A look back at my career to date through the lens of the managers I worked with along the way.
The screenshot is my former manager Shane O’Sullivan in ephemeral messaging app Slingshot back in 2014. Shane sent the photo of himself, and I replied with his other half.
Today I woke from a dream about getting a Meets Most Expectations rating (not good) after a fictional half at Facebook where I worked for seven years. Strangely, the setting wasn’t actually Facebook at all; it felt more like the Federal Aviation Administration (FAA) from work years past. That made me interested to explore thoughts and experiences from my career by writing about it.
I needed somewhere to start, so my first thought was to list all the managers I’d ever had. Managers (or as I used to call them, bosses) had never actually been an important factor for my work until I joined Facebook, but I thought that this might help me frame things around people. So I spent some time looking through LinkedIn, Facebook, and the web to recall some of these guys’ (and they were 100% dudes) names from years ago.
💼 Sega AM2
I moved back to Japan from Ethiopia at age 16, eager to leave the cult I was born into and focus on tech. My mom had set me up with a one-month job before I arrived (thanks, Mom!), which meant I wasn’t going to start out broke. The gig was to play a video game for 8 hours a day. Or more specifically, to test the nearly completed Xbox port and English translation of Japanese RPG Shenmue II, as 1 of 5 “Foreign Debuggers.” The game would become a cult classic, and I made it into the credits, yo!
Hiro san was “Foreign Debuggers Management Director.” He was friendly, showed us how to fill out bug reports on paper (I probably reported twice as many as anyone else, and included every instance of Japanglish I found), and he showed us all the Easter eggs so we could test those too. One I liked was a secret area where you could make money by gambling on duck races.
Hiro was taken back in surprise, and possibly a little worried about child labor laws, when partway through my time there I told him it was my birthday and I’d just turned 17.
💼 XPS Tokyo
Mike & Steve
These were two of four adults at what felt like a halfway home in Tokyo for ex-cult youth from The Family International. They ran a small moving company and would pay me and my peers per job. I spent a couple of months or so packing up homes and hauling furniture across the city, then took several weeks to build the XPS Tokyo website (for room and board) while learning about new web standards. Web development and graphic design were fun, and I’d frequently stay up all night working on the project. The result of this work was my first website, and it would continue to serve the business for more than 15 years.
💼 Tokyo IT Services (~2 years)
This was my first full-time job. Scott wasn’t the IT guy of the two partners at this tiny startup, so he was mostly irrelevant to my work. He wouldn’t have hired me either, since I was a kid without any actual IT work experience. But the main partner, Siddiqui, knew a good thing when he saw it. That good thing was a skinny 17-year-old who didn’t speak Japanese and had no education, but did have a fresh A+ (computer repair technician) certificate, endless passion for tech, and no working visa—great so they could get away with paying me ~$18k a year working in downtown Tokyo.
My salary (which felt like a lot at the time) covered whatever they or customers needed, from hardware and software repair/setup to office networking, web development and logo design (for the company and our customers), building my own desk (I was the first employee), and once helping to forcibly keep a pissed-off customer out of the office until the police showed up. Siddiqui had many great qualities, but he was a shyster and refused to refund broken equipment we’d sell. He also once made personal copies of a customer’s nude photos of herself, when she brought her PC in for repair.
One night someone smeared shit on the walls of the office floor’s shared bathroom. The next morning when it was discovered, Scott was respectful enough of me as a technical employee to clean it up himself. He’d later ask me “What was I supposed to do, I couldn’t ask you to do it.” My reaction to that was surprise, but I kept my mouth shut. From that point on I realized I could set boundaries about my work duties without being fired.
I saved enough from my time there to move to the States with $14k in the bank. Moving to the US would become one of the most critical turning points of my career and life.
💼 Network Designs (~4 years)
I’d just moved to Rockville, MD, and was taken in for a year by my wonderful aunt Jill and uncle Danny. I started doing house calls for PC repair around town, and had gotten myself a job with Best Buy’s Geek Squad—by that point I had a Microsoft certification as well, and was overqualified. But Danny told me not to go, and used his connections to get me into Network Designs, a small government contracting company in Vienna, VA. They hired me on the spot thanks to a directive from the dude at the top, and I started on an hourly contract at $30k/year as an in-house PC/server/networking technician.
Jed headed up in-house IT operations and various short-term contracts. I shared his office and worked most closely with him. He was kindhearted, a little grumpy, and more than a little bit country.
Mike wasn’t my manager, but an on-site tech lead. On my first day at the FAA he showed me the ropes for a couple of hours I think, then I was mostly on my own. I did well enough that the FAA asked to keep me around after the three months were up, and I never looked back from my new, unintended career as a programmer.
