When I moved to Boulder in the early 2000s, I worked a variety of jobs that, taken together, looked less like a career path and more like someone throwing darts at a newspaper’s classified section. I managed medical offices, did graphic design, worked retail, and eventually found myself driving a town car between Boulder and Denver International Airport. Of all the odd jobs I’ve had, that last one remains a favorite.
I love driving. I love being awake before everyone else. I enjoy talking to strangers, provided they’re interested in talking, and I’m perfectly content spending an hour in silence with someone who isn’t. The job was nearly perfect, except for the rather inconvenient problem of inconsistent pay. Apparently, enjoying your work doesn’t always convince the mortgage company to enjoy your arrangement.
Over the course of a year, I developed relationships with regular passengers, many of whom traveled weekly for business. We’d talk about everything from politics and philosophy to computers and the future of technology. I was in my twenties, endlessly curious, and more than happy to share my thoughts with anyone unfortunate enough to express an interest in hearing them.
One of those regulars was a man named Oliver.
Oliver and I frequently talked about technology, a subject I’d been fascinated with since childhood. One morning, he arranged a ride to the airport with several colleagues. What followed was an hour of enthusiastic conversation about computers, digital life, and where technology might be taking us. Everyone participated. We laughed, exchanged ideas, and thoroughly enjoyed ourselves. It was exactly the sort of ride that made me love the job.
When we reached the airport, Oliver informed me that nobody was actually flying anywhere. The entire trip had been a job interview.
Oliver and his colleagues had a technology startup, and they’d decided to see how I’d fit with their team. Apparently, an hour of me enthusiastically talking about computers was enough to convince them I belonged in the company. They wanted to hire me.
I had just interviewed for a job I didn’t know existed, with people I didn’t know were interviewing me, and somehow managed to get hired.
For someone who has never been particularly good at pretending to be anything other than himself, this was about as ideal a hiring process as I could imagine. No rehearsed answers about my greatest weaknesses. No explaining where I saw myself in five years. Just me, driving a car and talking about things I loved.
Naturally, I took the job.
Unfortunately, the dream of working for a technology startup and the reality of working for a technology startup turned out to be slightly different experiences. I’d imagined participating in the development of exciting new technology. Instead, I was mostly responsible for selling it.
It turns out there’s an enormous difference between happily discussing the future of computers with a stranger and calling that same stranger to convince him to purchase something. They’d hired me because I could talk to people for an hour without running out of things to say. Then they handed me a telephone and discovered I could barely stand to use it.
I was also, in retrospect, not exactly an employee of the month. I was young, drank more than I should have, and possessed an almost supernatural inability to repeatedly make unsuccessful sales calls. Each rejection made the next call less appealing, until the telephone itself began to resemble a tiny plastic monument to anxiety.
There’s probably a reason my phone has been on silent for nearly twenty years.
Eventually, my employment came to an end. The technology involved creating three-dimensional models layered over Google Earth, which was exciting for its time. The company eventually pivoted, laid off most of its employees, and moved into other areas of custom mapping. In fact, I only recently discovered they’re still in business today. Good for them!
I sometimes laugh thinking about how close we were to a very different technological revolution. Had the company started a year or two later and decided to develop applications for a strange new device called the iPhone, who knows what might have happened? Perhaps we’d have created something remarkable. More likely, I’d have been equally terrible at selling it.
But I wouldn’t trade the experience.
I got to work inside a technology startup at a moment when the possibilities of digital life seemed almost limitless. I learned about business, technology, and myself, including a few things that probably should have been obvious much earlier. I eventually went on to become an assistant dean of admissions at Naropa University and later opened businesses of my own. Looking backward, the entire experience feels like one of those strange little turns that helped shape everything that followed.
What fascinates me now isn’t that I happened to get the job. It’s that I had absolutely no idea anything important was happening while it was happening. I was simply driving some people to the airport.
How many moments in our lives work this way? How much of what we eventually call a career, an identity, or a life is simply the accumulated consequence of being ourselves in situations we have no idea will matter?
We spend an enormous amount of time trying to position ourselves for opportunity, carefully managing our presentation and imagining which decisions might lead somewhere important. Meanwhile, some of the most consequential moments arrive disguised as ordinary Tuesdays.
There’s something wonderfully absurd about being hired because you were completely yourself and then, quite possibly, losing the job for exactly the same reason. I suppose that’s the risk of authenticity. The qualities that make you appealing aren’t necessarily the qualities that make you employable. Especially when someone hands you a telephone.
I’ve always thought of that experience as a bit of synchronicity. Not because I believe the universe arranged an elaborate scheme to get me a short-lived job selling 3D maps, but because life has a remarkable way of connecting events that seem entirely unrelated until we look backward.
Sometimes the path only becomes visible after we’ve walked it. And sometimes an important job interview is the one where you didn’t even know you were applying.