Being a beginner again and always

For my next role, I should be looking at a “lateral” move, or even better, a “higher level” role. What if I did the opposite? What if I started over?

A lot of people are asking about what I’m going to do when I get over to Scotland. Where am I going to work? Am I going to continue with Microsoft? Are there opportunities with other gaming companies? 

I don’t have anything lined up yet, I say. This is followed by some knowing nods and smiles. I’m sure you’ll have no trouble finding something is a common response. I don’t disagree, but I also don’t want to agree so easily. I feel comfortable with where I’m at professionally, and that’s my issue. The expectation of most is that I will go for the equivalent of a “lateral” move, or even better, get a “higher level” role for my next job. What if I did the opposite? What if I started over?

Menu sketch
Me writing out the code and design for an accordion menu I would implement on my university’s homepage using Actionscript in Flash back in 2000.

Ever since I can remember, I’ve loved art and design, and grew up learning about it through the lens of games. My interest in technology was born of game consoles, PC games, and remote control cars. How interfaces and images appeared and were arranged on a screen, and how input devices manipulated those images, was inextricably linked with how I created and what I wanted to create. I was also (and am still) a meticulously organized person, and I’ve always held tension between those often opposing forces: the creative who dives in not knowing where something will go on one side and the cartographer charting a detailed plan on the other.

The intersection of this making and organizing is where my career in tech began. Around the end of 1999, I started to notice how much visual creativity and storytelling were happening online, and I wanted to be a part of it. A friend of mine was making websites, so I joined him and suddenly I was building and (over) designing websites for academic departments at my university. I also set-up my own site (, hosting it with a company called (solely because other web design artists were also using them). I was hooked by the combination of design and technology and freedom I had publishing on the web. Information taxonomy mixed with art! These were the days of figuring out how to bend table-based layouts to one’s will using single pixel spacers and CSS wizardry. The days of using FTP clients to publish a new version of WordPress and it’s MySQL back end. The days where Macromedia made Flash and the coolest sites had their menus and hero sections of homepages rendered with it. It was maddeningly hard to learn how to do it all and there was nothing else I wanted to do.

Scanned drawings for
Some layout sketches for my original blog. I wanted a unique style so I hand drew the UI and then scanned them in and cut them into table layouts using Macromedia Fireworks.

I’ve previously written about this time as good hard work, and it’s not an exaggeration to say that it’s the time in my life where I felt most creative, where I had full agency to learn, create and do. I knew there was no barrier other than time to making it happen. I was solving problems though experimentation, banging my head on the wall more often than not, and I was teaching and learning with others at the university technology department, and with like minded friends. My career at Microsoft owes itself to the momentum I gained during this time.

Early academic department website screenshots
Screenshots of some early departmental website designs I did. Bad by today’s standards but back then the web wasn’t as pretty as it is today.

I’ve never lost that love of creating and publishing work, and helping and supporting others use technology to create themselves. However, I’ve gotten further away from it as my career has progressed. Up until recently, It had been a long time since I was last making, designing and creating things with technology. My recent role (with Minecraft) has gotten me into making again, and non-coincidentally I’ve also jumped back into sharing my writing and illustrating online as a committed side-gig. It’s been amazing how it’s fueled all other aspects of my life and made me a better dad and a husband. The energy is flowing in the right direction, and I want it to stay that way.

“Energy cannot be created or destroyed, it can only be changed from one form to another.”

Albert Einstein

So what do I want to do for work next? I’m not sure but I know what I don’t want to do. Instead of looking for a job that’s lateral or “higher level”, I’m looking for something that will allow me learn something new. I’d like to go back to the beginning, to actually being a beginner again and having to figure something out from scratch. I’d like to learn how to design and implement new user interfaces, bring stories to life using narrative, illustration, music and some code, or create a new way for creative collaboration and sharing. I’d like to do it both for income as well as incorporate it in projects with my kids and their education. I’d like to do it with others, in a way that’s not crazy.

I’m not sure that this will lead to in terms of my next role, salary, etc. It could certainly lead to less money. It will almost certainly lead to some raised eyebrows. I know it will lead to a lot of new learning, new connections and great experience.

Beginning again might not make sense to most, but it makes sense to me. I can only hope it’s one of many more.

“Work hard” is advice with a short shelf life

I’ve experienced the value of hard work and the danger of working too hard. My work must work for me, not the other way around.

I come across the advice that one needs to “work hard” frequently in my reading. There are other, more sinister variants that are common too, like “Work harder than everyone else”, “Outwork the competition”, or “Do what it takes”. This is commonly offered as advice on how to be successful, as a desired trait for a job applicant, or as something someone did that made them stand-out and reach heights that others aspire to. While I agree that a strong work ethic is an important quality to develop early in one’s life, I think it’s vastly overemphasized as a means to be “successful” and can lead many people astray.

Working hard is often regarded as a perpetually active state, a super power that must constantly be deployed like Spiderman swinging on his web in each encounter. If you are fortunate, this feels effortless, natural and empowering. The results can often lead to thrilling highs, the high of exceeding your bosses expectations, of exhausted praise from peers and of big rewards. Unfortunately, there is a more-common-than-not flip-side to this. Working hard is also synonymous with putting in more hours, being constantly connected, and working because you “should be” and are expected to if you are really passionate about your customers/your art/whatever. Striving to work hard can cause one to ignore boundaries, be one-dimensional, have a distorted view of self-worth and ultimately chase after results and expectations instead of accepting (and appreciating) reality.

How does someone parse the good hard work from bad hard work?

In the year 2000, I was just starting my bachelor of arts in marketing and internet studies (my 3rd major, after somehow failing to apply to the art program and giving computer science a go for a couple of quarters and hating it). It was then that I discovered the web, a new to organize information and design using new creative tools, and it was all I wanted to work on website design. I loved spending time doing this and did so almost any chance I could get. I was energized by the work, and I was by all definitions “working hard”. This was good hard work. My personal life and school life flourished.

Contrast that experience with another around the year 2009. I was working as a member of a remote team on things I didn’t really care about, but that I thought were important for me to know and experience. I was meeting with teams from the UK, France, Singapore and India and thus was pulling crazy hours to make it all work. I was paying my dues and getting good experience, or so I thought. I was by definition “working hard”. This was bad hard work. My professional life stagnated and my marriage fell apart soon after.

The key difference between these experiences is that when the good hard work was happening, I wasn’t thinking about the work. I was thinking a lot about (and doing) what I was truly interested in, I was doing work that was aligned with my goals at the time, I was challenged, I was having other experiences at the same time that gave me breaks (college is good for that), and it all fed and amplified my sense of self-worth. Contrast that with the bad hard work phase, in which I started to ignore side projects, didn’t look after myself physically, felt my marriage deteriorating, and was in many general adrift.

I’ve had a job since I can remember, starting with working in my Dad’s shop before it was legal, to a steady career in retail in high school and college. Even in those early years of learning the value of hard work (and having it suck at times), my overall feeling was one of pride and agency in my future. It was good hard work.

I’ve wasted plenty of time stubbornly working harder and ignoring the signals that something is amiss, that my priorities are off, that my work is working me and not the other way around. I bet a lot of other people are in the same boat.

I love and value hard work, but it’s advice with a short shelf-life. Once you learn the basics, working hard comes for free when you are doing what matters most. Knowing what matters most is the real challenge. That requires dedication, discipline and focus. Committing to that is what life is about and to do it requires that you truly work hard.

(By the way, if you’re reading this, you probably don’t do hard work)