How To Make It Work As A Freelance Writer

A Portfolio Approach.

I have a lot of coffees and drinks with journalists thinking of going freelance or getting out of journalism altogether or doing some hybrid thing where they do a little marketing/branded content/ghostwriting and a journalistic piece every now and then. In my experience, this is less because anyone really wants to get out of journalism than because the ceilings on salaries for senior level people are pretty low by New York standards and as people accumulate mortgages and kids, it becomes harder to make ends meet.

But some people are just burned out, or want to try working on a passion project on the side, or just want to know if there’s an easier way to live and work. So here’s what I’ll say about freelance writing: it is very very difficult to make ends meet as a freelance writer in New York City — or any big expensive city. (And most of the major US media companies are unfortunately in big expensive cities.)

So how do you make it work? I’ve said this to a lot of people, but I don’t know that I’ve ever written it down, so here goes:

My advice has always been to figure out how to pay your minimum bills first and take any work that will allow you to do that in the least amount of time for the highest amount of money. This gig is your anchor gig. You don’t have to love the work (though you probably shouldn’t loathe it either), but it needs to pay decently and take up less than 50% of your time. It could be copywriting for a marketing agency, ghostwriting for an executive, whatever. Once you have most of your basic income accounted for, you can be choosy about what you’re doing for the love. (If you’re living in Bushwick with five roommates and have no kids or mortgage, you can be even more choosy.)

And line up the anchor gig (or maybe gigs) before you leave your job. It’ll give you a sense of security both financially and psychologically. The last thing you want is to get an assignment you really want and like that doesn’t really pay the bills and end up too stressed out about money to actually enjoy it or do it well.

So figure out what your minimum number is and look for work that will cover it, or mostly cover it. DO THAT FIRST.

Then when you’ve done that, make sure you have a way to telegraph that you’re capable of doing whatever it is you want to do and get paid for it. If you want to do humor writing, but no one has ever paid you to do that before, then you should probably write some funny things and put them online.

This, incidentally, is not what people mean when they say you shouldn’t write for free. What they mean is that you shouldn’t write for free for other people. Writing for free for yourself is a different animal. You’re the only one who benefits here and you control what you publish and how — and this is basically a passive advertisement for your talents. It’s there so people can find you with little effort on your part. If you’re already doing what you want to get paid to do as a freelancer, make sure people can find your work easily and consolidate it on your own website. Expecting editors to type your byline into the search box of various publications you’ve worked for puts the research onus on them, and they will not do it. They are busy and they don’t have time.

LASTLY, pitch the pubs you want to write for. If you’re already a journalist, you know how to do this and it needs no explanation, but I mention because it’s the last thing you should do in this list, and in my experience it’s the FIRST thing people try to do and while they’re waiting on editors or getting rejection letters or just taking forever to get or complete an assignment, they flail/go broke/etc.

So here’s what your writing portfolio should look like: half your time or less spent on activities that generate 80% of your minimum necessary income — your anchor gig — no matter what it is. It only matters that it’s part time and pays well. The rest of your portfolio (time-wise) is split between pitching and doing work for yourself that will passively attract more of the kind of work you want to do on a paid basis.

I should mention that I know these things because I’ve done it the wrong way, and have flailed, been broke, and so on. I do not recommend it. Unless you fetishize suffering and enjoy a good panic attack, it will not be fun for you. So listen to Shameless Pragmatist Spiers and look for a tiny bit of financial security before you pursue your art.

[I should also mention that this advice is intended for people who are not independently wealthy. If you are, by all means, go do your art, whatever it is. You probably don’t need to worry about these things. But you’re probably not asking me to drinks to find out “how to make it work” either.]

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