Jen A. Miller: ‘I'm going to be the Mercedes of freelancing’

The author and New York Times writer on how to increase your income and improve your attitude

When I first went freelance, I found that I kept asking myself, “Ok, but how do I actually do this?” 

There were plenty of blogposts out there talking about why you should take the leap into the freelancing, but few people spoke about what to do after you’d leapt. One person who was not only sharing her success as a freelancer but also explaining how she did it, was Jen A. Miller. 

Jen, who is based in the US, is a regular contributor to the New York Times, where she also writes their running newsletter. She’s the author of Running: A love story and also writes a brilliant newsletter which often features behind-the-scenes peeks into her freelancing process. On Twitter, she’s the boss of the freelance mafia, calling out bad client behaviour, sticking up for fellow freelancers and showing us all how lucrative and fulfilling freelancing can be. 

As a seasoned freelancer, she’s incredibly generous with her time and knowledge she’s gained over the last 15 years in this business. This interview with The Professional Freelancer is no exception – Jen talks candidly about how she made a six-figure income this year, why you should fire bad clients and how to recession-proof your freelance career.

TPF: You recently tweeted that you made six-figures as a freelancer this year. Congratulations! How did you do it?

JM: Thank you! I know it might seem like an arbitrary number, but it means a lot to me. I'll have been freelancing full time 15 years this coming January – phew!

I made this happen after having a really terrible year freelancing in 2017. I went through a lot of "life stuff," and went on a four-month road trip. While I did work along the way, I didn't market like I should have been doing. My gross for 2017 was about $55,000, which is quite low for me. When I finally settled back into a more normal routine at the beginning of 2018, work was scarce, and I panicked. 

I have been friends with Jennifer Goforth Gregory for a long time, and she offered to help. Even though I wasn't that interested in doing content marketing (which is her thing), a lot of the principals on how to find work are the same. She did a one hour consult and told me that a lot of what I was doing was good, but that I could do more. I was sending out five letters of interest (LOIs) a week, for example. She told me to send out 25 a week. I also read her fantastic book, which got my mind moving in the right direction. 

So I looked at what kind of work was best for me and my bottom line and realized I was not pitching myself as someone who could write about tech, cybersecurity and healthcare technology. I had fallen into that work a few years prior (an editor at a magazine for chief information officers (CIOs) followed me on twitter because he was a runner and convinced me to write for him, which is how I got started in that kind of writing) but I never proactively sought it out. 

I also found a list of editors at research institutions and publications – another kind of work that had always just come my way (my first job out of college was working for the University of Pennsylvania School of Medicine). So I marketed the hell out of myself: I sent a lot of LOIs (and then followed up at least twice); I scoured Journalismjobs.com, not to apply for jobs, but to learn about media companies I never heard of and got an anchor client that way. I also reached to regular clients to see if they knew of anyone else who could use me. I reached out to older clients to see if they had any work. I also asked for raises from some of my regular clients – and got some! 

My gross for 2018 was about $85,000 (I write an infrequent newsletter about freelance writing, and in it, I did a more detailed analysis). I carried it into this year and project I'll finish the year at about $120,000 – AND I still managed to take off the month of June to drive from New Jersey to California and back. Another thing I did for 2019: I participated in Gregory's annual marketing contest and scored the most points! So I haven't stopped marketing (though I admit I need to do another round - my grandmother suddenly died in September, I just ran the New York City marathon with my mother, so a lot has been going on).

In the years you’ve been freelance, how have you seen attitudes change towards freelancing as a career? 

I think we've always been seen like the scut of the writing industry, even if that's not the case. I don't think that attitude is ever really going to change so I've stopped getting mad about it, even if that message is relayed by other freelancers. I do think, though, that we've moved beyond content mills (with some notable exceptions but I don't suspect that'll work out). I wrote a long piece for Poynter about what it was like to be a freelancer during that era where I shared a lot of my feelings on it.

I'm going to be the Mercedes of freelancing. If someone else wants to be the Yugo, that's their prerogative. 

More important is changing my point of view about freelancers. I've decided that I'm going to be the Mercedes of freelancing. If someone else wants to be the Yugo, that's their prerogative. 

You often talk about the importance of firing bad clients – how do you actually do it?

A lot of the time, it's declining new projects they offer. That's a pretty passive way to do it, but it works. In the case where I have to fire someone mid-assignment: my litmus test is "is this project/person keeping me up at night, and not in the fun way?" If the situation is already there, and I just have had enough, I will tell them something along the lines of "I don't think this is a good fit and I'm moving on." I had another instance where my piece was delayed because of an editor shuffle, and when the new person got the piece, she knew that the process had been wonky but she wanted something entirely different and longer but would not pay an additional fee. I said that we obviously both recognized the long process and editor change had presented some complications and that I was choosing not to move forward with another draft. 

