The weird way I became a successful freelance writer 2

A newsletter subscriber recently asked me:

When you were first starting out, did you have any websites or reference materials that you found helpful connecting with people looking for freelance work? 

I’ve been thinking about this a lot, trying to come up with relevant tools and resources I used as a writing novice, and the short answer is: Nothing much!

Here’s the long answer.

When I first started out, I was 23 and my AmeriCorps stint had just ended. (It was a year-long program with the PTA-cheerleader-mom name of Project YES!)

I figured it was as good a time as any to try the whole “be a writer” thing, since I’d basically never had any other ambitions, which was convenient, because there are SO MANY CHOICES everywhere all the time. There’s 37 kinds of mustard even. It’s overwhelming.

My “plan” consisted of searching the gig section on Craigslist, which is where I saw the blogging opportunity of a lifetime: writing sex toy reviews for Early 2 Bed. I applied. I got it.

I was ecstatic even though that gig earned me zero dollars—I was paid in toys, which, at 23, I thought was the coolest thing ever. I did that for about six months and broke approximately half of the toys I reviewed, because evidently my vagina is made of diamonds.

Takeaway: We all gotta start somewhere. Don’t be afraid to write for cheap at first. You can raise your rates as you gain more experience and knowledge.

When not trolling Craigslist, I was cold-pitching blogs I liked and read, which at the time involved a lot of lesbian sites that are now defunct. Anyone remember Dyke Diva? Stuff Lesbians Like? The super-fun-to-say Dramanonymous?

These were mostly unpaid as well at first, but eventually, once I had a portfolio going, I started pitching paying places, including my local queer rag, The Windy City Times.

Not, like, journalism—no. I pitched them a short work of fiction. AND THEY TOOK IT. It was about a girl I dated who wanted to be Harry Potter. I got paid $25 smackeroos for it and was hooked.

And also broke. So around this time, I started looking for a “real” job with the intention of blogging on the side and continuing to build up my (incredibly gay) portfolio.

Takeaway: Freelancing is hard and sometimes you have to get a 9 to 5 job to pay the bills. This is fine! Also, you don’t need a fancy website or anything. I shared my work on my blog, which I am only a LITTLE embarrassed to tell you was on MySpace.

Through my AmeriCorps connections, I got a job at an education nonprofit by day, and continued to wax about butt plugs and lesbian drama by night. It was tiring, but it made for good conversation fodder at parties. No ifs, ands, or butts about it.

(That’s exactly the kind of terrible pun I have made throughout my writing career, despite every editor telling me not to. I DO WHAT I WANT.)

My roommate at the time was friends with a gal who worked for a website called (also now defunct), and one night, I was bragging to them both about getting “paid” to masturbate and she asked me if I wanted to be their new advice columnist.

Takeaway: Talk to everyone you know about your writing. You never know where your next connection, client, or advice column will come from.

I sent Centerstage a sample column and they loved it and I was suddenly given free reign to tell people how to live their lives! Me! A dumb 24 year old who broke vibrators regularly.

Centerstage was also a general review site, so I started writing restaurant reviews, bar reviews, theater reviews, and so on. I took anything they threw out, partially because I wanted the experience, but also, lez be honest, I wanted the free Appletinis and to see shows at Steppenwolf that I would never normally be able to afford.

Takeaway: Go outside your comfort zone. This will make you a stronger writer and possibly get you free Appletinis!

Centerstage eventually became pretty successful, and got bought out by the Chicago Sun-Times, which led to my first byline at a renowned daily rag (no offense, Windy City Times!)

After the Sun-Times came the Chicago Tribune, which is where I helmed an extremely poor-paying blog called Sex and the Windy City, on a new platform the Tribune was trying out called Chicago Now.

It was a pay-per-click type of arrangement, so I made approximately $.35 during my tenure. But, I made tons of friends and connections doing that blog, many of whom I still keep in touch with (and who have even interviewed me occasionally: See the Feast of Fun podcast.) I also learned about SEO, continued to review weird/cool shows like Naked Girls Reading, and even made some videos.

