How Do You Get Into Freelance Writing?

jan-kahanek-184676-unsplash.jpg

Originally written in 2015.  Edited and annotated April 2018.

Photo by Jan Kahánek on Unsplash


I didn’t intend for this guide to be anywhere near this long, but when I sat down, my entire year—which was devoted to freelancing—just poured out in one sitting.

Although a lot of this advice could be applied to writing in general, it mostly focuses on freelance blogging and internet content, which is both my job and the biggest emerging field for writers.  I can’t talk about noveling, ghostwriting or magazine writing, since I haven’t done those... Yet.

2018 Update: I ended up writing a novel, but I’ll be self-publishing it, if it hits print at all, so I’m still not qualified.

Anyway, after the aforementioned year, I’m just beginning to make an income that rivals what I made when I had a job.  And not a middle-class job, either: $9-an-hour shit work.

Why’d it take so long?  

One, because I don’t have a college degree.  Just like the regular job market, people are more reluctant to hire you without one.  You can still do fine without it if you’re persistent, but it does slow you down in the beginning when you have no other way to prove you actually know anything.

But the second, more important, reason is that I made a ton of mistakes.  Everyone makes mistakes, but hopefully, you won’t make the same ones I made.  

A lot of what you need is simple preparation.  Going into your potential new career with a few things figured out in advance will save you a ton of agony.  So, if I had to prepare a kit for the beginning freelancer, it would consist of these:

A niche

When faced with the question of what to start writing about, it’s tempting to say “anything I can get paid for.”  But you don’t. There are a lot of things you’re simply not qualified to write about unless you’ve had years of experience with them, and trying would just be a waste of your time and the client’s.

What do you do for a living now?  Or, if you’re unemployed, what was the last field you worked in that you liked?  You should probably start writing about that.

If it’s STEM, business, marketing, finance, nutrition, management, logistics, construction, real estate, or some boring-but-practical field like that, you’re in luck.  If you have a degree in any of them, even better. If you can find a way to write about them in an interesting way, holy hell you are a rich (wo)man.

Everyone wants to interview bands and talk smack about video games, which is why those clients can underpay and treat freelancers like shoe gum.  Trade publications, however, always need content about obscure technical subjects, and there aren’t many people who can provide it. If you can develop a passion for the finer points of high-volume data security or advances in CAT scanners, you’ll find low competition and very good pay.  

Note that I said “develop.”  Too many people have this romantic dream about finding the one field you were destined to work in since birth—the Mr. Right of careers—but it doesn’t work that way.  Passion is often something you have to nurture for a field that you might be “meh” about when you first start.  It often comes years later, grown from the satisfaction of working hard and getting good at your job.

Warning: Don’t go into a field you actively dislike, though.  

If you’ve never worked in a field you enjoyed (sorry), what are some of your hobbies?  Again, most of the fun fields like music reviews, art writing, and web fiction are oversaturated and pay very little.  But you can still find opportunities if you’re willing to explore their boring relatives. For example, I write about photography and graphic design.  In order to land these gigs, I had to break out of the parts of them I found fun and start studying light metering, color temperatures, design psychology, typography, things like that.  You might not be able to write about your favorite album, but you might be able to write about the music business.

Online marketing is a common starting point for beginning freelance writers.  It’s easy to get into, and if you’re good at research, you’ll at least find work.  The competition is brutal, so you’ll find it hard to make a living, but I still suggest you pick up an entry-level marketing gig on the side simply so you can learn how it works: you’re selling your services online and they need to be marketed.  For my first consistent gig, I spent about five months writing 3,500 words a week on ecommerce, and although it only paid two cents per word for work credited to someone else (a deal I’d never take now) the knowledge I gained during that period is invaluable, and I still use it every day.

A website

Stop reading this for a minute and open two new tabs.  In one, go to Hostgator. In another, go to Namecheap. In the Hostgator tab, find their cheapest monthly plan ($7 per month) and in the other, search for variations of your name until you can find a dot-com domain that isn’t either taken or squatted on.  If you can’t, go with a dot-net, but you should aim for a dot-com. I’d advise only using a novelty extension if you can make it form part of a word, like my webcomic, Yume-Hime, which uses the domain Yumehi.me.

2018 Update: Using a novelty extension is fine now.  Also, that webcomic’s defunct, don’t visit it.

For your website, you should use WordPress.  If you know jack-nothing about WordPress... You should still use it.  Many client sites will use it and expect you to post your articles to their sites with it, so you’ll have to learn it eventually.  Why not now?

