How to Do What You Love: Q and A with Freelance Writer Alissa Walker

Meet Alissa Walker. Today she is a design blogger at Fast Company’s website Co.Design, a columnist at GOOD, the associate producer of the public radio show DnA, and an organizer of Design East of La Brea, the monthly party she co-hosts. Alissa launched a freelance career for herself a few years ago by starting, simply, to do what she loves: writing, walking, and eating gelato.  Her blog at gelatobaby.com documents, over a picture of oozing horchata nectarine gelato, her adventures in writing and thinking about design, walking around L.A., and tasting new kinds of gelato. She’s been kind enough to talk to me about her career and offers some advice on how to do what you love and get paid for it.

On your bio page at gelatobaby.com, you mention that you returned from a two-month adventure in Europe knowing that what you really wanted to do was write. Tell me more about your experiences in Europe and how your time there helped you come to this realization about writing.

After trying to work in advertising as a copywriter, then taking a day job as a producer at a production house, I was doing a bit of freelance writing for magazines but was still too scared to leave my day job. I had spent the last few years before my trip promising myself that I would do some writing “on the side”—which, as we all know, never really ends up happening when work and life get in the way. So I planned the trip to Europe as a type of creative sabbatical to see if I could fully commit myself to writing every day when I had no other responsibilities. I booked a solo trip with no itinerary whatsoever—something I highly recommend that everyone does at least once in their lives!—and it was the first time I’d ever traveled alone or really ever been alone in my life. I wrote, of course, but mostly I learned so much about myself, and how I liked to spend my time: looking at beautiful buildings, walking down strange streets, going to flea markets, eating new foods (including lots of gelato!). I decided I had to try and replicate this experience back at home, and writing seemed like the best way to do it.

Would you say you’ve been pretty successful at turning what you love to do into a career? What have you done to make this possible? What advice would you give to someone who would like to do the same?

I think I have been successful when it comes to being able to get paid to write in a way that I genuinely like to write and about things I genuinely care about. I think the key to this is to start doing the kind of writing you love to do, every single day, even if it’s just on your personal blog, or even somewhere like Twitter. Just do it frequently and do it passionately. Early on, I was lucky enough to get a job as an editor of the design blogUnBeige where I was required to post stories 3-5 times a day. This allowed me to develop my voice and build an audience. If you’re writing enthusiastically and often, people will remember you, and the work (and the money) will come your way.

Part of the appeal of freelance work is that you get to be your own boss. So what is itreally like to work freelance? How much of your job would you say is doing what you want versus doing what others want you to do?

Freelancing is simultaneously the best and the worst idea in the world. Ideally, I’m my own boss, and can orchestrate my own hours and choose my own assignments. But in reality, I’m stressed all the time juggling my various commitments, trying to carve out time for my own projects, and making sure that I’m drumming up enough business for the future. I think the goal for any freelancer is a bit of stability, which comes in the form of a contributing editor or contributing writer gig. But with that you lose a bit of freedom, since you’re required to write a certain amount of stories each month or year, and more of them are dictated by the publication, not by your own personal pitches. I would say about half of what I write are my own pitches and story ideas, and about half come from my editors at various publications.

What is a typical work day like for you?

I get up around 6:00 or 6:30 and start poking around the internet for story ideas. I have to file several stories a day and they all need to be incredibly timely, so if I see a potential lead I have to jump on it quickly, emailing or calling the sources for more information, quotes or images. I usually write or edit two or three stories before lunch. My boyfriend, who is a graphic designer, also works from home (you can see where we work here) so we take a break and make lunch together, which I didn’t used to do when I worked at home by myself—cooking is my favorite thing and stopping work to do it makes such a difference in the day! Then back to writing and editing stories until it’s time to make dinner. Not very glamorous! But at night I often go to different events around town which is a great way to connect with friends, potential story sources, and other writers. And I think IM and Twitter are also really great ways to stay in touch with what’s happening. I feel like I’m pretty social for someone who sits at home all day.

