The 5-Minute Freelancer Q&A #18 — Andrew Braithwaite

In this regular feature, Story Board asks Canadian writers to share a few details about their work habits and their strategies for navigating the ups and downs of freelance life.

Andrew Braithwaite is a Canadian-born writer currently living in San Francisco. He’s written about food and wine, architecture, travel and culture for such publications as enRoute, Wine & Spirits, the Globe and Mail, Bloomberg Businessweek, The Walrus, and Reader’s Digest.

Andrew took the time to speak with Story Board this week about staying focused, the benefits of being a generalist, and the advantages of placing limits on certain aspects of your freelance career.

Do you think as a freelance writer that it’s better to be a specialist or generalist?

I’m definitely a generalist. For me, it’s the easiest way to stay motivated and excited about the things that I write about. Anytime I’m caught up in a lot of assignments on one topic, I get kind of bored. In terms of how to navigate the market, I don’t know whether being a specialist or a generalist is better. But in terms of actually getting the work done, it’s nice to have more subjects to write about just to keep yourself interested in sitting down at the computer every day.

I write a lot about architecture and I write a lot about travel and sports, so I guess I’ve specialized in a sense that I don’t do hard news or business writing. But I definitely like the variety of writing about different fields. I’ve actually been working on two big architecture stories since last weekend. The last six months have been very food- and wine-heavy, so I’m really excited about getting to think about something different for a while.

What’s the best thing you’ve done over the years for professional development?

I’ve gotten a lot better in the last couple of years at coming up with plans when I have an assignment. And by that I mean really laying out all the steps that it’s going to take for me to get that story done. Instead of having on my docket a one-line item which is “write story about blank,” which is how I used to approach things.

This happened partly through reading a book called Getting Things Done which is a task management strategy and partly because my wife works in business strategy. I think that being more strategic about planning my day and planning my week and planning each assignment, breaking each thing down into a long list of very small, manageable steps has been the thing that’s allowed me to take on more and bigger projects that I’m more excited to work on.

How do you keep it all organized?

I use a mix of analog and digital technologies. I still haven’t perfected the system of exactly where to put all of these things! I use things like Evernote and Google’s Task Manager, but I also have legal pads that are full of long to-do lists that I update every two weeks. It’s a mix of formats and not an exact science yet, but I’m working on it.

What’s the biggest challenge facing freelance writers these days?

I think it might be knowing where best to apply your energy and where to pitch. Things are changing very quickly in the digital world and things are changing very quickly, not for the better, in the print world. The wide array of choices and different formats that you can write to can get a little overwhelming sometimes if you’re trying to attack all of them.

I’m still very much focussed on writing for print publications and I think that might have something to do with the limits of space in print. It’s something that I’ve always thought is really important to how I learned to write. The idea in digital journalism of an editor telling you “write to whatever length you need to tell the story because we have all the space in the world” for me, personally, would be a nightmare. I think word counts and the limits of the printed page are one of the best things that a freelancer can have because you learn to tell a story exactly as long as you need to tell it.

So limiting your options helps you stay on track?

Funnily enough when you asked about being a specialist or a generalist… I think I’m actually the opposite in terms of formats. I’m much more of a specialist in terms of the types of places that I want to write stories for.

Do you do any corporate writing?

I do a bit of that. I really like doing it. It pays well and it makes it a little easier to take on the big stories that are more of an investment in your reputation but aren’t as good of an investment in terms of time versus money.

How do you find a balance between corporate writing work and journalism?

I haven’t had a problem yet where the corporate stuff is getting to be too big that it’s in the way of the writing that I like to do. I keep an Excel spreadsheet of month-to-month money coming in and what pieces I have coming out. This year I wrote an e-book that Canadian Writers Group put out. I’d been working on this book for almost two years but I needed a month-long stretch to really finish it. I think that one of the things that encouraged me to shut down some of my journalism was seeing some of those corporate projects that I had done this year in the ledger. It just gave me that feeling that I could turn off the journalism for a month and finish this project.

So that corporate work allowed me to work on the e-book, which is the exact opposite. It’s kind of a showpiece or a calling card that I got to write exactly the way that I wanted. The corporate stuff feels like something I can look to that I can say “okay I did that so now I can do something more personal.”

What’s your approach to your online presence? How important has it been to your career growth?

It’s changed a bit in the past two years. When I got the Canada’s Best New Restaurants assignment from enRoute, the first thing that they told me was “you have to go and scrub pictures of you off of the internet.” And in a sense it was kind of freeing. Social became a much more undercover thing for me. My face isn’t on it, and I try not to tweet about things as I’m doing them. I obviously can’t tweet “I’m at this restaurant reviewing it undercover,” that’s pretty much the number one thing that’s going to get you busted as an anonymous food writer!

But I do still try to invest in Twitter and I built a portfolio website myself through a company called Squarespace. I think that there is value in building a community of Twitter followers and a presence on the web. It’s good to have these tools to get your stories in front of other people’s eyeballs. But at the same time I’ve tried to be a little more careful about how I actually go about presenting myself and how I’m creating a brand of myself online.

Now I really like not tweeting or Facebooking about stories that are active. I think it helps me focus on them better if I’m not putting ideas out into this digital morass and then having to stick to those ideas as a story evolves. Each story is kind of like Fight Club. You don’t really talk about a story until it’s actually published.

• Andrew Braithwaite’s most recent published work includes the Canada’s Best New Restaurants feature in this month’s issue of enRoute and the CWG-published e-book An Inconvenient Fruit. You can follow him on Twitter at @agbraithwaite.