You Never Give Me Your Money…

I’m now well on my way to my three-month anniversary as a freelancer. It’s been a gas overall. However, I would say that compared to full-time work, the highs are higher and the lows are lower. There are the times when you’re sitting on your porch in the middle of the day counting the checks that come in the mail and others when you spend too much time corresponding with Accounts Payable and wonder if your biggest account is going to drop you and you’ll soon be applying to Uber.

I’m writing this after agreeing to a kill fee with Unnamed Publication. I worked damn hard on it, but life is just too short to work with an editor who doesn’t give direction and is basically batshit crazy. I also met with a marketer at an ad tech firm that promised me some blogging and ghostwriting opportunities. I also finally got a delinquent account to agree to write a check after I threatened legal action.

A typical day, in other words.

I knew going in that I’d spend a lot of time chasing down paychecks. It’s depressing that despite cloud computing, Gmail and a host of other modern conveniences that it still comes down to a power struggle: As a contractor, you don’t have much while the people who hire you do. You have to bank on their decency, which is often a foolish bet.

In the beginning, pacing was a problem too. I recall one morning waking up and realizing that I had basically nothing to do. Naturally, I went to Target and bought a printer. Within a few hours, some new assignment had come in and quickly extinguished my sense of existential angst, at least for a few hours. I’ve also suffered from the opposite problem: Gulping down meals in front of my laptop as I raced from one assignment to the next. That swallowed-a-golfball sensation of agreeing to work that I really don’t have time for. The mind racing at 2 AM about a mammoth feature that I hadn’t yet gotten a handle on.

That’s the dark side of this venture. The more heartwarming part is that I get to write about some interesting stuff and have the satisfaction of banging out an assignment worth a few hundred dollars in a few hours on my couch.

There’s also the knowledge that I have a marketable skill and don’t need to kiss anyone’s ass to make a living. And no boring meetings in which a room full of 10 people silently look at their laptops while one person jabbers on about meaningless rubbish.

The biggest benefit though is that as I look back on the past quarter, it’s not all a blur of the same workday stretched across three months, but a collection of weird moments. There was the Wednesday afternoon I pulled my daughter’s tooth out with a washcloth, a bizarre lunch in the Village with an ad tech exec in which I unwisely ordered a Moscow Mule and the morning in Vermont when I conducted a Skype interview with a guy in Germany as birds sang in the background.

All through it there was the threat of failure and the specter of career suicide mixed with the everyday triumphs of finishing an assignment or watching a payment materialize in my checking account.

In general, there’s more heroism, more conflict, more drama and more overall life than there was in the full-time route, at least, so far. It looks likely I’ll stick it out another three months at least. That means a mortgage will be out of my reach and this will be less a lark than a career move. I’m sold on it for now, though. After all, there’s always Uber.

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