A few weeks ago, I was in a work-related meeting where we were discussing skill sets required in a small team. At one point, someone said, “But we can’t be good at everything.” Since then, I found myself repeating that once or twice in some similar circumstance, but each time I say these words or something to the same effect, I wince deep inside.

As I was growing up, my parents, to their credit, tried to make sure I had a well-rounded education. I was given music and art lessons, and turned out to be quite good at these things in addition to being an A-student. However, the education system in the place where I was born was inherited from the British; your destiny is binary — you either end up in the Arts or the Sciences, depending on how well you did at school. (I’ve since learned this system is similar in many other places.) So, students who score good grades were streamlined into Sciences, and students who didn’t were cast into the Arts. If you were a Science student, your future is ripe for the picking, your oysters grown for you.

However, being someone who happened to be good at science and mathematics (it took me all the way until university before I started to loathe maths), as well as a performing musician when I began primary school, I couldn’t understand this arbitrary split of abilities and social rank, but I digress. At some point, I realised that to maintain a level of sanity, I had to make sure I could exercise both my artistic abilities and scientific inclination whatever I ended up doing.

I remembered one day when I came home from school and offered to help with dinner. My grandmother had always been nervous watching me cook because I was left-handed, and everything looked wrong to her. Out of nowhere, she said nonchalantly, “You’re such a good student, we can’t expect you to cook.” I remembered thinking to myself, “What?!” Even more surprising, she said it with a touch of pride. Maybe that was when it began — I refused to have my whole person judged upon one thing I did well, and wanted to do well in many things.

Recently, I was cleaning out my hard drive and found a random voice note I recorded at some point, probably for some essay that I never got around to write:

When I was in primary school, my headmaster thought I was smart enough to be a scientist one day. Looking back, I think he expected me to fill big shoes, maybe I could be like Albert Einstein or Marie Curie, but I think then that I really wanted to be like Leonardo da Vinci.

By the time I was getting into university, my matriculation score placed me in the top 3% of the state — probably not the best I could’ve done, but I didn’t really work all that hard, I was spending too much of my time playing in every single music ensemble the school had to offer. But that was alright, there were only two university courses my score wouldn’t have let me gone into: medicine and dentistry. Neither of these were of interest to me.

Throughout all these years, time and time again, my family repeatedly told me, “You can’t be the jack of all trades, master of none.” After awhile, I started calling myself a jackass of all trades.

And now, after more than a decade into my profession — which I stumbled onto rather than chose — I still hear this. Specialise, be really good at one thing. Don’t be a jack of all trades, master of none. You can’t be good at everything.

But I have the blood of a generalist. I was a fairly accomplished musician. In the realm of building for the web, I went from coding back-end systems, to front-end engineering, to designing user experiences, to leading teams, to project and product management. I wrote ever since my father thoughtfully gave me a book to fill since I was 7 years old, I sketched, wrote all the way through my difficult years, I learned to photograph the moment I could afford a decent camera. And thanks to my mother, I learned how to make things, and continue to pick up various different ways of making things. Later, I learned a little of the art of the barista, and learned how to silversmith.

If I hadn’t been a musician in an orchestra, an accompanist, or a soloist at times, I would probably not have had the ability know how to get people to work together, how it takes the power of many to create magic, how it takes careful listening, coordination and trust. If I had not graduated in computer science, I would not have come up with a team strategy that was inspired from programming for parallel processors. If I had not been a musician, I would probably never have been a good writer, communicator, teacher and speaker. What makes me a good cook is also what makes me a good project manager.

Somewhere in the way we view what we, as respectable members of society, should do with our lives, we lose out the moment we think of ourselves as a cogwheel that can be good at only one thing. So many of the skills we possess in one discipline translate to another, it seems ridiculous to limit ourselves and fool ourselves into thinking that we were each designed for only one thing.

It’s a little like mastering languages. When you begin to know a couple of languages, the third, fourth and fifth language comes easier, because suddenly you have a much more flexible model of the world through which you can adapt what you see and interpret. As you encounter new things, they either fit into something you already know, or you create a new mental model.

Doesn’t it stand to reason that if we could pick up very different skills, that we should be able to be more efficient learners, and be more adept in more of the things we do? In which case, why do we have a society that’s afraid of giving birth to generalists?

Update (Jan 7, 2010): Wow, for some reason this post is getting a lot of traffic after I’d even forgotten I’d written it. This post was a deep self-reflection, but I’m really happy to see that it appears to resonate with many. Also, seems like we lost some trackback info during our server crash a few months ago, so you may also be interested in follow up posts elsewhere:

• On Stephanie Booth’s blog: What if Generalist vs Expert was a Mistake?
• On my other blog, where I felt it’s more appropriate to take this thread: The Master of Many, Part 1 and Part 2.