Writers on Freelancing: Roundtables, Tips, and More

The life of a freelancer can be flexible and spontaneous, allowing you to choose your own projects, set your own schedule, and be your own boss. But freelancing requires more than simply a thirst to write — it takes hard work and discipline. Here are resources on the business of freelancing, with practical advice from seasoned pros.

“The Freelancers’ Roundtable”

Illustration by Kjell Reigstad
Illustration by Kjell Reigstad

“In Praise of Pitching,” also at Longreads, discusses pitching stories publicly.

At Longreads, freelancers Eva Holland, Josh Dean, Jason Fagone, and May Jeong chat about pitching stories, negotiating contracts, and breaking into a tough industry:

Do the work. There’s confidently sending off a pitch you’ve done your homework on, and then there’s just throwing shit at the wall to see what sticks. I think when young writers aren’t talking themselves out of things, too often they’re rushing things out half-baked instead.

Eva Holland


“Beyond Your Blog: Freelancing, Getting Paid to Write, and Writing for Free”


Deborah Lee Luskin is part of the New Hampshire Writers’ Network. On its blog, Live to Write — Write to Live, you’ll find resources under the freelancing tag.

In this Daily Post roundtable, Julie Schwietert Collazo, Caitlin Kelly, Kristen Hansen Brakeman, and Deborah Lee Luskin offer their perspectives on getting paid to write, and the flip side of this — writing for free and exposure:

The write-for-free model establishes a precedent that isn’t encouraging for those of us who want to write and get paid (namely, that both publishers and readers start getting accustomed to not having to pay for work). It ultimately devalues words — literally.

— Julie Schwietert Collazo

Julie Schwietert Collazo and Caitlin Kelly also comment on the business of writing on their personal blogs. Explore Julie’s “freelancing” tag at Cuaderno Inédito, her site on writing and editing, and Caitlin’s writing on Broadside Blog, from “The writer’s life: MIA sources, LOIs, the quest for ideas” to “Cotton years, cashmere years: what full-time freelance is really like.”


“On Picking My Brain”

Image by 10ch (CC BY-SA 2.0)
Image (cropped) by 10ch (CC BY-SA 2.0)

In a post from last summer, author Chloe Caldwell writes about receiving many unsolicited emails from new writers looking for advice or asking how she “got” where she is today:

It is insulting to ask writers how they GOT on VICE, or The Rumpus, because it implies they knew someone there, not because their work is good. I got in The Rumpus and Salon because I went to their websites and followed the submitting directions. The secret to writing and publishing, it turns out, is writing and publishing. Mostly writing.


“10 Non-Fatalistic, Real-Life Tips for Freelance Writers”


In a 2012 post on her personal blog, Alaina Mabaso compiles a list of tips for finding and keeping freelance projects across a number of writing fields:

Be willing to tackle a variety of fields and topics. A big reason I am able to pay the bills by writing is that I don’t let new arenas intimidate me. Arts, science, medicine, aviation, farming, business, architecture: whatever it is, I track down some experts to tell me all about it, and write that piece.


“The Business of Freelancing, Blogging, and Books, According to Author Jennifer Armstrong”

Image by Magic Madzik (CC BY 2.0)
Image by Magic Madzik (CC BY 2.0)

At love.life.eat, Felicia Sullivan also explores the freelance life — especially the financial aspect — in her freelance-life-careers category.

In this WordPress.com Blog interview with Jennifer Armstrong, author of the forthcoming book Seinfeldia: How a Show About Nothing Changed Everything, we asked her about the hard truths of freelancing, and how she makes time for her blog:

No matter how many times people tell you how hard it is to be a freelance writer, you never truly understand until you do it. I guess we all like to believe we’ll be the exception.

Explore more posts in our Writing, Work, and Authors topic archives.

March 7, 2016Business, Longreads, Work, Writing