If you’re a customization freak, it’s tempting to use Wix, as I did for my first site, but I’d suggest you resist that.  If you know absolutely nothing about web design and are determined not to learn, I can’t stop you. But you’re only cheating yourself out of experience.  

2018 Update: Squarespace and Carbonmade have become quality alternatives.  WordPress is still a great skill to have, though.

But for those of us who are willing to put the work into a WordPress site, learn some basic CSS.  That’s another skill you’ll need, because you’ll probably be doing a surprising amount of customization.  Myself, I’ve had to spend days making revisions to my own site, my blog, client sites, and my webcomic’s site, so I’ve found myself needing it a lot.

On your site will be...

A portfolio

Collect your best stuff and put it where your clients can see it.  Preferably a page with an easy-to-write URL.

You’ll want multiple portfolios, one for each type of client you want to attract.  If you’re interested in writing articles, blogs, and ad copy, have one portfolio for each.

And yes, I know this is the one step I’m still doing wrong.  Mine is simply a list of all of the things I’ve written, organized by subject.  Someday, I’m going to go through them, pick out the best ones, and find some way to display them at the top of the page, but today is not that day.

But what if you haven’t written anything?

One of the biggest catch-22’s faced by new writers is that you can’t get gigs without a portfolio, but you can’t build a portfolio without gigs.  This is similar to the “no jobs, no experience; no experience, no jobs” cycle faced by people starting a new career, but yours is much easier to break: Simply assign yourself a few topics relating to your chosen niche and write a few articles about them.  Three to five 500-to 1000-word pieces will do. If you’re knowledgeable about the subject and have a few topics in mind, you can do it in a day or two.

If you can find somewhere to put these online, great.  If not, you might want to look into...

A hobbyist blog

“Get a blog” is the “get a room” of freelancing.  It’s one of the most common pieces of advice you hear from self-styled freelancing gurus.  And it’s fine, but there’s a catch: you don’t want just any blog.  Personal blogs will do absolutely nothing towards improving your portfolio.  Professional writing clients don’t care about your corgi—although I’m sure she’s adorable—or how well you can describe last night’s snowfall.

The only reason for a writer to start a personal blog is the same reason anyone else would: to talk about your personal interests to your friends and whatever randos happen to wander in.  Tumblr’s great for that.

But for your business, you want a themed blog, preferably one that offers your readers a tangible benefit: teaching them how to do something they want to do better, or keeping them up on the news of your chosen field.  From this point on, I’ll call it a “hobbyist blog.” This doesn’t mean it has to be about a “hobby” in the common use of the word. If you’re interested in finance or medicine, blog about Wall Street or the issues facing nurses.  But the principal is the same.

The point is to attract people interested in the topic, convince them that you are a knowledgeable person with interesting things to say about it, and eventually draw in an audience that will interact with you.  This is good for letting clients know you’re the kind of person who can draw in readers and continually put up stuff they’ll like, since that’s what they’ll want you to do for their sites as well. It also shows you can write things that are genuinely helpful and informative for other people, not just muse on your own thoughts.

The theme should be something related to the field you’d like to work in.  I want to move towards writing about writing, art, design, and the internet itself, so I started a webcomics blog, which lets me do all of those.  

It should also be a topic you’re interested in and want to know more about.  While passion isn’t essential to your day job, you should have it for the subject you choose to blog about, since that’s what will inspire you to go above and beyond when it comes to both writing great articles and marketing them.

If you can do all of these, you should be able to impress clients.  Webcomicry got me my second best-paying job, with Tuts+, just three months after I started it.  

If you end up finding unprecedented success with  your blog, you can even monetize it. If it ends up being a runaway smash hit, you can make it your day job, although to be honest, that’s not likely.

Come to think of it, I suppose you can also do the same thing with a Youtube channel, but I have no experience with that, so I can’t judge.  Also, even if you are scripting your videos, it’s a different medium that text-writing clients might not be as interested in. It might end up starting you on the path towards videography, though, which is an even more in-demand field right now.

A Twitter

Facebook sucks for business pages now, unless you have an ad budget, but Twitter is more important than ever.  I know it can be a pain if you don’t have an audience already, talking do dead air with nary a like or retweet to show for it.  I willfully resisted it myself for years.

