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4 Terrible Things I Learned about Freelancing in 2013

In a lot of ways, 2013 will go down as a kind of annus horribilis for me, both personally and professionally. The end of this year has found me laid off (twice), broke in a new city, worried that I might lose the car I worked so hard to pay off, accumulating debt again, taking on a sketchy roommate, and generally feeling like I’m trapped back in my post-college years again.

Basically, I found that many of the things I thought were secure and a sure thing in my life were built on some frightening mix of quicksand and fire ants. Super intelligent fire ants that will crawl into your brain and convince you that you’re talentless, unloveable human garbage before pulling you down to the depths.

One of those big changes was losing the stability of a full-time job and embracing freelance work. Moving from the comfort of a 9-5 work environment into the instability and tumult of freelancing has been a particular challenge. Anyone who’s made that transition knows that it’s moving from the safety and security of knowing where your next paycheck is coming from to having to be like ODB when it comes to your cash.

And as I attempt to crawl free of this year and into 2014, I thought I’d reflect back on some of the lessons I’ve learned as a freelancer. By the way, this isn’t going to serve as some how-to-get employed guide, because if I knew that, I wouldn’t be sitting here writing this piece.

"I Know Nothing" by JoeConde

4. Don’t be Afraid to Chase Down Your Would-be Employer (or Boss)

So, you’re out in the freelancing wilderness, and you’re hitting up the job boards, Craigslist – anything – to find your next gig. As a creative, they’re going to be few and far between with plenty of other candidates swarming to them, but hey, even with declines in the rate of part-time unemployment, the U.S. is still in an under-employed economy.

What that means is that you can’t just rely on your well-written cover letter, expertly-produced resume, and slick portfolio to get the the interview (let alone the job): you’re going to have to follow up with the employer. And even if you somehow get the interview, don’t be afraid to follow up to find out what your would-be boss’ timeline is for filling the role you want.

I’ve gotten good at sending out resumes and crafted-to-perfection cover letters. The thing is, I’ve sent out a ton of them only to get radio silence from my potential freelancing overlords, and there’s a soul-crushing rhythm to it that I’ve had to get used to: send out my resume, expect radio silence for a month, possibly an interview that’s rescheduled, then rescheduled again, cancelled, set up again, and finally conducted and forgotten about.

Or worse, you do get the job and your boss is the type that doesn’t respond to an e-mail or phone call about some critical work decision. Or a second. Or a third. It’s a frustrating shift from my full-time days in a studio where I could walk over and talk to a colleague or supervisor and resolve things pretty quickly, but in my new and nebulous life, I find myself having to play bounty hunter in order to get approval for time-sensitive projects or a simple piece of information about a complex problem.

And there’s a reason for that…

"Submerged" by 2DForever

3. No One Loves You and You’re Doomed (Don’t Take it Personally)

Or, out of sight, out of mind. Despite some changes in leadership, I thought I had, what seemed like a pretty good relationship with one of the companies I’d been freelancing for off and on over the last couple of years. I’d been creating a steady stream of content for them, was friendly with my supervisor, and I’d – to my mind, at least – established myself as loyal and able to come through in a pinch.

And I understood that circumstances would change when that gig got dramatically reorganized and less work would be coming in (although the dramatic pay cut was somewhat unexpected). What I didn’t expect was how incredibly mercenary and stifling things would become: I’d gone from having creative freedom to having to work within much narrower parameters for an audience I wasn’t necessarily comfortable with.

That was one of the big shocks: learning that as good as I (thought I) was before, it was always possible to be thrown back to square one, that in spite of all of my previous hard work, I would have to reestablish myself with not only the audience, but with the people who’d been signing my checks over the years.

Maybe it should have felt liberating, but it actually caused a kind of psychic whiplash because…

"Freudian Slip 2." by Andrew Nawroski

2. You Don’t Get to Be Yourself Anymore

I’m a narrative game designer, comic writer, editor, blogger, journalist, reviewer, cat sitter, and short order cook. Okay, I’m not a short order cook, but 2013 has been the year where I’ve had to convincingly wear a lot of hats to even just have a conversation about a job. When I was working full-time, being flexible was the virtue that my bosses sought. Now, it’s being several different people with multiple competencies – it’s learning to be chimeric while still making a convincing case that you’re an expert at the job title.

What’s been most anxiety-inducing and off-putting isn’t that I’m expected to know how to do all of the things listed in the job description, it’s all of the small ways that I’m not the person they’re looking for because my experience has been so varied over the years.

Seriously, I’m at the frightening point in my professional development where I’ve been doing things long enough to establish a reputation, but not quite long enough to fit the job description. I’ve spent nearly a decade in the game industry in numerous creative and editorial roles and it’s been the same with my online writing. I’ve become what I’ve always feared: a jack of all trades, and a master of none. I’m not an expert, I’m not the number one guy at anything, just someone who’s really, really good at a lot of things (and that old standby, “ready to learn”).

So I find myself having to massage my resume into something that fits, only to ultimately have an interview where it’s clear that what the potential employer is looking for isn’t what was listed in the job description. It’s learning, suddenly, that you’re not good enough and that you’re competing with a dwindling number of candidates who are.

Of course, this isn’t a problem relegated to the freelance world, but the next one is…

"For sale" by henribanks

1. It’s Not Yours Until You’ve Been Paid for It

My earlier note about keeping in contact with your bosses becomes a little trickier when you’re dealing with a pitch environment. You’ve come up with a bunch of great ideas, some kind of fantastic proposal, only to find it used without your permission, or somehow absorbed into something that your employer was – they claim – planning to do already.

Look, I’m going say flat out that I don’t believe anyone I’ve worked with has been out to screw me or take money away from me. While I don’t subscribe to the egalitarian notion that ideas are ephemeral and belong to everyone, I know that there’s a narrow pool of them and two people can independently arrive at the same pitch for the same narrow concept.

But I have been in situations that felt a little hinky, and that’s made me more cognizant than ever that I need to keep a paper trail for everything. Every pitch, every proposal, every idea, every invoice – all of it. It’s not paranoid, it’s just the price of doing business when at any given point in time management or payroll might change or your employer might simply lose track of some work that you’ve done for them.

And that’s, of course, the grownup way to be, but trapped – at least for the moment – in the freelance economy, it’s hard to not feel a little paranoid. Anytime a check is late or your boss goes MIA for a couple of days, leaving you to wonder what’s happened with your work. Was it not good enough? Are they even using it? Do I even have a job?

It’s bracing: you don’t want to be paranoid and over-protective of your work, at the same time, you want to guarantee that you’re being compensated for your hard work. Again, it’s a lonely existence – you don’t know who to trust, and because you’re not part of team, there’s no one to depend on but yourself.

Maybe in the near future I’ll have some sage advice or tips on how to weather freelancing, but for the moment, all I can leave you with is this: don’t expect it to get any better, but don’t be afraid, either. The surest way to fail is to quit or not even try.

"i'm not done" by pinkglove

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