How could this happen?

tl;dr: How did a musician and graphic designer become the manager of a team of highly skilled digital technologists at one of Canada’s largest media companies?

How could this happen?

I was recently asked how I got where I am. It took me long enough to explain that I though I better write it down.

How did a musician and graphic designer become a digital strategist and manager of a team of highly skilled digital technologists at one of Canada’s largest media companies?

I could trace it back to when I got my first account with an Internet Service Provider and my first 28.8k modem in 1994, but it actually goes further back than that.

It began when I was five or six years old, but really got going when I was about nine.

The Blue Computer

Almost as far back as I can remember, we had a computer in the house. I was very young when my father built what I always considered the ‘Blue Computer’ – a foot-tall rack filled with circuit boards and ribbon cables. This was a project he worked on with several of his colleagues at work, electrical engineers and HAM radio operators who could see the future was going to be in bits and chips, not in analog circuits.

By Konstantin Lanzet (CPU collection Camera: Canon EOS 400D) [GFDL (, via Wikimedia Commons

It was an 8080 based computer. I know this because there was a 12 inch by 12 inch circuit board dedicated to the central processor, which clearly had the numbers 8080 stamped on it. Several more boards were dedicated to grid upon grid of memory chips, which totalled something like 16 kilobytes of RAM. There was a board dedicated to interfacing with a very clicky keyboard, and another board dedicated to running the tiny monochrome CRT monitor. The rack that housed this monster was painted blue, which is why I thought of it as the Blue Computer.

My father had hauled this computer from Toronto to the interior British Columbia in 1980 when we moved there, and set it up next to all his Heathkit HAM components in his radio room in the basement of the townhouse we lived in there. He packed it up again and moved it back to Toronto in 1981 when the economy collapsed and he had to give up on his western dream in the hard light of needing to feed his family. He had several 4-inch binders filled with photocopied manuals detailing how to program in Assembler.

So I was comfortable with the concept of computers from a very young age but the fact is that I never really did anything with the Blue Computer. It was something my dad played with from time to time, even showed me some of things he could make it do, but it never had much impact on my life other than knowing in a vague way what assembler was. I went on drawing pictures and building increasingly complicated Lego scenes in my basement playroom.


All that changed in 1982 when my father came home from work one evening with an unmarked cardboard box. My curiosity was piqued when he opened it and started pulling out it’s contents.

First came a bag of capacitors, in all sorts of different sizes, shapes and colours. Then an even larger bag full of resistors, hundreds and hundreds of them. Then other things I couldn’t properly identify: sockets, bus bars, spools of wire, ribbon cables and many different connectors. Then a box came out of the box. A low, lean square that, when opened contained several bare circuit boards, each individually wrapped. Then came the piece de resistance: a beige wedge shaped box.

By Bilby (Own work) [CC BY 3.0 (], via Wikimedia Commons

I wasn’t entirely sure what I was looking at at the time, and then he handed me a thick binder full of schematic diagrams and documentation. On the first page was a striped coloured apple with a bite out of it, and futuristic text that said Apple ][+

My father and his colleagues had purchased Apple ][+ clone kits. They were inexpensive compared to the real thing, and even other clones because they came as a box of parts that had to be assembled. They also didn’t come with an official Apple name plate or anything like a ROMchip. Apple hadn’t been able to protect their electronics from copying, but the ROM was covered by copyright so clone makers couldn’t sell them legally. It turned out that this wasn’t going to be an issue for my dad and his friends.

He spent a few weeks pottering around, soldering and building until at last we had something that looked like a computer, missing only that precious ROM chip (and an official name plate, which it never got). But the ROM was being taken care of too. Unlike most consumers or even avid technicians, my father and his colleagues had access to something rare and useful: They had access to a EEPROM (Electrically Erasable Programmable Read-Only Memory) programming machine.

They were able to not only copy the ROM chip from a borrowed Apple ][+ but even modify it slightly. Once inserted into the socket on the main circuit board (and I swear I heard a choir of angels) my dad snapped the lid closed, ran the RCA cable to the selector switch on the back of the television, and flipped on the switch. The television immediately burst into light, and then almost total darkness. Centred at the top of the screen in place of the stock ‘Apple ][+’ was the word ‘APPLEBAR’, a silly play on our last name. Not only was this now a functioning computer, it had a dad joke displayed on screen every time the thing was turned on.