If you already have one, you might want to start a separate one for your writing.  The people who'll be following your writing are not the same as the people who will be interested in your personal life, and they won’t want to be exposed to all your “lol went to applebees”, “lol got turnt up at a party”,  “lol took a poop” tweets.

2018 Update: Yes, I know no one says “turnt up” anymore.  If they even did then. Also, this is less true now.  When I first wrote this, there was supposed to be a clear separation between your personal views and your business writing, but in the current political climate, the trend seems to have shifted towards breaking the “professional veneer” to comment at least comment on social issues, even on accounts that were previously kept all-business.  Maybe, instead, just never tweet about getting turnt up.

“But don’t you post about your personal life on your Twitter?”  Yes, but I try to do it in a way that someone who doesn’t know me would find funny or interesting.  Same goes for anything I retweet. And although I’ll use f-words sometimes, I try not to dip into actual vulgarity.

The main reason to have one isn’t to attract clients, however, it’s to network with people.  Right after email, Twitter is the second-best way to get in touch with people you want to interview or pitch to.  It might arguably be even better than email, since you can’t go on too long, bore them, and have them toss it in the trash.  (Unless you send a long string of tweets, but that can be resolved by just not doing that.)

Not to mention that even some famous and prominent people tend to handle their accounts themselves, where you’re more likely to have to go through receptionists and hired social media managers in other channels.  

I’ve managed to talk to some of my favorite musicians and comic creators through Twitter.  I’ve also reached out to people who’ve expressed interest in hiring me for projects. And yesterday, I had an interview with Hiveworks CEO Jojo Stillwell via a long back-and-forth, which I was later able to edit down and piece together into an article.

A pitch strategy

Don’t rely on sites like Elance and Odesk.  There is little to be found on them but disappointment.  (More on that later.) Relying on sites that have public submissions pages is also not the best idea, since they probably get deluged with offers from other writers.

Your best bet is in finding corporate blogs that could use writers and pitching to them.  Often, blogs that are already active but primarily written by one person who seems overworked (you can tell by the content quality), or blogs the company has let lapse recently, are good targets. 

Same goes for established businesses whose blogs are surprisingly crap, if you think you can do a better job.

You’ll need to find the name and email address or Twitter account of the person in charge of the blog—usually someone with a title that involves the words “content,” “advertising,” “marketing”, “outreach,” “social,” or “editor,” and message them.  

First, you should send them a general inquiry letting them know who you are and asking them if they’re open to accepting pitches.

If they have a submissions page, or you know from some other source that they’re accepting pitches, you can skip straight to sending them a letter.

It doesn’t matter how many pitches you send out to various sources, as long as you can bring in enough work to support yourself, but don’t overextend yourself either.  A good general rule would be “if you don’t have enough consistent income to know where your rent’s going to come from next month, keep pitching.”

And if you use form letters, there’s no reason you shouldn’t be able to send out five to ten queries a day until that happens.

Form letters

You will kill yourself if you have to write hundreds of applications from scratch.  

So you need a form letter that includes a link to your website and portfolio, and a section where you can fill in why you’re qualified for this particular job.  Try to include enough variables to truly personalize it: the less you can make it look like a form letter, the better.

More likely, you’ll need more than one.  I have seven that I use for various purposes.  I keep them on my Google drive to ensure the formatting and links will be carried over smoothly to Gmail, and that I’ll have access to them on public computers should anything happen to my laptop.

I could spend a while telling you how to structure it, but instead, I’ll just post three of mine and let you figure it out.

Don’t copy them word for word.  Dick move bro.

If they have a submissions page...

SUBJECT LINE: Guest Post Pitch: [Topic]

Dear [Editor’s Name:]

I’m a freelance writer specializing in blog posts and article writing, [optional: with a niche in X].  [I currently write for X, Y, and  Z.]  [or]] I just discovered your blog, I’ve spent [an amount of time reading it] (I particularly liked [article or aspect X] and I’d be really interested in contributing.

[I’ve heard you accept guest posts, so I’d like to propose one that I think would really connect with your audience.]

[It’s called X], and it would be about [Y, Z, and Z.1], [and I could flesh it out by adding [Z.2.]\

A full list of my clips can be found on my website, but here are the the two that I think would be most relevant to this subject:

  • [Clip 1]

  • [Clip 2]

Let me know if you think this would be a good fit for your blog, and I’ll start working on it right away.

