Although my mom had enrolled me in a couple of art camps and classes when I was a kid, I was definitely not one of those instinctively drawn to it. I had classmates who spent all their free time (and much of class) doodling in sketchbooks. I immersed myself in text, reading books, writing notes, programming computers. Well, I’d been mindmapping since grade school, so visual thinking was already part of my life – but it didn’t captivate me as much as text did.

Here’s how I rediscovered drawing.

2007. J- had been looking forward to getting a Nintendo DS. Since there were some interesting games with cooperation modes and one of the stores had a decent sale on Nintendo DSes, I bought myself one as well. I immediately loaded it up with an application called Colors DS, which let me draw using the Nintendo’s stylus. It was a lot of fun.

This was fun, so I started drawing on paper too. It wasn’t nearly as awesome, but it was a good mental challenge.

I got into drawing my presentations on a whim. In 2008, I was a technology evangelist and web developer at IBM Canada. I was passionate about how social business systems like internal blogs and communities could transform the way organizations worked. An IBMer in New York told me that whenever she went on campus tours, the students she talked to simply couldn’t grasp the idea of why anyone would want a social network at work. To help her out, I put together a presentation.  I figured – why not make my rough storyboard the actual presentation? So I drew it on my DS and made this:

People liked it. A lot. And they wanted to know how I made it, so I made this:

And then I started sketching most of my presentations, because it turns out you can get away with stick figures instead of bullet points even at IBM:

I had some space in my opportunity fund. Since I was drawing a lot more than I used to, I decided it was time to invest in tools. I didn’t think I had the hand-eye coordination for working on a Wacom tablet attached to the monitor, so it was a toss-up between getting a tablet PC or a Cintiq tablet that lets you draw on a screen. I sprung for the Cintiq 12WX, reasoning that it would let me keep upgrading the computer it was attached to instead of locking me into something with limited upgrade capability. Using it with Inkscape was great, because I could tweak my drawings until they kinda looked like what I had in mind.

When Slideshare organized a Best Presentation Contest, I thought, why not? I didn’t think I stood a chance in the “serious” categories, so I went for the self-introduction one instead.

I won, which was a little mind-boggling. My prize was an iPod Touch, which I immediately used for more drawing.

In 2009, I made a couple of other presentations that got pretty popular: The Shy Connector:

and A Teacher’s Guide to Web 2.0 at School.

I helped organize lots of innovation workshops at IBM. I started drawing there too. It turned out this is called graphic facilitation. I took notes at other people’s presentations. This one is from Gary Vaynerchuk’s talk at DemoCamp in Toronto:

Getting a tablet PC made a huge difference in how I drew. The Lenovo X61 was my first tablet PC. I bought it second-hand in 2010 and started drawing right away. For the first time, I could draw digital notes at meetups.

In 2011,  I switched to using Autodesk Sketchbook Pro. I even started giving presentations using it.

I looked at other people’s work for inspiration, and I played around with my own. I really liked how Exploding Dog and Hyperbole and a Half managed to say so much with simple figures and vibrant colours, so I tried that out.

I still don’t feel particularly confident about colour, though. Seriously, I have the computer figure out complementary colours for accessorizing. So I draw mostly in black and white, like in this three-word life philosophy.

If you compare how I draw now (black and white stick figures, with some colour for accents/highlights) and how I drew in 2007 or 2008… there’s not that much difference. I still draw stick figures. I still don’t have a lot of depth or fancy layouts. I still don’t use pressure sensitivity. My lines are still a little wobbly. I use fewer colours, even. I like the colourful explosion of my Katamari drawing! I should make stuff like that again.

The main difference is that I know my tools more, I guess. I know how to set up a grid so that my text is mostly straight. I work with brushes so that my lines look clean and confident. I work with layers so that I can redraw or erase or move things around. I know that digital drawing works out much better for me than paper does. I know that I don’t have to be an “artist” and I don’t have to make art – I just have to make something that makes me smile.

From time to time, I’m a little bit envious of friends who doodled and drew their way through years and years of practice, and who can now make these beautiful drawings just from their imagination. It’s okay. I can draw well enough for my purposes, even if I probably draw worse than my 7-year-old self could. =)

So that’s my “evolution”. I haven’t actually made much progress in terms of drawing skills, because I haven’t needed to. Simple stick figures turn out to be enough. In fact, I probably won’t try to draw amazingly well, because I want to keep things approachable for people. I want people to look at this and say, “Hey, I can do that.” If anything, I’ve probably only grown in terms of vocabulary, confidence, and understanding. That’s just a matter of practice, and I’m looking forward to getting even better.