Monday, June 6, 2011

Five steps to becoming a freelance writer.

When I was in the first grade, our teacher made us all stand up and tell the class what we wanted to be when we grew up.

"A fireman," said the boy next to me, predictably.

"A marine biologist," said the little overachiever in front, the one who always wore tight ponytails and tucked in her t-shirts.

"I would like to be Janet Jackson," I told the class.

And it was true.  I grew up watching Star Search and listening to Rhythm Nation, so at age six, these influencers were as strong as any on my future vocation plans.

But what I didn't know, was that my fanciful imagination -- that I could become a pop star, that I could become a Jackson, that I could become black -- was actually steering me down a different career  path.  Writing.

Now I've had a lot of jobs between my teens and now, but writing has always loomed in the background.  Pre-Internet, I hungered to see my name in print, in a story byline.  I freaked out when my very first column ran in the illustrious Hoof Print Weekly (published by Alamo Heights High School).  It was a story about a local car repair place, and how they had been in business since 1973.  Aren't you dying to read it?

Twelve years since my hard-hitting mechanic profile piece, I have written for a variety of outlets.  Some of which you've heard of, some you definitely haven't.  The most well-known are probably TreeHugger and Planet Green, both owned / operated by the Discovery Channel.  In 2009, I also had a brief stint writing for The Village Voice's now-defunct feminist blog.  These days, I'm still freelance writing, and while it's hardly enough for me to quit my day job, I'm still angling for bigger stories in bigger media outlets.  I've been rejected a lot, but I do feel like I've got the game down.  Since several friends and blog readers have asked me lately about freelance writing, I thought I'd share what I've learned so far on this textual journey.

Here are my five essential tips to becoming a freelance writer:

1. Decide what you want to write about.  Ok, this probably seems really obvious.  But seriously.  Take a moment and write down what three topics make you feel completely jazzed.  This is important, because it will help define your direction as a freelance writer.

While some of us daydream about a spread in Glamour, others are shooting for a column on or in The Wall Street Journal.  Do you want to ask people in positions of power the hard questions?  Or do you want to test-drive recipes with chefs?  Forecast Spring 2012 runway trends?  It changes for me all the time, but right now, my top three story topics are:

  • Interviews with writers and visual artists
  • Food, both restaurant reviews and chef profiles
  • Essays on becoming a grown-up
I admit that last one is pretty open-ended.  But the thing I want to point out here is that in addition to topic, think about format.  Do interviews make you excited, or make you cringe?  Do you actually like reviewing restaurants?  Or would it be annoying to stop in between bites and take notes on what you just ate?  Ross gets irritated with me all the time when our food comes out, tantalizing and piping hot, and as he's reaching for his fork I slap his hand away so I can take a picture of his plate.  So think about that too -- how the shape of certain pieces affect your research process, before you ever sit down to type.

2. Consider an internship.  I got my first magazine internship when I was well out of college.  I was in graduate school in California, and I was 24 years old.  It was at a new, local city magazine in Sacramento, and my editors came from Money Magazine and In Style.  I worked for free and, due to the miniscule staff and multiple overnighters spent at the office, I pulled my hair out a lot.  But in exchange, I got this awesome, New York school education in magazine journalism.  I learned about all the boring aspects of freelance writing, like fact-checking and copy-editing (if you've read this blog for any amount of time then you can tell I still need lessons on copy-editing), and I also collected all these splashy, well-designed clips.  When I came back home to Austin and was trying to get my freelance writer thing happening, I scanned my clips into PDF's:

 My first food writing column, courtesy of my Sactown internship

So what I'm saying is, think about a part-time internship.  For those of us who work full-time, that may seem unrealistic, and I hear you.  But if you do have 10 hours a week to spare, interning at a media outlet will give you some freelance writer street cred.  Mostly though, it will give you a spread of nice clips, and that's really what I'm driving at here: Trading your time, for free, to get your name in the byline of an established media outlet. 

3. Write for free at first.  Not just because it's a down economy.  But again, when you're starting out, you just want to build up your clips.

When I first moved back to Austin, I got in touch with the editor (now my buddy) Matt Swinney at the late Rare Magazine, and sent him my clips.  He said ok, I could write for them, as long as it was cool that they didn't pay me?

I said that was fine, and proceeded to write for them for two years -- four stories per monthly issue.

I also asked Austinist if I could write for them, and eventually, they said yes.  That wasn't paid either, but I wrote a cocktail column and got compensated handsomely in complimentary spirits tastings and boxes of liquor mailed to my home.

My column at Austinist, The Informed Drinker

(Now that I think about it, why did I ever give that column up?)

When my old editor at Rare moved to Launch787, I blogged for them for a while.  Also for free.  In the end, it was only after I clocked in two years of free writing that I started getting offers for paid work.  I linked to that very column above when I applied to Planet Green, my first paying writing job.

So the next time a new website (or a magazine) launches, contact the editors.  Ask if they're looking for contributors.  Be up front with them, let them know you're trying to build up your clips and would be willing to trade your free time writing for them in exchange for some bylines.  

4. Blog and networkThe Village Voice blog editor found me via my blog.  So if you're blogging now, keep it up -- and start chatting with other writer bloggers.  (I say "writer bloggers" since not all bloggers aspire to be freelance writers.)  Use Twitter, and don't just chat with writers -- chat with publicists.  They're eager to turn you into a media contact, so they can eventually pitch their clients to you.  I'm a publicist too, so I can state that with authority!