C.S. Jones
[My phone number]

sea.ess.jones@gmail.com
TheCSJones.com
@thecsjones

If they don’t...

SUBJECT LINE: Do you accept queries from freelancers?  If so, what are you looking for?

Dear [Editor’s Name]:

I’m a professional blogger and content writer, I’ve read your [magazine/blog/website] recently, and I’m very interested in contributing.  [Optional compliment on specific article.]  

Are you open to queries from freelance writers?  If so, what are your current rates and submission deadlines?  And are there any specific types of articles you’re most interested in right now?

Thanks for your time,

C.S. Jones
[My phone number]
sea.ess.jones@gmail.com
TheCSJones.com
@thecsjones

If I’m answering an ad on a job board...

SUBJECT LINE: Guest Post Pitch: [Topic]

Dear [Name]:

I’m a freelance writer specializing in blog posts and feature articles].  In the past, I’ve written [X and Y], which I’m confident have prepared me for this position.  I hope you’ll find my unique voice, my keen eye for nuance, and my prior experience with [X and Y] helpful as well. 

A full list of my previous articles can be found on my website, but here are the three that I think would be most relevant to this subject:

  • [Article 1] (with link)

  • [Article 2] (with link)

  • [Article 3] (with link)

I’m available anytime, so let me know if you’re interested, and I can begin writing right away.

[Optional: I prefer a rate of [five/seven/ten] cents per word for this kind of work, although that’s negotiable, so if you object to it, please let me know your budget and we can work something out.]

Thanks for your time, and I’m looking forward to hearing from you.

C.S. Jones
[My phone number]

sea.ess.jones@gmail.com
TheCSJones.com
@thecsjones

Bit more advice...  

I shouldn’t have to tell you this, but just in case:

Do

  • Actually read the ads and mention something they’re looking for.

  • Maintain a polite and professional tone in all your correspondence with them.

  • Thank your clients often.  Not too often or it starts to get weird.  Once at the end of each important message works.

Don't

  • Agree to work for free unless it’s a one-time assignment and you’ll get some tangible benefit out of it, like the chance to post a column on a high-traffic site and link to your blog or portfolio.

  • Get cocky and say anything like “You’ve found your new writer right here,” or “I’m really in demand right now, so you’d better book me quick.”  Clients don’t like the smell of douche.

A client database

Make a list of clients you’d like to pitch to, and already have pitched to, along with their editors’ names and contact emails, and links to their submissions pages.  Keep it on your Google Drive, somewhere near your file of form letters. Also, use a spreadsheet for it. I didn’t, now I have to reformat the entire thing from scratch.

I have occasional research periods where I spend a day just hunting for sites to pitch to and adding them to my file.   Have a section for sites and a section for print markets, and a separate section for fiction markets if you want to pitch those too, and organize them by topic.  If they have any special instructions for pitching, note those.

Here are some premade lists you can draw from:

2018 Update: I’m sure some of these are outdated by now.  Sorry.

It’s worth noting, however, that the competition for these jobs is far higher than cold pitching to potential customers of your own volition.

Not on this list...

...Is a “freelancing site” profile.

If you haven’t seen them yet, there are tons of these places.  Personally, I’ve used Elance, Odesk, Guru, Blogmutt, TripleCurve, Typebroker, Freelancer.com, and Scripted, and only the last one was worth a shit: There’s a test you’ll have to pass, but that’s part of why they’re good.  They only let people in who are at least decent at writing, which means there’s much less competition from the “Write many English for America monies” crowd. You won’t be able to rely on this site alone, though, so keep that in mind.  Also, get a Business specialty if possible: those bring in the most work. Don’t just go for Art/Design and Entertainment, like I did.

On those other sites, there’s too much competition from both sides: most of the high-paying gigs are taken by career writers, often with English degrees and literal decades of experience, and most of the low-paying gigs are taken up by freelancers from developing countries who take less than a cent a word for copypasted and never-proofread content.  That kind of work has been devalued to the point where you’ll never make rent in any western city off it.

If you have a video camera, however, you can try the DiPiazza method of working job sites, which I’ve heard is really effective.

You’ll also have more of a chance if you’re willing to invest money into these sites right away, before you even start working, which will give you an advantage by giving you more “credits” and letting you see your competitors’ bids and undercut them.  Two things, though:

  1. If you’re a broke-ass beginner, I can’t recommend you pour what little money you have into something that may never see returns.

