The gig economy is obviously an economy of mercenaries. The connotation is explicit in the term freelancer, which literally meant a mercenary knight in the European Middle Ages: a “free lance” with no fixed allegiances. The label mercenary is nearly always applied pejoratively (by missionaries of course), in terms of shallow motives like maximizing money. Can we reclaim the term in a positive way, and construct a better understanding of it?
A good place to start trying is with the story of John Hawkwood, a major but obscure figure in the history of 14th century Europe, perhaps the most famous freelancer — of the literal knightly variety — that you’ve never heard of. In a very literal sense, he was the OG indie consultant (the “gangster” part being quite literal).
I’d never heard of him until last month (I learned about him in Barbara Tuchman’s A Distant Mirror, a book about the Black Death and the 14th century), yet he was at least as important in shaping the fate of Europe through the tumultuous decades after the Black Death than many far more famous people I had heard of. Including kings like Edward III of England, Charles V of France, and the popes of the period — Clement VI, Innocent VI, Urban V, and Gregory XI.
His was also arguably a more consequential role than famous mass populist movements like the Jacquerie commoners’ rebellion against the nobility in France.
There is an obvious reason for his obscurity. Hawkwood was a mercenary. A very powerful and important mercenary who often led armies of thousands, but a mercenary nevertheless. And while history is often written by both winners and losers, it is rarely written by the mercenaries who shepherd its less glorious chapters towards resolution.
This is of course a point directly relevant to us. The history of late industrial modernity may be written by/for/about the “kings and popes” of our time — CEOs and Presidents/Prime Ministers — or by/for/about the “commoners” (in the form of say the history of the labor or social justice movements), but it will not be written by/for/about consultants or freelancers. But as in the 1350s-90s, a post-pandemic period that very much resembles today, ours may in fact be the most significant role for a while, even if not recognized as such by the history writers.
Because freelancers today, as in the 14th century, are necessarily, definitionally, mercenaries. In the stories of history as written by winners or losers, it is the fate of mercenaries to be cast in a role that is worse than the good or bad guys in any account: shadowy figures who refuse to pick permanent sides, and subvert, through their very presence in the story, any claims to absolute rightness made by missionaries on all sides.
Then as now, mercenaries were simply outside of the false consciousnesses of the many mutually inconsistent missions they participated in.
The White Company
Admirable as they are in their own ways, missionary leaders like Steve Jobs cannot be role models for indies. We must look in the shadows of history to find the interesting figures we can learn from. John Hawkwood is one such.
Hawkwood’s story is a story of relentless pursuit of greater personal agency through decades where grand missionary campaigns were unraveling in the chaos that was the post-Black-Death world. Details of his life are sketchy, but as best as we can tell, he grew up a commoner, and fought as a longbow archer in early battles in the Hundred Years War leading up the Black Death. He got knighted somewhere along the way, and in the chaos after the Black Death, rose to the leadership of one of the most important free companies of mercenary free lances of his time, known as the White Company (Arthur Conan Doyle apparently wrote a historical novel about them — it’s on my list to read now).
In one sense, especially later in his life, Hawkwood was a corporate CEO — roughly the Erik Prince of his time (but unlike Erik Prince, not born to wealth and privilege). The White Company was superficially rather like the Blackwater of its time: in the thick of the action no matter who was winning or losing.
But in another sense Hawkwood was a true freelancer in the sense we gig economy people use the term. Despite the name, the free companies of mercenaries in the 14th century were nothing like modern private security corporations or even contract-staffing agencies. They were loose networks of at-will, exit-over-voice affiliation closer to open-source projects, or like large networks of individually negotiated subcontracts. This, incidentally, is exactly the kind of structure we’re trying to create with the Yak Collective (which just released its second report, The Old New Home, go check it out).
The “indie” unit of the 14th century military market was the self-provisioned and metonymously named lance (used similarly to “suit” today): an organizational unit consisting of one man-at-arms, one squire, and one page (non-combatant).
Aside: I’m going to start calling my subcontractors on gigs squires and pages going forward.
Lances were free agents themselves, either working by themselves, or signing up for larger campaigns under the leadership of people like John Hawkwood, and bringing on their own subcontractors. But they were not bound to their temporary masters by any grand moral notion of fealty, or to a broader culture of gallantry as the knights of the established nobility were. They were unapologetically just lances for hire, willing to fight for the highest bidder. Which is another way of saying they were skeptical of the grander self-serving justifications driving the missions they fought for.
In his post-Black-Death career as a freelancer and leader of freelancers, Hawkwood featured in almost all the important battles of the late 14th century, often changing sides within a single battle, based on who could pay (or failed to pay).
To a very significant degree, the free companies, rather than the traditional nobility with their vassal troops, shaped the history of conflict in the back half of the 14th century. In fact, a top political objective of kings and popes in starting conflicts between 1350-1400 or so was to try and make the (once useful, but now inconvenient) free lances go somewhere else. Because if they remained unemployed, they simply turned to brigandage wherever they happened to be, preying on nobles and commoners alike (you can see a similar behavior today among a certain class of indies in which I count myself — between gigs they tend to write stuff calling bullshit on the cynically manipulative empty pieties being spouted by missionaries in the paycheck world; a sort of intellectual brigandage).
