The best job I’ve ever had was my pizza delivery job at Pasquale’s. Well, in 2007 that was the best job I’ve ever had. What wasn’t to like?

  • Tips are great.
  • A free meal every shift.
  • Driving a car around is fun.
  • No boss breathing down my neck while I’m out on delivery.

After moving to Florida, I had to find a job fast or else the old bank account might start running backward. So, I thought about what I liked to do. Well, I liked cars. I walked into a Volvo dealership and as it turns out, they were looking for a Porter. If you don’t know what a Porter is, they wash your car and deliver it to the front when it’s done at the dealership. They also generally do a laundry assortment of undesirable tasks no one else wants to do. A “gopher,” so to speak. There was a lot to like:

  • Driving new cars all day.
  • Free lunch on Saturdays.
  • Enjoying the great outdoors for most of the day.
  • Great camaraderie with co-workers.
  • Learned enough dirty and off-color jokes for a lifetime.

After a year, I had gained residency in Florida, which made it much easier to get into UCF and not drown in the out-of-state tuition. At UCF, with a semester under my belt in Film, I started searching for yet another job. Would this be the Best Job Yet?

No. Regal Cinemas, I vow to never upsell popcorn again. This was the Worst Job Ever, and I hope that designation sticks for the rest of my life. Awful hours, especially when we had one car and Sarah would need to pick me up at 2:00 AM after a movie ended. Awful pay, near as makes no difference minimum wage. And a corporate structure that seemed, to me, to be set up entirely to disparage and demean. Yes, my drawer is off by a dollar. No, I don’t think I want a demerit point for that. I quit after a month and a half.

There was not a lot to like.

It took me until 2009 to get a job I enjoyed as much as Pasquale’s, although for wildly different reasons. It was my first office job, a place where cake was served to celebrate July birthdays and Dilbert was pasted up on cubicles. It’s also where I first learned to do web development, finally getting a bite of the forbidden fruit that sparked my insatiable appetite for learning the depths of technology. What wasn’t to like?

  • Free coffee & soda.
  • Dilbert jokes.
  • Great autonomy.
  • I got to stretch my creativity by making videos.
  • Learning web development.
  • Feeling appreciated for the work I’m doing.

By 2012, graduation from UCF was looming and I was not sure if I should stay or go. The economy was still slowly recovering from the recession, so the options didn’t seem to be wide open.

For the best chance for both my now-wife and I to get a job, we wanted to relocate to somewhere with more opportunity. We both interviewed in the Washington, D.C. area to see what kinds of post-graduation professional jobs we could get. With both some software development experience and a radio/television production degree, I applied to both video editing and software development jobs. Thankfully, Ronald Gregory gave me a chance at Interface Media Group to do web development, despite my thin resume in that area. What wasn’t to like?

  • Working in Washington, D.C.
  • Salary position + benefits.
  • Learning C# and strengthening my CSS, HTML, and JavaScript knowledge.
  • Worked on a project that ended up in a Smithsonian museum.
  • Hot chocolate at Pret-A-Manger on the way to work in chilly weather may be the closest thing to heaven on earth.

All was not sunshine and roses, however. After three years of the commute, and the weather in D.C., Sarah and I were ready to move back to Orlando. I wanted to see if I could hang out my shingle. Would this be the Best Entrepreneurship Job yet?

Well, no. After one contract job that went very well, I realized how important the business side was. Relying only on my technical know-how wasn’t going to make that venture successful. I was not filling up the sales funnel while it was draining, so I had no more work lined up after that initial contract. Still, there were some great perks:

  • Set my own schedule.
  • Work from home.
  • Very fulfilling working directly for a client.
  • Great sense of pride for the work accomplished.

But, with no prospects in the pipeline, it was time to find something a little more stable. That’s when I interviewed at Nebbia Technology.

And what a ride it’s been. When I started, we had no permanent office. I started as a fifth to add to the existing four people. Over the course of three and a half years, we got an office, grew to thirteen people, expanded our office, and was acquired by New Signature. We increased revenue and profits in that time by leaps and bounds, not always in a linear fashion. I can’t give enough credit to Chelsea’s tenacity as a head of Business Operations for keeping all of us technical people employed in those early years. And, of course, Esteban’s leadership in shaping the company into something worth acquiring. My own failures in starting a business has given me a lot of respect for those non-technical responsibilities.

Speaking of important non-technical roles, I also can’t thank Hannah Schaffer enough for making our lives so easy in her Operations role, and for shaping the Nebbia brand as Marketing Coordinator. Also, Alyse Hyatt, for coming on board as our Project Manager, and playing a key part in greasing the gears to make it so we could focus on what we do best: delivering.

And, boy have we delivered. I’ve worked with clients who have multi-million line code bases, who are looking for build & release pipelines, to automate, to move to the cloud, to create hiearchical picker extensions for Azure Devops, and who knows what else I can’t remember.

I honestly marvel at how the team is chock full of experts and technical powerhouses, yet there’s nary an ego to be found. A dream team. It will be incredibly hard to leave when I know how easy it is to work with everyone there. Nebbia Alumni include Mikey Cooper, Brian Hall, Clementino De Mendonça, Cliff Chapman, Phil Hagerman, and Jeff Truman. I have appreciated working with every single one of you, and have learned from each of you. The team that I’m leaving now, Facundo Gauna, Justin VanWinkle, Ryan Buchanan, Troy Micka, Chris Ayers; thank you so much. Mostly, for laughing at my horribly punny jokes. But also, for teaching and inspiring me.

Although there is never a “right” time for anything, this feels about as close as I can get. I know I am leaving the team at a time when they are very able to succeed without me. I know with Esteban’s leadership, and the weight of New Signature behind them, they have the capacity to truly change the world.

So to them: go out there and teach ’em that software development doesn’t have to be drudgery. That all the Sev 1 late night all-hands-on-deck anxiety fests don’t need to happen. That the pointing fingers and rolling eyes and feeling stuck and being bored to death in silos can be replaced by celebrations and high fives and talking to users. I’m counting on you, team. Go out there and show ’em.

While it’s difficult to leave the best job I’ve ever had, I’m comforted by the knowledge that I’ve done it before. And each time, the next thing has never quite been what I’ve expected. Every job has managed to teach me something about myself, about what fulfills me, what I’m capable of, and each have given me the experience and confidence to take on the next thing. Now, I’m excited by the prospect that, maybe, the next position I’m taking will also be the best job I’ve ever had.

Stay tuned for next week, when I talk a little bit about what’s next for me.