Thanks for getting this far! If this is the first part of my series on my experiences between being a fresh BA grad to a decently successful DevOps engineer, you can read part 1 here. If you've already read part 1, let's not tarry. There's much more in my memory castle to explore.
Part Two: Kind of a Real Job
One thing I wanted to focus on before we move forward was my brief experience with a now-defunct small company called PC Specialists. Since it's currently defunct, I have no issues with mentioning it by name. It was a small shop operating out of a neighborhood abutting the western edge of the city, where the traditional Chicago two-flats gradually transform into forest preserves, golf courses, and eventually the suburbs. We serviced small clients without IT departments of their own: tiny operations on shoestring budgets who couldn't afford a full-time spread of employees (or even a single tech). This was part of what made the job fun.
My initial (and final) interview took place in the owner's basement. The 'offsite datacenter' was a room adjacent to his tool closet, humming with what was then top-of-the-line RAID systems and NAS drives. We talked for what might've been twenty minutes about the differences between bits and bytes, and he handed me a CD copy of VMware and Windows Server 2008. This is what brings me to my first corollary of getting into this world: take what chances you can get. Sure, you may have shown up in a suit when your boss looks like he just rolled out of bed. But the experience you obtain will be paid back. Eventually.
Our clientele was an interesting bunch. Some were educational companies staffed in actual executive buildings. One was a hair shop whose walls were made of chicken wire overlaid with plaster, forming a functional faraday cage that prevented cellphones from working inside. One happened to be one of the largest food storage manufacturers represented in the Middle East, somehow making money off both the western-aligned Arabs and Israelis at the same time. While I didn't love the staff much there, I had to appreciate their business acumen. Again, take what you can get. And as a second corollary, learn wherever you can.
One of my colleagues was a gruff gentleman who we'll refer to as Sol. Sol had worked as a lineman (one of the men and women who hang high-tension electrical and data transmission wires), and would gladly provide gruesome details of exactly what happened when you fell off an electrical pole and caught a creosote-laden splinter through your palm. He would also tell me the best way to stay warm when the wind in Chicago whipped up into the mid-hundreds in the dead of winter. You'd better get used to pissing yourself, he told me on one drive to an all-too-distant job site. Despite his particular nature, he was incredibly knowledgeable in the immortal ways that networking functions on a basic scale, and provided me with the initial knowledge that eventually got me through obtaining my first Network certification. He was Cisco certified himself, and strong as an ox, as you had to be back when a 'small' office server could weigh up to 150 pounds. I haven't heard from him in many years, but I hope he's doing well.
This was also the place where I learned all about virtualized computing. While functionally this concept dates back to the 1970s, it took off in the pre-cloud era when small, stressed IT teams were eager to squeeze every drop of compute they could out of outdated chassis before being forced to upgrade to newer and more expensive hardware. The concept for the uninitiated is this: one big computer can run multiple programs inside it. One of those programs (called a Hypervisor, itself a play on Supervisor) can itself simulate a totally separate computer, running its own operating system and performing its own tasks discretely from the host unit. While I've come to learn of many other ways to do this, it was the bread and butter of how I helped to power the business.
Most of what we would do was go into a building, find the heaving core compute module of their business (typically a smoke-stained piece of beige hardware wheezing out hot air like a jet engine), plug it into a USB drive, copy its entire stack over to a sleek, silent, new machine, and charge them for the privilege. While the work would hardly fit me anymore, I do miss the days of constantly meeting new people in new businesses and making their days easier. But we'll get back to that later.
Part Three: Enter the Discount Factory
Unfortunately, the irregular hours and constantly shifting schedule led me to search for a different position. And when I found it, my brain felt ready to pop. It was a brand-new, totally hip startup in the River North neighborhood. While the founding CEO was ousted right around the time of my hiring, it felt like a wild opportunity to pivot out of the hardware space and into what was surely the future: something based in software, wireless communications, and mobile technology. I just had no clue what I was getting into. For now, we'll call this company the Discount Factory, because it's still in business. If you want more clues as to what it really was, check out the first episode of Mr. Robot, where Angela's boyfriend makes a brief reference to it, and if you're quick, you'll catch it.
My job there was to help clients operate one of our products that had not yet been integrated into the overall Discount ecosystem, which I'll call Panini. As our clients liked to angrily joke over a heated discussion, it was a POS (Point of Sale) app for the iPad that would let a restaurant owner track bills, register credit card information, close out checks, monitor tables, the works. You could even map out entire restaurant floor plans to determine exactly who had ordered what. I wouldn't be surprised if more traditional systems had worked this out already, but we would have significantly undercut the market costs if only the service itself had been slightly more resilient. But we'll get to that later.