At the time in order to actually load software onto the computer, one had to attach, via a 1/8” mono audio cable a standard run-of-the-mill cassette player. To say this was slow would be an understatement. This wasn’t good enough for him, so my father acquired a full-height 5-1/4” floppy drive and got it hooked up. With two additional modifications, this clone became the most transformative piece of electronics to ever happen in my life.

First he added two telephone jacks to the ‘chin’ of the machine, to which two ‘paddles’ could be connected via standard telephone cables. These paddles consisted of two bare metal electronic kit boxes with potentiometers and momentary switches. Together they acted as a joystick, one controlling the vertical axis and Button 1, and the other the horizontal axis, and Button 2. This enabled my sister and I to play games like ‘Choplifter’ jointly, though it did take a lot of yelling at each other and teamwork to get any good at it.

Later my father built a real joystick with which both axes could be controlled by one person, and gaming became a different and wonderful experience. I was the first of my friends to have a computer of their own, and we gamed extensively. Lode Runner, Wavy Navy and Transylvania were personal favourites, as were the Ultima and Wizardry games.


I loved digital gaming, but what really fascinated me was the idea of computer graphics. I wanted to draw pictures on the screen like those I saw in games. After pestering my father about learning how to do so, he one day came home with a thick binder again full of photocopied pages. It was a manual for Apple BASIC, and my first introduction into programming.

I spent weeks learning BASIC, and weeks more figuring out how to use it to draw pictures on the screen. I would draw pictures on graph paper, then program out the individual pixels to produce my first digital art. I got pretty good at BASIC too. Control structures and subroutines were interesting. I started writing short text games that mimicked Zork. They were silly, but they were fun and I learned a lot. It was a powerful feeling, being able to make the computer do something I told it to.

Before long several of my friends had computers in their houses too. One of my friends had a very sexy Apple ][c which I always coveted for its tininess and its pretty white case, but most of them had Commodore 64s, which had similar capabilities but a far different operating system. One time a friend and I spent three hours on the phone relaying Sargon chess moves to each other while my Apple ][+ played against his Commodore 64. It was always close, but the Apple won every time. In between moves we talked about how cool it would be if computers could just talk to each other over phone lines instead of him and I needing to translate the moves and type them in. We talked about how we could avoid long distance charges by chaining a bunch of computers together.

Rock Lobster

By 1987, the Apple][+ was no longer enough for me, and I took years of earnings from my newspaper route and with my dad’s assistance purchased an Amiga 500. For those who don’t know their computer history, the Amiga was a groundbreaking combination of hardware and GUIsoftware at a time when monochrome DOS and a clunky keyboard were the primary way people interacted with computers.

By Bill Bertram (Own work) [CC BY-SA 2.5 (], via Wikimedia Commons

It came complete with ‘high-res’ monitor (736×483), 512k memory upgrade to 1MB, a second external 3-1/2” floppy drive, a mouse and an Epson dot matrix printer. And it was code-named ‘Rock Lobster’, which sounded cool to a 14 year old. I remember my dad asking me if I was sure I wanted to spend this much of my money on this kind of computer, one he didn’t know very well. Maybe I would be happier with an ‘IBM compatible’ like the ones he used at work? I assured him this was what I wanted and spent two hard years worth of earnings without a moment of regret.

Several of my friends had upgraded to Amigas from their Commodore 64s so the Amiga was wan easy choice. We could share tips and tricks and not least of all software. It didn’t take us long to figure out how to pirate video games by using an external floppy drive that allowed us to duplicate disks track by track, defeating most common methods of copy protection back then. It wasn’t right, but we were young. At least we figured it out ourselves. One friend even ran a BBSon his Amiga, and we would call into it on our 1200 baud modems to leave messages for each other and play early versions of MUDs.

No line numbers

It was with my Amiga that I was first introduced to the C programming language, and then very rapidly to C++. I had two friends who were heavily into programming and they started showing me the ropes. After coming to grips with the idea that there were no line numbers, I began to catch on. I wasn’t as fast as they were – they were taking computer science classes while I was studying art and music. But I did get it.

