"YOU'RE A WHORE!" and the perils of a freelancer's life

To cut right to the chase, I ended up at wework summer camp somewhere near the top of that bubble and ran into a guy I knew who ran a dev/design agency. His director of operations or chief of staff or whatever glue person nanny role was one of those young women who are on the surface very sweet, and also very reserved, so that you can never see what wheels are turning beneath that sweet surface - but you can see that they are, and furiously. She was half holding him back as the intensity of our conversation suddenly and inexplicably skyrocketed as we stood on the beach of a lake in upstate new york with college mashup DJs blaring in the background and everybody drinking the canned wine sponsoring the party, because I had mentioned freelancing.

“If you have clients,” he insisted, “you’re a whore.”

“Ok,” I said. Despite having gone to school in Boston I didn’t yet have the radar to clock when somebody was very drunk. “Maybe.”

“No, you’re a whore!” he shouted. “They tell you want they want, you do it, you’re a whore!”

“Do you mean me personally, or like, all of us?” I ask. To his majordomo: “Does he mean me?” I haven’t been in a fight in ages. Adam Neumann would probably be stoked.

“He doesn’t mean you,” she assures. “He’s just kidding.”

But he isn’t kidding. About five years later I wrap up with a fairly long client engagement and it strikes me that he was completely correct, and he was probably just a few years ahead of me in realizing it, and it was eating him, and he needed me to agree so that we could - I don’t know, commiserate and share the desolate camaraderie of two people who have sold out their sacred gift for money. Sorry, man. You could have been a little more articulate.

What you pay for versus what you want

It’s no secret to anyone who’s looked at marketing for thirty seconds that you don’t sell the product. You sell the vision of the buyer with the product. The Corvette is not a way to drive fast, the Corvette is a way to become the kind of guy who can score a second wife with implants. But it would ruin the experience to actively go out and buy yourself a pussy wagon, you’re an independent forty-five year old residential heating oil executive. Your financial planner says you’re on track to be a millionaire before you retire. The emotional part of you recoils from reaching directly for the thing you really want, so you need to find a proxy. You need to seduce yourself into pursuing your own desires.

We don’t belabor the point, but it’s an important one. Very few goods or services are bought for the value of the good or service. Those are called commodities, and you get them by the barrel or bushel or kilowatt-hour. Everything else is bought for its commodity value plus its signalling value to other people plus - maybe, I am here to argue - some true value the laundering of which is the true purpose of the whole transaction.

Startup founders often seem to have this multi-motivated purchasing problem. Especially once they’ve been funded, they’re so tied up reporting to investors on the one hand and managing staff on the other that it’s so exhilarating for them to work with somebody who’s been in these trenches dozens of times, who they don’t owe anything, who owes them nothing other than the work above the dotted line. They didn’t set out to find a work buddy and venting partner, they set out to resolve a persistent flaw in their pipelines that none of their staff seem to be able to put away for good. But en route to the solution to the material problem they find, maybe, a solution to the spiritual problem: they’re lonely.

Whores

The most interesting tales prostitutes tell have to do with the real services they provide their clients. Not the kiss and tell, in a depressing industry I find an unexpected heartwarming thing: a lot of the time, guys buying sex are only using the buying of the sex as a proxy to get someone to care about them. But you can’t buy somebody to care about you¹, so you buy a couple hours of a woman’s body, and use it as an opportunity to ask for her heart. It’s a constant refrain in working girls’ assessment of their job. A prematurely jaded twenty-six year old posts on her blog, “a lot of guys, they just want somebody to listen.” You’d picture her knocking back a gin as punctuation, straight, if she didn’t reside in a culture that prefers research chemicals to gauche old toxic alcohol.

I have now performed exactly fifty client engagements as a freelancer. Sometimes I find myself thinking about that guy up in the finger lakes, and what the real value is that I’m providing to my clients, especially over the last year as more and more of my job becomes wrangling agents and not actually creating something from nothing through the carpal of my tunnels. Because when I’m in a one-on-one with a founder harried by back-to-backs and the sixteen-months-to-live timeline of the venture-backed lifestyle, what’s top of mind for them is rarely the thing they hired me to build. They know I’ve got that on lock - “great, wow, tell me what I owe you” - and more often than they’re eager to “run something by me”. A problem with an employee, an uncertainty about an investor or a new opportunity for the business. And, first and foremost, a pitch with a plaintive request embedded in it: believe in me. This isn’t your first rodeo. Do you believe in this?

And it dawns on my that I’m maybe one of the only people they can trust. I’m a free agent. I don’t rely on them for a paycheck; I’ve got my own clients. They don’t rely on my for investment; they can be honest. I’ve seen the dirty little secrets in their git history, the old passwords in reflog and handwritten apologies in code comments, the spit and the duct tape that makes the gleaming machine they present to the outside world work. They’ve trusted me with root to their baby, a far more intimate commitment than the way most people would experience a mere hookup.

They want to know how their problems rate against other companies I’ve been with (breathless, proud, nervous: “so how do I stack up?”) and how those companies and especially their founders solved similar problems. I’ve been at clients’ birthday parties, apartments, ski lodges, brunches, and post-divorce nights out. They want to hire me, to give me equity, to bring me on board, and the calculating cynicism with which I face their offers has given me empathy with the plight of the beautiful woman. Because I don’t want to be put in a position to have to calculate your potential value as a unicorn, man, I want to do a job and get paid. My work is good but it’s not as if I’m pushing the frontiers of computing. Let’s be honest, here.

At the end of the day, what’s the difference between me and the girl renting her body? I value the product of my mind and the yield of my time far higher than my material substance. I blur these lines just as much and probably far more than a working girl. They are technically hiring both of us for the product of our work but really for the human connection we provide to a lonely person. We each know this. She makes peace with it, somehow, but I can’t. I find myself, finally, understanding why that agency guy was looking for a mirror to grab, and shake, and shout: “YOU’RE A WHORE!”

Only if you behave like it

This is overwrought nonsense, of course. It’s not Corvette’s fault their customers are who they are. And anyway the client-services provider, be they therapist or prostitute or freelancer, has two options: extend across the contract to meet their clients’ real needs, or stay on their side of the line and deliver only what was promised. Once I realized what was happening, I’ve stuck scrupulously to my guns. For one thing, it’s good business. A naive freelancer might think they need to tell their client they’re the greatest business since since John Company, but an experienced one knows that founders are masochists, and love nothing more than to be told that they’re full of shit, and that they’re better than the derivative trend-chasing their investors have forced onto their roadmap.

We love stories about marginalized people, because the margins are where the action happens. The ronin, the prostitute, the pirate, the cowboy, the freelancer. What makes you seek freedom above stability? Does corporate work really rob you of the ultimate freedom over your own time and opinions? If so, what do you do when your pirate ship necessarily docks back in port and needs to interface with the real world from which prosperity and contracts and consumer goods come? Do they don the kayfabe of the enchained, pretending and being pretended to, or hoist the colors and remain their own master?

That’s how I’d answer my fellow up in the finger lakes. You may be, man, and I’m sorry. But what you’ve bought with your risktaking is the right to meet the world with integrity, and it’d be a terrible loss if you didn’t use it.