13 things I’ve learned in 13 years of freelancing

This January marks the anniversary of me quitting my regional magazine editor job to freelance. I thought I’d do it until I went broke, but 13 years later, here I am.

So here are 13 things I’ve learned along the way. Freelancing can be the best job in the world – if you run your business right. Here’s what you need to know.

1. You are not destined for penury. Freelance incomes are all over the map, depending on the writer’s goals, if the writer does this full or part time, or even what kind of year the writer is having. In my best year, I brushed up against $100,000. In my worst, half that. But if you treat this like the business that it is, you can make a tidy living working for yourself (and while you may lose some clients, you can’t lose your job as so many full-time reporters have). So while you may glance at the next “freelancing is the worst” article that is bound to be published by someone who tried it for a few months then bowed out, don’t take it to heart. A lot of us have been doing this and doing this well for a very long time. We’re the ones you should be talking to. And take that attitude with you when you pitch publications. They want good writers. They aren’t doing you a favor by giving you work. They need us as much as we need them.
    
2. Don’t work for free. Ever. Would your plumber repair your faucet in the hopes that you’ll post the picture on Facebook to be seen by someone who may offer paying work? No. Would your doctor remove that mole in exchange for being in your good graces? Of course not. Anytime someone asks you to work for free, ask yourself if your doctor or plumber would do it. The answer is probably no. The only exception to this rule is if you are writing for yourself — though you’re better off publishing that article on your website than with someone who is running a business without paying for your labor. Don’t fall for the “we can’t afford it!” line either. If they can’t afford to pay their writers, they can’t afford to publish. I’m not shy about this stance either. When I called out Amy Pohler’s Smart Girls for the practice, asking them if they changed their minds from their no-stance pay when they launched, they blocked me on Twitter. Smart girls – and boys – don’t work for nothing.    
    
3. Think per hour, not per word. I have written for popular newsstand magazines that paid what looked like very high fees. But when I calculated the time it took to do their layers of revisions (sometimes telling me to put it back to the way it was without recognizing that I wrote it that way in the first place), the demands for rewrites to be done over holiday weekends, and the fights to get paid within six months of the story being run — they’re not worth it. You don’t see my name in those publications often now because they’re money losers. That’s also why I evaluate clients on a per hour basis, not per word.
    
4. Figure out your finances. In December, I collected more than $10,000. In January? $1,500. You must know how to navigate the waves of work and money that come in. Otherwise, you won’t last long, or you’ll bury yourself in debt. I’ve tried budgeting apps, but they never quite worked for me. Instead? The Money Book For Freelancers, Part-Timers and the Self Employed. The authors get what we do, how our income varies, and their system of where to put your money when has worked for me. Also: You most likely will need an accountant. Freelancer taxes are confusing (and the new tax bill doesn’t make things easier). Pay a person to help you; it could save you money and a lot of frustration in the end. One more thing on the money end: Whenever someone asks me how much they should save before going freelancing, it’s always “more” because one bad thing can slice your life — and your ability to work — into shreds.
    
5. Books should fit into your freelance life, if you chose to write them. I’ve written three books, and each one was tied closely to my freelance work. I made sure of that: My first two books were travel guides, and I used the things I learned while writing the book to pitch stories. I made a lot more money on freelance stories about the region than I ever did on the book, but having the book published made me a recognized expert, which got me a lot of those assignments. My last book was a running memoir, a book contract I got in part because I wrote a running column for The Philadelphia Inquirer at the time. Now, at the end of every New York Times running newsletter I write, the book is mentioned. I’d like to think that I’ll write a bestseller someday, but I’m also realistic, so I make sure that whatever books I write fit into my other writing, too.
    
6. It’s not a competition. A few weeks ago, I went to lunch with another freelance writer. Some of our clients overlap, and I offered her advice on how to form a tighter relationship with one of those editors. Never did I think “ugh I’m losing work because I’m giving her inside information.” That’s because we’re all pitching our own ideas from our own experiences from our own point of view. The two of us may pitch that editor the same idea, but never from the same perspective (this is also why, most likely, that publication did not steal your story idea). I never would have stayed freelancing this long if I hadn’t given a hand up — and gotten many hands up — from other writers. And if you encounter someone who raises their battle ax at your presence? That’s not someone you need to know. Move on. On the flip side: If you find yourself jealous of what another writer is accomplishing, shut that down. That negative energy is not going to help you and your business, and most likely, you and that writer were never going to follow the same paths anyway. You do you, as the kids say.
    
7. Meet your editors. It’s easy to see editors are gatekeepers bestowing assignments from up on high, but they’re like you: people trying to get the best story published. One way to cut down on their aura of all-assignmentness is to meet them in person. This has been easy for me because for most of my writing career, I’ve lived within a two-hour train ride of New York City. But I know two writers who fly to New York from Hawaii to go to a writers conference and, while there, meet their editors too. One reason I ran the Chicago Marathon in 2012 was because my biggest client at the time was based there. I may have limped into the building the next day for our meeting, but they were far more impressed with my feat than I was that they paid a good chunk of my mortgage that year (and then they assigned me some running-related stories even though their publication covered personal finance). Traveling to meet your editors is a business expense – and you may have some fun (or get a marathon medal) in the process, too.
    
