My friend Johannes and I were recently chatting about the jobs we had before becoming web developers.

As I was describing all of the random things I’ve done for a paycheck I thought to myself, I should really write this down…

Mid 1990s: amateur janitor at Cornell Orthotics and Prosthetics in Salem, MA

I was around 15 years old and rode my bike here after school to do basic cleanup work; I swept floors, took out the trash, wiped down counters, etc. My only real lasting memory from this job was discovering who Tom Petty was because they played his tapes in the manufacturing area over and over again.

Mid 1990s: general employee at the Roller Palace in Beverly, MA

In the beginning I worked at the skate rental desk, handing out skates and making minor adjustments or repairs. Eventually I became a skate guard out on the roller rink, blowing my whistle at the fast and the furious.

Side-note: I dated a girl who worked at the snack-bar, which is where cool kids would ask for a ‘suicide’ (a drink made from every flavor in the soda machine) and pizza slices with mustard on them (don’t ask; kids are weird).

Mid/late 1990s: shop assistant at … I can’t remember the name

In my last year of high school, the job placement person got me a job at a nearby auto mechanic that only worked on those big oil trucks that deliver heating oil straight to homes. Like my first job I was basically a janitor, however the two brothers that ran this place treated me well and made me feel like one of the team; I really enjoyed my time here, short as it was.

Late 1990s: salesperson at Circuit City in Danvers, MA

I started where they start all new salespeople: in the ‘Ace’ (accessories) department, where I sold small-ticket items like cordless phones, portable tape and CD players, batteries, etc. Later I transferred to the home audio department, which felt a tad more dignified. It was here that I met some great friends—including the Best Man at my wedding—one of whom became a roommate in my first apartment.

Early 2000s: salesperson at Michaud Mitsubishi in Danvers, MA

There was this one really bad day at Circuit City where I simply quit without giving notice—as of today I can’t remember why. Regardless, on the way home, without thinking, I pulled into a car dealership to ask for an application and a day later I was selling cars. That job…ugh…it was absolutely terrible and wonderfully life-changing at the same time: somebody who worked here convinced me to take night classes with him to learn web development at UMass Lowell. If you know me now, you know how that turned out.

If I hadn’t mindlessly pulled into that car dealership, hadn’t landed that job, would I be a web developer today?

Early 2000s: customer service rep, then assistant manager, at Sprint PCS in Danvers, MA

I quickly left the car dealership and landed a job at a mobile phone store. At first I was a customer service representative, and later I was asked to be the assistant manager. My only strong memory of this job is it’s where I was on September 11th, 2001.

Side note: I continued taking the web development night classes while working here.

Early 2000s: salesperson at Tweeter in Danvers, MA

Yet another salesperson job. I sold high-end home audio and video equipment, but I was fizzling out; my desire to talk people into buying things was gone. I had just met Sharon and was focusing on increasing my meager web development skills in my free time. While it was neat to be surrounded by high-end equipment, the job was commission based and I had fizzled out, so I made almost no money.

Side note: the web development night classes wrapped up while working here.

2003: truck driver for Moynihan Lumber in Beverly, MA

Despite being done with the night classes I was not yet ready to apply for jobs in that industry, so I found myself another regular job. This time, however, I was hell-bent on doing anything other than being a salesperson again, so I landed a job driving a big delivery truck for a local lumber company. If you purchased windows, doors, or millwork from Moynihan Lumber in 2003 and asked for it to be delivered, there’s a fairly good chance I pulled into your driveway and dropped it off. To be honest, I loved this job because I was alone most of the time, I got to drive a big truck, and I was doing manual labor (which I enjoy)…it was like nothing I had done before and I would’ve stayed longer if it weren’t for the potential to earn more money via web development.

Side note: I spent many nights and weekends continuing to learn more about web development while working here.

2004: web developer for a now-defunct financial company in Beverly, MA

I finally had the confidence and maybe the skills to apply for a web developer position. After applying for a bunch of beginner roles, I landed at a financial company and was tasked with designing and developing their website. I was in heaven. I can’t even describe what it felt like to land that job, to hold an almost wizard-like status in the eyes of the people I worked with, and to be paid (decently) to do things I genuinely loved doing.

2005: web developer for Net Atlantic in Salem, MA

After the now-defunct financial company earned its now-defunct status, I landed a new role as a manager (and web developer) of a small team at Net Atlantic. This job became very stressful very quickly as there were four of us and we each juggled 4-8 website builds at a time. I had no say in the sales part of the process and, as a result, I didn’t last that long.

2006: web developer for a now-defunct agency in Salem, MA

This was the first job that seemed to match my general expectation of a cool web agency; everybody was happy and having fun, the money was good, the client list consisted of names most everybody had heard of, there was a pool table and a keg of beer, the lunches were free (most of the time), etc. I really loved this job and the people I worked with—in fact, it’s where I met Michael, and he and I (and Johannes) now run our own agency, but more on that later. The only reason I left this job was because…

2008: self-employed web designer/developer at Boston Web Studio in Salem, MA

…I decided that I’d like to try doing it on my own. I put on my this-is-a-huge-risk pants and started my own one-person design and development agency called Boston Web Studio. The timing was great because Sharon and I were recently married, we lived in a very affordable apartment, and we didn’t yet have children; our expenses were low and we would survive if the first handful of months were shaky. Over the years my client list increased as did my income—it was wonderful and I was happy.

In 2011 and early 2012 I subleased office space from my friends Michael and Johannes while they ran their small agency, Booyant. Being in the same office space, we became good friends and would occasionally subcontract client work to each other where helpful; I would tackle some of their front-end development overflow, and they would assist me with design and back-end development challenges that were above my pay grade.

2012: self-employed front-end developer and partner at The Outfit in Beverly, MA

In mid 2012, Michael, Johannes, myself, and two designers decided to shut down the small agencies we were running and start a new one together—that’s how The Outfit was born. These last 13 years have been a wild and fun ride; here’s hoping we keep it going for another 13 or more… but not too many more, because retirement sounds nice.