Tricksters, Hackers, and Schemers

Thursday, August 20, 2015

by Kent Aitken RSS / cpsrenewalFacebook / cpsrenewalLinkedIn / Kent Aitkentwitter / kentdaitkengovloop / KentAitken

In literature, trickster characters are the rule-breakers. They cross boundaries, put others outside their zones of comfort, and question authority. They "playfully disrupt normal life and then re-establish it on a new basis." They're often set in a world such that the rule-breaking appears, to the audience, to be understandable - if not downright virtuous.

In society, the tricksters might be the civic tech, NGO, social entrepreneurship, and hacker communities. Hackers, in this view, are those who take things apart to understand them and reconstruct them to suit their needs, be it technology, institutions, or machinery (try these pieces by Tanya Snook or David Fleming for this take). Dealing with government is just one lever to pull towards achieving their goals.

Inside organizations the tricksters may be called innovators, or perhaps mavericks or "rebels at work." Less flatteringly, they might be called "headstrong" or "naive".

There's always conflict between tricksters and those around them, including other tricksters with different levels of willingness to break the rules. The Fantastic Mr. Fox (the character in the image, above) revels in tricking farmers out of chickens until he realizes that his actions are endangering the other animals in his community by provoking the gun-toting farmers. In many stories, a common theme is discord between members of the counterculture: some people are willing to do anything to reach their goals, and their friends have to stop them from compromising their principles. Ideals and goals don't always get along.

Wither rebels?

Brett Scott's recent piece The hacker hacked gets into the conflict faced by the first group, those outside large businesses or institutions. 
"We are currently witnessing the gentrification of hacker culture. The countercultural trickster has been pressed into the service of the preppy tech entrepreneur class. It began innocently, no doubt. The association of the hacker ethic with startups might have started with an authentic counter-cultural impulse on the part of outsider nerds tinkering away on websites. But, like all gentrification, the influx into the scene of successive waves of ever less disaffected individuals results in a growing emphasis on the unthreatening elements of hacking over the subversive ones.
 In this setting, the hacker attitude of playful troublemaking can be cast in Schumpeterian terms: success-driven innovators seeking to ‘disrupt’ old incumbents within a market in an elite ‘rebellion’."
(See also: "The best minds of my generation are thinking about how to make people click ads." - Jeff Hammerbacher)

I highly recommend reading the full piece. For one, it's as a fascinating take on the arc of the technology and digital world - once considered a disruptive, democratic, playing-field-leveling force. Two, there's an obvious parallel for anyone trying to remake an organization around themselves.

The trickster's dilemma

Akin to hackers being subsumed into the tech entrepreneurship scene, change-wanters will face a practical dilemma in efforts to drive change. Sometimes, after years of suggesting X project, someone will say "Ah, now you have your chance to put your money where your mouth is: we'd like you to do X. But by our rules." This invariably means that you won't actually get to spend much of your time on X, instead worrying about HR, finance, proving the value of X, building partnerships, and navigating internal politics. And you'll realize that they're using a different definition of X. But, you're finally getting the chance, so you can't rock the boat now. You need to succeed, even if it's not exactly what you wanted to succeed at, to gain the credibility for future such projects. Besides, if you decline the opportunity they'll ask someone else anyway, and it won't be done as well. You're stuck.

Last year I had the opportunity to speak on a topic I was passionate about and I was pumped. When I accepted, I heard the parameters: it was an "un-panel," and I'd be "randomly" selected from the audience to ask a question and then join the panel. My question was scripted and a speaker would magically have a presentation ready to answer it. I backed out, but the principles versus impact debate is rarely so lopsided.

So you believe in change and doing things right. But do you do things less than right for the opportunity to do things right in the future? Or dogmatically stick to your guns, but end up alienated from the organizations and people that can facilitate progress? Do you stay as a garage hacker, or join an organization that limits your freedom but expands your impact?

Ryan Androsoff was recently musing about whether the W2P (web 2.0 practitioners) community in the Government of Canada had withered, and he captured the discussion. It seems I'm not alone in viewing the people in that community as innovators and schemers, but that they've moved on to "operationalizing" their goals or simply "doing."

In the US, the Presidential Innovation Fellows program exists to get bright and talented tech experts into government to revamp systems, build tools, and shake established mindsets. My anecdotal evidence from conversations with public servants south of the border is this: one, that the "not-quite-in-government" position allows the freedom to question established practices and push through solutions. Two, that institutions have had problems following through and maintaining Fellows' projects after they leave. The program was made permanent this week, which could help the latter problem - but might hurt the former advantage.

For the Fellows and W2P, there's a power in being distant enough from portfolios that you can truly speak your mind. Once institutionalized, operationalized, or made responsible, these Fantastic Mr. Foxes may realize that other animals are counting on them and that playing with the rules - even if virtuously done - isn't the right approach anymore.

Which is not to say that accepting positions of responsibility is inadvisable. It's actually the core of the public service ethos. It's why we're here. If you have a meaningful job and your work actually impacts citizens then it comes with responsibility. But there will be constant tension: is the value you had as a trickster being left behind?

A last word about naiveté

Naiveté is the true enemy of tricksters, hackers, and schemers. But it comes in two different flavours.

  • Failing to understand or appreciate the value of "the way things are". Ever complain about something and have a friend respond "Actually, there's a perfectly good reason for that"? The more you learn about something, the more you'll see both its flaws and its virtues. If you're trying to change things, you have a responsibility to understand them.

  • Failing to understand or appreciate the value of ideals. There's a reverse-image naiveté to the above and it manifests in Machiavellianism, acting as though everything is strategic, pragmatic, and political. As bad as the naive tricksters, the naive institutionalist can't tell when the tricksters are right, and falsely believes that the rules of the game can never change.