Aside: Since the FAA was in DC, working there was also great for my commute. Although it was only a 20-minute drive from Rockville to Vienna, I didn’t have a car. So I’d been using a patchwork of public transport that took two hours each way between the two buses (including walks to and from) and two trains (that routed me into and back out of DC).
William joined the FAA contract not long after me and was immediately the best programmer there. He was a role model for me and we became close friends. He quickly became the tech lead for day-to-day work, then guided me into taking over his role when he left.
John was the first person I worked with at Network Designs who was more of a full-time manager instead of being hands-on. We liked each other, but he was focused on contracts and clients. He didn’t work on-site at the FAA, was rarely involved in what we built, and mostly deferred to me as the tech lead for things like hiring and day-to-day team management. I never received a meaningful performance review (I’d write my own), but I did frequently negotiate for more pay.
While working at the FAA, Network Designs sponsored me for a Top Secret government clearance. …Yes, officer, I had tried marijuana exactly 5–7 times before (the amount I’d heard was safe to admit), but the last time was years ago, I’m pretty sure, and there were definitely no harder drugs (let’s not talk about Tokyo clubs). And no, I was not a member of any organizations that planned to violently overthrow the US government.
When I asked the guy who interviewed me what he would do if I said yes to that last question, he said he wasn’t sure since no one ever had.
I never ended up using my clearance while there, but it would help me get my next job.
💼 Vykin (~3 years)
I joined Vykin to move to Iraq for a programming (ColdFusion and ActionScript) contract there. Vykin had programmers and IT/comms technicians supporting a company called Global Linguist Solutions, which provided about 10,000 translators for the US military. If I recall, about 8,000 were local Iraqis, and the rest were from the States. Our database tracked something like 80 different languages they spoke, though Arabic and a handful of others were the most relevant.
While in Iraq, the bases I stayed at would get mortared most days, and on days with particularly heavy incoming fire (or when they had intelligence about upcoming attacks) they wouldn’t let us into the chow halls for food unless we came in body armor. My housing was a shared bunk bed in half of a military-provided trailer without running water—a nice upgrade from the plywood box I slept in for a little while, or the tents where I’d slept communally with soldiers and other contractors in Kuwait. On the flip side, this was the only time in my life I had my own office, even if a bullet did come through the ceiling once. Fortunately, I didn’t often need to travel between bases, but my peers who did would sometimes have their military transport helicopters shot at, or vehicles in their convoy blown up. All of this felt new and interesting, and the risks never bothered me.
Scott Dritz & Phillip Galinski
Scott was a programmer/manager who worked from home in the States. Phillip was the manager on the ground in Iraq, and was an IT/comms guy who focused on that work. He was also a ping pong legend. Both were good dudes.
💼 O’Reilly Media
Andy was my editor at O’Reilly Media, and I worked with him on both editions of Regular Expressions Cookbook. He wasn’t actually a manager, but the closest thing to it and my main contact in the company. For better or worse, though, he wasn’t that involved after the beginning. That seemed disappointing at the time since O’Reilly Media claimed their editors worked closely with authors all along the way, which was supposed to be the reason they didn’t accept already-completed manuscripts.
💼 Facebook (7 years)
Brian Rosenthal, Arash Nikkar, Shane O’Sullivan, Ian Bavey, Vladimir Kolesnikov, Sridhar Iyer, Arvind Mani, & Dmitry Sokolowski
Something like 10 years into my work experience, Facebook was the first place managers made a significant difference on my career development and personal growth. Maybe they’d always been more relevant for others around me, but I was (and would continue to be) largely self-directed. Maybe I never appreciated enough that I didn’t have managers who made the workplace suck.
In any case, this was the only job where I’ve had meaningful performance reviews, where managers saw the people side of their work as a discipline to master, or where I had regular one-on-ones with managers who focused on more than just my day to day work. This was transformative on my thinking about work and was why I ended up going into management myself, halfway into my time there.
I had eight managers over seven years at Facebook, so I won’t go deeply into each one. But I’ll say that Facebook engineering leadership as a whole was a densely packed collection of highly impressive people. That applied to my managers as well.
- Brian, Vladimir, and Dmitry were the ones I most wanted to emulate in my own work.
- Shane, Ian, and Arvind I most wanted to learn from.
- Brian was my first manager there, and it took me about six months to fully internalize that he wasn’t my boss. This was an inspirational dude, and everyone loved him. He dedicated himself to constantly improving as a manager, and liked to experiment in the process.
- Arash was my manager for a couple brief periods only, and I think I under appreciated him at the time. Hindsight fully changed this. Plus his cool tattoo sleeves inspired me to want my own.
- Sridhar was the only manager I’ve ever not gotten along with. He was always a nice guy and I’m certain he’s a good manager for most (plus I know I was sometimes hard for leadership including him to work with), but at the time we had some big disconnects and never found a way to work effectively together.
Good times, good people.