What happens from there depends. Sometimes I get a partial fee, sometimes a full fee. A handful of times, I've had to eat the fee (I have a fund set up to cover myself in such instances). I sometimes fight for more, but if I'm just tired of it, I don't want to throw good money after bad (i.e. my time) It's never really pleasant, but I refuse to have someone take over my life like that for a freelance gig.

I once had to give up a regular gig – I wouldn't consider it firing of a client but a moving on because it didn't work for me anymore, and I had been offered a better opportunity. I met the editor in person (because the publication was local and he's a friend) and told them why I had to move on. He completely understood and appreciated me telling him that way. 

How did you start writing for the New York Times?

I sold my first piece to the NYT in 2006, to a section that no longer exists! I started writing for them more regularly in 2010, which was soon after the "Well" section started. That's who I write for most now, mostly because that's who assigns and editors the running newsletter, which I write weekly. 

You were a freelancer during the last recession – what tips do you have for recession-proofing a freelance career, given there’s likely another one coming our way? 

I thought about that a lot when I was re-setting my business at the beginning of 2018, and concerns about a recession are part of the reason I have turned more towards technology writing and doing work for research institutions. I think they will be more stable in the next recession, especially those research institution that have endowments. Yes, I do have my regular NYT spot, but I don't do as much consumer-facing work as I used to because I find that it doesn't pay as well when you consider how long each assignment takes (and I include pitching and getting paid in that timeline) and be more of a pain in the neck, but also because I don't want to rely on it when it comes time for recession-related cuts.

I don't have the patience to be treated like dirt anymore. It's not worth it. I turn down work all the time.

I don't think you can entirely recession-proof a career, so I try to have low fixed costs, especially since I live alone – there's no other income to prop me up. So, for example, I recently bought a new TV after primarily watching shows on my laptop and iPad. I wasn't worried so much about the cost of the TV, but more about what it would do to my monthly expenses because I knew it'd make me want to get Hulu for example. I live in southern New Jersey, in a suburb of Philadelphia. While it's not the cheapest place in the US to live, I'm not paying NYC or DC or Bay area prices. I bought this house in 2018. It's lovely and perfect for me, but it's also way cheaper than what I could have afforded. I don't expect to make $100,000 every year – recession or not – so I don't live like I will.

What do not enough freelancers do enough of? 

Treat their business like a business. We shouldn't be flattered that someone wants us to write for them. We should form partnerships with people who both need our work and value what we do. They're more likely to treat you with respect. I don't have the patience to be treated like dirt anymore. It's not worth it. I turn down work all the time. If it doesn't fit with my business and my goals, I'm not going to take on that work.

When I was in graduate school, I did part-time marketing work for a local construction company mostly because – I'll admit it – my dad is an executive there. But I knew the people and the material and how to write construction so they kept me on and I wrote for them for years as a freelancer. One job was to help them write proposals, and I learned a lot by sitting in on executive conversations about them. They talked about what fee they wanted to charge, and how they would refuse to cut their fee just to get into the door because it didn't make sense in the long term. They also turned down the opportunity to work with a lot of big companies because they knew they were not good to whoever they had hired before. I know one person's writing business is not constructing multi-million dollar buildings, but a lot of the same concepts apply. 

What’s the balance of the work you get assigned versus pitched? By this point – how much cold pitching are you doing? 

I don't cold pitch much anymore. Part of this is that with a lot of my clients, I don't have to. They give me the assignments. This is fantastic because it saves a lot of time. I don't really assess clients based on per word. I figure out how much I make per hour, and if I don't have to pitch, that per hour number goes way up. I am also approached often about covering topics editors know I can write about. Whether or not I take those assignments depends on if the client and my work fit with my business.

I don't technically pitch my running column, but I do usually have a back and forth with my editor on what I should be writing about that week.

I have a really great set up with the NYT, and I write for a lot of different sections of the paper, so that is most of what I do for consumer-facing writing. Almost all of the rest is what I call B2B or business journalism. It's still journalism, but for a niche audience. I did that breakdown for last year in my newsletter, and I plan to do it again at the end of 2019.

What do you need to sustain a freelance career over the long haul?

I've said many times before that I'm not the best writer in the world, but I do enjoy the business side of things. That's key. Most people who don't stick around can't get a handle on that. And that doesn't mean they're weak or bad – it's just not for them. Also, I cannot recommend enough The Money Book for Freelancers. I have a financial planner and an accountant, but this is what taught me how to work with rollercoaster freelancer income. It is a must for anyone who wants to do this.  

Next week’s members’ post will be another instalment of Ask A Freelancer, a series in which I address any and all questions about freelancing. If you have a question for the Ask A Freelancer series, simply reply to this email with it.