I continued writing small text games, which were now a little more involved than my first efforts in BASIC. I also wrote several small utilities that made my computer even more useful. But there were distractions too. With the Amiga, I had access to a painting program called ‘Photon Paint’ which allowed me to draw incredible bitmaps at unheard of resolutions and colour depths on screen without having to write code. This was a major revelation for me, and I created a lot of digital art, which was where my heart always lived. But it did mean I wrote less code.

Adolescence intervened, and I wrote even less code. Music had always featured in my life, but instead of just playing classical music on a piano, I discovered guitar and bass and most importantly rock and roll. That meant less code. A couple years after high school I went to college to study graphic design where I was introduced to the Macintosh. The Amiga was arguably a better computer, but the software on the Mac was better for what I wanted to do – which was create graphics and design. Photoshop and Illustrator were tools too delicious to ignore. Less code.

The thing is, you never really forget how.

What’s this WWW thing?

In early 1995, I had finished college and was looking for graphic design work, along with a million other recent grads. I was offered a job doing design work for the “World Wide Web”. Not being 100% sure what it was all about, I did some research and decided to take the job. Given the state of the economy at the time and the lack of graphic design jobs available, it seemed the right course of action. The design work was easy enough, as was the basic HTML available to us at the time. Testing was done in the predominant web browser of the time, Netscape 0.98b. They were good times. It felt like the wild west, and anything was possible.

When Netscape released LiveScript and then renamed it JavaScript later in 1995, things got really interesting. We were finally able to start scripting the front-end of websites, the part people interacted with. Because of my previous C++ experience, I was asked to do most of this JavaScript work. I didn’t have a lot of trouble picking it up. I was now officially a ‘web developer’, though still more often called a ‘web designer’. I even wrote a few simple and painful CGIbackends for sites in Perl.

JavaScript led to more complex JavaScript. HTML led to dHTML and later XHTML and HTML5. Standards compliancy became a thing. Accessibility became a thing that I cared a lot about. AJAX happened, enabling the front end of a website to interact with the back end in a new and powerful way. New languages were learned, from Java to PHP to Ruby to Python. Best practices were discovered and optimized and Web 2.0 became a thing. These were exciting times for the web, and exciting times of professional growth for me. We were both coming of age.

Eventually I had been around long enough to be considered a ‘senior’ front-end developer. I was hired by one of Canada’s largest media companies to help modernize and innovate the front-end of several high-traffic sites. My grasp of graphic design was considered a bonus, because it meant I didn’t have to check back with the designers to clarify potentially vague concepts in their design work.


I didn’t know until I had started there that the morale of the development team was very low and turnover was exceedingly high. In fact on my first day I was informed that both the people who had interviewed me three weeks ago had quit yesterday. My boss was fired less than a month after I started there and I was asked, as one of the senior developers on the team, to help hold the fort down until a new Director of Development could be hired. A week later, I went to the CTO and told him that I was interested in applying for the position. After five interviews with various stakeholders, I was given the job.

Having been part of the team and understanding where developer frustrations were coming from, I made some changes to the way we worked. Some of those changes were subtle, some were as seismic as changing development paradigm from traditional waterfall to an agile process. These changes stabilized the turnover rate and morale improved. In my entire time as Director there I had no voluntary turnover and grew the team to full capacity for the first time ever. Productivity skyrocketed. I didn’t get to write as much code as I would have liked, but I learned to delegate to and trust in other talented developers and oversee things from a more strategic point of view. I learned how to help those developers grow and achieve their ends. I guess I learned how to be a manager. Instead of building websites, I now built teams that built websites.


I’ve been a manager for seven years as of this writing, first at that newspaper and then at a startup where we did some amazing work with some excellent people. Eventually I came full circle and am back at The Toronto Star, the same newspaper I had delivered when I was a kid. Now I manage a technology team comprised of designers, developers, QA specialists and cloud operations experts. I am part of the larger leadership team dealing with digital strategy. And I’m loving every second of it.

There it is. Drawing pictures on a television screen using Apple BASIC to leading digital strategy in twenty simple steps.

I wonder what the next twenty will be like.