For the first few years of my freelancing career my business practices were a little bit of a mess.
That’s not quite right. My business practices were a total disaster. No surprise though, because like many journalists (and lawyers for that matter) I’m no businessman. I’m good at analysis, at writing, and at finding stories, but not good at marketing, operations or any of the other dozen little things that go into running what is very much a one man enterprise.
So my pitching was scattered, my editorial relationships were all over the place and every April I owed the IRS a bunch of money.
The results were predictable. Despite publishing several pieces a week I struggled constantly. When I decided to add copywriting and thought leadership to my portfolio I barely had any idea where to start. And I was tired all the time, because that’s what stress does to you. It gives you a constant, draining, exhausting sense of anxiety. It robbed me of the joy I should have taken in a dream career that I had spent years working towards.
I went freelance out of a love of personal freedom, but was too busy chasing my own deadlines to enjoy a life without bosses. I went freelance in order to pursue projects that I believe in, but was too caught up just paying the bills to look at the big picture. I went freelance to see the world and the people in it, but was too overwhelmed by the process of pitching and finding outlets to land the stories that would put me on an airplane.
This is the story of how I got my act together and cleaned that up. It’s not short, but hopefully it will prove helpful to a few people.
Remember why you do this. That goes doubly true in journalism.
This is a mantra I had to repeat a couple of times before digging into this project because, I’ll be honest, I was burnt out. I had had my fill of corporate clients suggesting unethical practices, editors demanding more than they were willing to pay for, and an overall industry that felt dedicated to squeezing every last unpaid syllable it could get from me.
Combined with the struggles to be a good journalist in an era focused on content and quick-consumption media and it was enough to make me want to quit.
But I got into this business for a reason.
I became a journalist because I genuinely believe in the power of our profession to do good. We are educators and investigators. Yes, we hold the powerful to account, but we also build communities and publicize businesses. We chat with school boards, attend zoning meetings, celebrate weddings, mourn obituaries, photograph beloved pets, interview high school actors, pick over tax proposals and put events in context.
Good journalism helps shape the world by helping people learn more about their place within it. Great journalism builds empathy, helping readers to see each other as people instead of just strangers from strange lands.
This is work worth doing, even when you’re up late sending out pitches or hear back from an editor who wants personal essays instead of reporting.
Just remember that for every article you write, someone out there is thrilled to see their name in the paper. A reader learned something and an editor paid the bills in an industry that’s worth fighting for.
Never think you know everything.
For years I had told myself I knew what I was doing and I wasn’t entirely wrong. I do still make a living as a freelance journalist after all. With no small modesty, very few people succeed at that.
I wasn’t very happy though, and was nowhere near as successful as I wanted to be. To start fixing that the first thing I did was look for for advice from other, more successful people than I.
Now, that doesn’t mean taking everything at face value. One of the difficult things about learning how to freelance is that, in the Internet age, it has become as much a lifestyle brand as a way of doing business. The web is absolutely filled with “here’s how I quit my 9-5” websites, and if you dig a little deeper most of them make their money by selling advice on how other people can quit their own jobs. It’s like a terrible, digital pyramid scheme.
But there are best practices, and it’s good to learn them. My life would have been considerably easier if I’d done so sooner than I did. A few of the resources I found useful were:
- The Freelancer by Contently
- John Scalzi’s Whatever
- The International Freelancer
- The Freelancer’s Union
- The Columbia Journalism Review
Data, data, data! I cannot make bricks without clay! – Sherlock Holmes
By the time I settled down to do this I had lists everywhere, and none of them were much good. I had halfhearted, half-assed collections of contacts and potential outlets scattered across my desktop, Word folders, Excel sheets, bookmarks, Trello and Google Docs. None had more than a handful of entries.
All I can say to that is UGH. It hurts to think about how many opportunities I probably left on the floor because it took me so long to get organized.
Here’s the thing about record keeping: It is tedious, time consuming and a pain in the neck to maintain. Then, when you actually want information, you’re desperately glad you did it. I had not done it, so every time I pitched a new outlet or reached out to source an article I was essentially reinventing the wheel.
This is particularly tough when it comes to finding outlets to submit to, and here’s why: Quickly, think of five places you’d submit an article to, any article at all.
Bet you a nickel all five were outlets you read often.
Run that exercise again and I’ll bet yet another nickel that you come up with a lot of the same names all over again. Let’s go to 15 cents, because I’m willing to also bet that most of those names were among the majors. Whether you read the Times, Buzzfeed, Fox or Vice, those are indeed excellent bylines… and also some of the hardest in the industry to get.
Yet when brainstorming new outlets for every single pitch, the odds are you’ll start over again each time with the outlets you read. Just think about how many hours that wastes, cycling through the top (least likely) outlets before looking back up every other editor who might be interested in your work.
So I created three lists on three Excel spreadsheets:
On this sheet I list every outlet I can find to whom I could, would or do pitch. I record their name, the subjects they publish on, specific style (news/blog/etc.), contact information, any editors I have a relationship with, whether they’ve published my work, our last contact and any general notes.
This sheet helps me figure out who I’m pitching to without having to stare at the intimidating search screen of Google over and over again.
On this spreadsheet I’ve begun tracking every single pitch I send out. I record the name, the outlet, the editor I reached out to, the date, the date I sent any follow up, the date of any response, and whatever response I got back. I also have a section for additional notes and, if they run the piece, what I got paid.
I mark every pitch as “Pending” until I hear back. If no one gets back to me, I’ll put that on the sheet, same if an outlet accepts it. If an editor has any comments, they go in the notes.
