The ups and downs of being a freelancer

My life is ridiculous. In a good way, mostly. And it has been that way for the last year and a half. To illustrate, here are some of the activities I engaged in over the span of a recent week:

• Took a tour of a decaying castle on an island in the Hudson River.
• Dressed as a taco and sang murdered David Bowie’s Space Oddity at Joe’s Pub, while being pelted with 144 sticks of chalk. This silliness was all in pursuit of a URDB world record.
• Did an interview on the flight deck of the USS Intrepid, then had a few chats with serving members of the US Navy.

• Attended a six-hour burlesque workshop, during which I learned seductive glove removal techniques and discovered that my personal goddess is the Hindu Sarasvati, patron of intelligence, cosmic knowledge, creativity and the arts.

All of this was “work”. This is the life of a freelancer. And it is all very charming and whimsical — until you visit a medical practitioner and get told that your ultrasound will cost $5,600 because you have no health insurance.

Hello, sailors! Pic by Leah D’Emilio.

Becoming a freelancer is one of the biggest shake-ups I’ve ever experienced. It’s fun yet stressful, lazy but tiring, and the wild variation in income from month to month is a rollercoaster of budgeting angst. But all up, I love it. And I don’t think I could ever work nine-to-five in an office again.

If you’ve considered ditching your job and seeing what the freelance thing is all about, here are a few things to roll around in your head. Let’s start with the positives.

• No set routine, aka, who cares if you wake up at 11am and eat cake for breakfast? For many people, being able to set your own hours is the main appeal of freelancing. I can’t deny that it feels rather delicious to spend most mornings sleeping in. But lack of routine can also be a downer. I actually like being told what to do. I like having a place to go to and a time limit in which to get things accomplished. When you are the master of your own destiny, work hours tend to bleed into leisure hours.
• Creative and intellectual fulfillment. Every one of my jobs — I have five at the moment, ranging from copyediting to video presenting to writing about burlesque — is something I believe in and enjoy doing. This has a major effect on my enthusiasm for life.
• Being able to work wherever you like. I’ve worked on projects while sitting under a tree in Central Park; in the reading room of the New York Public Library; in other countries; and, frequently, from a supine state in my own bed.
• Crowd avoidance. This is a small thing, but it’s a pretty swell feeling to be able to go clothes shopping at 2pm on a weekday or get a seat on an 11am train that would have been packed at 8:45. Avoiding the rush-hour crowds makes you feel like the rat race does not apply to you. (‘Cause it doesn’t! Yeah!)



Another day at the office. Pic by Bob Geile.

Now, some downers:

• Idleness. Compared to full-timers, I don’t work that many hours per week. But here’s the rub: when I’m lolling about in a semi-conscious stupor of a morning, or idly cruising the same batch of 10 websites over and over, part of my brain is freaking out about how lazy I am. “Do something!” it screams. “You’re falling behind! It’s embarrassing! DO THINGS!”
  
  This is, ironically, the stress of idleness. It’s especially pronounced in New York, where everyone is a Type A young gun overachiever who is constantly trying to prove how busy and important they are. Comparing yourself to such people flings you into a spiral of self-criticism, where you become so preoccupied with chastising yourself for your laziness that you don’t have time to do the work you are punishing yourself for avoiding. (Like most human behaviour, this makes no sense.)
• Social isolation. Sometimes I really miss working at CBSi, because every day there was such an interesting, funny bunch of people within a ten-metre radius of my desk. When you freelance, you need to make a concerted effort to connect with people in your industry, or you can feel out of touch and socially maladjusted. If you’re prone to introspection, the long periods of solitude can make you a bit loopy.
• The need to sell yourself. For some people this is easy, but I struggle with it, big time. I’m from the land of self-deprecation. The idea of emailing a stranger and telling them they should hire me because I’m fabulous is anathema to my culturally mandated modesty. But you have to do stuff like that when you are self-employed. A hefty dose of self-belief is crucial, but if you are doing something you are really passionate about, it’s easier to frame it in the terms of your work, rather than your personality or ego. Think about a problem someone has that you can solve. That approach is always more effective than “check me out, I think we both know you want me in your life”.
• No employee benefits. I have no health insurance. If I get hit by a rogue moped, need a root canal or come down with appendicitis, I am totally screwed: the resulting medical bills would total way more than five years worth of tertiary student debt. And it’s not just the emergency-type stuff that’s pricey. Things like new glasses or the Pill or even basic check-ups are similarly exorbitant. In many cases it would be cheaper — and faster — to fly home to Australia, go to a doctor and fly back. So, that sucks. If you’re in a country where the cost of healthcare is not tied to your employment status (wow, what a concept!), you may have it easier. But here in the USA, being a freelancer means either paying a heap of cash for personal insurance or taking a gamble and staying uninsured.
• The financial rollercoaster. A batch of cheques will come in, you’ll think you’re rich and will go spend all the money on cocktails and monocles. Then a few weeks later you’ll go to pay your rent and realise there’s nothing in your bank account. Whoops.
• Taxes. Nightmare.

So, should you become a freelancer? If you can handle all of the above, sure. It’s a lifestyle that comes with creative freedom, a lot of sleeping in and the satisfaction of charting your own course.

Got questions to ask or experiences to share about being self-employed? Get commenting, tiger!

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