Quit Your Media Job Today: A Freelancing Endorsement

Luke O'Neil, at work in his office
Luke O'Neil, at work in his office

On Friday afternoon I got a frustrated message from a fellow music writer. AOL Music, she said, was closing down. Soon thereafter employees of the media property, including Spinner editor Dan Reilly confirmed the news. "Well, we all just got laid off," he Tweeted. "AOL Music is finished."

My first reaction, which is, sadly, a common one for all of us in the media of late, was "Oh, great, another one bites the dust." That was followed by a note of sympathy for my friends and colleagues employed by the various AOL music sites. We could spend a lot of time pouring one out for our lost publications lately, that is if any of us had money to pay for the beer in the first place. A similar scenario played out a couple months ago when the Boston Phoenix, the venerable alt-weekly that I had written for for years, shuttered. In a big picture sense, the city itself was rendered poorer the instant it closed down. In another sense, all of my friends there were rendered literally poorer.

See also: Advice For Aspiring Music Writers: Quit Now

Around the time of the Phoenix's closing I was party to some of the outcropping of sympathy, with colleagues in the industry checking up on me to see if I'd be alright, money-wise. Sure, it was a little blow, I would say, but it's the full time staff I was really worried about. I'd emerge relatively unscathed ultimately, and many of my fine colleagues have already landed on their feet elsewhere, but that wasn't a fluke on my end, it was a vocational fail-safe mechanism cultivated by design for just this increasingly likely outcome. A freelancer by its very nature is a hydra-like beast, or a system of disconnected terrorist cells -- cut off one head and the other lives on; in fact another one grows back quickly in its place. I couldn't imagine working any other way.

The life of the freelancer is often regarded with skepticism by more traditional job-oriented media professionals. "Isn't it scary out there, drifting unanchored to anything stable?," my desk job-having friends have always asked over the years. As a matter of fact, it's the exact opposite. In the current media jobs climate, it seems a lot less responsible to me to put all your word eggs in one publication basket, especially since all of the baskets are going out of business.

But stereotypes about the life of the freelancer persist. A recent Fast Company piece outlined the ideas behind Why Freelancers Are So Depressed. Among them include feelings of confusion over who you're actually working for. For a certain independent-minded worker, that's exactly the appeal. Frustrated with the demands you're getting from one editor? Don't take their assignment that week. How many people at traditional jobs know the pure joy of saying "No" to work? You know the old saying about football: if you have more than one quarterback you don't really have any? It's the same for bosses when you're a freelancer.

The Fast Company piece goes on to outline other typical fears about the freelance life: the work/home blur and social isolation among them. While I'll admit there's a certain something lost by not, you know, actually seeing any human faces for eight hour stretches a day while you're at home, there's also this: not having to see any human faces for eight hour stretches a day while you're at home. I'd list off a few of the common grievances that most people face in the office environment, but I don't even know what they are anymore. Do people still complain about the fax machine not working all day and not clean out the refrigerator?

It's been about 10 years since I last had an office job; it was an editing gig, where I lasted for about 3 days, and ended when a group of new co-workers came over to explain excitedly that there was pizza in the break room. I just can't sit here in a place every day and watch people get excited about pizza in the break room, I thought, and promptly walked out. You know why people get so excited about pizza at the office? Because they're such miserable, soul-crushing places that literally any bright spot dulls the oppressive weight. When you work from home the entire world is your break room.

Admittedly there are problems chasing down payment from time to time, but if you properly diversify your working portfolio, you can spread out the risk. That's one of the most basic tenets of investment strategy, so why wouldn't it make sense to do the same with your actual source of income? At least I think it is, I'm a freelancer so I've never had a 401k.

See also: Advice For Aspiring Music Writers: Don't Quit, Just Don't Suck


The idea of working in one dedicated media job, shlepping to the same desk every day, over and over again, for years, is on the way out anyhow. It's something I've been trying to explain to my traditional workplace colleagues. By the end of the decade, more than 40% of the entire workforce will be made up of freelancers and the self-employed one study suggests. As Quartz writes on this very topic, the Scarlet Letter of the freelance life is being scraped away. "Traditionally, being self-employed used to come with a social stigma; you were self-employed if you couldn't get a 'real job.'" What does having a "real job" even mean anymore?

If that doesn't convince you to unburden yourself from the outdated job model, consider freelancing this way: it's the closest approximation to a life of promiscuous dating that most of us get after we're married. Each assignment at a new publication brings with it the same sense of gratification and excitement that a new sex partner does, each pitch brings with it the thrill of the chase, and convincing a new editor to take a chance on you is an act of seduction. Maybe all of that seems a lot sexier because I'm sitting at home writing this with no pants on.

Now, we could certainly debate whether or not publications treating people like me as permalancers as a means of getting around paying for benefits is a good thing, and whether or not this is a healthy model for the American worker on the whole, but it's definitely a beneficial idea for anyone who likes the idea of cutting their commute down to zero miles and eliminating all of the stresses of the normal office environment. You should be looking out for number one anyway, because no one else, certainly not your employer, will be -- particularly all of the media outlets closing down out of nowhere and instituting massive layoffs over the past few years.

I'm not saying it's an easy choice to make, and it does stake a certain steeliness to commit to going it alone. It took me a lot of years, and a lot of side gigs along the way before I could get to this point of freelancing zen. It also helps if you're actually worth a damn, and preferably not just starting out. As I've written before, I'd still advise young would-be arts writers to find something a lot more stable to waste your life on, but if you're mid- to late-career it's a no-brainer.

I realize this all sounds like the type of spam you'd see on the comment section of a website that you're probably reading right now at your desk job, but it's true. You can do it too: Make Money From Home! Quit Your Job Today! Just don't, you know, take any assignments at any of the places I write for. I need all the work I can get.

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