The result: I can know who I’ve pitched to, my success rates and what the editors asked for in response. I can also tell if I’ve started to fall behind on my pitch rate. (See below.)
On this spreadsheet I keep track of everyone I know in and around the industry aside from editors. These are my contacts and sources to whom I reach out for stories, again so that I don’t have to reinvent the wheel every time I need to get quotes for a story.
On a second page of this sheet I keep track of companies and PR firms. Like my outlets list, this lets me track both ongoing and potential work in my capacity as a copy writer and thought leadership expert.
Then I created a Trello account. Here I keep track of ongoing projects, which comes in incredibly handy for larger works. For example, when I wrote this piece I was preparing a reporting trip to Puerto Rico. On my Trello board I have a project dedicated to the pieces I’m writing down there and what it will take to bring them together.
Like organizing my work into lists, using project management software for my individual articles helps me think of them in discrete packages instead of as stories that generally need to happen.
The Numbers Game
I just. Wasn’t. Sending. Enough. Pitches.
For me, pitching is the worst part of this job. While I love finding and developing stories, that’s the minority part of what pitching actually entails. The bulk of the work you do to land a story involves writing out an eye-catching e-mail that editors might love (that takes plenty of effort). Then taking up the intimidating task of researching outlets it might be perfect for. Then sending the idea out there and waiting for it to get a response. Then following up. Then trying again someplace else.
Now, it gets easier with editors you’ve worked with before. Particularly for beat writing around the 1,200 word or less mark, once an editor gets to know you they’ll usually prefer elevator pitches of 1-2 sentences.
Otherwise, though, pitching is a slow, time consuming process. What’s more, you need to send out a lot of them. Some writers estimate that even a successful freelancer only gets a hit rate of about 25 percent, and that feels about right.
So I needed to be sending out four pitches for every one article I need to write to make my monthly income. Guess what? I wasn’t sending out anything close to enough.
I also wasn’t doing enough to build my professional network, especially given that I work remotely.
One of the biggest challenges with working in modern journalism is the degree to which it relies on relationships. While this has always been true, it has only gotten moreso as opportunities for journalists grow increasingly scarce. This problem is compounded by the fact that I work remotely and have almost exclusively electronic relationships with my colleagues.
As a result maintaining and building my professional network is absolutely essential, and I hadn’t been giving it nearly enough time.
That needed to change.
It starts with a social media presence. Now, I’m not much of one for social media. I don’t find Facebook particularly interesting, and I rarely have anything worthwhile to say in 140 characters or less. (Frankly, aside from “I love you,” “bathroom’s to the left” and “I’m allergic to shrimp,” I think few people do.) So instead I polished my LinkedIn page and started a small Medium blog which sends updates to my otherwise moribund Twitter account.
I began attending events in my local area, meeting as many colleagues face-to-face as possible and from them making as many connections as I could get.
I did the same thing with editors, corporate contacts and other journalists I get to know. Once I work with someone long enough to have developed a relationship, I reach out to ask for if they would be comfortable introducing me to their colleagues. I never do this early, as it simply makes everyone uncomfortable. (Build the relationship before asking for favors.) I also do as much business over the telephone as possible, as it makes for a much more personal connection.
Building long distance relationships is hard, and this is still an area I’m working on. It is, however, absolutely necessary to having a career as a freelance writer.
I love being a journalist, but I would also like to do two more things in my career: teach university classes and write books. These are both long standing goals, and the truth is that they have both fallen by the wayside.
That’s not acceptable.
Career stagnation is a risk for everybody, but it’s especially dangerous when you get caught up in the day-to-day of your work. For me, my waking hours had become so taken up by simply keeping the wheels on the operation that I never had time to think of the bigger picture. I just spent all day, every day worrying about finding my next byline and keeping the lights on. It didn’t leave time for trying to develop an academic reputation beyond my bylines, nor could I even think about starting a manuscript of my first book.
That’s how you find yourself still doing the same thing year in and year out.
The answer was time management. I needed to get better at managing my days and needed to get better at ending them too. Instead of working 12 inefficient hours per day, I focused and began working 8-10 good hours.
It didn’t just give me back raw time. Getting my schedule back on track freed up my mind for other work in the evenings. I could think about other things again instead of constantly fretting over what I didn’t get done at 2:00 that afternoon.
These are goals I haven’t achieved yet, but I fully intend to. I love being in the classroom. Teaching students, whenever I get the opportunity, is one of the great joys in my life and I look forward to the day when I can explain how they should contextualize law and policy in their own lives. The same goes for writing my books. I have begun my first novel. It’s a story that I am genuinely excited to tell, and every night I get to indulge in the joy of writing something sheerly for the fun of it.
Neither of those futures would be possible if I hadn’t sat down and gotten my head around my own career. It’s also been a long time since I used the word “joy” to describe my career at all, no less twice in rapid succession.
The truth is that writing has always been a business and these days it’s harder and harder for those of us in the industry to keep that at arm’s length. That’s neither unclean nor amoral, but it is a problem because the skillsets that make us good analysts, thinkers, investigators and storytellers don’t necessarily translate to marketing or client service.
But as a freelancer that’s exactly what you have to do. You are a retail location owned and operated by a one man team. Your product is words and your customers are editors, businesses and the readers who count on you. It’s exactly what you have to do because the dirty little secret has always been this: You can write the best article in the world, but it won’t make a difference if nobody reads it.
So, I decided to get better at finding people to read my work.