10 Questions Writers Must Ask Before Quitting Their Day Job

"The thing is, most writers don’t quit their day jobs, like you did, to start full-time writing and promoting their first books. But sometimes that’s what it takes to be successful.”

It was a simple observation, but something I’d never really thought about until my editor mentioned it over dinner last summer. Given how hard I’d worked the previous two years to sell, write and promote my first tome, I couldn’t imagine having succeeded had I not devoted all my time to the endeavor. And that’s the irony. Had I not quit my job to devote myself full time to my first book, it might not have been successful, and I’d be no closer to realizing my longtime dream: namely, quitting my job to write full time. This career conundrum is shared by many writers, especially as the publishing industry demands we do more and more to promote our work and ourselves before, during and after the book deal. So when do you roll the dice—or do you roll the dice?—and quit your day job to become self-employed as a full-time writer and promoter?

I put my head together with a number of gifted writers—some full-time, some part-time, some somewhere in between—to come up with the answers. Or, rather, to come up with some very important questions: the ones you need to ask yourself before taking the plunge.

Let me answer this for you: Of course you don’t. Nor is there any guarantee you’ll be successful even if you do devote yourself 24/7 to your writing. But working at it full time can definitely increase your chances for success, particularly when writing and launching a new book, and especially if you write nonfiction. Novelist Lisa Tucker says, “You need to draw a bright line between fiction and nonfiction right from the start,” as the expectations can be drastically different. Today’s nonfiction writers generally devote significant time to promoting their books and building their platforms. Demands on fiction writers’ time are often less—though good platforms can help them just as much.

[How To Write Novels When You’re A Parent]

“Heck, yeah!” you’re probably saying. Be careful what you wish for. Or, perhaps more accurately, make sure you know what you’re getting into.

Although Tucker has been writing full time for the past seven years, she wrote and sold her bestselling first novel, The Song Reader, while teaching full time. She found the balance it provided to be an asset. “It was a great job because it gave me a grounding in the objective world, where problems could be solved—rather than the murky, beautiful mess of a novel,” she says.

Brian Dzyak’s first book, What I Really Want to Do on Set in Hollywood, came out in 2008, and at the time what he really wanted to do was write full time. But he kept his day job as a film cameraman for financial security, and now that he’s had a taste of the publishing world, he’s not so sure he still wants to take that step, even if he could afford to. “I thought that writing full time would mean, well, writing full time,” Dzyak says. “But at least with nonfiction, so much time is spent promoting your book and doing other things, like giving speeches and seminars, in order to make a living from it.” Dzyak is currently working part time on a second book. He hasn’t ruled out writing nonfiction for a living—and he’s keenly interested in writing screenplays—but he warns that authors have to stay grounded. “Sure, you need to run after your dreams, but you also need to be realistic about what that really involves.”

This is the sword of Damocles hanging over most writers as they weigh their options, particularly in these harrowing economic times. As the author of The Ultimate Cheapskate’s Road Map to True Riches, I thrive on—and in fact now earn my living writing about—the art of living happily on less. In my case the decision to quit my job for a writing career wasn’t influenced much by financial angst. I knew exactly how much (well, actually, how little) I needed to get by. Between the income from the freelance writing jobs I was already doing, my first book advance and what I felt I could expect in additional writing-related income, I made a low-stakes wager that I could swing it financially.

But everyone’s situation is different. Generally, quitting your day job solely based on a first book advance is ill advised, as you have no track record of actual sales/royalty income; plus, there’s always a chance you’ll default on the publishing contract and forfeit your advance. Regardless of your situation, I’d recommend having at least six to 12 months of living expenses in the bank before you do anything drastic. That’s a safety net to allow time to re-enter the job market if things don’t work out. And even if things do work out, you’ll need funds at the ready to cover periods of weak cash flow—a common occurrence in the lives of most full-time writers.

Most successful writing careers are built over years—and endure for many more. Are you truly prepared for the long haul, to stick with it through all of life’s changes, good times and bad?

Romance novelist Kathleen Gilles Seidel has been writing more or less full time for 25 years, and last year she released her 14th novel, Keep Your Mouth Shut and Wear Beige. When she first made the commitment to her writing career, she had the financial security of a bread-winning husband. She kept writing when children came along, albeit at a slower clip so she could savor motherhood. With the death of her husband in 2007, Seidel’s life took another turn. “Be prepared to constantly reinvent yourself and your writing,” she says, “because the market, your readers and events in your life will all change around you. There’s nothing you can do about that, but you can choose to change with them. Be realistic, but always keep writing.”

