My Journey Here

Mar 15, 2017

How many times have you told yourself that today will be the day? Today will be the day you get up a little earlier to make a great breakfast. Or that after work, you will certainly go for a jog, so long as you’re not worn out and brain-fried by the end of the day. Maybe you want to read that book over there on the shelf, but the sofa is just so inviting, and you’ve been meaning to start binge-watching that 6-month-old show everyone stopped talking about. Perhaps you’ll even start writing that amazing novella that’s been stuck on page one since college. I mean, you could do all of these things on any given day if you wanted to. Maybe tomorrow…

Well, today is my day – 36 years in the making.

For about 17 years now, I have known that the type of career path I have been on was not the right one for me. I did not feel it immediately. After all, I was lucky enough to be connected to a great family friend who hooked me up with a wonderful internship at a global bank in downtown Chicago. This was easy; I was a smart kid, just out of his first year at university and things were already going my way. Fast-forward to the end of the summer and I was sick of the packed train rides. I did not look forward to huddling in my cubicle and poring over some risk formula. I had tasted the morning routine, the mid-day break to shovel some fast food into my mouth, the rush out of the office to make the express ride back to the suburbs, all while being a tooth upon a small cog within an enormous financial machine.

I was 19 then. I was told this is how life is, and how life will be for almost everyone with my privilege. It was my destiny (unless I wanted to be a doctor or lawyer). I’d get my degree, find a job, hole up in my cubicle (and eventually office) for 8+ hours a day, get 2 weeks of paid vacation, discounted health insurance (the glory!) and a 401k to ride with me for 50 years until that sweet day arrived where I could retire and cash out. Whatever else happened between that time I got to work and the time I left didn’t matter, so long as I did a good job, impressed the right people, and got some promotions along the way. I carried on with this vision ingrained within my being. “Just be successful and everything will be fine.”

Success was a broad vision, but a narrow scope. It basically meant, to me and those around me, that I just needed to make some money, be great at my job, and make more money so I could do more-money-stuff with it. I was a “gifted” student through my elementary years and didn’t do too bad during high school. My time at university hit me – hard. I didn’t excel like I was used to. I wasn’t interested in my major topics; at least, not enough to try really hard. I went through the motions of life and school to get out as soon as possible and make it into the workforce. Becoming successful would be the easy part.

Of course, I got into the workforce during the mini-recession of 2002, so plans stalled for a bit. After a period of unemployment (there was a back-office gig there somewhere) I worked as an intern at a locally headquartered firm doing “data analysis.” Really, all this meant was updating some spreadsheets for the accounting and finance teams and filing some paperwork. After two-and-a-half years at this “temporary” position, I escaped (YES!) to a large, national, multi-billion-dollar telecommunications company. Sure, the title wasn’t great, but I was going to start from that position that I was wholly overqualified for and show them how smart and talented I was and I’d be a manager in no time. I’d probably become a director in record time, maybe their youngest ever. I mean, c’mon I was super smart and talented, remember?

After 8 years, I quit my position at that company. I had done the things I was supposed to – make an impact, be a team player, never say no, stay late when needed, come in earlier than most, be the subject matter expert on everything related to my title (and even some that weren’t). I worked on some huge projects, got a couple promotions, and grit my teeth every day knowing from day 1 that this environment wasn’t a fit for me. I didn’t feel things were happening quickly enough, or at the pace I felt was befitting of someone of my age and particular talents. I wasn’t yet that manager (I had passed on an opportunity I felt wasn’t up to my caliber, and got passed over for a couple others), so I saved up enough money (I knew I would be doing this far in advance) to survive for a few months and took the leap. I was an analyst still. Something generic and relatable to almost everything I could find posted on the internet. I’d find work. And I did.

