Jack of All Trades, Darn Good at Some

Photo: Ming-Chih Kao

There's a pretty longstanding preference in business, school and even hobbies that I feel like I've been fighting against my whole life: specialization. Whenever talking to recruiters or employers, they always seem disappointed to not find their ideal hyper-specialist.

You know the one. The guy who has 6 years of experience in C# integrating Oracle, a CRM system with 9 customers worldwide and their custom inventory system. In other words, the guy who started there 6 years ago and just burned out and left.

In college, there's a push that you choose a major as soon as possible. In graduate school, medical school or law school, there's a deep push to choose a speciality: heart surgeon or patent attorney.

In many hobby communities, there's a deep sense that many of the people there are seriously dedicated to *that* hobby and that hobby only. They *are* hobby photographers, model train engineers or collectors of obscure fast food receipts.

Now, I'm not going to speak against specialization in any way. I think that people who really find themselves in a specialty are fortunate. It's just that, like being an introvert in an extrovert-oriented society, those of us who are naturally drawn to a more interdisciplinary or "generalist" approach to career, life and hobby can often end up feeling fairly misunderstood.

The title of this post comes from a common refrain I've heard more often than I'd care to count. When I explain how much I enjoy dabbling in lots of different areas, it's usually only a matter of time before someone, usually in a sing-song voice, chimes in with, "Jack of all trades, master of none".

However, my conversational partner has NEVER finished the statement with the rest of the quote: " . . . though ofttimes better than master of one". That particular nit aside, by listening to the push for specialization and pursuing my own interdisciplinary path anyway, I've always ended up happier than when I caved and attempted forced specialization.

And, it's resulted in finding that, while people may not explicitly ask for generalists (even actively rejecting anyone labeled that way), they nearly always value the things that *come* from being a generalist.

In talking with other generalists, I've found that one of the surest ways to tell if you're a generalist is the frequency with which you're asked the question, "Why do you know that?" followed in close proximity by "How do you know that?".

When those questions pop up, as long as the generalist isn't being annoying, it's usually because an observation from some other area of life seemed relevant. However, because most of the group has never had a "reason" to, say, read books on neuropsychology and economics despite having no obvious reason to do so, they aren't in a position to see how a principle weaves across those disciplines and into choosing the appropriate dessert.

Party conversation aside, what I've found most surprising is how generalization can actually lead to its own kind of specialization. In my career, I've essentially ended up a specialist in integration and problem solving by working with a wide variety.  It's as though there are 2 approaches to specializing.

One is the obvious one where you get a quick overview of a topic and you then choose a specialty and pursue it.

The other is a bit more of a wandering approach where you pursue lots of different things until eventually a specialty sort of just pops up. And, what I'm finding interesting about the specialties that arise this way is that they'd be fairly difficult to achieve any other way. I know because I'm often asked how you could teach problem solving skills and admit that I'm stumped for a real answer.

Scott Adams posted this summer about deliberately embracing this as a career strategy and I found myself nodding along vigorously. Rather than picking a pre-defined niche and attempting to beat out everyone else who chose that niche to get to the top, he suggests picking (whether deliberately or through experience and wanderlust) 2 or 3 things and getting reasonably good at them.

In doing so, the combination becomes your own specialty in which you can easily distinguish yourself. And, to me, an ongoing quest for cross-disciplinary learning and working lets you turn that 2 or 3 combinations into a richer tapestry as you get older.

I'm still mulling over how I think about this particular dynamic, but the conclusions I'm seeing and coming to over the last few years really resonate wit.h me and are something I'm embracing