Finding comfort in the uncomfortable

The company I co-founded is now ten years old. Prior to this, I had never held a job for longer than three years. And yet, despite the fact that the riskiest career move I’ve taken has turned out to be my most stable one, at no point in the past decade have I felt truly comfortable at WAM. Ten years of ostensible success and zero days of feeling at ease. That sounds like a horrible way to work.

But, like adrenaline junkies — the ones that don’t feel alive unless they jump out of airplanes plunging with a small but measurable probability toward their own death — I’m addicted to the feeling.

I wouldn’t have expected that growing up. As a first-generation American born to parents that scraped by to raise their two sons in the U.S., I learned to study hard, find a stable job — you know the stereotypes.

My plan was to go into a hard science. Yet, all through grade school and high school, I had a passion for the arts. I loved creative endeavors. I drew. I painted. I wrote. I calligraphed. I designed. I just assumed that part of my life would whittle away when I turned 21. I wasn’t sad about the prospect. Just like you eventually decide to stop wearing sweatpants in public, it was simply a natural progression in life. But, something happened in college that, unbeknownst to me at the time, forever shaped my work identity.

I began dabbling in HTML and web design. I got confident enough to ask people to pay me to design for them. The summer after my sophomore year (1999), I landed an internship in Chicago for a new web development startup. They had an official-looking website and a small handful of clients. Taking a summer internship at a startup was a small venture outside my comfort zone. But, it was, at worst a three-month excursion. By September, I’d be back on track studying toward that scientific job I planned on marginally enjoying.

On the first day of my internship, I walked into my new boss’s duplex on the north side of Chicago. 3538 Marshfield Ave. wasn’t an office building, it was some dude’s house. I buzzed the door hesitantly. There, I met Matt. Later that day, he told me the company was no longer going to consult with clients. They were, instead, going to build a startup in the then-nascent online shipping space.

This guy must be crazy, I thought.

He introduced me to a lanky guy named Charles. Charles was 19 — a year younger than me. He had the smirk of someone perpetually pulling a prank on you. I would come to find he wasn’t there for the summer. This was his full-time job. He’d been working there with Matt for over a year since graduating from high school. College was never in his plans.

This kid must be crazy, I thought.

During the middle of my sophomore year, I had picked up a web design gig with a student-run storage company. There, I met Mark — a 26 year old database programmer-in-training while still working full-time as a product manager for an engineering company. A few days into my internship, Matt asked if I knew anyone that worked in databases. I did. Mark came on-board a few days later. A few weeks later, he’d quit his well-paying current job to work full-time at this startup.

I ended up interning at PaxZone through my senior year of college. Charles left at the beginning of my senior year. Though Mark and Matt remained, the company eventually folded just as I graduated. But, I had been eternally reshaped. I had seen three different people do things I would deem well outside my comfort zone — starting your own business, foregoing a college education to work for a startup straight out of high school, and quitting a well-paying job to work for one. I, on the other hand, had nothing comparably risky at stake. I’d go on to get my college degree and find a software development job the following year.

A few years later, I felt the itch again. I’d gone through a layoff, a year of freelancing, another corporate gig, and a second round with another startup. About a year after Craig and I connected, he began formulating the idea of starting a new business. We were both looking for a change. But, I had just received an offer from Razorfish as a developer. The position, salary offer and opportunity looked great. It was a natural step for me in my programming career.

The other option was to help start a web business from scratch. No position. No guaranteed salary. No guaranteed work. Nothing. I’d be starting this with someone who was newly married, had a baby on the way, and had just come back from a four-year sojourn in Germany.

This guy’s crazy, I thought.

I was ready to take the comfortable job. I know plenty of folks who think like me. They’d like to start something new but never do. Straying from their natural path (self-imposed or otherwise) is daunting and risky. As we get older, the inertia of life makes that force all the more stronger. But, the experiences from my past steered me in the other direction.

Uncertainty becomes a lot more comfortable when you surround yourself with people that thrive in it. I’ve had the fortune of stumbling upon those folks throughout my career. And, perhaps coupled with my own approach to things, it’s the collective balance that keeps this project of ours moving steadily through the uncertainty that I’ve grown to love.