The Freelance Writing Survival Kit

Dakota Sexton 

My friends don’t normally come to me for serious advice. Like, ever. I usually provide a brain trust of a million different, but equally bad, dating-related ideas. If my life were a romantic comedy, this would mean I don’t have it together and am otherwise a clueless or jaded best-friend/supporting character that will never find love unless fate pairs me up with someone who is equally hopeless and probably both wildly sweet and also somehow a really big lost cause.

But I digress. This is about writing advice.

When friends ask about that, I have different answers. And I hold onto different helpful writing-related tips and articles. Almost nothing beats Richard Morgan’s essay “Seven Years as a Freelance Writer, or, How to Make Vitamin Soup.” In it, Morgan describes how he pitched fancy magazines like Playboy and Details while still living with his parents in Apex, North Carolina. During the same decade, he also has to make vitamin soup, mostly by mashing up a multi-vitamin with a bunch of garlic salt in hot water. (Sexy!)

If you need more inspiration than that, there are tons of practical, online resources. Among the best: Ann Friedman’s #Real Talk From Your Editor column for the Columbia Journalism Review. MediaBistro publishes a weekly How to Pitch column that provides advice on pitching to a single publication, which also includes tips from the publication’s own assigning editors. Chris Guillebeau has been writing to his readers about freelancing and budget-friendly travel hacking tips for years as a blogger (and he writes totally affordable books on the same subjects as well). There are also ultra-cheap Skillshare courses on everything from Humor and Personal Essay writing to how to pen a 10-minute film short.

What’s missing for me? More articles that detail how exactly to pretend to be professional when you need to invoice a client, especially for hourly-paid freelance work. Or when you haven’t been paid. Or how to get an interview transcribed affordably while sleeping. There are tons of budget-friendly applications and services for all of this, though. Below is a list of just a few of my favorites.

For Organizing Tax Deductions

I’d guess that “butt-loads” is the correct term for how many expenses most freelance writers could write off. Except I don’t really know that many people who actually do it. There’s an awful lot of effort required. And what if you get audited? A service called Shoeboxed wants to let you have your cake and eat it too, though, by letting people scan or mail in receipts and other business-related documents. Shoeboxed then trades you an IRS-accepted image to use for each document, plus provides other selective benefits.

For Writing and Editing

Have you heard of a writing app called Scrivener? Supposedly, a bunch of fairly-reputable writers think that it’s pretty cool. I’ve also tried it. Instead of recommending it to any other gullible people, however, I’d like to create a drinking game. It will punish you whenever you can’t remember how to do something really basic, and the game will also punish you whenever you can’t find a tiny piece of research because it was hidden in a sea of panels and/or obnoxious different boxes.

You could blackout for half of the day doing this, or just try out Editorially or iA Writer. Both are dreamy, well-designed writing apps that focus on minimalism and typography. They format text using a web-friendly language (Markdown) that easily converts to HTML without the additional garbage code other applications (Microsoft Word, Pages, and even Google Docs) unintentionally create.

When you finish a draft with Editorially, you can also easily invite friends and editors to read, comment, and edit your work. And as a bonus, there’s version control options built into both programs to reassure even the most paranoid and/or obsessive writer.

For Invoicing and Time-Tracking

Do you need to be paid for an article or something else you did? As a joke, try signing a contract and just cross your fingers. Someone might know you need to be paid, because magic. But if that doesn’t work out, try using Harvest. It’s an online and app-based service that can track task-based time and also help you invoice clients—repeatedly, if necessary. After creating a project and, optionally, toggling task-based timers, Harvest can generate an invoice that's automatically populated with all the relevant info you need.

If your client/publisher doesn’t still rely on billing practices that probably once originated in some kind of dinosaur age (like the 70s, or possibly just whenever the publication was founded), Harvest also helps you to accept payments online using Stripe.

For Email Reminders

Getting ahold of editors is hard. We’re busy, we get really distracting stomachaches sometimes, and it’s just hard to make yourself remember to keep reminding us to get back to you in the first place. That’s where Boomerang for Gmail comes in. After installing it in Gmail, you can set up automatic email reminders for any outgoing email. If say, an editor doesn’t get back to you in a week, a “boomerang” will let you know.

On the flip-side, if you don’t have the time to answer an email, you can set up a boomerang to hide an email for a few days.

For Transcribing Audio

Until recently, I transcribed all my own audio interviews. Other editors I knew just assigned that work to our interns, but I was personally too embarrassed to do that. Now as a freelancer/unpaid-and-non-glamorous editor, getting an intern to do it is obviously no longer even an option. There are professional transcribing companies (notably Casting Words), but the cost is usually out of the question on freelance money. Yet there’s hope: Mechanical Turk, a service launched by Amazon about 5,000 (actually 9) years ago.

As a “Requester,” you can post an entire audio file online for one person to transcribe or upload 6-7 small segments of the same file for multiple Turkers to complete—using one set of instructions. Get more tips on maximizing the service here and here.

For Your Health

For the most part, I don’t try to use a lot of health-focused apps. But I do use f.lux, a free app that adjusts your screen’s brightness automatically based on info you provide on your current room lighting.

For General Productivity

I name-dropped an app called TeuxDeux more times than anything else last year. It does one thing: lets you keep an online to-do list of everything you’re supposed to do in a given day. If you don’t cross a task/priority out, or delete it (the app lets you do both), then it automatically rolls over to the next day. That’s it.

It’s simple, but it works.

And if you spend a lot of time on the internet (you must), just set all new windows in your browser to open to TeuxDeux’s task listing and you’ll be constantly reminded of what you’re supposed to be working on. Alternatively, you can also download the TeuxDeux iPhone app.

That’s all. You should now have all the tips you need to bother every gainfully-employed editor in America, or at least the ones that matter. (Kidding! Sort of.)  

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