Let me give you another example.  Years ago, I became friends with one of Austin's most beloved social queens, Rose Reyes.  She works at the Austin Convention and Visitors Bureau, and has always been a big supporter of my blog.  When SheKnows contacted ACVB looking for local Austin writers, her team recommended me -- and voila!  That's how I got that new gig I mentioned on Friday.

(And, PS, Rose and I met through absolutely normal, non-fabulous circumstances: I babysat her kids.  If any of you know Rose in real life, you'll be pleased to know that she had incredible shoe taste back then, too -- seven years ago).

5. Pitch ideas appropriately (and name your price).  This is the stage I am at now: Approaching outlets who have never run my work, and pitching them story ideas.  Sometimes it works (like with Austin Monthly a few months back), and sometimes it doesn't.  Meaning, a LOT of the time it doesn't.  But I'm still going for it.  I'm still Googling editor's names and email addresses, and sometimes I'm shamelessly calling the website / magazine office and straight up asking to speak to somebody about a story idea.  You have to have balls in this line of work.

It also helps if you've first made friends with one of the outlet's existing writers, who may kindly offer to introduce you to their editor.  Again, this is where Twitter can be your friend!  Find writers whose work you admire -- and whose writing homes you admire -- and make nice.


That's it!  Ye writerly wisdom from a humble foot soldier.  Some freelance writers have amazing connections, like a sibling or parent at a media company; for the rest of us, freelance writing involves a slow, patient execution of the steps above -- and lots of free labor.

One more thing.  Beyond the thrill of seeing one's name in print, I can honestly say that I've met some of the most interesting people through interviews, and a few who turned out to be my very good friends -- designer Rene Geneva, vintage princess Sarah Jessica Dean.  So when you're not getting paid in ch-ching, at the very least, you're probably getting paid in intriguing company.

good luck!


Angeliska said...

Loved this, Tolly. Thanks for sharing your experience and advice!

Peter Tsai said...

Yet another awesome post Tolly - while your post is catered towards freelance writers this could really helpfule for anyone doing any kind of freelance work.

Thanks for sharing your personal experience / blueprint for success.

I like your point #1 - it's super important for everyone. I think a lot of people don't really think about what they really get excited about before jumping into a career field - They put the money first and as a result aren't inspired in the content they produce.

Also, rhe to free or not to free debate rages on in other circles - refreshing to hear about it from a creative writing perspective.

Also, definitely agree that blogging and networking can help everyone!

Austin Eavesdropper said...

@Angeliska -- I'm so glad you found it helpful!

@Peter -- No problem! (PS, you'll be shooting for Food & Wine Magazine in no time. Then, request me as a writer to your editor. ;)

It's so true that people don't always think about what they actually WANT to write about ... including me. One time, I wrote an article about a device that played predatorial bird noises to scare off grackles. ? Look out New York Times.

Courtney said...

this is a great post. when i was little i said i wanted to write and illustrate children's books. but wanting to be janet jackson is infinitely cooler.

Dad said...

My advice: Just write. And post anywhere you can.

My niche is any issue that affects baby boomers -- as long as it is humorous.

Go to and read about diapers for adults; where boomers should retire; and required reading in high school.

That Chelsea Girl™ said...

Great tips, Tolly! My dad is a freelance writer in his field of expertise (firearm engraving), and I think these rules apply for anyone that wants to write. Take care!

Christi @ Rumination Avenue said...

What I came away with from this post is-grow some balls. For me, it has been difficult to state my objective "I want to see my name in print."

Aaand, getting off my duff and cold calling is right up there with ramming wood underneath my nails.

How do deal with NO response? How many times do you follow up? A follow up post that would be helpful are etiquette tips for rejection or no response. Yes?

Austin Eavesdropper said...

Courtney -- Girl, I think you're the one with the cool ambition. If you do ever turn your dream into a reality, then call me! I just so happen to be a book publicist. ;)

Daddy, I read your post on Moby Dick. My favorite line was, "I read the whole thing. Moby effing Dick. Can you believe it?" I'm pretty sure I Tweeted that.

Chelsea -- Whoa, he is? I didn't know that! So cool. Is that his main job, or does he do it just for kicks on the side?

Christi -- Yeah. Pitching yourself is completely scary (still).

But, it's easier once you've accomplished the whole clips thing. If you've got some, then you at least have a bit of ammo to use in your pitch. Something that says, "I'm not lying, I really can write here." I recommend writing an editor first (before calling), telling them a little about you, and asking if you can pitch them a few story ideas. The worst they can say is no.

Speaking of which, the biggest lesson I've got out of rejections is: People's minds change. Austin Monthly ignored me for a while. Then they got a new editor, and asked me to write a story. So if you get a "no," don't give up -- simply leave that outlet alone for a while. Minds (or, staff) could change.

But every time I get a no, I always, ALWAYS write back and thank them for their consideration. Graciousness goes a long way in this world! Then, I send them an anonymous computer virus.

(Kidding about that last part.)

Jada said...

Tolly, I really enjoyed reading this post. I giggled at the Janet Jackson part! :) I'm currently studying English literature in school now, and I'm def. considering becoming a freelance writer. I love your tips, thank you! :D

Minestrone Soup For the Teenage Soul

Austin Eavesdropper said...

Jada, it is such a pleasure to have you drop by here! I discovered YOUR blog via The Flowerchild Dwelling!

No problem at all on these tips. And, don't let anyone tell you the English major is impractical! Articulate writing is needed in any job environment. That's what I told all the business majors, anyway ... before I threw a copy of Pride & Prejudice at their head.

You'll be a wonderful freelance writer!

lk said...

Great post, Tolly - so very true!