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6 Things I Wish I'd Known When I Started Freelancing

by Matt Hershberger Apr 3, 2017

1. You have to exercise. This is not an option.

When you work from home, it’s easy to slip into the habit of staying inside all day. This is really, really bad for you. And not just for your physical health — for your mental health. In the first couple years of my freelancing life, I slipped into a depression in large part because I was isolated and wasn’t working out. Not everyone’s depression is the same. But mine virtually evaporates when I start exercising regularly. If I want to be productive, I no longer consider it an option.

2. Go ahead and spring for the accountant.

Between estimated taxes, the self-employed tax, and keeping track of all of those tiny checks, you’re going to lose track. I have now messed up my tax return two years running while using TurboTax. This is not TurboTax’s fault — it’s a cool program. But it’s not totally idiot-proof, especially when you’re self-employed. Next year, I’m spending the money on an accountant. Every other freelancer I’ve talked to says it’s the only way to go.

3. Get on the phone with your colleagues, even if they live on the other side of the world.

Decentralized workplaces are pretty cool. They afford a lot of flexibility, and it’s nice to be able to live pretty much wherever. But you need to talk to your coworkers, and not just about work stuff. Think of setting up “water cooler” chats with your coworkers and writer friends so you can hear about their lives and learn a bit about who they are. This is for mental health as much as it is for networking.

4. Connections matter almost as much as your writing does.

There are a lot of good writers out there, and in the end, the one who gets the job is the one whom the editor can rely on. If you’ve produced great work for an editor, they’re going to want more, and if you’re going head-to-head with an equally good writer they’ve never heard of, you’re going to win based on the connection.

When you can, meet people in person. You don’t realize how little you know about a person whom you’ve only interacted with over email until you’ve met them. People who can put a face and personality to your name are going to be more likely to give you jobs.

5. Take time to work on high-quality stuff.

I’ll let Glenn Greenwald say it:

…Be a little bit willing to sacrifice some short-term work for longer-term benefit. I know this is really hard to do if you’re trying to pay rent, but instead of taking every single job you can and just turning out copy in order to get $250 checks here and there, try and work in a more substantial way so that what you’re producing is more geared towards quality rather than quantity.

This is an incredibly easy trap to fall into — it’s exciting when a publication asks you for more work. So the impulse is to churn stuff out. But while this gets you money in the short term, it dilutes your portfolio in the long term. Do you really want the first article when people Google your name to be a viral clickbait piece? Or do you want it to be of something you’re well and truly proud of? In the long run, a few high-quality pieces will take you further than hundreds of low-quality pieces.

6. Value what you do.

It’s easy to forget, in the slog, what writing is. It is the act of taking something that’s in your brain and putting it into someone else’s. Do you realize how amazing that is? Do you realize that there is nothing closer, in this world, that is closer to magic?

It’s easy to forget the magic of what we do when you’re in the slog of churning out work, or agonizing over a sentence or a turn or phrase. It’s easy to forget when Twitter and Facebook are spitting out billions of words a minute. It’s easy to forget when advertisements use words to mislead us, or politicians use words to confuse us, or trolls use words to anger us.

It’s easy to forget that the work of writing is sacred. That’s why it’s hard. That’s why it has to be done.

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