How To Be A Freelance Writer

*Not a full-proof, expert guide. Just some observations.

This is my third freelanceversary, if such a thing exists, meaning I began freelance writing as a major source of income three years ago. I had always been terrified of freelancing — because it is literally like walking a tightrope without a net below— but now it’s hard for me to imagine not doing it.

Is freelancing for everyone? Probably not. It’s not easy, but it’s also not impossible. I’m not an expert at freelancing by any means and I’m learning things about it all the time. That said, here are some of the things I’ve learned over the past three years that others might find helpful and/or entertaining.


Do not pass go. Do not collect $200 — because you will likely owe money. Just pay your taxes and get a business license.

Keep Track Of Everything

Filling out Schedule C for the first time has a weird affect on freelancers. It turns you into a tracking machine. You will keep every receipt. You will manage so many spreadsheets. You will constantly think of tax write-offs. You will obsess over your finances from sunrise to sunset and even while you sleep. This is part of your job now.

Time Management Is Key

One of my screenwriting professors in film school (of all places) always told my class, “Work expands in the time allowed.” When I caught up with him years later and told him about what I was up to, he asked how I managed it all — and I told him I was merely following his mantra. Basically, if you manage your time realistically and wisely, you have more time than you think you do. This is harder than it sounds.

And despite what some people believe, sleep is not overrated and you should definitely get some.

Have An Anchor Gig

An anchor can relieve a good amount of the financial worries (but not all of them. They will always be there, sorry). I have been lucky enough to have found some anchors, and then have a little food blog I started in 2013 grow into something that generates some income. It has allowed me some stability to pursue hobbies, like actually using my Master of Fine Arts degree in ~dreams~, I mean, screenwriting.

Don’t Depend On One Gig Entirely

One of the great benefits of freelancing is that you can switch gears all the time. You become an expert at juggling and multitasking. But one of the worst mistakes you could make is to place so many expectations on one gig to pay your bills and even sustain your self-esteem. Don’t do that. Editors can smell that desperation — it suddenly emits from every pitch you submit and every interaction you have — and personally, I had more rejected pitches during that period than any other. Embrace the fact that you can switch gears and pursue other passions.

Don’t Expect To Get Paid On Time

Oh, you really think that check is going to arrive when they say it will? Excuse me for a moment.

Bunny thinks you’re funny.

Yes, there are some great companies that do pay on time. But also, there are some companies that will make you wait seven months and ignore all your queries about the mythical check they owe you. Even if the client regularly pays on time, don’t count on the money being yours until it actually clears in your bank account. You will learn this the hard way.

One Gig Often Leads To Another

Here’s a fun story: Once upon a time early in my freelance life, I e-mailed some really dumb pitches to a pretty prominent website and they rightfully got rejected. About a year and a half later, that same website e-mailed me saying they loved my work at the current website I write for and wanted me to pitch them — they even set up a profile for me at the site before even accepting my ideas. They wound up accepting a few of my pitches. Another story: I kept pitching this one story around and it kept getting rejected. Eventually, an editor accepted it and it got pubbed! So, the lesson is…

Never give up, never surrender.

You Are Allowed To Say No

At first, it’ll be exciting getting all these gigs! People like your work, they really do! Yay money! But part of freelancing is working with lots of different personalities and juggling lots of different projects. There are only so many hours in the day and so much patience you can have before you get stressed out. If something isn’t a good fit for you or your schedule, it is totally OK to say no or to cut ties. If you’re feeling sick, take a day off and rest. If your family is in town or it’s your SO’s birthday, it’s OK not work for a little bit.

I’m not saying you won’t feel guilty and obsess about how much money the day off is costing you. You will definitely do that. It’s definitely going to be hard, but do it fast, like ripping off a band-aid.

No One Else Will Understand You (Except Other Freelancers)

Your full-time employed friends will wonder why you can’t hang out on a whim or do favors for them like you used to. They simply won’t understand that when you say “I’ve been swamped with work all weekend,” you literally were trying to make a deadline so you can pay your rent. You will turn down invites and you will watch personal e-mails sink and disappear in your inbox quicker than quicksand. You will forget many birthdays. You will take many naps.

Your friends will get butthurt and some will probably stop talking to you, but you’ll find solace in other freelancers who get you. And they all won’t get you, because every freelancer’s career in different, but bonding over invoicing is always a good starting point.

Your Social Media Profiles Are Business

If your social media accounts are public — and even if they’re not — people will find you. PR people, people who want to network, and readers who think you are the worst person on the planet for writing about Drake. The readers will find you, and they will let you know how much you suck (one of my favorite reader love letters will always be: “Drake sucks and you suck”).

Do I even have to tell you that social media is a minefield right now? I don’t even tweet a lot anymore and I still get mean @ tweets about articles. But that’s how it goes.

Have Fun With It

Embrace the one time in your life when you can wear jammies, eat take out, and watch an entire season of Master of None while you are getting paid to write.