This is going to be a personal post, and it’s long, and I’m writing it mostly to get it out there, so if you aren’t into the whole “career journey memoir” thing, feel free to skip this one.

Would it surprise you to know that I applied to the Rhode Island School of Design and for a non-trivial number of years thought that I would have a (likely struggling) career in the arts and graphic design? In fact, I have done a few freelance graphic design gigs, and for a few years I ran a home business restoring old photographs (that probably deserves its own post).

So how did I wind up writing ColdFusion for a living?

As many programming stories do, mine begins with Java.

I wrote my first line of code when I was very young. I am not certain of my exact age, but I was younger than ten. I learned how to launch GW-BASIC on my dad’s IBM desktop (the kind with a green monochrome monitor and two 5 1/2" floppy drives) and write that first program everyone writes:

10 PRINT "Hello"
20 GOTO 10

I learned how to increment and decrement values and create scrolling patterns on the screen. Interestingly, even as I was exploring programming concepts, my goals always tended to be visual, and I think I still have that tendency today.

Years passed and I taught myself other languages. Perl, Visual Basic, mIRC Script (who remembers that one?) and yes, PHP. None of that knowledge earned me any money, but it was almost all of what I did in my free time. I wasn’t deeply into sports, or video games, or in a band. I wrote code for fun.

My first tech job

Eventually I lucked into a tech job. It was actually luck: I had a high school friend whose father and uncle had started an insurance software company decades ago. The company had global reach, had made tons of money selling mainframe software, and had a small office in my home town. They were looking for anyone with half a brain to do rote work converting terminal-based input screens of their program to GUI dialogs using Java and Swing. It was an hourly gig with no contract term; “come do this until we decide we’re done.”

This was all part of a series of strategic initiatives to overcome the fact that in 1999, nobody wanted to buy an IBM mainframe anymore. On top of that, their software was written in COBOL, and, as you might recall if you’re as old as I am, there was something worrying anyone who ran important COBOL programs in 1999.

The “Y2K bug,” as it was called, was in actuality the dramatic lack of foresight that led COBOL programmers of decades past to allocate only two bytes for year values and the associated anxiety about what would happen when those values changed from “99” to “00” and millions of lines of code assumed it to be “1900.”

So, in the frenetic atmosphere of COBOL consultants suddenly making a king’s ransom to sift through millions of lines of old code looking for dates, and the company’s looming inability to sell any new installations of their product, I put on whatever could pass for “business casual” and started my job “writing Java.”

I have to put it in quotes because what I was actually doing was following a very specific set of step-by-step instructions in a thick binder.

1. Open this terminal emulator and follow these steps to reach screen X.

2. Open IBM VisualAge for Java and create a new Swing dialog like this.

3. Place input controls onto the dialog such that they resemble the layout of the terminal screen.

4. Type in the following specific Java incantations to wire up the data to the controls.

And that was it, for eight hours each day.

I worked with three other people. One, a close friend of mine to this day, also got referred in through our mutual friend whose dad owned the place, and would end up working a series of career-defining tech jobs like me. The other two were just folks looking for work, and happy to have it.

So there I was mindlessly typing in whatever was written in this binder. What I immediately came to realize was that only a human could look at a terminal screen and compose a usable GUI form based on it, but a lot of the typing I was doing was redundant. A computer could do that.

We had to give the controls very specific names, which presumably aligned to identifiers in the underlying COBOL that ran the terminal representation, but once we had created the GUI controls and typed in their names, we had to type a line of Java code for each control, repeating that field name twice, that would sync its value with the “middle layer” that connected the GUI to the mainframe.

What irked me was that I was doing this work that was repetitive but also derivative. Some part of me that had been recreationally programming for eight years was offended to have to type the control names into the GUI editor and then type them two more times in the Java code.

Why do twice what you could instead do once?

—Abraham Lincoln, probably

Always work to reduce your toil

Being the industrious and resourceful young man that I was, I somehow discovered (and I honestly have no memory of how I figured this out) that IBM VisualAge for Java had a plugin architecture and that you could write Java code to automate all sorts of functions of the editor, or to modify projects.

I got to work.

Instead of creating new screens, I literally stopped doing my actual job and started writing Java to automate part of my actual job. I don’t think it actually took very long but I really can’t recall the details. In the end, I had written a plugin that added an item to the package context menu in the IDE. Once the GUI form was created, I could right click the appropriate underlying code file, select my custom entry, and all of the data sync code would be instantly generated.

This will save me hours! I thought, triumphantly. Bursting with pride, I showed my colleagues.

My good friend thought it was awesome and, at least in my recollection, he was duly impressed. The other two got mad. “We’re paid by the hour!” they exclaimed.

What happened next changed the course of my career and life in a very real way.

I got laid off

We kept creating GUI screens, using my new plugin, until one day the word came down that our project was getting canceled. As noted, we were hourly employees with no contract term, so it was over for us.

Well, it was over for them. The manager of the team called me into his office on the day of this news and offered me a full-time job. With a salary.

I enthusiastically accepted. As I recall, it was almost a poverty wage, but I was still living at home with my parents and figuring out what I wanted to do with my life, and a job is a job after all. They wanted me to start immediately.

I was installed in a team of other full-timers who had been working, in parallel, on a web-based front end for the product. It seemed to me that someone higher up made the call that building two new front-ends at once was a waste of time and money and decided to bet on the web, which was probably smart.

