Last Saturday I was in Texas giving a talk at Dallas Drupal Days. The morning after I got up early to go mountain biking with Tom and Dave from Level Ten — the conference anchors; thanks guys! — and their friend Peter, who really set the pace on the ride. It was a lot of fun, and as you can see I had a few brushes with the terrain. Turns out my street biking skills don't translate super well to the offroad context in terms of maneuvering, but I was mostly able to keep up and the road rash (tree rash, actually) was totally superficial.

It got me thinking about risk. I've got a fake tooth stemming from a pretty messy bike wreck in Brooklyn back in 2003, and my chosen mode of transport has gotten me into a number of other other scrapes. I commute daily on the gauntlet of Market street, which is a chunky combination of traffic, potholes and trolly tracks, and enjoy the daily challenge, but the odd moment of jamming between busses aside it doesn't really raise my hackles. By contrast, riding up and down creekbeds and over roots and rocks felt downright dangerous.

The perception of risk is in part about experience; urban street riding is all about tracking multiple changing variables — the timing of the lights, the position and momentum vectors of traffic, the odds that someone is going to open a car door, etc — in the context of relatively flat/even/vanilla landcape, whereas mountain-biking is about maintaining momentum and clean lines of action as the landscape throws challenges at you. Both activities carry risk, but the one I'm used to feels (relatively) safe.

Really I wasn't thinking about biking. I was thinking about the part of my presentation the day before where I reflected on my work-life over the past decade and concluded that I'm more or less ruined for "regular work" — meaning a 9-to-5 type job — at this point. When I put that in the talk I meant it to be about attitude, which is true, but later I started thinking about how it applies to my approach to risk as well.

From my perspective, taking my career in my own hands feels legitimately safer than tying it to any big company. I'm absolutely confident in my ability to execute, and while being adventurous in business means some ups and downs, that feels much less risky than going inside a large institution were I won't have any control and might be left out in the cold at any moment with no marketable skills. It's totally tautological, but I want to say "because I'm comfortable with risk, risk is less risky" or something.

Some of this is generational. Actual credentialed social scientists have excessively documented the shift away from The Company Man as a mainstay of the workforce; this isn't really in doubt at this point. I was also influenced early in my career by the elephant and the flea polemic — which is more about how this can work in the favor of creatives and entrepreneurs, and less about how big companies have started shafting their long-time employees by shedding obligations/etc. These trends are real.

But I'm more interested in that tautology-ish sentiment. Human beings have egocentric tendencies, and I'm no different. I reflexively assume other people are like me, which clearly isn't the case. Moments like this are interesting, where I have to situate myself within the broader spectrum of people to try and figure out what's really going on. I have an almost prejudicial preference for DIY/new/creative activities — for getting close to the edge. That's where I thrive, in large part because I'm comfortable there, which isn't the norm.

To look at it from a different angle, it's another spin on another much more famous tautology: there's nothing to fear but fear itself. If you're unafraid, opportunity blossoms. You can get acclimated to that kind of environment, and once it starts feeling like home there's no place else you really want to be. Why give up home court advantage? For me, playing it safe feels more dangerous.