I distinctly remember my mother’s voice over the phone, “Why can’t you get a real job like washing dishes at a restaurant?” She said after I gloated about being paid to repair a computer and help fix some software for the first time ever. At the time I was 13 and it was my first ever paid job over the summer making a whopping $75. I had to file a special document with my school and the state to allow me to work for money in a local computer store and my father reluctantly agreed to sign. It was the start of a very long and difficult career in technology.
Over the next 5 years I would fumble my way through various contracts which were dubiously executed by an underage software developer. I lost count how many times I got screwed out of money from clients that found out I was under 18. The money I did get I blew on computer parts and ridiculous phone bills from dial-up internet. The late night calls to an attorney family friend who specifically told me: “You aren’t signing anything until I see it first” after one particularly bad screw up. My father believed in me, yet he did not want to co-sign much of anything I proposed and so I put on a good front for clients. To my dad I was an ambitious kid full of drive and ego, yet ignoring basic guidance on performing effective contract work.
Looking back, I was reckless and it was a wonder things turned out the way it ultimately did in my career. I went back to retail after narrowly escaping the legal ramifications of a poorly handled contract. Realizing I needed better people skills that can’t be obtained behind a computer monitor I worked at the local game store to make ends meet while I took a break from software. At one point I got my lucky break to join Apple retail by a chance meeting of the local store manager who eagerly insisted I apply. As I started my career at Apple, the allure of writing software for money came back again. Around that time I also started dating someone special who would one day become my husband.
The big push came from one of the Apple store managers who sat down with me to conduct my annual review. This meeting was different because they knew me fairly well, yet they had little direct insight into my review as I was not their direct report. He threw up his hands and said, “Aaron, I’m going to be honest with you. You are too smart for this job and I don’t ever see you getting the chance to join Apple corporate like you have been wanting to. They won’t know how smart you are and I think you’d be better off finding a software position elsewhere.” It was a bucket of cold water I needed to wake up and retry that career I wanted to have in the first place. Within a couple months I was applying for software developer jobs in the Chicago area because my new boyfriend wanted to move away from Florida the moment he graduated.
We both got lucky and landed jobs at the same time with two different companies. I gave my notice at Apple and we moved up to Chicago over New Years Eve. My first real salaried position started me at $30,000 as an apprentice developer working for various clients. During that time I would propose to my boyfriend and get married in that same year when more states began to pass equal marriage laws. Within six months I was promoted to a full developer and receiving a raise all the way up to $85,000 a year. It was shortly after our company holiday party where I showed up in drag on a dare. Many of my co-workers thought it was hilarious, however one of them did not take very kindly to it. I got a reality check about being openly queer in tech shortly into the new year. Suddenly I became “Difficult to work with” despite glowing reviews from the client I was working with and insistence I continue my work on their project. I would soon be put into a room with the CEO and office manager where I had to make a choice. Take 2 weeks pay as severance and sign a non-disclosure for a year to keep quiet or walk out the door with nothing. That was one of the worst days in my life and I almost quit working in software entirely that day.
Over the next few years I would burnout pretty hard and walked away from an amazing tech community that boosted my social confidence, laid the groundwork for my latest job, and gave me so many great memories and friendships. I also had aspirations to get into tech leadership at Packet and soon realized it was never meant to be within six months. Applying elsewhere for leadership roles usually came with the response “Where is your past leadership experience?” I hit my breaking point and decided it might be time for another break from software.
At the start of 2020 I joined Datadog as a Tech Evangelist with an amazingly talented team. The plan was simple. Take my $150,000 in salary plus signing bonuses over the next 4 years and put them into savings. After it all matures, take a big break and go do something else for a while. Doesn’t matter what it is, just find a new passion. In the mean time, enjoy all the travel and speaking opportunities. I jokingly called it my “victory lap” in tech. Rack up a ton of miles to use on future vacations and the big tech break later on. Then the pandemic took the world by storm. All my new job travel plans evaporated overnight and I was chained to my desk with zoom being my only window to the world. I fell into a massive depression about my situation. It wasn’t until June of 2020 where I started wondering if 4 years was too much time to wait to leave technology.
I had been home brewing beer and hard cider for years at this point. Back in 2012 we received a homebrewing starter kit as a late wedding gift from my older brother. He got it for us because I was always curious about how he made mead for his wedding years back and I kept putting off trying to make some of my own. “Now you don’t have any excuses,” he said over the phone when I unpacked everything in the kit. We eventually made our first beer which was a mild success. Then we tried making cider after reading about some recipes and the simpler process to creating it. Cider is everywhere during the fall season in Chicago and we gave it a shot. The first batch was not great and we knew it could have been better. With some tweaks to the recipe we created something amazing and magical. It was a delicious cinnamon cider that was rich and not overly sweet. More like liquefied apple pie filling with a very strong kick because it was around 10% alcohol by volume. Sharing it with friends and getting that glowing feedback became the start of a new passion in my life.
Something many don’t know about me is my family history around bars and restaurants. I’m a third generation restaurant and bar kid which is to say my family has owned and operated those establishments for the last two generations. Going all the way back to 1966 with my grandfather starting the first of many bar and restaurant locations around the city of Chicago. Many of the family gatherings would happen at the bar or the kitchen within the bar too so I was unusually comfortable around alcohol as a kid. We never got into the production side of things by making our own alcohol, but they were really good at selling it.
For years my family has purposely kept me away from joining the business and for many good reasons. Alcoholism has taken it’s toll on my family along with all the other industry related problems that I might share at another time. If you read Anthony Bourdain’s book Kitchen Confidential I can tell you from personal experience that a lot of what he describes in there is still true to this day. The kitchen and bar service industry is an interesting place and not for the faint of heart. Yet, I still was attracted to it and always joked with my family that if things hit the proverbial fan, I’d be running a bar somewhere because at least I knew how to do that thanks to them.
So now that you have some of my history, I am writing to you today to let you know I am going to take a big break from technology. Looking back, I am glad to have had the experiences and friendships along the way. Without those I don’t think I would have had the perspective and drive that I do now to be successful. Some of it was incredibly painful. However, the magic of creation in electronic or digital form will never cease to amaze me and I’ll be carrying that through into my next adventure. What is that next adventure? Well, I’d like to start the world’s first furry owned and operated cidery and perhaps the first openly queer one in the United States at least. That was always the plan when I joined Datadog, but 2020 kind of accelerated those plans. Right now feels like the right time to make that leap. I’ll still be around technology of course. Just not in the way I have done so for the last couple of decades of my life.