  2. That race to the bottom of the pricing barrel is exactly what’s killing freelance writing as a valuable career, and I hope you won’t participate in it.

Surprisingly, one job site that constantly gets slagged off, but that I’ve found is actually pretty good for landing a quick gig, is Craigslist.  If you live in or near a major urban area and are willing to pick up odd jobs, you can make some quick side money off of it.

There’s less competition from foreign markets, and you often get to work with the client in person.  If you have a DSLR and enough working knowledge to pick up photography gigs as well, even better. Same goes for any other artistic or other skills you might have: I was able to make $2k in two weeks doing man-on-the-street interviews for a marketing gig, which paid for a road trip.

A lot of people advise against Craigslist because there are so many people offering unpaid gigs, and for reasons unknown to me, you might be tempted to break down and take one.  Simple: don’t. Problem solved.

A way to get paid

All my clients use PayPal.  I have Stripe and Hiveage accounts as well, which took me forever to set up, but no one ever uses them.  Sometimes I’ll bill clients via Hiveage and they’ll send me the money via PayPal instead. Go figure. I also have a PayPal debit card so I don’t have to wait the three days for it to transfer into my account, and I recommend you do the same.

Other markets will have different ways of paying, but they’ll usually walk you through what those are and how to use them.  Scripted, for example, pays by check like it’s still the golden age of journalism and their writers are all sitting in an underlit room typing with two fingers, wearing beige fedoras with press cards tucked into the brim, and puffing comically oversized cigars.

2018 Update: This is probably no longer true, but I don’t want to lose that simile.

I’m not qualified to give tax advice, since it varies so much from state to state and person to person.  The most important thing to remember, though, is to set aside a quarter of each check for taxes. Even if you don’t make enough money to get hit with that much income tax, it’s a good thing to have.  If you can’t afford to set that portion aside, that’s a fundamental problem with how you’re managing money, and you might want to look into getting a part-time job until you’re in better financial straits.

Some other things you should have

  • A Google Drive, if you didn’t infer that from all the references to them.  Computers die all the time, and the last thing you want is to lose vital client information to a hard drive cock-up.

  • A working knowledge of MS Word and WordPress keyboard shortcuts.

    • In short: besides the obvious, Ctrl-C, Ctrl-V, Ctrl-F, Ctrl-Z, and Ctrl-S, you’ll be using Ctrl-K, Ctrl-A, Ctrl-B, Ctrl-I, Ctrl-E, and Ctrl-H a lot.  Know what they do.

  • Typing training.  Start now. If you have an old Mavis Beacon disc in your basement, dig it out.  If not, Typeracer works.  You’ll naturally get faster and more accurate the more you write, but there are things you can do to speed up the process.

  • Some serious Google-Fu.  The world of internet writing is far too fast-paced for you to research things manually, so your Google game will have to be on point.

After you’ve done all this

Your primary goal should be to find and keep a few consistent clients who will keep your rent paid, while leaving yourself just enough free time to pitch better and better gigs.

In the past, most freelance writers made their living working for magazines.  Those days are largely over. The magazine world is painfully slow and difficult to get into.  With the glut of unqualified writers flooding editors’ inboxes, expect to wait months for a response.  If you get one at all, that is. More and more print markets are just falling back on staff writers or unpaid interns.

But if you can land a magazine gig, that’s pretty kick-ass and can serve as a life-changing addition to your portfolio.  Tip: get a copy of the Writer’s Market. It’s about $25 for a hard copy, but only $9.99 on Kindle.

Finally

Don’t quit your day job.

If you’re currently unemployed and need money now, get a part time job.  Remember, it took me a year just to earn a base income, and even if you don’t make the same mistakes, you might make different ones, so don’t gamble on your ability to do it faster.

I know from personal experience that losing your apartment really hurts your productivity, not least because drifting around trying to find coffee shops to work in (your parents don’t have WiFi) eats up a lot of time.

Also, remember that this is just a guide to how to get started, not to the whole process.  More experienced writers have told me that there’s even better money in copywriting and pitching corporate clients, but I haven’t gotten around to researching all that yet.

2018 Update: I spent two years away from freelance writing, working normal jobs and such, but expect more as I get back to it.

Finally finally, If you’re coming here from anywhere besides my website, check out more of my work at TheCSJones.com, or follow me on Instagram.

Thanks for your time.  

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