I Thought Success Looked Like This

For most of my thirties, I was obsessed with looking successful.

I don't think I understood that about myself at the time. I would have told you I just liked nice things. Good clothes, good restaurants, nice cars, expensive watches. I worked hard, so why shouldn't I enjoy what I earned?

But the watch was different.

It was a Rolex Submariner. I bought it when I was 34 after the best year my business had ever had. I remember sitting in my car outside the dealer for ten minutes before going inside because even though I could afford it, spending that much money on a watch still felt insane.

I bought it anyway.

The first few weeks, I couldn't stop looking at my wrist. Not because I needed to know the time. Half the time I checked it, I didn't even register what time it was.

I liked what it said about me.

I grew up in a house where money was always discussed quietly. My parents weren't poor, but there was never much extra. I wore my older brother's clothes, we rarely ate out, and vacations meant driving somewhere we could come back from the same day. My father worked six days a week for most of my childhood.

So when my business finally started making real money, I think I became determined to prove that I had escaped that life.

The watch became part of that.

I'd wear it to meetings. Dinners. Weddings. Even places where wearing a $10,000-plus watch probably wasn't particularly smart.

I'd notice when people looked at it.

Sometimes another guy would recognize it and say, "Nice Sub."

I'd pretend it wasn't a big deal.

"Thanks, man."

But inside, I loved it.

It sounds embarrassing now, but I think I genuinely believed people respected me more when I wore it.

A few years later, I took a trip to San Diego with some friends. We rented a house near the beach for the weekend. Nothing crazy. Mostly eating, drinking, sitting outside and pretending we were still young enough to recover from staying up until two in the morning.

Saturday afternoon, we walked down to the beach.

I remember taking my watch off before going into the water.

I didn't want salt water or sand getting into it, which is funny considering what the watch was designed for. I wrapped it inside my T-shirt and put everything near our chairs.

We swam for maybe twenty minutes.

When I came back, the shirt was there.

The watch wasn't.

I thought one of my friends was messing with me.

"Okay, who has it?"

Nobody knew what I was talking about.

I emptied the beach bag. Checked underneath the towels. Shook out my shirt. Checked my shoes even though there was absolutely no reason the watch would be inside my shoes.

Nothing.

For the next hour, I completely lost my mind.

I walked up and down the sand staring at the ground. I asked strangers if they'd seen a watch. I went through the bags again. Then again.

My friends were helping me, but eventually one of them said, "Man, it's gone."

I got angry at him for saying it.

That night, everyone wanted to go to dinner. I didn't.

I sat at the house searching online for the serial number, insurance information, police reports, pawn shops, anything I could think of. I kept calculating what I'd paid for it and what it was worth now.

But underneath the money was something else.

I felt embarrassed.

I remember looking at my bare wrist at dinner the next day and actually feeling less successful.

That's the part I still remember.

Nobody had said anything. Nobody cared. These were my friends. They knew exactly who I was with or without the watch.

But somehow I felt like something had been taken from me beyond the object itself.

For the next few weeks, every time I got dressed, I'd look at my wrist. I considered immediately buying another one, even though replacing a stolen luxury watch was not exactly an emergency.

One afternoon, I was having lunch with my dad.

He knew I'd lost it and asked if I'd found it.

"No."

"That's too bad."

Then he kept eating.

That was it.

I laughed and said, "You know how much that thing cost?"

He looked at me and said, "I know. That's why I never understood why you wore that much money on your hand."

There wasn't some profound speech after that. My dad isn't that kind of person.

We started talking about something else.

But I thought about what he'd said for a long time.

This was a man who had worked six days a week for years, raised a family, paid his mortgage and somehow put his kids through school. I had never once seen him wear a watch worth more than a couple hundred dollars.

And I'd somehow convinced myself that the thing on my wrist was evidence that I'd accomplished something.

I eventually received an insurance payment. I could have replaced the Rolex.

I didn't.

I bought a regular watch for a few hundred dollars and put the rest of the money away.

I'm not going to pretend I suddenly stopped liking nice things. I still do. I still notice a beautiful watch when somebody is wearing one. Maybe I'll buy another expensive one someday.

The difference is that I don't need it to introduce me anymore.

The Rolex wasn't the problem. It was just a watch.

The problem was how much work I'd made it do for me. I wanted it to tell strangers that I was successful before I ever opened my mouth. I wanted it to prove that I'd made something of myself. Maybe, in some strange way, I wanted it to prove that all those years of watching my parents worry about money hadn't followed me into adulthood.

Losing it didn't change my life.

But it showed me something about myself that I probably wouldn't have admitted otherwise.

For years, I thought I was wearing the watch because I had become successful.

It took losing it to realize I had been wearing it because some part of me was still afraid I wasn't.

So if you're reading this and you're chasing the car, the watch, the house, the clothes or whatever else you think will finally make people look at you differently, there's nothing wrong with wanting those things. Work for them. Enjoy them if you get them. Just don't make the mistake I did and let them become proof of what you're worth.

Because eventually the watch comes off. The car gets sold. The clothes get old. Money comes and goes. And when all of that is taken away, you're still left with the same person underneath it.

Spend more time building that person.

Become someone who doesn't need a logo on his wrist, a certain car in the driveway or a number in a bank account to feel important. Become someone whose character speaks before his possessions ever get the chance.

I still like nice watches.

I just don't need one to tell me what I'm worth anymore.