The Freelance Life: Tips on Staying Sane

By Necee Regis

I was tempted to put quotation marks around the word “Sane” in the headline of this post. Because who in their right mind would choose freelance writing as a profession? (I’m tempted as well to write: “profession.”)  But I’d rather leave all snarky witticisms aside, and proceed with the knowledge that anyone who embraces art as a career has got to be a little bit crazy. And I mean that as a compliment.

To earn a living as a freelance writer I need to wear many hats, or juggle many balls–pick your metaphor. With no trust fund, employed spouse, or sugar daddy in my life (at the moment!) I need to cobble together an income from many sources. Thus my to-do list for a week often looks something like this:

Compose handouts for travel-writing class-email to Mary Ann

Submit photos for Portland story to Anne @ Boston Globe

New travel pitches to Anne (Quebec City, Eataly, PEI)

Menus for Berlin/Liebman bar mitzvah

Advertise Miami apt sublet on Craigslist

9:40 Wed-Genius Bar @ Apple Store-Fix iPod

Write/Submit LA story to Wash Post

Artist statement/images to WCCC


I’m aware that in many ways I have it easy. I mean, I only have myself to organize. I don’t know how some of my fellow writers who are parents do it. (I admire them more than they know.) Still, the freelance life in any form–with spouse or not, kids or not–can be stressful. In order to manage all this and not go bonkers, I’ve developed some strategies to make it all work.

1. Make Lists. (See example, above.) Writing a list of things to do is immensely helpful. It not only clearly spells out the tasks at hand; it can alleviate some of the free-floating anxiety that accumulates when one has many diverse commitments and deadlines. Basically, list-making can give you a sense of control by knowing exactly what needs to be accomplished in a given day or week. And the satisfaction of crossing something off is a little serotonin rush of its own.

2. Make A Schedule And Stick To It. Okay, I know, this isn’t easy. And life, as they say, has a way of making other plans. What I’m suggesting is to create a general template of how best to organize an otherwise unstructured day. Otherwise, two or three days will disappear in the blink of an errands-running/meeting for coffee/chatting on Facebook eye.

Tailor your schedule to when you know you work best. Some people write better at dawn, others in the evening. My template is something like this: Drink espresso, check email/Facebook, swim laps, run errands, eat something, write-write-write (usually 11:00 a.m. or noon till 6:00 p.m.) dinner and fun time, sleep. Repeat.

3. Write Smart. Being a freelance writer is a lot like being a competitive oyster shucker. In the latter, results are determined by both time and presentation, and the best competitors strategize to balance speed with perfectionism. In other words, you can’t just be fast. You have to be fast and clean.

It’s the same with writing. I have to balance writing fast with writing well. Though I think of myself as a slow writer, I don’t have the luxury of endlessly contemplating every verb and adjective. I do my best to avoid clichés, maintain a consistent tone, and narrate my story in an interesting way. At some point I must determine that my project is done, and move on.

4. Reach Out to Friends. Writing at home can be a lonely endeavor.  Maintaining contact with the world outside your own four walls is good for your psyche and, I’d argue, makes your writing more interesting. In this way, Facebook is a godsend to freelancers, as it acts as a virtual water cooler where pals can gather for a break. (On the other hand, Facebook can also be a huge time suck. Use judiciously!)

5. Exercise Regularly. I don’t know about you, but I often find that I’m slouching at my desk, and hardly breathing. Exercise can relieve the stress and tension that comes from sitting at a keyboard many hours each day. I don’t care what you do, but do something. (Put it on your schedule!)

6. Minimize Expenses. Freelance income is sporadic, so one has to learn how to maintain a satisfying lifestyle without worrying all the time about paying bills. If you can minimize expenses, you’ll have money to save for when times are lean, when emergencies arise, or when you need a well-deserved splurge. Every so often, it’s good to take a hard look at your expenses and delete any unnecessary costs. For example, do you need a cell phone AND a home phone? Some people do, but I decided I didn’t and saved $70/month by dropping my landline.

7. Network. The way to get more work is to make and maintain professional contacts. Social media is great for this–Twitter, Facebook, Linkedin–though they aren’t a substitute for meeting people face to face. Professional organizations like Media Bistro and Grub Street often sponsor get-togethers and workshops where you can meet and mingle with fellow writers, editors and agents.

8. Be Madcap. Every now and then, do something unexpected. Skinny-dip in the bay at night. Sing “Row-Row-Row Your Boat” on the subway and see if anyone will join in. Write a letter to Charlie Sheen’s agent to see if you can ghostwrite his new book, Apocalypse Me. (No–wait–I’m doing that! Hello, Charlie? Call me! I’m sure I’m less expensive than those Hollywood hacks.) There’s no better way to maintain your equilibrium and sense of humor than allowing your inner-Goofy to roam free.

And now, if you’ll excuse me, I have to go and cross something off my list.

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Are you tempted by the freelance life? Do you live it? What tips can you add to balance work and pleasure?

["The Juggler," Oil on Panel, 1981, by Michael Parkes]

A freelance writer with an MFA from Mass College of Art, Necee Regis is a frequent contributor to the travel and food sections of The Boston Globe and The Washington Post, and has also been featured in the Los Angeles Times, American Way Magazine, Spirit Magazine, The Globe and Mail, and the literary magazine, Tin House. Excerpts from her novel, Glitterbox, were published in Gulf Stream: New Voices From Miami (2003) and in Hacks: 10 Years On Grub Street (2007). She is currently polishing her second novel, and welcomes all serious queries from agents, interlopers, thrill seekers, and her mom. She lives in Boston and Miami Beach.

About the Author

GrubWrites is a space for the writing and reading community to share ideas and seek advice, a place where writers at the very beginning of their careers publish alongside established authors. Book lovers, we bring you reviews, recommendations, and conversations with exciting new authors to keep you up to speed on all things lit. Writers, this is your one stop shop for expert craft talk, opinions on how we learn and teach writing, and essential advice about the publishing industry.

Plus, we want to hear from you! Our ongoing call for submissions is open to literary community members of all types and persuasions. We want to hear from students, teachers, authors, readers, editors, agents, publicists, and any devotee of the written word. If you have something to say about writing, reading, the publishing industry, or anything related to the literary world, this is the place to voice it. We’re particularly committed to advocating for a diverse range of voices in the literary marketplace and raising the visibility of writers from under-represented communities.

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