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10 Things I Wish Someone Had Told Me About Freelancing

Several times in recent years, a former journalism instructor has asked me to come talk to his class. I’ve always somewhat awkwardly postponed this, mostly because for a long time, I wasn’t sure I had much to say about freelancing or journalism or writing or anything else that would be remotely helpful to anyone. I pictured a classroom full of eyes blankly staring, fingers tapping and swiping for something more interesting than me trying to sound like I knew what I was talking about.

I wasn’t sure I was really the freelance model of success my former instructor seemed to think I was. Did he want me to tell his students I’d been chasing a $350 invoice for a newspaper story for months? That all the hours I’d put into reporting, writing and editing that story worked out to about what I used to make foaming lattes at Peet’s? How I was pretty sure that “freelancing” was Latin for “never-ending tsunami of rejection”? (Actually, we’re apparently named after medieval mercenaries. Bet their invoices got paid faster, though.)

But it occurred to me recently that after eight years of freelancing, about five of which it’s been how I eat and grudgingly pay the Comcast bill, I might have actually learned some things. So I started thinking about what I wish someone had told me back when I was a 23-year-old naively setting off down the freelance path.

Here’s what I came up with.

1. You won’t make any money off your own words.

Yes, there are exceptions. I recently ruined my morning by reading a New York Times story about a 30-year-old waitress who landed a six-figure book deal. And occasionally you can find an organization with both the budget and the moral compass to pay a reasonable sum for your carefully crafted 3,000-word essay on the various uses for yak meat. But for the most part, freelance rates are kind of like Anna Wintour’s haircut or my love of stretchy pants—they haven’t changed since the ‘80s. (Actually, it might be worse than that. In 2002, the National Writer’s Union found that in real dollars, freelance rates had declined by more than 50 percent since the 1960s.)

It took me a few years to accept that it’s nearly impossible to make a living off of writing alone. Sure, there are the assignments here and there that make you think, “Yeah, this could totally work.” But then that assignment ends, and you’re back to explaining to an alt weekly why no, you will not write them a blog post for $40.

My solution to this is to simply spend more of my time working with other people’s words, charging an hourly rate for things like editing, research and fact checking. (Clients are generally willing to pay a decent hourly rate for these services while writing is almost always a flat or per-word rate.) I try to make time for my own writing and reporting, but honestly it tends to take a backseat to the stuff that pays the bills.

2. That doesn’t mean you should give up and start handing your words out for free to anyone who asks.

See my rant on that issue here.

3. You’ll spend a lot of time on things other than words.

Freelancing is running your own business. By yourself. And yes, you can wear pajamas in your kitchen while you do it, but running your own business is still a hell of a lot of work. Be prepared to spend hours invoicing (and re-invoicing), reading and negotiating contracts, keeping track of expenses for taxes and performing other housekeeping chores.

Also, learn how to read a contract so you know what you’re signing. They’re usually not that complicated, but you want to know enough to decide whether to ask that the indemnification clause be removed or a kill fee added in. And get this settled BEFORE you start the work—you’d be surprised how many clients will send you a contract you didn’t know existed after you’ve already started a project. And that’s not a great time to be negotiating terms.

4. The rejection will never stop, and you don’t want it to.

Failure may be trendy these days, but I’ve been good at it for years. Seriously, I could wallpaper my apartment with all of the “Thanks, but I’ll pass” emails. This was really hard for me at first. When you’re just starting, it’s hard not to interpret each rejection as someone saying you’re not good enough to be doing this. It took probably three or four years before my brain learned to channel rejection as motivation.

Other than letting the rejection pummel you for a few years until you don’t feel the blows anymore, here’s my advice:

Don’t slink away after the first “no.” More than once, I’ve had a client express zero interest in my first pitch only to immediately accept a second idea. Hell, I’ve pitched myself as an editor or researcher to the same client for a couple of years before getting a contract.

Pitch stuff even when you’re almost certain it’s going to be a no. I’ve had editors surprise me a few times by accepting pieces I was sure they would hate. Maybe I didn’t know them as well as I thought I did. Or maybe they just had a really good burrito for lunch that day and felt like saying yes to something.

