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.

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Writer For Hire

After what seemed like forever of standing in front of my dresser determining what outfit wouldn't be too unbearable to wear, it finally happened. Somehow, in the blink of an eye, summer decided it had had enough and when I woke up on Saturday to a 54 F degree sort of morning, I knew the time had come again for sweaters.

As pleased as I am at the weather's turn for the chillier, as much as I adore the faint nip in the air whispering of fall's impending arrival, fall means changes in more than just the weather around here. In less than two months I'll be wrapping up the day job for the season and returning to the lowly little desk where I sit right now to attempt to eke out a living with my fingertips and my brain. Oh geez.

While I'm thrilled to be nailing new freelance gigs every few months, the truth is even with the new gigs, my freelance earnings make up a mere fraction of what I need for winter wages. Which means I need more work. Which means I better get looking.

It also means I somehow need to transform this into a productive work place again.

Notice all the piles scattered on the desk and on the floor? That's how this summer's gone. When I've finished with something it just gets thrown into a pile to be dealt with at that magical time known as "later." As the summer's progressed, some of the piles have achieved "teetering" status. I work well in a general hodgepodge that only I can make sense of, but this is getting out of hand, even for me.

The mess of a desk I currently sit at is just the cherry on top of a hefty dose of confusion and frustration.  From my experience with queries it can take 9 months to a year to get an affirmative response. In truth, I should have started the whole "look for winter work" project last winter. Why did I wait so long to start putting serious thought into this? And since my winter writing partner from last year decided to move to India (!), it'll be a truly solo venture this winter.

Luckily, a good friend gave me the Rick Allen print below, called "The Trapper's Daughter Crosses the Lake", yesterday.

I propped the print up on my desk, within view when my laptop is open. When I look at the print I see a young woman doing what I want to do: heading across the lake, chin up and looking forward into the unknown. No floundering, no self-pity, just a bag packed with all the tools she might possibly need and a confident stance.

Maybe as I glide across this vast unknown on my trusty loons' backs, I'll do so with "writer for hire" printed in bold letters on my back.

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Breathing Room

This sounds kind of dumb, but sometimes I forget that I'm a writer. You know what I blame? All the writing.

I'm not sure what I expected when I signed on to "be a writer." Maybe mornings spent in front of the laptop, calmly sipping my tea while rearranging the characters and plots of my imagination? Maybe long, leisurely walks spent searching for inspiration?

One thing's for sure; I didn't expect I'd be hauling my arse out of bed long before my mind wanted to be awake to plunk in front of the computer to tackle the latest writing assignment: trying to feed myself breakfast with one hand while typing with the other, frantically shaking the words in order before it was time to get dressed for my "real" job.   

It's been quite the month or so, now.  There's been one freelance assignment on top of another to deal with. Good news for my portfolio. Bad news for those awful black bags under my eyes. Then throw in some pretty impressive humidity to top it all off and it's been kind of tricky to catch my breath.

But this morning I sat down at the computer and realized I had no lingering writing obligations hanging over my head. No commentary, no article, no guest post to write. For the next week and a half, I'm assignment-free.  These morning moments at the computer are mine.

Actually, more than just these morning moments. For a little while, I'm blessed with total control over my "non-work" hours. A very good thing indeed, since a certain favorite berry is ripe and ready for the picking.

Here's to the lazy, carefree days of summer. May your berry buckets grow full and heavy. May there be plenty of room to stretch and take a nice deep breath.

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Being A Tourist in Your Backyard

Yesterday, as the result of an exciting new freelance opportunity, I had an excuse to spend the night downtown in my hometown. The NYC trip of April had started to fade into “far away” and frankly with the vast amount of highway construction along the one getaway route out of town -- Hwy 61 -- makes a quick day trip anywhere outside of the county anything but quick. Schedules have been consistently chaotic so we’ve pretty much hunkered down in the woods.

Time for a change.

Last night, even though I was only an hour away from the cabin and about five minutes away from my parents’ place, I was anxious for the excuse to shake things up a bit.

