Obliquity and Luck

I have a slight confession for some of you: I’m an occasional smoker; perhaps more than occasional.

Last night I finished my last cigarette and took a cab home from the co-working space I’m renting to help me stay on top of things. It was late, I had just spent several hours in a row writing and sending emails and I was on the phone wrapping up some of the day’s details and catching up with a friend. As I got out of the cab, I went to put my cash away in my wallet and found it missing. My cab receipt was already in the wallet and I had no idea what cab company, let alone what car number I was in. I quickly ran to chase down the cab as it turned the corner, but it was for nothing… that cab was long gone.

I walked a few blocks home and quickly turned to my computer to start cancelling cards and rapidly re-order them as I’m due to be in Boulder, Colorado next week to help run the Learning Registry Plugfest. As soon as I got on my bank’s website, the phone rang… it was a stranger asking for me, saying that they found my wallet, and after asking some questions based on the contents of the wallet and where it was found, confirming they had my wallet, they invited me to walk over to their house and pick it up. They were super nice, refused to take any offer from me to thank them for being so kind as to find me and spare me a huge hassle of running around to the DMV and all my financial institutions… and they lived right up the street from Walgreens. After stressing out about losing my wallet, I really needed a cigarette.

My unsavory vices aside, as I was walking over to this house to pick up my wallet, I couldn’t help but be reminded of a recent conversation I had with Thor Muller (@tempo) about his ideas for structured serendipity and a concept he introduced me to, called obliquity. Thor described obliquity in this way,

Given a complex set of challenges, you have a higher likelihood of reaching your goals by aiming for something else.

That probably makes either absolute sense to you or no sense at all. No sooner did Thor share this with me than it registered that obliquity is a pattern that has been part of my life since I was a young adult.

In my last post, I wrote how “over the last couple of years I’ve encountered a lot of professional and personal challenges, met them head-on and even with my failures, I’ve gained so much from doing so.” What I’ve gained overall is in large part due to obliquity, but there’s something more.

I have lots of opportunities for this kind of growth that come my way. These opportunities don’t come because of some special privilege or power. They come because of luck: I’m a very lucky person.

I’m lucky that there are so many good people in the world who happen to make connections into my work and life just when I need them (sometimes when I don’t even know I need them).

I’m lucky that I’ve been able to recognize the opportunities when they come my way: to borrow from American Football, that I can “find the seam and go vertical.” I’m lucky that I have this drive within me to want to apply the ideas I have, so I practice finding opportunities to which I can say “yes, and…” rather than “no, but…”

And apparently, I’m lucky that I live in the Midwest, where strangers are friendly more often than not. I’m lucky that someone found my wallet probably five minutes after I lost it and they called me. I’m lucky that they lived right near a Walgreen’s.

Apparently, I needed a pack of cigarettes. ;)


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Andrew Krzmarzick

Interesting to bring this concept into learning. So often we want to achieve efficiency in learning by teaching with a methodology that transfers knowledge as quickly as possible.

But what if we took people the long way around? What would we discover if we explored related material that indirectly addresses the ultimate learning objectives?

My hunch is the learner would be surprised by serendipity…and satisfied by something akin to cigarettes…and maybe, just maybe, that more adventurous way of learning would become addictive. 🙂

Aaron E. Silvers

@Andrew That’s exactly the approach, brother. If we’re going to create learning experiences, there needs to be opportunity for that self-awakening. That “a-ha” moment where one recognizes that there’s more truth out there than what’s been at-hand.

Faye Newsham

I’m a big believer in serendipitous research. I’ve written my best papers with the spiffy-est resources by wandering around a brick and morter library and pulling out books that just catch my attention from random shelves. I’ve found new ways to consider the problem and solution, what an entirely different segment of research thinks about the same topic, and put 3 and 7 together to get 42… it isn’t efficient, sensible, or even lucky…it’s happened too many times for mere “luck.” I must admit that I frequently look at electronic media resources for options for serendipitous views. I’m more likely to use a tool that gives me options to just look around (and target exactly what I want) over one that only does it one way. I recently received a gift certificate for a dinner coupon website. I could search type of food and location but I couldn’t just look for a specific restraunt (which I might have traveled to if I knew it was an option). By limiting my ability to “just look around” or search on options I cared about, I left the site frustrated and will likely leave the $25 gift on the cutting room floor.

Aaron E. Silvers

@Faye I’m with you. Reading your comment the first thing that pops in my head is the notion of how networks of people work in many ways like the neurons in a brain work. The more connections one can make, the more new ideas can strike seemingly out of the blue (in the brain, this is a lot like how dendrites form). These “discoveries” are serendipity. Getting people together, stirring people up… there are lots of ways to encourage serendipity.

One way that never seems to work: silos and walls. 🙂