Best Advice From Freelance Writers and Editors, 2021
plus last chance to save 40% on subscriptions
Hi writer friend,
It’s now been nearly two years since I started One More Question. When I hit publish on the first issue, and sent it out to about 15 friends, my simple plan was to write an essay on writing every week. As the list of subscribers grew, I started including pitch calls and deadlines for things like grants and fellowships.
There are now over 2,000 of you on the free list, and about 250 paying for a monthly subscription. Those numbers have motivated me to keep finding ways to offer you more honesty and insight, more value, and more perspectives on what it’s really like to make a living as a freelance writer. And to do that fully, it was important to share perspectives other than my own.
This past year, that’s really been the focus—bringing you advice and stories from writers who do all different types of writing. Through Q&As and guest posts, they’ve shared what works for them, the mistakes they’ve made along the way, and so many lessons for all of us to benefit from.
As the year winds down, it is such a joy to look back at the many writers I’ve published here, and all of the collective wisdom we’ve gained from each other. So, now seems like a good time to round up some of the best nuggets of advice shared by our fellow freelancers in 2021.
I hope you are looking back at your own work this past year with some combination of pride and conviction to keep doing the damn thing. No matter how much you wrote, or how much you didn’t write, you kept showing up and finding ways to be a working writer, or to keep tinkering away at your creative projects, or maybe just continuing to learn and ponder while you focus on other things. All of that is worth celebrating.
Thank you for being here through whatever your writing journey has looked like.
The Best Advice on Making it Work as a Freelance Writer 2021
On tackling a big creative project…
Don’t be intimidated by the longevity of the project. If you start working on it now and write 300 words a day, you’ll be at 109,000 by this time next year. You have to start chipping away at your projected word count and get something on the page. You’ll thank yourself in a year from now for having the chutzpah to take on the task. — Megan Walsh
On applying to fellowships…
Don’t try to tailor your application to what you think the organization wants. Be frank and honest about what kinds of stories you want to do and what you want to achieve. Ultimately, a fellowship is a kind of investment in yourself and you should only invest in an organization that is really willing to invest in you as well. — Sarah Sax
On juggling multiple projects and topics…
You will not finish everything. I’ve learned that some days, one project will take a lot longer than anticipated. If that happens, trying to abruptly switch to something wildly different will not result in your best work. Turn off, re-charge and try again. — Jeremy Fuchs
On protecting yourself when writing personal essays…
Writing is catharsis. I need to do it as much as other people need to hear the stories. But I need to feel safe doing so. There are certain publications I won’t pitch to because I know the personal stories they feature are there for people to mock rather than empathize with. And now I’ve added certain editors to that list. — Olga Alexandru
On bread baking as a productivity tool…
According to psychologists, the baking process induces a sense of calm and may even promote creativity. For me, there is a deep benefit from periodically getting back into my body to focus on a manual task. When good writing often feels like an unguided trip into deep space, especially the early stages, the feeling of dough in my hands is grounding. — Lynn Curry
On advocating for yourself…
As a freelancer especially, I don't have someone else I can turn to that is going to speak up for me. I have to be the one that takes the initiative to speak for myself, whether that's in relation to clients, negotiating contracts, pitching, or even just in everyday life. It can be nerve wracking for sure, but it's definitely one of the most important things I've learned at a whole new level this past year. — Paige Lyman
On writing and parenthood…
As a parent, it’s important to have some time for yourself. And as a parent who’s also doing creative work, I believe setting aside time for creativity is an important form of self-care. For me, it’s even more important than other self-care activities I do like exercise, meditation, and even just vegging out watching TV. — Lyle McKeany
On specializing…
Don't be afraid to geek out on things. Frequently my coaching clients say things like, I don't want you to think that I'm a weirdo, because I know and read everything about this one thing. But [hiring managers] want people who are obsessed with their stuff—that's what makes you highly qualified! So be the weirdo. And reach out. And you know, don't be afraid. — Chandra Turner
On getting invited to press trips…
I recommend being proactive and reaching out to PR firms that represent travel clients you are interested in working with. Email them to meet for a coffee or just send an introduction with samples of your writing — that is another way to get on their radar and up the chances of being invited on a press trip. — Nikki Vargas
On tracking your hours…
I track my hours and have a spreadsheet that calculates my hourly rate along the way for each assignment. That helps me see if a project is actually worth my time and really guides my decisions about what work to take on in the future — and when to negotiate for more. — Mike De Socio
On the decision to apply for an MFA…
