There’s no such thing as a free(lance) lunch: Alexandra Kimball

There’s no such thing as a free(lance) lunch is a series that asks professional freelancers the questions you want to ask them.  Think of it as having coffee with everyone at the same time. This week: Alexandra Kimball.

Who are you, what do you do? What’s your speciality?

Alexandra Kimball, Toronto. I write longform nonfiction: essays and journalism, for online and print magazines. Some memoir. There are different terms for this: literary journalism, longform journalism, magazine journalism, etc — I’m actually not sure what to call myself. I usually just say I’m a writer. I like most topics, but mostly, I’m comfortable with mental health and addiction, class politics, and fashion.

How long have you been freelancing?

A little over a year.

How did you/What made you start freelancing?

After I graduated, I applied for in-house jobs at magazines and newspapers, but nothing ever came up. I wound up working a series of “peri-media” jobs: creating content for a marketing company, doing communications at a non-profit, and writing copy for websites. Sometimes I had to double-up these jobs, but when my schedule was lighter, I would pitch ideas as a freelancer to magazines.

Eventually, they started taking my pieces, and after a couple of years of this, I had a decent if small portfolio and a few connections. In 2011 I got an inheritance — this is all documented in a rather whiny but sadly accurate way here, — which allowed me to pay off my student loan and put aside a couple of months of income. I used that time to pitch and write my first few pieces as a full-time freelancer.

I figured if I wasn’t getting regular work within three months, I’d go back to some sort of communications job, but thankfully that wasn’t necessary. I had a vague idea at that point that I may go in-house at a paper or magazine, and I still might want to do that, but nothing’s turned up so far.

How did you sell your first piece/pitch your first job?

I wrote freelance pieces for local magazines as a grad student, and then later while I was working various copywriting and communications jobs. I guess the first thing I wrote that really opened doors was a series about Toronto Fashion Week I published on the Walrus Blog in 2010. I got that by emailing a pitch to the online editor, and thankfully he opened and read it! After I had those clips — clips with a known, respected national publication — it was a lot easier to publish.

What are the pros?

Over in-house work? I get to set my own limits — I don’t have to write anything I don’t want to write. As someone who has written probably millions of words of marketing copy, I can say with 100% sincerity that this is a blessing. Everything I write I am fully gung-ho about, it’s all authentic and I’m happy to have it in my portfolio. I can choose which publications I work with, and turn down assignments if I don’t feel right about them. I get to work with different publications, and different editors, which I think is more intellectually challenging. Like all good work situations, freelancing — for me — is a very conducive situation for learning.

I’m a pretty serious night owl — 11:00 p.m. to 4:00 a.m. are my prime writing hours (though I do try to do interviews during the day). While I’m working, I like to pace around my living room, and talk to myself out loud, like a prisoner in solitary. I don’t know why but I’ve always done this, and it’s compromised both roommate and job situations. So my work behaviour is definitely most compatible with freelancing.

What are the cons?

It can get lonely  I’m pretty introverted, but sometimes I’m just starved for human contact! I wish I could go into an office maybe 1-2 days a week just to be with other people. Ideally these would be my research days, doing interviews and reading. Then I could retreat back into my midnight pacing cave to get the writing done. I don’t think jobs like that exist though.

Let’s talk networking. Some people think of it as a dirty word. What do you think about networking and how do you do it?

I always felt like an asshole, trying to network or even saying that word. Like I think of some jerk with a Bluetooth headset and a blazer sans tie who speaks in 100 per cent early-2000s corporate jargon and has a repertoire of different handshakes…I don’t know. It smacks of marketing, and thus insincerity, and I guess I’m naive and obnoxious enough in my own right to think that insincerity or self-promotion is fundamentally incompatible with what makes for good writing.

That said, of course you have to network, you have to meet people who can help you publish, right? I have a Twitter account, and a website, and I belong to some associations that have networking things which I really should start attending. All of that is good, it will help you get work. So I guess, get over the awful connotations of marketing and just do it.

Is it really who you know when you freelance?

That’s a big part of it. But I’ve gotten to know people who have helped me because they’ve read my writing, so you don’t have to be born knowing people, you can still do it via your actual work (I hope).

What do you think about the ‘pick your brain over coffee’ invite? Do you do it?

Yes, because I am freelance and oh so lonesome I could die. Kidding…kind of. I like meeting other writers and editors, and part of that is the fact that I don’t get to do much of that while freelance. The other thing is that I find that talking about my ideas out loud helps me refine them.

Do you think you have to have a certain personality to freelance?

Introversion will certainly help, I think. Also, this is probably common knowledge, but sometimes you don’t get paid for…upwards of a year? So you have to be OK with that flux, with things not happening on a set schedule (including payment). Perhaps most importantly, you should be able to motivate yourself. There’s no one there telling you to meet your deadlines or to check up on your progress. You have to be good at setting your own schedule and enforcing it.

What are your tips?

Be persistent and shameless. If you want to write for some specific publication, pitch them over and over even if you don’t hear back. Don’t be afraid to ask for more money or to meet with people in person…advocate for yourself, basically. This can feel really awful and embarrassing but if you want work, you may have to be a bit pushy. I don’t really do enough of this as I should, though I’m getting better.

Oh, and get dressed! If I stay in pyjamas all day just because I work from home, I will start to feel like a loser, which in turn will mess with my momentum. When I put on normal clothes, I feel more professional, and thus more motivated. The key is to remind yourself that you actually do have a job, because when you work from home and have limitless freedom, it’s easy to lose sight of that.

Do you think freelancing is a viable way of making a full-time living?

Aiiiiiii, it’s possible, but you really have to know what you’re doing. Most freelance writing assignments pay peanuts, and there’s more and more high-profile work that pays nothing at all. So if you have a regular roster of high-paying gigs you can count on, you can make a living, but you really have to be able to depend on those assignments. The most successful freelancers I’ve heard of supplement their lower-paying writing work with higher-paying corporate writing gigs, or a semi-regular thing like a column (and some columns pay very well). So, difficult but possible, I guess. Though if you can pull it off — absolutely rewarding!

You can read Alexandra Kimball’s work at her website.


Free(lance) lunch is a weekly series published every Monday. If you are a freelancer and want to be featured on Free(lance) lunch, please email





No Comments

Sorry, the comment form is closed at this time.