How this 6-figure freelancer cracked the code to happiness

Hello friends! I’m moving this week (Yay! But also ughhhhh), so I’m pulling from the archives of my all-time favorite installments of the FWT series “8 Questions With …” featuring one of the most successful — and most content — freelancers I know: Jen A. Miller.

Jen has been a freelancer for more than 21 years, and in that time she has unlocked one of the holy grails of the freelance life: finding a perfect work/life balance while still making bank.

But how?! Read on to find out, then check out Jen’s newsletter, Twitter, Instagram, LinkedIn, and Bluesky.

I’ve been a full-time freelance writer for 19 [edit: now 21, congrats Jen!] years as of January, and while I’d like to say what I write about, the answer is a lot — and my focus changes as my interests do. For example, when I started out, I wrote a lot of travel stories about New Jersey, and then for a while, I wrote about running. Now I’m more focused on specialized science work. I’ve also written three books in the traditional fashion, the last one being the memoir Running: A Love Story. And I write about how to be a freelancer through my free Notes from a Hired Pen newsletter, and a series of $10 ebooks: How I Made $135,000 in One Year of Freelancing, Where to Find New Freelance Writing Clients and Turbocharge Your Career, and Freelance Writing for Laid-Off Journalists (and Those Who Want to Quit).

I love love love freelancing. It has led to an ideal work/life balance for me. I generally work about 30 hours a week, and I take off a month every summer to go on a long road trip visiting national parks. It’s not the easiest way to make a living if you don’t like or are uncomfortable running a business, but it’s been an ideal career for me.

I’ve been writing for a few different titles at Industry Dive, a B2B publisher, since 2019. I found them by looking at full-time job listings at journalismjobs.com. I wasn’t interested in a full-time role, but I search there occasionally for media companies I might not hear about otherwise. They were advertising for an editor for Construction Dive. I used to work in that industry before becoming a full-time freelancer, and I had previously written for other construction publications, including Engineering News-Record, so I sent them a letter of introduction. That’s a short intro about me, my experience, and relevant clips. After a bit of back and forth, my name was passed on to editors at a few of their other verticals, including CIO Dive and Supply Chain Dive, and they’ve been an anchor client ever since. Funny enough, I didn’t start writing for Construction Dive until last year. 

It starts with a sad story — just a warning. In August of 2023, my previous dog, Annie Oakley Tater Tot, died very suddenly. I was inundated (of course) by the Rainbow Bridge, which I ended up writing about for Slate in December, a story that included interviewing the woman who wrote the poem (yes, she exists!) and also Rachel Bloom. I wrote about the pitch process in my Notes from a Hired Pen newsletter, so you can see exactly how the story came together! I point out there, but also worth saying here, that I don’t pitch a lot anymore because most of my work comes directly to me, but I do when something’s important, as this one was. (And to end on a not-sad note, I adopted a dog a month ago — Bonnie the Button. She’s very cute, as you may imagine).

I wrote a story that ended up running longer than we thought, so I asked for a bump up in fee, and I got it. I also had been having a series of conversations with an editor I worked with for a long time about how the publication’s rates were not up to par with what other similar companies  were paying me, and she finally got the budget to raise my rate. 

The benefit of these negotiations is that I’ve known both editors for a while, and they are also familiar with my freelance writing instruction, and know that I encourage people to ask for more. They don’t take it personally (nor should they!). I have also asked new clients for a slight pay bump over what they’ve offered me, and I can’t remember a time someone has said no. It’s one of those things that has just gotten easier over time.

I’ve been doing this for almost two decades, so a lot of work comes to me, either through previous clients or referrals from them. I’m still writing for one of my first freelance clients, in her role at a different organization. I am big on sending letters of introduction, which are those short emails with a few lines about me and clips (and then I follow up on those emails twice). Since I write for a lot of specialized science publications that generate their own ideas, this has been an effective way to get my name and my work in front of them. How often this leads to paying work varies. I don’t hear back from a lot of people, but I’ve gotten assignments as quickly as two hours after sending an email, to as long as three years. 

I’m at the point where I really don’t pitch much anymore because, again, I’m working with editors who come up with their own ideas. Pitching can also mean a lot of work to toss ideas into the void. I think of it as a necessary evil when I have something I really want to write (like with this essay I wrote about learning to surf at 40 — that finally got me into Oprah!). But I’d say that I pitch about 10% as much as I did when I started freelancing.

But when I do pitch, my success rate is much higher than it used to be. That comes with being very selective in what I pitch, getting better at pitching over time, and knowing a lot more people than I did when I started out.

Lucky for your readers, I already broke this down — I do every year when I write a piece for Notes from a Hired Pen about the previous year.

Here’s the breakdown:

This has changed a lot since I started doing this kind of tracking. I don’t write for consumer publications nearly as much as I used to, which was my choice. I’ve shifted more into the science writing side of things, and a lot of that just happens to be for association publications like Clinical Laboratory News, and medical and engineering school publications, like Stanford News. In a way, it goes back to where I started. I initially went to college to study marine biology, then switched to English Literature. Then I worked for an Ivy League medical school while getting my master’s degree, also in English Literature. I like the work, it pays really well (because you need specialized knowledge to do it, and there aren’t as many writers vying for those spots), and I learn so much! 

I hesitate to offer advice to new freelancers, because it’s been so long since I started, which was really in 2002 as a senior in college, when I freelanced on the side for beer money.

But I always tell people to start by mining their own networks. This is especially true for people who have been in the working world before — including, but not limited to, laid-off journalists. Whenever I’m scrounging around for new work, I make a list of every single person I know who might be able to offer freelance work — or knows someone who does. I advise other people in that situation to do the same thing. LinkedIn is really great for this. I once found an anchor client when I realized someone I knew from the local running community was the marketing manager for a major Philadelphia law firm, and writing for them helped pay my mortgage for years (and when I didn’t want to do that kind of work anymore, I passed along the name of a friend new to freelancing who had a legal background, and now it’s helping her pay hers!).

Of course, you should do things like network with other writers, and pitch, and send letters of introduction, but when you start with who you know, the lift is just so much easier because you don’t need to tell them how great you are — they already know.

It took me some time to figure out the financial side of things, about how to roll with the highs and lows of when money comes in. I cannot recommend The Money Book for Freelancers, Part-Timers and the Self-Employed enough — I still use their system of separating every single check into buckets, so now 60% of each check is already earmarked for something else the moment the direct deposit lands or check clears (though I do the breakdowns manually). I see so many talented freelancers get tripped up on the uneven income of it all. Their system has helped me so much. 

Also, I always remember that it’s not personal. Freelancing involves a lot of rejection, and while a “no” still stings sometimes, I realize that editors are just people trying to do their jobs, and I’m just a person trying to do mine, and those things don’t always line up. 

Two things: First, if the way an editor acts is so unprofessional/mean/disrespectful/what have you (and that includes being chronically late payers) that it’s keeping you up at night, and not in the fun way, fire them. They’re not worth your work or time, no matter how famous a publication they work for.

And second: You don’t need to live in New York City (or some other expensive city) if you don’t want to in order to make it as a freelancer. I decided early in my career to stay in South Jersey in an inner-ring suburb of Philadelphia, near where I grew up, to keep my overhead costs low. Would my career have been different if I chose otherwise? Of course. But I also own a (small) house with a (small) yard, and I live in a community I love near the people who are important to me, and that to me is golden.