Things I Wish I'd Known Before Freelancing

A friend recently reached out on her blog for some advice on starting freelance writing. It got me thinking.

I've been dabbling with freelance writing since I was a college sophomore. In those early days, freelance writing was something I dipped my toes into each summer. It wasn't until a year or so after graduating that I actually waded in. The deeper I wade, the more I've learn, and some of what I've learned sure would have been nice to know while I was still sitting on the shore.


1) It's Never Too Early To Think of Taxes 

Maybe I've been dabbling in the freelance writing world too long, because boy was I surprised last year when my freelance earnings last year bypassed what the IRS considers hobby earnings and had to be claimed on my tax return. I'm only grossing a couple thousand dollars annually, so I don't bother to pay quarterly taxes yet.However, your life will be infinitely easier come tax time if you've actually spend the year acting like you'll be making oodles of writing money that the IRS'll want to know about.

You should:

• File a W-9 with every freelance writing job contract.    
• Track your mileage on freelance assignments. 
• Keep all your receipts for office supplies and other freelance writing related purchases. 
• Hold on to those thank you letter from any charitable donation you've made over the year. (Despite being poor I do make a couple of those every year.) 

2) The Books Will Help . . . to a Certain Extent 

There are all sorts of writing books out there. Some will provide you with helpful insight you'll return to again and again. Others, you won't even finish. You've heard this hundreds of times by now, but no book has the power to transform you into a freelance writer. Time and perseverance are the only fail proof ways I know of to become a freelance writer.

That said, there are a couple books, I think every beginning freelance writer should have on their bookshelf, or, even better, their desk:

 
You should also purchase, or at least subscribe to the online listing of the current year's Writer's Market. The book is the definitive listing of literary agents, small presses, trade markets, literary markets, magazines, and contests. If you have no idea where to start submitting your writing, this 1000+ page puppy will give you so many possibilities your head'll spinning after 15 minutes of leafing through its listings.

As you become more comfortable with the query process, you'll become less dependent on this massive tome. While I haven't bought the book for a couple years, I'm extremely grateful for both the advice Writer's Market gives on how to query probably and the eye-opener the book was about how much possibility still exists in the print world.

3) Query Thoughtfully

It's very easy to read through the paragraph descriptions of a publication in Writer's Market's listings and think "Oh my goodness, that one piece I wrote would be perfect for this magazine. I'm going to query them immediately." Hold. Your. Horses.

There's a little rule when it comes to querying. A rule that says you should be familiar with the publication before you query them with an article. Luckily, in this internet age, you don't necessarily need to head down to the library to leaf through back issues. A couple minutes spent poking around on a publication's website should give you a pretty good idea of whether or not your writing would be a good fit. It's also a good idea to do a search of the publication's website to see if they've published anything recently on the topic you'll be querying about. Chances are pretty good that about half the time "that perfect match" of a publication won't be at all what you thought.You're not necessarily wasting an editor's time by sending in an ill-fitting query  . . . you're wasting someone way more important's time: yours!

4) Your Queries Aren't Just Another Drop in the Ocean

It's really easy to get down on the query process. If I can use an ice fishing analogy, sometimes it feel like you're going ice fishing on a fish-less lake. You spend all this time crafting the perfect query, you send it off and then you wait, and wait, and wait. Most publications won't tell you they're not interested; after a certain point, you can assume you won't be hearing back. That said, you should never give up hope completely on a query unless you've heard a definitive "no" back on it. I've gotten assignments out of queries more than a year after I sent out the query, which, to me, makes the whole process worthwhile.

However, if you want more instant gratification (and less pay), pursue online freelance writing opportunities which are more prevalent than traditional print ones.

5) Recognize Writing As A Part of Your Life

Write daily. Figure out a process for getting queries out on a regular basis. Find other writers to hobnob with, both on and off-line. Subscribe to a writing magazine. (I get Writer's Digest although, I've heard better things about Poets and Writers.) Look into continuing education possibilities. If you only have time to read on writing publication a week, subscribe to C. Hope Clark's Funds for Writers e-newsletter. That lady knows what she's talking about.

6) It will take a lot of time

If you want to be a freelance writer, you need patience. Lots and lots of patience. Because, you guessed it, if you're spending years waiting for people to respond to your queries, making it as a freelance writer is one of those "slow but steady" sort of things.

One of the best things I did when I was getting serious about making a living as a writer was analyze the local writing market for opportunities Now I have a regular (paying) gig writing features for a small monthly publication and I write a biweekly commentary for the local radio, which does not earn me pay, but sometimes results in awards.

How about you? Is there a newsletter for a local nonprofit you could help with? A small monthly magazine that you could be come a regular contributor to? 

Start small and build as you go. In the process, you'll hone your writing chops and build a portfolio.