We’ve all heard about the health insurance crisis in America, but as a full-time writer you’ll probably confront it firsthand. Many writers start by continuing their previous employer’s health coverage under the Consolidated Omnibus Budget Reconciliation Act (COBRA) of 1985, a law that typically allows you to maintain coverage for up to 18 months if you pay the (expensive) premium. Others find coverage through plans offered by professional organizations such as the National Writer’s Union and The Author’s Guild, though most of these groups offer coverage only in certain states. Other writers either secure insurance through a spouse’s employer or purchase it on the open market. The latter is often the most expensive way to go, but you might find it’s the only option.

Get 15 of our most popular resources for writers
(where you'll find answers to all your writing questions)
for one low price. Limited time offer.Order here.

Ellyn Spragins has been writing full time for almost three decades. She worked as a journalist and editor for major publications, including BusinessWeek, Forbes and The New York Times. But she quickly corrects me when I refer to her as a full-time writer. “I’m a full-time entrepreneur now,” she says. “Although, yes, my business is built around writing.”

Spragins wrote The New York Times bestseller What I Know Now: Letters to My Younger Self and two other nonfiction books. She’s parlayed the former into What I Know Now Enterprises—which offers seminars and lands her 15–20 speaking engagements a year—and she emphasizes the need for entrepreneurial and business management skills in addition to writing ability. From marketing yourself to filing quarterly tax reports to budgeting your time and money, writing full time is a business and needs to be managed as one.

Any type of self-employment can be a lonesome pursuit without the companionship of co-workers and others for your daily fix of human contact. But writing is, almost by definition, a solo endeavor, and doing it full time can leave you feeling isolated. Online interaction has, to some extent, become many self-employed writers’ stand-in for face-to-face contact. But it’s satisfying only to a point. Seidel recommends joining a local writing group, getting involved in community activities and treating yourself and a friend to lunch once or twice a week.

[5 Important Tips on How to Pitch a Literary Agent In Person]

Who doesn’t want to be his own boss? Again, be careful what you wish for. Staying on task is just one of many challenges that come with working independently. Tucker admits that a lack of feedback and an unstructured work environment can sometimes be obstacles to overcome rather than perks of self-employment. Spragins still struggles with the gravity of knowing that only she is responsible for charting her future and advancing her career; there’s no corporate ladder to climb and no one else to call the shots.

Having the support of family members and friends can tip the balance between success and failure. And failing to consider the impact of your decision on the important people in your life is the difference between self-employment and selfish employment.

For Dzyak, that’s been a primary consideration as he ponders the possibility of someday writing full time. “Pursuing any career that doesn’t involve an established salary is a significant risk for anyone, single or married with commitments,” he says. “There is so much more to consider, from your own finances to the business aspects that will keep your career alive and growing.”

And while having a spouse with a steady income can certainly help ease the financial transition into a full-time writing career, leaning on that spouse for too long can test even the strongest marriages. Communication is key.

My motto has always been, “Plan for the worst, but work for the best.” Don’t focus on failing. But have a contingency plan—or several—ready to go before pulling the plug on your day job. Knowing what other options are available should your venture not work out is only common sense. It’ll also give you tremendous peace of mind and allow you to focus on the top priority: succeeding, so that you’ll never need to implement Plan B.

This guest post is by Jeff Yeager. Yeager's the author of the bestselling book How to Retire the Cheapskate Way: The Ultimate Cheapskate's Guide to a Better, Earlier, Happier Retirement. His first book, The Ultimate Cheapskate's Road Map to True Riches: A Practical (and Fun) Guide to Enjoying Life More by Spending Less, was published by Random House/ Broadway Books and was the #1 Personal Finance book on Amazon.com. His work is also featured on his website UltimateCheapskate.com. Yeager was dubbed "The Ultimate Cheapskate" by Matt Lauer on the NBC TODAY Show, where he occasionally appears as a guest correspondent. Follow him @JeffYeager.

Thanks for visiting The Writer's Dig blog. For more great writing advice, click here.

Brian A. Klems is the editor of this blog, online editor of Writer's Digest and author of the popular gift bookOh Boy, You're Having a Girl: A Dad's Survival Guide to Raising Daughters.

Follow Brian on Twitter: @BrianKlems
Sign up for Brian's free Writer's Digest eNewsletter: WD Newsletter