Dare to Dabble

I don’t think I’ve ever heard the word dilettante used as a compliment.

Even the dictionary seems weirdly derisive (emphasis mine):


a person who cultivates an area of interest, such as the arts, without real commitment or knowledge.

But I think to be a dabbler (a synonym of dilettante) is to be a good thing. To dabble is to explore what’s out there. It’s to be curious.

I think most people stop being curious because of a certain fatalism. The assumption seems to be that I can never know/see/do it all, so why try? Of course, those who say this are right: a dabbler will never achieve everything. Or anywhere near everything.

If achievement were the point, this might be a concern, but it’s not. To try something even though you know that you are going to absolutely suck at it is a thrill. It’s like jumping off a cliff into the ocean when you’re only mostly pretty sure that it’s definitely hopefully deep enough to not kill you. It’s like moving to another country or winning a race.

Or at least, that’s how I feel about it.

Recently I had the chance to act as a mentor to someone at work. Setting aside how weird it is to think of myself as a mentor, he asked me a question about how far he should pursue his formal computer programming education.

My advice to him was to choose one keystone skill that he wanted to be an expert in, and a few supporting skills, and a wide array of miscellaneous interests. Here’s what I meant:

The Keystone Skill

To be an expert at something is a great joy, and at the same time a maddening never-ending quest. In some inescapable ways, it frames how you think of the world. Whatever this skill is, it takes so many hours to become a true expert you’ll inevitably start thinking like the other experts in your same field (a true disadvantage of expertise). This is why supporting skills are necessary.

The Supporting Skills

Supporting skills stop the mind from being myopic and widen the breadth of creative influence. They don’t have to really be in any way related to the keystone skill. Creativity can come in some strange intersections, as is argued in the Medici Effect. Personally, it seems there is a correlation between the exceptional skill of some computer programmers and the high diversity of hobbies they each have.

The Miscellaneous Interests


The Zen Buddhists would call this the “beginner’s mind.” It’s a state of mind which means not taking things for granted. The more knowledge you have, the more expertise blinds you to small changes or unconventional solutions.

Leadership gurus like to talk about things like “stepping outside your comfort zone.” Well, that’s what dabbling is. It’s a programmer learning design, or a designer learning programming (as a colleague recently did).

The Use of Dabbling

I don’t think I’ve ever seen dabbling yield less than remarkable results when used sincerely. Dabbling is not an idle pursuit. It is active and inquisitive.

The dabblers I know are fascinating people. In most ways, they vary. Some are introverts, some extroverts. Some are secret artists, others genius engineers. The one thing that makes them all similar is that they find a way to combine their keystone ability with supporting skills and dabbling to create something truly unique.

This blog is a result of me trying to follow in their footsteps, and deconstruct the actual process of learning a skill in the process. Some of the posts are personal logs of successes and failures in learning new things (from musical instruments to foreign languages). If you’re here for more practical reasons, when you sign up for the mailing list I’ll send you a 7-email series of the most important lessons I’ve learned in 10 years of dabbling.

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