Takeaway: Failures are necessary. Indeed, they are the only way to really learn and grow. With every shitty assignment, with every unsuccessful experiment, I was learning how to be a writer and a business owner and how to advocate for myself.

Chicago Now was a wash, but it led to future advice columns at AfterEllen (the editor, Trish Bendix, was also a Chicago Now blogger) and the Redeye (the Trib‘s entertainment rag).

I was still working my education nonprofit job throughout all of this, because I liked it, and, well, I was afraid of making the leap into the scary unknown of full-time freelancing. Until I was forced to.

My girlfriend and I decided to leave Chicago and head to the wilds of San Francisco in 2009. You might remember that era as the worst economic recession America had ever seen. Great time to leave your secure job and start over in a place I knew nobody!

I don’t know why I had such confidence about this move, but I was pretty sure I would be okay in San Francisco.

I went back to being broke for a while and made a coffee date with one of the only people I knew in SF, who was—OF COURSE—a former Chicago Now blogger. Her name is Marian Wang—total badass reporter and you should read her stuff. She works for Last Week Tonight with John Oliver now.

Marian happened to be leaving for New York and her job at Mother Jones was opening up and she thought I should apply. I did. I got it. HALLELUJAH. No more croutons for dinner!

MoJo led to more connections and more assignments and opportunities and, years later, to my first book. (They even interviewed me about it because they are awesome.)

My freelance writing career felt pretty solid at that point, though I have on occasion stumbled back into the 9-to-5 realm—not out of fear this time, but because I was interested in the unique challenges of trying to make an arts blog thrive, for instance, or managing an alt-weekly, as I did at SF Weekly and the East Bay Express, respectively.

Nowadays, editors and publications often reach out to me first, I get to choose assignments that are interesting to me and turn down stuff that doesn’t, and I’m not worried about starving. It’s a pretty sweet deal.

And hey, I’m still writing niche things about lesbians, so some things never change.

Further Takeaways

Tennis star Arthur Ashe once said: “Start where you are. Use what you have. Do what you can.” I like this quote a lot for just about any endeavor, but especially for freelancing.

It’s easy to get bogged down in strategies and tactics—learn to optimize your SEO! Start a webinar! Grow your following on Instagram!—but that kind of stuff is going to take your attention (and precious time!) away from what matters: Writing.

I’m not against using tools or anything, but if my roundabout path to freelancing success taught me anything, it’s that I didn’t need any complex lead incentives or a pimped-out LinkedIn profile to find my way (though I’m sure those probably do help).

Instead I started where I was (INCREDIBLY GAY) with what I had (BUTT PLUGS) and did what I could (WRITE STUFF).

In a way, starting out is perfect because, to steal from Bob Dylan, when you got nothin’, then you got nothin’ to lose.

So start somewhere. Try things. Email people you don’t know. Don’t ask, “But how?” Just do something!

Slightly more practical advice

Write about what you think about obsessively. Use LinkedIn Publisher or Medium or Tumblr if you don’t have a website yet. Create a portfolio.

Make an ambitious, slightly crazy goal for yourself. (My current one is to write two books in 2017.)

Be ready to fail a lot and to embrace the unknown. The only way to succeed is to be willing to fail over and over again.

Peruse freelancing platforms available to you, like Upwork or ProBlogger or (GOD BLESS IT) Craigslist.

When you write to a potential client, just remember to make your pitch all about them. What can you offer THEM? How can you meet their needs? Tell them how you plan to solve their problem(s) and they’ll be much more receptive to writing you back.

Network with other freelancers—not just writers but editors, artists, coders, sous chefs, anyone. You never know what might lead to a gig or a steady paycheck.

And lastly, don’t obsess about writing the most perfect, beautiful thing that makes the angels sing and lands you a movie deal and cures cancer. Writing is a process that takes years to fine-tune. Most of it is trial and error. You throw shit at a wall and see what sticks. Even veteran writers are sometimes surprised by what was uber-successful and what flopped.

For instance, best-selling author, podcast prodigy, and blogging guru Tim Ferris once marveled that his most popular video is one in which he shows people how to peel an egg without peeling it. Like, whut?

Throw shit. See what sticks.

(Someone put that on an inspirational t-shirt.)

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