I was sitting in the back of an Uber a few months back when the driver and I started chatting.
He was in a punk band, did the Uber thing on the side when he wasn’t on tour. But he was
about to head back out on the road. His band had signed a record deal with a big-time label.
They’d spent months in the studio recording. Now the record was about to be released. The
tour was mapped out across the country over the next several months.
I was impressed. Usually when you meet an Uber driver in a band, they don’t have a record deal
on the books. (Side note: I googled the name of the band after we got out of the car. His story
checked out. I found the music video to prove it.)
But while I was impressed, he was clearly not. Yeah, it seemed great when they first got the
deal, he explained. But everything just moved so slowly after that. Ten months to make a
record, then months longer to produce it. Then the marketing and the planning. Now, they
were finally about to hit the road to play music he now considered dated. It wasn’t fresh and
new. It was carefully crafted and finely tuned, and he just wasn’t feeling it.
He told me that it had been his dream to get signed by a record label. That was all he ever
wanted. And now that he had it, he didn’t really want it. He had been working so hard toward
that goal for so many years.
He didn’t understand how to live with a goal he’d already achieved.
I sat in the back of the car thinking about how crazy this all sounded. Here was this young guy
— maybe 25 years old — who had achieved what so many people aspire to but so few of us get
to have. And he wasn’t happy.
Suddenly I knew exactly how he was feeling.
So I broke out some advice a friend of mine had given me awhile back — advice I hadn’t taken
but thought was profound: I told him, sit down with a glass of wine, a bourbon, a cup of tea,
whatever, and think back on what you’ve accomplished since you started the band. Then, write
it all down — the big things and the little things. The first time you played to a packed house.
The first time you stumbled on someone listening to your music. The moment you signed the
record deal. The music video you shot with record label money.
Chances are, you’ve neglected to celebrate all those moments, I continued. And when you take
the time to reflect on all the amazing things you’ve accomplished, it’ll blow your mind.
I started my business in August of 2017, and since then, tons of amazing things have happened.
But if you ask me on an average day how it’s going, I’ll probably sigh and tell you I’m hanging in
there. That owning a business is hard. That I feel overwhelmed and inundated and uncertain
more often than not.
But the reason reflection — our seasonally appropriate word of the month — is such a powerful
thing is that it forces us to take stock of what we’ve done, where we’ve been, how far we’ve
come. And when it’s out there, in black and white, written out in a nice, neat list of hell-yes-I-
did-that accomplishments, you can’t ignore it.
When you’re driven, you get accustomed to keeping your eyes trained ahead. You’re going for
the next goal, and once you get there, you move on to the next. But what’s the point in hitting
your goals if you never take the time to celebrate them?
I say that as someone who has yet to make such a list myself. But maybe this month is my
As for the Uber driver, the recipe for reflection seemed to resonate with him. He thanked me
when I got out of the car. And he smiled. But you never know. Reflection is sometimes easier
said than done.