans, turtles, crocodiles—and tree roots you can’t even imagine.

We went river rafting and ziplining. (And yes, it’s safe for certain 80-year-olds to zipline.)

In the middle of the hot springs in the rainforest, something kept coming back to me—something I’d overheard our tour director, Ronny, say under his breath:

“Don’t sell expectations.”

It felt especially true there. One minute the sun is shining, the next it’s pouring. Sometimes it’s your day to see monkeys. Sometimes it’s not.

Ronny is exactly right—it’s not good to sell expectations. But it made me think about how powerful it is to reset them.

Sitting in the hot springs—and later in a pool with an Imperial Original—it took me back to high school. I remembered a conversation on the way to the Nike outlet with a close friend. We both agreed we were going to make a lot of money. We didn’t know how, but we felt optimistic.

This was 1995—before what most of us think of as Silicon Valley tech money.

It was just… hope.

The weekend after we got back from Costa Rica, I ran into that same friend at our kids’ basketball games. We’re still close, and he’s been an invaluable advisor to both me and my wife.

It turns out that after selling his business and surpassing our high school goal before turning 40, he’s now taken a job turning around a company in a similar space.

What I love about that is—it has very little to do with money. He’s working on something that aligns with his skills and brings him fulfillment. He’s having fun.

If I could go back and talk to that 15-year-old hunting for Nikes, I’d tell him:

I love your optimism.

It’s good to have money.

But think about how you want to feel.

Think about feeling safe.

About being loved.

About finding time for things that make you feel the way shooting a basketball makes you feel.

About spending time with the people who matter most.

Because the truth is—

You can hit every goal you set at 15…and still miss the point.

Or you can find yourself in a rainforest, three generations deep, watching your 80-year-old mom zipline—and realize you're not missing anything.

Pura vida.