If the rejection ever does stop, either you’re the most successful freelancer ever or you’re not really putting yourself out there anymore.

5. Used to the rejection yet? Good. Now you can deal with the criticism!

As pretty much anyone who has ever put words on the Internet knows, criticism is impossible to avoid. Whether you’re writing about the local community college or street clashes in Cairo or your own family, there will be people out there seething with rage as they scroll.

So, all of those voices that are keeping you from hitting publish, all of those nasty things you’re afraid people will say? Oh, they’re going to say those things. They’re going to call you and say those things, email you, post on Facebook, probably discuss your lack of talent over brunch this weekend. The sooner you’re OK with that, the better.

For me, the tricky part of criticism is that it’s hard not to become numb to it, to block out some of the constructive stuff along with the bizarre and the downright nasty. I’m still not very good at this to be honest, and I don’t know many writers who are.

6. Fake it till you make it.

There is no room for modesty in freelancing. You need to be able to pitch yourself as the greatest thing since cold-brewed coffee, whether you believe it or not at that particular moment. As a recovering perfectionist, it took me a while to break free of my irrational fear that someone somewhere would be thinking, “Who the hell does she think she is? She’s way out of her league here…” It’s true that confidence comes with experience—just don’t sell yourself short in the meantime. Pitch publications that you think are out of your reach, go after stories that seem too big, ask for more money when you think you deserve it, just keep aiming high until you believe that’s where you deserve to be.

7. Take breaks.

When you work from kitchen, it’s easy to keep typing with one hand as you use the other to eat whatever you just found in your fridge for lunch. Work can bleed into the evenings and weekends until you start to see Sunday as that annoying day when your work cafe is overcrowded with all of these inexplicably happy people in workout gear.

This is not good. One of the main perks of freelancing is the flexible schedule, and you should take advantage of it. I still have a pang of guilt when I go for a run at 2 p.m. or make a trip to the grocery store on a Tuesday morning. There’s a voice in my head that says I should be working every second of every day. But you know what? That voice is stupid. I know I’m more productive when I take breaks, that my brain actually does better work more quickly when I make time for yoga classes and laptop-free lunches.

8. Find a mentor.

I don’t know how anyone survives without a mentor. By mentor, I mean someone in your field who sees your success as an extension of his or her own and does everything possible to propel you forward. Someone who inexplicably has your back in any situation and is always willing to take a break from his or her own stuff to deal with your stuff. This person is equal parts life coach, cheerleader, editor, colleague and friend.

How do you find these amazing people? Well, it might feel a little awkward, but you have to start by asking. Shoot your potential mentor an email asking if you can buy him or her coffee. When this person offers advice or work opportunities, pursue those opportunities with everything you’ve got. Show mentors that you’re invested, and they’ll invest in you, too. And then remember to pay it forward someday.

9. Don’t put all your freelance eggs in one basket.

Clients can vanish at any point, so don’t rely too heavily on any one in particular. Budgets get slashed, news organizations shut down, stories fade away, that one editor who really liked you moves on—if anything is certain in freelancing, it’s that everything ends at some point.

Just the other day, an editing contract I was hoping to renew ended due to budget constraints. Though I’m disappointed because I liked the client and the gig, I also have others to help fill in that gap in my paycheck. And I’m always looking for more in case those go away, too.

10. This might not be how you live forever. That’s OK.

It takes just the right blend of work ethic and insanity to make freelancing work. This isn’t a lifestyle for everyone. If you find yourself feeling stressed out all the time or really wishing you had coworkers, it might be time to send out some resumes. I’ve spent essentially my entire adult life as a freelancer, and I’ve had some amazing experiences that I wouldn’t trade in for all the office gossip and 401Ks in the world. I love the flexibility of working from anywhere, being able to hop on a plane to go visit friends or family anytime I want. Freelancing and I were made for each other. But even I can’t promise you that we’ll be together forever. Or even five years from now.

Right now, though, I’m going to sit here at my kitchen table in yoga pants, drink my tea, send another email chasing an invoice, type some more words and then maybe make it to the grocery store before the rest of the city gets off work.


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