And the very best part was that my friend Kati agreed to be my travel companion. Since I sometimes look at as Andy as he walks through the door at the end of the day and think, “oh, do you live here too?”, you can only imagine what effect being uber busy and living an hour away from town has had on friendships. There was some much needed catching up to take care of.

We made the most of the time we had. For supper, we cooked up some wonderful homemade pizza. Then, once I was sufficiently full of cheese, pepperoni, and root beer, Kati suggested we go spend the rest of the evening playing some pick up soccer. While I was playing, I felt like I was 16 again, albeit, missing a bit of that handy hand-eye coordination I had back then in my soccer playing days. Today I feel like I’m about 60. Ya know, who needs knees anyway?

This morning, after a fitful night of sleep in a strange location, we headed down the street for a bit of breakfast. Afterward, although there were plenty of things I could have been doing, we opted to play tourist a little bit more. There are a couple new businesses in town and although I’d written preview pieces about both businesses' openinga, I hadn't been inside yet to get a glimpse of the final product. We poked around in those two stores, along with a few other gift shops, then headed out to the lighthouse.

In the end, we decided if you were really, truly a tourist in this town, it wouldn’t be half bad. I guess that's not a surprising conclusion to reach when the skies are blue, the conversation is pleasant, and there's nothing that truly needs to be done except enjoy the warm sun and gentlest of breezes.

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I Will Buy You A Garden

“I made you something,” Andy said when I got back to the Shack on Sunday. Cranky from my five-hour drive back from the Twin Cities and feeling (somewhat melodramatically) as though I’d arrived up at the very end of the world, I raised my eyebrow.

“Yeah? What?” I asked.

I’m not sure what I was expecting. Maybe, a necklace made out of bubble gum wrappers?

It turned out to be a lot better than a bubble gum wrapper necklace.

While I gallivanted in New York City, Andy constructed a raised garden bed at the cabin where we’ll be spending the summer. My mother gave me some flower seeds for my birthday in March and at the time, I didn’t know quite what to do with the seeds. While I’ve been dreaming of a garden all winter, the Shack is located in a shady valley that doesn’t appear particularly agriculturally viable. But my new summer job has lead to shift in residencies for the summer where the raised bed Andy built as well as the pre-existing terraced beds with warrant plenty of digging in the dirt this summer.

Sometimes the grass is greener on the other side of the fence.

Now that the means exist to have a bit of a garden, we’re faced with the dilemma of deciding what to plant. Although it’ll still be awhile before any seedlings can be put out in the garden, we’re a little behind on starting seedlings. I really don’t want to bite off more than we can chew when it comes to garden maintenance, so I want to be as smart about this project as possible. One of my concerns is that the garden is as sustainable as possible.

Gardening seems the ultimate sustainable act, but gardening can generate a ton of largely unusable plastic waste. Just think of all the dinky little plastic 4/6-pack containers you accumulate on a trip to the greenhouse. Molly over at the Snyder 5 has a great idea on how to use egg cartons to start seedlings: Composting for Newbies. That’s so smart! I need to pick up some potting soil from my parents’ house tomorrow and then I plan to start a batch of flowers in an egg carton tomorrow evening.

We plopped a few tulip bulbs – excess favors from coworkers’ wedding last September – in the perennial garden last fall. Like most things you “plop” in the ground, I promptly forgot about them. So it’s fun to see all three tulips poking up now.

I have a cold, probably just travel fatigue catching up with me. We’re also in the process of moving out of the Shack for the summer. Our bedroom currently looks like a suitcase vomited in it and my desk space is a teetering cityscape of notebook towers and paperclip ponds. I should spend the evening organizing, but I’m more keen to plant my sweet pea seeds in the far corner of the raised bed.

I’ve gotten back to work. I have some calls out for an article that needs to be done by the end of the week and as long as I actually get some calls back, I think it has potential to be a really good article. I’m also in the process of setting up some interviews for my radio project and my current priority needs to be hammering out a draft of a commentary.

Speaking of commentaries, here’s my recent effort.

A college colleague got in touch with me yesterday regarding a freelance opportunity for the website he edits. My interest is piqued, but I need more details before I make a commitment to any more work.

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