What kind of advice would you give to writers who are trying to get started in the world of freelance? What skills would you say are important to have, and how might one go about practicing those skills?

The most important thing you can do as a budding freelancer is to practice writing and pitching every single day. As story ideas pop into your head you should treat them this way: Write something short and pithy about an aspect of the story on your blog, so you can sort through your observations and get down all the details. Then transform that little idea into a bigger story pitch for a publication:  do your research on exactly where it should be placed, decide what makes it very timely, and get a really smart pitch written and out the door. Even if the pitch doesn’t pan out, you’ve realized why the idea was important to you and you’ve figured out your own take on the issue. You’re practicing your writing and developing a point of view at the same time, which is really important for a freelancer.

If I’m really interested in freelance and travel, would you say a freelance career makes it easier to travel than otherwise? What challenges/difficulties might I encounter? In your experience, is it possible to find freelance work that will pay you to travel?

I think there used to be more of those jobs where you got to go on free trips, but sadly budgets are getting smaller for all stories, even travel ones. But I think to prove yourself to these kinds of publications that are going to pick up the check for your vacations, you’ve got to really prove yourself to them as a tour guide. And that means treating where you live, your own neighborhood, as a travel destination. Try to pluck out amazing experiences, restaurants, events, and stores in your neighborhood and introduce them to a wider audience. This will show your skills as a curator and editors will realize that they can trust your opinions and advice when they assign you that story far, far away.

Between your column “Design is a Verb” at GOOD, your own blog and website, your public radio show DnA, de LaB–the monthly party you co-host, and the various conferences you attend and/or speak at, you must be very busy all the time. How do you fit it all in? Got any good strategies for effective time management?

Only say yes to things that you want to do, then none of it will ever feel like work. You’ll go into every day excited about everything you have to do and you’ll have no problem getting it all done.

It seems like you’ve become quite an authority on things to do/places to see in LA since you moved there. How much exploring did you have to do before you felt comfortable writing about the city?

That’s a really interesting question because I still don’t think I feel comfortable being an authority on LA. I’ve only been here nine years, and I have so much more to explore! But I think that’s the way I approach the city: There’s always something new to write about, or a different way of looking at something that’s been around forever, or a perspective that I have that’s unique because I am (somewhat) new to Los Angeles. From the first moment I got here it seemed like such a special, magical place, and that feeling has never really gone away for me. It surprises me every day.

Is it unfair of me to ask you what your favorite kind of gelato is?

Not at all unfair, although it’s difficult for me to pick just one! Here in LA, it’s whatever is in the case at Scoops (712 North Heliotrope Drive, LA), which is about to open a second location. Their salty chocolate and brown bread flavors are a killer combination. They catered my most recent birthday party where I had gelato beer floats. I often go to Mozza (641 N. Highland Ave., LA) for their olive oil gelato and this insane dessert called the caramel copetta, which has carmel gelato, marshmallow and Spanish peanuts. Finally, while it’s not technically gelato, I am obsessed with the flavors, concepts and people behind Coolhaus, an architecturally-inspired ice cream sandwich truck that roams LA. They have a dirty mint flavor with real chopped mint that’s so good for summer, and sometimes they even serve it on brioche buns, which they did for my birthday party the year before. That’s exactly how I used to eat it in Italy. Five times a day.

Do you have any more general advice about building a career around what you love to do?

Two pieces of advice. 1) Brand yourself and/or your company in a way that references what you love. In my case, I went for the gelato, and people everywhere send me gelato tips, gelato stories, gelato recommendations, even free gelato! 2) This goes along with what I was saying about writing every day about what you’re passionate about: If you want to get paid to do something, just start doing it for free. I started co-hosting a monthly design gathering here in LA called de LaB and once we gained some momentum, people were asking me to organize and moderate events for their groups. Now speaking at and curating events has become a big part of what I do for a living.

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