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Freelance Writing: Things I Wish I’d Known Before I Started

by Dakota Kim 

Freelance Writing: Things I Wish I’d Known Before I Started

If you’re a new freelance writer, I’m going to let you in on a secret I wish I’d known when I started out: Freelance writing is about so much more than writing.

Freelance writing is also about who you are as a person and your perspective on the world. It’s about how you brand yourself and what you’re known for. It’s about who you know and how you use those contacts. It’s about how willing you are to explore, be open and take chances. It’s about how business savvy and tough you are. And it’s even about how good you are at things that are not writing.

In this two-part series, I’ll first give you advice on acquiring the mentality of a freelance writer and seeing the big picture of your career. In the second part of the series, I’ll discuss how to handle the business and financial aspects of freelance writing.

Here’s are my tips on having the right mindset and approach:

1. You’re going to need the thick skin of a battle-worn, feisty old alligator.

You will face constant rejection as a freelance writer, especially in the beginning. If I cried over every spilled-milk rejection I got, I would no longer be a journalist. I just keep on keeping on like a battle axe, optimistically and strategically looking for opportunities.

Freelance writing is about who you are as a person and your perspective on the world. It’s about how you brand yourself and what you’re known for. It’s about who you know and how you use those contacts. It’s about how willing you are to explore, be open and take chances.

The amount of time you spend writing may be a small percentage of the amount of time you spend pitching. You are essentially a salesperson. There are warm calls and cold calls — know how to do both, although you’ll most likely get the majority of your assignments through someone you know.

2. Know how to brand yourself.

Do you want to brand yourself as a certain kind of writer, or are you more of a generalist? I would recommend a mixture of the two tactics. While I focus on healthy vegetarian and Asian food as well as subversive underground arts, I’ve done some financial, business and technical writing as well.

You may want to milk your unique characteristics as, say, a street photojournalist who photographs street fashion and culture from her bike. But you should still be able to take assignments in other areas, like tech and education. In that case, focus your website and social media presence on street culture, but include a diverse range of clips in your e-portfolio.

Speaking of social media, your Twitter, YouTube, LinkedIn and in-person branding should be fairly consistent, but each platform should offer something special and unique about you so that people will have a reason to visit each of your social media presences and not get burned out on repeat posts.

dakota kim

Dakota Kim


3. Be open.

Assignments can come from the strangest of places. Some of my most interesting and highest-paying assignments have come from colleagues of friends, or aunts of acquaintances. I’ve met the people who would lead me to assignments in the oddest of places — including while working in a French bistro and while taking a trapeze class.

4. Reach out.

I am pretty fearless – I’ve messaged writers I admire asking to meet so I can buy them a drink and receive an hour’s worth of mentoring. And some of them have accepted, and gone on to give me assignments because they thought I had an interesting perspective and we got along. Now, I have the opportunity to help young writers who are starting out and it feels great.

Like other industries, people often hire you as much because they like you as because you are a skilled writer, so be friendly and likeable. Have some questions in your pocket when you meet, and maybe even give the writer some pitch ideas.

5. Do weird things.

Have an interesting personal life and you’ll have great fodder for pitches.  I attend performing arts shows, flashmob dining events, event expos and sci-fi conventions. I always keep my ear to the ground and ask friends what’s going on. I’ve written about everything from Asian-American clowns to techy gardeners who tweet. Being open to new experiences and curious about the world will take you a long way. And the contacts you make in various worlds will help you procure assignments. After all, it’s much easier to get a freelance assignment when the editor knows you can actually get the interview with the famous musician, mysterious tattoo artist, reclusive art collector or non-responsive cult chef.

Being open to new experiences and curious about the world will take you a long way. And the contacts you make in various worlds will help you procure assignments.

6. Polish your digital writing.

Journalism isn’t romantic anymore. The days of expensed three-martini lunches with glamorous sources are mostly over, and print publications are crumbling before our eyes. Buzzfeed is more important to most people under 35 than The New York Times. Hone your media skills and learn to pitch for digital. Take a class, ask friends, and read articles online about digital journalism.

7. Develop additional skills.

Having additional skills, such as photography, videography, recipe development, info visualization, graphic design, web design, SEO, foreign languages or investigative reporting, can really up your pay level and make you more desirable to editors. Take a food photography class or even consider a journalism course if you have the money.