I found a small “start-up” company in the city working in sales software. They had a technology stack I wanted to dig into. They had the culture I wanted to be a part of. My boss was amazing – bright, talented, passionate, experienced, humble. My co-workers were cheery, cultured, and (for the most part) loved what they did. A year into that gig and I was fairly miserable once again. Not because of the environment, not because of the culture, not because of the tech I was (or wasn’t) using. Not because I hadn’t learned a great deal on the job (I did!), and not because of the nice paycheck I was receiving. But because of what I was doing day in and day out just wasn’t for me. I had known this, remember? 15 years had passed and I was used to this. Insert / analyze / export, build presentation, improve processes, repeat. Intersperse with some side-impacts and friendly interactions.

It’s fine, this was life. I’ll get something else. I’ve got the connections and the knowhow, I’m equipped to jump to that leadership role I was destined to have. Lo and behold(!), I get that opportunity with another company. This jump takes me back into finance (meh… at least it was technology) but look, a director title! Yes… this was it. I knew the environment wasn’t the right one I wanted to be in. But hey, I could get this title at this company, ride it out for a couple years and keep my hot commodity status before jumping ship and doing great things again.

After day 1 on the job, I knew it was a mistake. I needed change. Fully. Wholescale. Tear it down and build it back up. I lasted a total of 6 grueling months. And I do mean grueling. The life I knew I never should have had was finally taking its full toll on me. It was now that I realized there were many times throughout these years where my prior positions completely impacted my mood and well-being (and likely altered my memory of how great and deserving I was of all this corporate praise I so yearned for). It was here, with the title I wanted, the disposable income I enjoyed, the office I looked forward to, that I finally took a deeper look within.

“I must be willing to give up what I am in order to become what I will be.”

That quote is (likely incorrectly) attributed to Albert Einstein and was the starting chapter title in a book I had read. It stuck with me for a couple years after that reading, rattling around my head here and there.

There was one thing in the back of my head through these years that continued to try and knock some sense into me. At age 12, I was lucky enough to have my own PC. A relative rocket ship at the time, a full 8MB of RAM, 66 MHz 486 processor (once you pushed the “turbo” button) and the newest version of DOS installed. More hard drive space than I could ever imagine I would fill. I can’t tell you how many times I broke things editing config files so that I could play Wing Commander with every bell and whistle enabled. But I’d tinker (and hope my dad didn’t want to use the PC) and fix it all up. I continued my love affair with computers thereafter, buying new parts, saving up whatever I could for new games, tinkering all the way. I’d ogle at the large, imposing C++ or C# tomes at the bookstore (but never did anything with). I dove into the internet age head first; bulletin board services and text-based RPGs were my playground, slow modems and all.

I built my first website during my first internship. It was basic and built by hand in Notepad using a gigantic “Learn HTML the Easy Way!” kind of book. I remember using frames, and spacer gifs, and really impressing the resident tech / IT guy who had been trying to build this thing for the department for a while but never had the time. I enjoyed that. I also built an intranet site at the other company I “interned” at after I graduated. It was more a glorified front-end of the network directories for engineers to access from all across the company, but it worked. I even designed the whole thing to mimic what the global site looked like, with some added improvements (to me) that made the thing just look a bit smoother, more polished. People loved it. This was 2003, remember? Images were sliced up and put into various table or div tags and the evolution of web design with CSS was in its infancy.

I carried on with this hobbyist approach to building websites through 2010 or so. Just some simple pages that required minor updates for family businesses and local organizations I was a part of. Nothing spectacular, but functional in scope and I tried to keep up with the design trends at the time. But I had that career to focus on, remember? Unable (or unwilling) to put in the time to follow changes in web technology, I set that all aside. If you’ve been following the timeline, that’s when things REALLY took off.

Today, I am unemployed (again, by choice) and enrolled in the part-time web developer course at Bloc ( Attending a boot camp and turning my old web dev hobby into a career had been on my mind since I first read of Dev Bootcamp a few years earlier. I didn’t think I could afford to do so at the time, since I had to save money so I could quit my job then and get a new job with relative comfort. All of that changed with my prior position. I thought through this decision long and hard, and while I do not see having web development be my defining role for the next 20 years, I want it to be so in my near term. I want it to fuel my ideas that I’ve kept stifled. I want it to be my gateway drug into a wider world of impacting and developing burgeoning technologies.

I look forward to broadening my scope, and vision, of success as I continue on this journey.