Make no mistake — OG freelancers like Hawkwood were not nice people. They were at least slightly evil. The general historical view of them is as roving gangs of brigands just living off protection rackets in Europe, in the wake of the devastation of the early part of the 100 years war and Black Death. This view is correct.
What is often forgotten though, is that the missionaries they worked for were no better and often far worse. They just had better PR, based on expensively manufactured justifications for engaging in exactly the same behaviors labeled “brigandage” when practiced by the free companies. Often their behaviors were far worse.
Free Companies and free lances also didn’t come out of nowhere. Many members of the free companies were in fact former nobility and even clergy, who had lost everything in either the “normal” missionary battles of the previous decades, or to the devastation of the Black Death. The OG freelancers were also the OG laid-off collateral damage of “missionary” warmongering, as well as those hardest hit by the impact of the Black Death.
Missionary Endgames
As I noted before, the only real difference between people like Hawkwood, and the missionaries they served, was that they didn’t bother to manufacture elaborate and flimsy justifications for their actions.
Manufacturing justifications for “just” wars was a huge preoccupation with the missionary nobility of the time. Justifications were often based on claims to titles, and relied on marriage or ancestry links, and complex rules of inheritance. The role of the church was to make up these rules to its own benefit. The definition of “just cause” usually favored the highest bidder.
Today, “just causes” are often rooted in claims to charismatic leadership, with the literary-industrial complex of the business world playing the role of the church, manufacturing, via TED talks and cover profiles in magazines, fawning justifications for behaviors later revealed to be significantly less noble than claimed.
These justifications that drove 14th century warfare were very much the kool-aid of the time. They operated in much the same way corporate kool-aid does today.
And as with any larger theater of activity — be it 14th century warmaking or 20th century business building — competing kinds of kool-aid didn’t mix well. Which meant that the endgames got really ugly.
Then as now, mercenaries were the products of missionary endgames. The periods when the kool-aid wears off, and the hypocrisies small and large of the various missionary justifications are revealed for what they are, but the battle still needs to be fought through to a natural conclusion.
The end of this period is particularly poignant. Following a struggle over the papacy between two factions after the death of Gregory XI, the Catholic Church went through a period known as the Western Schism, when two candidate “antipopes” — Urban VI and Clement VII, excommunicated each other, leaving the church in an indeterminate state for decades (they should really be called heisenpopes).
Both were awful, violent warmongers, and though both laid claim to the religious mission of the Catholic church, the schism was entirely about political and economic power. Unlike in the reformation a couple of centuries later, there were no significant doctrinal differences, because doctrine wasn’t the central concern. Both sides were simply out for power.
And unsurprisingly, the free companies and people like Hawkwood played a big role in this particular endgame.
I find this both grimly hilarious and highly validating. Missionary endgames reveal the true nature of missionary postures. The idealism that seems so solid, virtuous and noble at the beginning of a mission is often revealed to be thin fictions overlaid on motives far worse than those of unapologetic mercenaries. The endgame violence missionaries unleash in service of their ideologies dwarfs the more pedestrian brigandage mercenary postures can devolve into.
Yet everybody must live through both beginnings and endings.
Missionary beginnings showcase the aspirational best side of humans, but missionary endgames usually reveal the worst they are capable of. When missionaries grapple with each other in an existential struggle for dominance, they can lay waste to everything else.
Mercenaries are not heroes. But they don’t claim to be either.
Mercenaries are not virtuous, noble people. But they don’t claim any particular virtue or nobility either.
But often in history, they end up acting more heroically than people claiming to be heroes, and exhibiting more virtue and nobility in practice than missionaries.
And not because they are better people, but because they have no choice but to do what they must to continue the game to natural and logical conclusions, long after the missionaries have smugly declared victory, or admitted defeat, and gone home. Because unlike the missionaries, mercenaries typically have to live with the consequences of their actions. They have no safe havens to retreat to once missions unravel, but the fighting continues.
So what then is the essence of the true nature of mercenary postures? What makes them not like the caricatures perpetuated by missionaries? Can we define the idea of a mercenary in terms of a consistent definition with an internal logic?
Trick question. Those games of abstract definitions are for missionaries pursing fragile ideals with varying degrees of hypocrisy and cluelessness. If a posture can be defined in terms of a set of abstractions at all, it’s a missionary posture. To be a mercenary is to defy such clean characterizations.
To be a mercenary is to pay attention not to the abstractions, but to the actual story. To be a mercenary is to not just pay attention the scenes historians put into the spotlight, but to what’s happening in the shadows, both in space and time. To be a mercenary is to believe in life rather than abstract conceptions of it in terms of clean-edged missions with clear beginnings and endings. To be a mercenary is to trust revealed preferences, and actual behaviors, over claims to virtue and grand intentions.
The mercenary is not necessarily anti-idealist. Just someone who plays by “trust, but verify.” The mercenary is not merely about the money, but someone who understands that money is a proxy for the reality principles actually driving conflict, whether in business or war; a surer indicator of patterns of ground truth than missionary claims and kool-aid dreams.
To be a mercenary is to be the yang to the yin of missionaries in the infinite game of life. If this means never being either hero or villain in any story, so be it.
I’m going to continue to develop this line of thought, and look for more interesting historical examples of freelancers and freelancer modes of being and working. If you know of any, send me pointers.