Work that feels like play

I followed my curiosity, and here's where I landed...again.

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When I enrolled in college, my dad gave me just one piece of advice: “Study whatever you’re interested in, because it’s not gonna matter anyways.”

The older I get—and the further I’m removed from my college years—the more I’m finding that to be true. Not just in my own life, but the lives of my peers, as well.

According to the Federal Reserve, only about 27% of us end up working in the field in which we graduated. So the vast majority of us—myself included—have wasted hundreds of hours, and thousands of dollars, pursuing something of little use. For the rare few who actually ended up working in their field of study—and actually enjoy it—I envy your clairvoyance.

So I followed my dad’s advice. I pursued my curiosity in college, rather than money or prestige. My classes were a breeze. Each day, I was itching to get my butt in the seat. To listen to hour-long lectures, and fiercely scratch away at my note pad. During this time, I scored the highest grades of my life. It was like four years of falling through a black hole—I couldn’t stop my curiosity even if I tried.

The material, however, was utterly useless in the real world.

In the years since graduating, I’ve worked a half dozen jobs, in a half dozen different industries, trying to find my way. I worked in IT and sales. I’ve done some marketing, some photo editing, and some software development. But the most lucrative career I’ve been offered, lay at precisely the intersection of those useless skills I learned in college.

Escape competition by finding your play

The legendary investor Naval Ravikant has a saying that, your biggest competitive advantage is finding the things that feel like play to you, but look like work to others. That’s because play is the precursor to obsessions, and it’s very hard to compete with someone who is obsessed.

Play is the gamer tapping away late into the night, it’s the athlete pushing their body to its limits, it’s the software developer writing out lines of code by hand. It’s the activities that—despite their intensity—leave us feeling more energized, rather than drained afterwards.

I pursued play during college, but soon thereafter, abandoned it. In the adult world, other considerations had to take precedence. Considerations like rent and lunch. Money and play seemed to be at odds.

At least, that’s what I thought.

People and writing

Two years ago, I started hosting people. At first, it began with small gatherings. But with time, these gatherings became more frequent, more intentional, and much, much larger.

I enjoyed being the host; listening to peoples stories, and occasionally sharing my own. As the group expanded, I began to meet people who were more fascinating, and thoughtful, and compassionate than I could’ve ever imagined.

Around that same time, I also started writing. There was no real purpose to it. I was just pulling at the loose string of curiosity. The precursor to a minor obsession.

I started—as weird as it may sound—to read about writing. Then, I’d wake up early, slide out the front door, and make my way to my favorite coffee shop to write. There, time would evaporate.

As the size of my events began to grow—writing revealed its purpose. It would codify the values of the group I was hoping to establish. It would be the medium I’d use to distill the lessons learned in our community.

Rediscovering play as an adult

Building this community and developing my writing, are sources of personal joy. The byproduct, of which, is a company I created called Startup Social. But it didn’t start out that way.

For the first year of its existence, I never considered Startup Social a tool for making money. To me, it was a bit like reading or going to the gym. It was something I did for fun, with no real expectation of outcome. Now don’t get me wrong, hosting hundreds of events, and writing a new article every week wasn’t easy. But despite the intensity, I always felt more energized afterwards.

Then I realized—almost two years in—that community and writing are my play.

Which might have been why, when my dad told me to study whatever I was interested in, those are the things that I chose.

A real life anthropologist

I majored in Anthropology in college. It’s a field that gets no love, and I’ll never understand why. Some of my favorite classes had names like: Lost Tribes and Sunken Continents, Human Sexuality, Forensic Identification, and Ethnoarchaeology.

A seasoned anthropologist travels to the most remote parts of the world, at risk of life and limb, to be a fly on the wall. They listen firsthand to stories and traditions, and document what makes a people unique. They do so in an attempt to untangle the mystery of human existence; why we fight, and love, and lie, and create.

After years of observation, they return back home with one thing left to do. They must codify the values they’ve learned, in writing.

I studied what I was interested in, and in doing so, I was ultimately reunited with those same interests nearly a decade later. Albeit, in a very different form.

You can’t think your way into play, you have to act

I turned away from Anthropology after college because, it’s not a job. Not in the traditional sense, at least.

Yet, all these years later, I discovered that the most lucrative skills in my arsenal, are the exact same ones I was told made me unemployable.

I can’t even begin to recall how many times I’ve tried to convince myself that I enjoyed more lucrative fields. I believed I could thrive in finance, then law, then medicine—only to have my actions reveal otherwise.

I don’t believe—not even for even the most introspective among us—that we can intuit what feels like play and what feels like work. In my experience, the realization has been much more visceral. I had to get my hands dirty. I had to explore through trial and error. My actions—rather than my thoughts—revealed the truth of my preferences.

There was no track in college for hosting 600+ person tech events, or curating dating salons, or designing instructional workshops. Had there been, I’m not sure I would have ever signed up for it.

But by following those curiosities, those little whispers, that hinted “Hey, this could be interesting?” I ended up in the same place that I began.


P.S. If you’re curious, I also minored in Business. Startup + Social. Life is weird.

P.P.S. If you’ve made it all the way down here and don’t feel that you’ve just wasted five minutes, consider hitting the Like button on this essay.

It helps others find it. And it makes me happy.

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