Two Flavors of Technical Opportunists: Missionaries and Mercenaries

“Missionaries and mercenaries” has a pretty intriguing ring to it, huh?  I wish I could claim credit for it, but I heard about it on this podcast with Ribbonfarm creator Venkat Rao.  Apparently, entrepreneurs use this pithy phrase to make a distinction among themselves.  I’ll explain in more detail shortly.

First, however, I’d like to do a bit of explanatory housekeeping.  In the coming months, I’m going to make some changes to my life.  Specifically, I plan to wind down the management consulting in favor of creating content (products) and offering productized-services.  This may sound a little crazy to you.  It would have sounded crazy (or naive) to me up until a few years ago.  Why trade a high profile consulting career for… an unknown?  So I want to explain myself before I lose sight of the fact that I might need to explain that to people.

On “Trading Hours for Dollars”

I’ll tell a quick story to clarify.  A few years back, I’d decided to leave a CIO position in favor of consulting as a free agent (which may also sound crazy, but it worked out).  As I looked to build my book of business, I was chatting with fellow Pluralsight author John Sonmez about the jump he had made away from full time employment.  He said something during that conversation that I’ll never forget, when I asked him about how he finds consulting work.

“To be honest, I’m trying to get away from trading hours for dollars.”

When you listen to the podcasts I listen to, read the books I read, and talk to the people I talk to, you’ll hear this a lot.  At the time, however, I had never heard anyone say that.  I probably replied with something noncommittal like, “oh, that’s awesome, man.”  Meanwhile, I recall thinking to myself, “I don’t even… wat?”

These days, I completely get it.  Back then, I didn’t.  And so I want to start bridging the gap before the curse of knowledge consumes me and I just assume that everyone shares my perspective on hourly work and the corporate condition.

Developer Hegemony launches on May 2nd, and people have been asking me what comes next.  Well, among other things, I plan to pursue a line of business wherein I help support people executing their plan to achieve developer hegemony.  But before I can do that, I have some mental groundwork to lay.  And that brings me back to missionaries and mercenaries.

Opportunist Escapees

If you’ve only recently come to read my blog, understand that I mean something deeper than the dictionary definition when I talk about “opportunists.”  I explain in depth in this post, but this graphic should suffice.

Most simply, opportunists are those who maneuver their way to the top of the pyramid-shaped corporations.  The C-suite consists exclusively of these folks, but you’ll also find them at all levels of the organization.  I think of those working their way up as “ascendant opportunists.”

But wherever you find them in the corporate hierarchy at the moment, you’ll find that all of them have ceded good faith with the organization.  In other words, opportunists ascend rapidly by coming to understand the essential bankruptcy of the corporate advancement narrative.  They arrive at their positions and status through the lonely recognition that the normal corporate rules are for the idealists and pragmatists around them.  They chuckle internally, behind a careful poker face, at the notion that companies can have such things as “missions” and “values.”

If you really want to dive deep into the psyche of the opportunist, my book talks about this archetype and the other players in detail.  For our purposes here, I want to talk about what happens to these players when they exit the game.  (And make no mistake, they’re the only ones who ever do this side of retirement.)  What fates await opportunists that exit pyramid-shaped corporate life?

Missionaries and Dents in the Universe

Close your eyes and picture an “entrepreneur,” particularly in the world of tech.  I’ll wager that you’ve pictured Steve Jobs in his garage or Mark Zuckerberg in his hoodie.  Maybe, if you’ve followed the news of late, you picture the apparently-Caligulan culture of Uber.

How about if I say, “aspiring entrepreneur?”  Do you then picture people working in open office plans, furiously trying to turn ideas into convertible notes and rounds of capital?  Can you hear them planning “scale” and “exits”?

First and foremost, understand that you have pictured opportunists, whether or not they succeed in entrepreneurship.  These people play only by the corporate rules they, themselves, create for the benefit of idealists and pragmatists to be hired later.

But also understand that you have (probably) pictured missionaries.  Now, before I go further, understand that the canonical categorization more or less boils down to “selfless versus selfish.”

[Missionaries are] all about “the big idea” and partnerships that last, and they understand that “this business of innovation is something that takes a long time” — it’s a marathon, not a sprint.

In other words, “are you in it for the love of your vision or for your pocketbook?”

I’m going to take a contrarian perspective and embrace the mercenary.  Quoted in the article, Doerr even describes him as “opportunistic.”  Yep.

But before we get to the mercenary, let’s close the loop on the missionary.  Missionaries dedicate their lives to higher callings, eschewing all trappings of this world.  They sacrifice of themselves and all of their time for the vision of putting a dent in the universe.

Mercenaries and Enough

Let’s now consider a spin on the vilified mercenary.  The entrepreneurial world Taylor’s article represents apparently thinks only in terms of the funded startup world.  In Elon Musk, you have a man of vision and a missionary.  He exists nobly to explore space and save the world from fossil fuels.  In Travis Kalanick, on the other hand, you have a mercenary.  He enables a culture of sexual harassment and squabbles with working class people over money.

But what if we abandoned the idea that all ideas worth having involved dents in the universe?  What if we consider a new flavor of mercenary, sometimes called a “lifestyle designer,” who simply wants enough?

For instance, consider Amy Hoy, who coined something called 30×500.  She describes the meaning of this set of dimensions as follows.

Uh… like, how much money do you need to happily live on?

…

Welll, if you skip the [venture capital], and figure out a way to get only 500 people across THE ENTIRE INTERNET to pay you $30 a month, that’s $180,000 a year. Pre-tax, sure, but that’s a pretty nice salary, no?

Amy argues (and understandably) that $180K per year should be enough.  No cold fusion rockets, self-driving trucks or electric cars.  Just “get 500 people to pay you $30 for something.”

In his book, the 4 Hour Work Week, Tim Ferris coins the term “lifestyle design.”  In essence, he says, figure out exactly what you want from life, and consider that enough.  You think you want unqualified riches, but maybe all you really want is a Mercedes, and 12 weeks off per year, instead of 2.  Your actual desires don’t require winning the lottery…. or the relatively roundabout path of founding a company that grows virally to billions in market cap.

Figure out what you want.  Call that enough.  And then figure out how to get it.

Opportunists in the World of Developer Hegemony

Alright, I’ve established that not all entrepreneurs need shoot the moon to have a good life.  But what does this have to do with John’s statement about trading hours for dollars?  And why do I need to unpack all of this before I release the book and before the curse of knowledge consumes me?

Well, put simply, developer hegemony calls for developers to become opportunists and then mercenaries.  Now, I don’t mean to discourage you from seeking funding for something big, nor from staying employed in the traditional sense.  Life offers us lots of paths from which to choose, and you should pick one that makes sense for you.  But I do mean to say that the path of empowered developer hegemony involves a march out of pyramid shaped corporations and into an autonomous life of enough.

That developer hegemony life of enough comes more easily when you shrug off the layers of management.  And it comes more easily when you figure out a better means of providing and accounting for value than dollars for hours.  (After all, do you really want to get valued and paid using the same paradigm as a guy, standing on a busy street, dressed like a giant donut, and holding a sign for some diner’s grand opening?)

I cover a lot of the mechanics and details in the book.  And, I’ll start covering even more of it in the months and years to follow.  But for now, understand a foundational truth that has taken me a long time to learn.  And, understand it before I forget how to bridge the gap.

When faced with the choice of “rat race, clawing my way up the corporate ladder until 70” and “risk it all on a long-shot to build the next Slack,” you have a third option.  And in the future, I’m going to talk a lot about how to exercise it.

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