8. Always network. Meeting your editors is one of those ways. So is going to writer conferences where you’ll meet other writers like you, and editors, too. I met my agent at the 2014 American Society of Journalists and Authors conference. I’ve gone to that conference almost every year of my freelance life, and every year get an assignment from a new contact that more than covers the conference fee and travel to and from. You can also find your tribe online. That might be a Binders group on Facebook (though I have found some pretty terrible advice on there too and don’t belong to any anymore myself). That might be the forums of ASJA. Or it may be, like it has been for me, Freelance Success. Wherever you go, find a place to talk about best practices and get inside information about publications, including other writers’ experiences, and in the case of ASJA and Freelance Success, interviews with assigning editors.
    
9. Always market. Even if the assignments are flowing, you can’t put this off because one day you may, through no fault of your own, lose two clients in two weeks that make up $20,000 of your annual income (as happened to me — true story). How do you market? Sending pitches of course. I also send letters of introduction to trade magazines, write my newsletter and use social media to share my work. I started writing for Poynter after I was interviewed for a story, then asked the writer if she liked writing here, and if she would mind passing along the name of the editor to pitch. Most recently, I started using Linkedin, which I had shrugged off before, because some people I want to write for hang out there. If you don’t know where to start, Ed Gandia’s International Freelancers Academy may help. I signed up when he ran a promotion offering two weeks' access to the site for $9. That was enough for me. The full gamut of services may be right for you.   
    
10.  Fight for your rights. When I sold my first story to Rodale, they sent me a contract that asked me to give them all rights for all eternity. I asked for a better contract, which they immediately sent. They had one. I just had to ask for it (though I don’t know if that’s still the case now since they have been purchased by Hearst). Asking that one question has led to thousands of dollars in re-print fees when other Rodale publications used my work (often after I found them re-used and alerted the contract manager, who said, point blank, that the editor most likely used it without telling me because everyone else gave away their rights so they didn’t bother to check my contract). It’s important to keep the rights to your work, even if, as happened to me last year, an editor told me that everyone required writers to sign away all rights. He’s wrong, so I turned down the assignment. Another editor told me I wasn’t a big enough name to negotiate with — and I got my agent involved. I’ve only encountered two publications in the past five years who wouldn’t budge on the contract. Can it be uncomfortable asking for a better deal or more money? Sure. But the more you do it, the more used to it you get, and the better off your business will be.
     
11.  Don’t work for assholes. I had a fraught relationship with a well-paying regional publication where the editor would send back comments on stories that were longer than the stories themselves, often with insults. When I won an award for one of those pieces, I let him know, and his reply was that he was surprised because he didn’t think it was good enough for the publication to submit (but boy did he make sure to pose with me for photos at the awards reception). Worries about that editor kept me up at night, so I fired the publication. I took a budget hit when I did, but I have never regretted cutting someone who treated me like dirt out of my writing life. Instead, I used the time wasted on them to find clients who treated me better — and getting a good night’s sleep.
     
12.  No, you can’t drive them to the airport. As soon as you plant your freelance flag, friends and family will come out of the woodwork asking you for favors: Watch their kid, drive them to the doctor, go shopping because they’re playing hooky that day. That’s because they think your schedule, especially if it’s obvious that you have a non-traditional one (like I do since I run in the middle of the day) is open for revision if they need a favor. No, it is not. You have a job, and if you’re busy running them to the airport, you’re not doing it. Freelancing opens up a world of opportunities to do things that others can’t because they are anchored to the 9-5 workday. For example, I’m writing this to you from a riverfront cottage in Daytona Beach, Florida, because I decided to opt out of an east coast winter. But you can’t be so flexible that you’ll break. That’s not to say you should tell your mom NO! if she’s in a bind, but get used to saying you can’t — because you really need to work.
     
13.  Go to the movies in the middle of the day. “But Jen you just said don’t drive people to the airport!” That’s doing a favor for someone else. Going to the movies in the middle of the day (or for a massage or a haircut or a daytrip to a national park) is a favor you do for yourself. This is a hard job, and can be both mentally and physically exhausting. It’s okay, if you’ve just filed a string of stories, or you’re pitching your face off and not hearing back, to go to a 10 a.m. movie. I have seen "Captain America: Winter Soldier," "The Great Gatsby," "Magic Mike XXL," "Saving Mr. Holmes," "Doctor Strange" and a half dozen more. There’s the practical side to this practice — that it’s not a bad idea to get out and experience a different kind of storytelling — but it’s also just fun. Even though I often say it’s the best job in the world, freelancing can be maddening. You deserve Chris Evans and popcorn for lunch sometimes.