It was here that I got my first exposure to more professional-grade software that carries me to this day: I cut my teeth on using Splunk, Confluence, Slack, ZenDesk and Salesforce. As my individual contribution grew, I got more comfortable picking up the phone and dealing with difficult customers. Sure, bar owners can be a rough-and-tumble crowd. Sometimes you could clearly detect slurring words and stumbling consciousnesses. Sometimes you had to tell someone to climb up a ladder into an attic to confirm a cable was connected to where it was supposed to be, or inform an elderly customer that they were clearly participating in fraud. Sometimes it was deadening. But mostly, it was informative.
After a few weeks of training in the 9-5 timeframe, I moved into the late-night sphere, working from 3 PM to 2 AM 4 days per week. And as much as I reflect on it as a painful time in my history, it was fun. I worked with about two other colleagues, and the pressure cooker made us tight as thieves while we supported various barkeepers, restaurant owners, and other angry people. I typically got home around 3 in the morning, spent a few hours decompressing, and slept until 10 AM every day. It was a good gig for a young man. And it helped me learn wherever I could: stuff like what a decent network looks like, what a recursing IP address resembles, and how to deal with a tough customer.
But working weekends wore me out, and eventually I had to go. So I talked to one of my old colleagues from PC Spec, who was then working for a large investment conglomerate that had just acquired a local real estate company. And that's when I actually entered the IT universe.
Part Four: Hello, I'm IT
Finally! I made it into the vaunted halls of the desk in the sunless corner where the guy who hooks up your wifi hangs out. Apparently I'm still a legend at this place due to my snappy responses to stupid questions; which leads me to my next corollary: be nice. Being an asshole is always a tempting option. When you are a vendor of expertise and power, the stupid and the powerless tend to be seen as an annoyance rather than your bread and butter. It doesn't pay off in the long run, and I'll explain more about this later.
This was a local agency that employed lots of independent contractors who ran their own books of business. Unfortunately, this also tended to mean that there was a lot of favoritism, i.e. ranking certain clients above others. When they said jump, you didn't even ask how high before catapulting yourself through the roof. Which in turn led to feelings of exhaustion and regret: had I made the right decision? I'd gone from being a respected, battle-hardened veteran of nighttime bar rescues to a baseline grunt whose primary job was to be hassled by people who had created Outlook calendars so convoluted that they stressed our local servers to the breaking point. And our job was to make them happy so they made more money. It could be soul-crushing.
Thankfully, my technical chops continued to be sharpened at this point. It's where I met my lovely wife (then girlfriend) who told me straight that she wasn't getting married to a server-room scrub without certifications or a potential future. I'm happy that she sat me down and made me think about what my future would be at this point; if we hadn't engaged in those hard discussions then, I don't know where I would be now.
After lots of studying and one anxiety-inducing test session, I successfully gained a Network+ certification. This will be important later. The unfortunate side affect was that this did not manage to change my position or prospects significantly at the organization: despite being ostensibly a 'network engineer,' I stayed at helpdesk. After a fascinating bit of corporate overhaul, I got a seat at our downtown office, where I spent lots of time staring out windows to the insides of massive blocks and watching tradesmen enviously as they worked on rooftop infrastructure. Eventually, it was time to move on. I loved my management and (most of) my colleagues, but the demand wasn't where I wanted to go in this environment. Which leads me to another lesson: let go when the time comes.
It's well worth noting that no job is forever, and an employer will only continue to permit you the pleasure of showing up to your desk in the morning so long as you provide value commensurate to your salary plus a healthy percentage. When that dips too low, it's their job to terminate your employment. Heck, since IT tends to be viewed as a cost center (never mind what would happen if they were gone--it's like considering your nervous system a cost center since it uses up so much energy compared to what you get out of your digestive process), you're under an extremely strong microscope. I learned from several colleagues over the years that clinging on for dear life and zealously guarding your expertise only extends your lifeline, it doesn't make it infinite.
So I leveraged my new certification to find a job out in the suburbs. And that's where my future began to collide with the cloud, which is a chapter that I'll save for our next meeting.
Thanks again for reading; please don't hesitate to reach out if you have any questions, and have a great St. Patrick's Day!
May the wind ever be at your back. 🍀 🍻