At 36, I’m finally starting my dream career

After 14 years of selling enterprise software — a professional career on which I’ve built my entire adult life so far— I’ve made the commitment to realize my dream of becoming a software developer. I gave my notice at work, and with that, there’s no turning back.

Over the course of the next six to nine months I’ll be devoting myself full time to completing an online software development training course through Launch School. By this time next year, my goal is to be employed (and hopefully paid!) as a software developer. And maybe, if I’m lucky, that job might even be working for a company like Basecamp, an organization that I admire tremendously.

So how did I get here?

Well, the truth is, I’ve never actually liked or wanted a career in sales. I just sort of fell into it. After high school I wanted to become a video game designer and even moved cities to go to art school. I studied animation, programming, audio production, art history, game design and other related disciplines within the craft. I loved it as was even pretty good at it. But, as fate would have it, my career in video game design would not materialize. Instead I would go on to work a variety of odd-jobs until finally landing in sales. What started as a minimum wage job cold calling internet service providers to generate leads for a small software company, turned into a 14 year career. Despite my aversion to the work and the inner conflict I felt, I finally started to make some decent money. And before I knew it, one job led to another, paychecks grew, things got comfortable and I was stuck.

In regards to programming, I was a bit slow to discover just how awesome it could be. My first exposure to coding was through a high school technology class. We were using Turbo Pascal to create small, procedural programs like a command line calculator and other simple applications. I found it interesting, but it didn’t quite pique my interest enough to keep it up. My second exposure to coding was during college. We learned the basics of C++, but never really pulled it all together to create something interesting. It wasn’t until a few years later — when I started to take an interest in how websites were developed — that I truly discovered the magic of programming. After a bit of Google’ing one day (or maybe back then I was still Yahoo’ing?) I came across Codecademy. Their website made it super easy to start coding immediately, right in the browser, and before I knew it I was making simple games, writing programs and bringing life to the text on the screen. It was like this whole world of infinite creative possibility had finally revealed itself to me. It felt like I was creating something living from text and with that I was hooked.

Over the next six years or so I began to dabble more and more with programming. I played around with free online courses, took a few semesters of programming classes at my local technical institute, BCIT, and even considered quitting my job to take one of those 12 week programming boot camps. In the end, I was still too nervous to quit my job, so instead I opted for a online boot camp and that’s how I discovered Launch School (although at the time it was called Tealeaf Academy).

What struck me as different right away from the other boot camps I had looked at was how pragmatic and authentic they came across in their website. (As someone who has worked in sales all his life, I have a very well tuned bullshit detector.) They weren’t painting some idyllic picture of how, in just a few weeks (for a mere $10K-$20K of course), I could be a programming superstar in high demand! Quite the opposite in fact. Instead, their website focused primarily on describing all of the unglamorous aspects of what it takes to become an great programmer: The repeat revisiting of fundamentals required to increase general fluency. The importance of focusing on the things that don’t change in software development as opposed to just learning the latest flashy language or framework. And finally, that becoming a great programmer takes time. Lots of it. It’s a journey, not an endpoint.

Sure, you can pack a lot of education into 12 weeks of 12 hour days, but how much are you really going to retain going at that speed? You need time to absorb new concepts and paradigms. You need time to practice what you’re learning. Time to reflect (and sleep!).

I’ve played the piano since I was seven years old, and I can tell you that it wasn’t during my lessons that I grew in skill. Mastery came through practicing for hours a week, playing the same song (or few bars of music) over and over and over again. Slowly building the muscle memory required to push my skills to the next level. And while short term boot camps do seem to land some people jobs, I don’t just want a job as a programmer. I want to know these languages well enough to bend them to my will.

I learned a lot over the six months that I worked through the first two of three courses that were available through Launch School then. My intuition was correct and this was the right style of learning for me. Slow, methodical and deliberate. I even got to the point that I was able to build a simple CRM application of my own design. But again, just as I was about to begin the third and final course, life got in the way. This time it was a trip to Europe, and by the time I got home and went back to work, I had lost my momentum. Ugh. So close.

Well, flash forward a couple of years to today and I have finally had enough. I’m tired of going to work every day feeling disconnected and dissatisfied. I’m tired of wondering where I’d be today if I had just taken the leap to fully commit to my passion a year or two ago. I’m tired of knowing that I have a set of skills and interests that, if fully explored and exercised, will lead me to the sense of engagement and fulfillment in my career that I know is possible. Today, the risks associated with quitting my job and going in 100% are finally outweighed by my desire to fully realize my potential. It’s both terrifying and exhilarating.

Going forward I’ll be using this publication to provide updates on my progress. I’ll be sharing all of the highs and lows that I expect to experience along the way. From time to time, I’ll probably also include some of my personal thoughts on sales and business. If you’d like to connect or ask questions (maybe my situation is familiar to you?), please feel free to comment and I’ll do my best to respond in a timely manner.

Well, I think that’s it for now! The next steps are to finish out my remaining two weeks at work and to pick up a new Macbook (as my last one was recently stolen). From there, it’s on to completing the preparatory work required by the Launch School program so that I can get started on the course in earnest.

Thanks for reading and stay tuned!