So I went from writing Java and dragging GUI controls around to learning Javascript and “DHTML,” which was all the rage in those days. This went on for some time, though I can’t recall how long. Long enough that I built a rapport with the other two guys on the project and with my manager, a colorful Scot, who would frequently use jargon from his home country such as “jiggery pokery,” which amused me to no end.

All the while, the company was in negotiations to be acquired by a large UK-based firm, and ultimately it went through. This meant a substantial golden parachute for my friend’s father and uncle who co-founded the business, but it also meant massive layoffs for many others, including me.

I forgot to mention PHP

During most of the time I was dragging GUI controls around in IBM VisualAge for Java, I was bringing my laptop to work and spending every free moment writing very bad PHP code. This was in 1999, so PHP didn’t have objects yet, and people were running around directly referencing $_GET and $_POST to the delight of hackers everywhere.

At that time, it was very popular to get an account on LiveJournal and essentially put your diary online. Some people posted frighteningly personal things, others opined about their hobbies and interests. In retrospect, this was the beginning of the “blog” as we know it today, though as the name implies most of these “journals” were more exhibitionist than educational or theatrical.

I briefly had a LiveJournal, but I fancied the notion of having one whose entire appearance and feature set I could control. Such is the megalomaniacal bent of many programmers. So, I wrote one. I used PHP because it was the hip thing to do, and much easier than Perl for making websites.

When I was working that office job copying and pasting Java, I was rewriting the entire online journal site from scratch, having run afoul of so many of my bad past decisions that it was simply untenable to me, and because I had a lot of time on my hands as a teenager.

Knowing PHP as well as I did by then would turn out to be a boon for my career, but of course I had no idea at the time.

My second tech job

After getting laid off, I started a two-year graphic design degree at a local community college (one of the best things I’ve ever done, in honesty), and kept programming for fun and restoring old photographs for money.

During this time, another friend-of-a-friend told me about a startup he was working for that needed a new corporate website, and asked if I’d like to help out with that. The company had perhaps five employees and occupied a low-rent incubator space in a building owned by one of the two large state universities. They offered me some near-poverty wage to work for a few hours a week on this website project. I enthusiastically accepted.

I used PHP, of course, and I enjoyed bringing their brand to life with CSS, which had become sort of a side passion of mine, merging my nascent graphic design leanings with my enjoyment of code.

By the time the website was all but complete, the CEO offered me a full-time position with a salary to continue doing web-related work for them. The pay was just OK. I enthusiastically accepted. This would begin an incredible five-year journey from our tiny incubator office to an acquisition by a giant consulting company, a move to a large and beautiful office, working for one of the best managers I’ve ever had, building increasingly complex web applications effectively by myself, and eventually my only real experience with burnout, panic attacks, and the first time in my life that I quit a full-time job.

My third tech job, and learning ColdFusion

I have so many fond memories of working for that startup, but after the acquisition by a large consulting company, things started to go south. It was not as a direct result that I started to grapple with burnout, but it was timely that my well-being caused me to look around for something different.

I followed another good friend of mine to a different startup where he’d been working for over a year by then, and before long the previous startup was gone. Erased from the parent company’s web presence.

The new startup was cash poor but reluctantly agreed to pay me a couple thousand less than I was previously making. In spite of taking a modest pay cut, I moved to the waterfront city where the company was located and began some of the best years of my life.

I learned ColdFusion on the job, wrote whatever features were desired, helped create an entirely new product from scratch, redesigned the company’s logo, made amazing new friends, met the woman I’d end up marrying, and had a vibrant social life that in retrospect sounds absolutely exhausting.

I worked for that company for seven years, so I could write reams about my experiences there, and about ColdFusion (which I may do, separately). What ultimately pulled me away was my that my friend who had referred me moved up to Boston to take a job at an even bigger company.

I took over his role, which was somewhat more senior than mine at the time, and carried on for nearly another year before electing to try out at some other places. I took a couple interviews, including at the company my friend had gone to, and ultimately ended up following him there.

My fourth tech job, and returning to PHP

This company was rounding out a long-term initiative to translate their entire system from Classic ASP to PHP, so I narrowly avoided having to write a single line of ASP (though I ended up having to read a lot of it to figure out bugs).

This was how I wound up working in a Boston high-rise office building with free coffee and snacks and writing PHP every day. Again. Of course, by now, PHP had objects and everyone was deeply embracing OOP and MVC and separating their business objects from their view layers and so on, but I was delighted to just be in Vim all day, hacking code.

The rest, as they say, is history. I ended up staying at that company for another five years, so there are reams more after this, but I’ll save it for another time.

When did I know?

The question is, when did I know that the programming I was doing for fun for years and years could be my job?

I think it was that moment in 1999 or early 2000 when I had created the custom IDE plugin and my whole team got canned except for me. I realized then that not just being able to write code, but also being able to see problems and fix them, had real value. Value beyond a paycheck; value that set me apart.

That experience also reinforced years of hacker behaviors that I had acquired. Always trying to figure out how things work, always trying to make things better or easier, always trying to solve problems by myself. Programming, in that way, was perfect for me.

I’ve had an absolutely staggering amount of luck in getting to where I am now, and I owe debts of gratitude to friends and colleagues who have trusted me beyond my expectations. The industry and the world have changed since those days, and I want to write a post about that, too, but I’ll leave you with these words of encouragement:

• You can write code for a living
• You don’t actually need a college degree (though it helps)
• The one thing that has created the most repeatable opportunity for me in my two-decade career is staying curious