8. That said, J-school isn’t necessary.

It’s helpful for the connections and it may help you find a job in journalism afterwards, but as far as the loan debt, it may not be worth it unless you want to be a hard-hitting investigative reporter or a broadcast producer. I was accepted to J-school at Columbia and Berkeley, but was unable to attend either due to financial constraints. Now I know a lot of people who went to J-school who are making 30k per year at a publication in New York trying to pay New York rent, or who are trying to get by as a stringer in China, and others who aren’t working as journalists at all but as private investigators or corporate researchers. Ask yourself whether you’re good enough at interviewing for jobs, pitching and networking to go it alone without J-school.

And watch out for the sharks who try to sell you $300 writing courses on how to pitch – sometimes the class is worth it, but sometimes the teacher is just looking to make money, and you can learn a lot of that material online or via networking contacts.

Have confidence and give your writing business a shot before you donate all your money to the ivory tower.

9. Consider the long game.

Sometimes it’s better to focus on your own blog than spend your time pitching to publications. If you find that publications in your field aren’t paying well and you’ve got other sources of income, you may want to look at the long game and develop your blog in hopes of attracting advertisers or a book deal.

Write down your objectives and goals. Where do you want to be in three months, six months, a year, five years and ten years? Then work backwards to establish all the general, then specific, steps you’ll need to take to get there. Put calendar reminders on for three months, six months and so on with your objectives so that you can measure your benchmarks. Have you reached 10,000 unique pageviews on your blog by three months? Have you made $1,000 in advertising by one year?

Also, not all self-help books and websites are trite. They’re often helpful because these people have spent a lot of time thinking about how to accomplish goals. One of my favorite entrepreneurs and career coaches is Jen Dziura of Bullish, who has taught me a lot about running my own business and working to achieve my own goals, not those of others.

10. Remember that success often comes with time, age and experience.

I started writing a teen column for my hometown Illinois newspaper, The News-Gazette, when I was 13. In my late teens and early 20s, I wrote probably over a dozen low-paid articles in internships and for friends’ websites and blogs. I progressed on to slightly less low-paid articles in my mid- to late-20s. You become a better writer – I look now at some of my pitches from my 20s and laugh. Now in my early 30s, I have almost 20 years of experience as a freelance journalist and am finally getting great assignments in publications like the San Francisco Chronicle and Momentum Mag. If you’re young and looking to succeed, skip some of those weekends out with friends and take the assignments that require you to stay inside working on a sunny beach day. Freelance writing requires years of hard work, patience, experience, innovation and building of contacts.

If you’re young and looking to succeed, skip some of those weekends out with friends and take the assignments that require you to stay inside working on a sunny beach day. Freelance writing requires years of hard work, patience, experience, innovation and building of contacts.

11. I never guessed how much I’d fall in love with what I do.

I love being a writer – a journalist, a creative writer, an essayist, a recipe writer, a cookbook author and a blogger. It’s what I’ve done since I got my first journal from my mom at age 4. It’s been thrilling, from interviewing some of my favorite bands like Au Revoir Simone and Lissy Trullie at SxSW, to being in the second row at New York Fashion Week, to sampling mouthwatering cuisine by tastemaker chefs like Soozee Nguyen of Soozee Cooks. I’ve surfed, I’ve met elephants backstage at the circus, and I’ve been paid to travel – all because I’m a writer.

So I have zero regrets about all the hard work I’ve done, all the failure and all the rejections. Personally, I think being a writer is about striving to understand life and loving people, and also about being generous and wanting to share stories with others. A story will be so amazing, you just know you have to share it with as many people as possible.

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There’s not just one right way to become a successful freelance writer, and how you succeed varies depending upon the culture you’re working in and the field of writing you want to specialize in. But if you’re determined, open, savvy and tough, freelance writing can be a very fun, rewarding career that enables you to explore the world and share the fascinating things you learn.

In part 2, I’ll explore money and finance lessons I wish I’d known.

Dakota Kim is a freelance journalist covering the arts, style, business, food and travel. Her work has appeared in SalonThe Huffington PostBedford + BoweryThe Wall Street Transcript, and various in-flight magazines. Tweet her at @dakotakim1.