One of the biggest incentives for going to grad school is the opportunity to work with people whose writing inspires you — and that’s true of both classmates and faculty members. Fate (and the admissions committee) gets to decide who your classmates will be, but when it comes to faculty, names and credentials are listed right there on the school’s website, along with their genres and areas of expertise. These are the people who will (hopefully) hold your hand and shape your work for the next few years — and also the people who will sit at that long, scary table when you defend your thesis. It’s worthwhile to at least poke through their work and see if you’re on the same wavelength. — Jamie Cattanach
On building a portfolio for higher paying work…
I think of my journey as sort of a family tree where I took one aspect of my life and turned it into an article which could be used as evidence that I can write another type of article. It went from personal parenting essays and branched into two sections: service parenting articles and divorce content. Service branched into medical, educational, and financial articles which were not necessarily related to my role as a mom. — Laura Wheatman Hill
On starting a side hustle…
Start small. It’s okay to have big plans — I literally have dozens of documents and spreadsheets for ideas and other stuff for the future — but you are only one person with a limited amount of time. You can do anything, but you can’t do everything. — Daniel Levitt
On doing work you love…
You have to love this job to make it work for you. You will also probably have to build your own brand while you’re at it, because editors come and go at the snap of a finger. I have seen major outlets take my pitches and assign them to staff writers. I have been chastised for turning in assignments ahead of deadline. I have had my work exploited for zero pay. And I have had countless drinks with other writers who have had the same experiences happen to them. My best piece of advice? It’s exactly what I tell them, and it comes from an infamous former mayor of Memphis: “Shake the haters off." — Joe Sills
On finding mentors…
Find people who are doing the job you want to do and just reach out and ask if you can take them out for a coffee or have a chat over Zoom. Some people won't respond, but others will -- and those of us who've benefited from the help of others along the way are usually pretty happy to pay it forward. — Paige McClanahan
On developing new skills…
I committed to learning each day, which is essential to making more money and buying more time for writing. Just 15 minutes a day. I’ve been doing that for a decade now, and the difference is incredible. I can come to my clients as a strategist and a consultant as well as a writer, which means I can charge more per hour and buy more time for creative writing. — Paulette Perhach
On responding to edits…
The only thing *I* [as editor] want is to know why a note doesn’t work for you, so I can be better at helping you get where you want to go. You’re the one driving the car; I’m just helping navigate. If you think my directions are shitty, tell me. Your name goes on it, not mine. You have to love it. — Michelle Weber
On writing (or not writing) about trauma…
It’s easier to speak truth to power and be ok when you have personal and professional support networks, sources of internal and external validation that aren’t tied to income or bylines, an understanding of one’s toxic traits and foibles. It’s necessary, too, for the successful essayist to find new methods of self-interrogation, to understand fully if you’re engaging with yourself in your work, and how your work is impacting your ability just to be.. — Meghan O’Dea
On all the other work…
I learned that freelancing is really running a business. There’s so much administrative work that’s a part of the job - pitching, responding to emails, onboarding, invoicing - all of it takes time, so that’s why I think it’s really important for freelance writers to negotiate rates to cover some of those hours spent doing administrative work. — Mariette Williams
On interviews and edit tests…
Learn the publication’s voice and intention behind publishing a piece—that can really set a good tone, if you approach an interview or edit test coming in at the publication’s level. Looking at the previous intern or fellow’s impression on the magazine is another huge one. That research is akin to pre-reporting if you’re writing a story—basically it’s extra work, but you’ll thank yourself for doing it. — Kevin Johnson
On making the time for big stories…
There’s an ebb and flow with long-term stories. For me, they always start slow. I do research in between other work and start looking for and contacting sources. Then depending on the story timeline, most of my interviews end up happening in the same span of 1-3 weeks. I can mostly do interviews while managing other work, unless there’s travel involved. I only occasionally travel for stories, but if I am, then that usually takes up 2-3 days. I transcribe interviews and compile notes in the midst of doing other work. — Adina Solomon
On embracing a niche…
Specialize! The sooner you niche down, the sooner people start to remember who you are and what you do. It's just easier to remember when you're all in on one very specific thing. — Kaleigh Moore
On working towards those big dreams…
Do one small thing each day that gets you closer to that dream. Do your morning pages. Can't sleep at night? Use that time to picture your end goal. Then, take one step towards that goal. Want a New York Times byline? Start reading guest essays and think of topics you might be able to write about. Write a few lines down every day. Eventually it will be something you're proud of, and then one day, submit it to the editors. If you don't hear back, you're no worse off than you would have been had you not actually done the writing. — Amy Shoenthal
That’s all for this year, friends! If you’ve enjoyed One More Question, it would mean so much to be me if you forwarded this issue to a writer friend or shared it on social media. Reaching new subscribers is what helps me keep doing this work—and I am really looking forward to doing a lot more of it in 2022.
And again, thank you so much for being here.
Stay inspired,
Britany