So You Want to Quit Your Day Job

It’s the dream for many writers: quitting the job (or jobs) that pays the bills and writing full-time.

The unfortunate fact is, writing alone doesn’t pay a livable wage for many writers and authors, especially those early in their careers. Even traditionally published bestsellers and award-winners aren’t able to quit their day jobs right on getting an advance—and if you followed the #PublishingPaidMe discussion, you’re aware that there are vast disparities between the advances paid out.

For indies and self-published authors, smaller or no advances can mean an even longer journey to that dream of quitting the day job. However, the dream is still possible to attain with work and preparation.

At the most basic level, quitting the day job means becoming self-employed. So what goes into making it work?

Dreams come true when they’re grounded, at least somewhat, in reality. Every rocket needs a launchpad. Some of these grounding factors will be obvious, but there may be some that come out of nowhere either immediately or once you think you’ve settled into your new situation. All of them fluctuate over time.

Let’s address the big one: money. Unless you find a generous patron, you’ll still need to pay rent and bills. Rainy day savings and retirement funds need to be considered. Then there’s insurance, business investments, lifestyle …

When was the last time you really broke down how much you were spending and where? When you’re no longer employed by someone else and give up the relative predictability of a paycheck for the greater freedom and potential of self-employment, you’ve got to have a solid relationship with your money.

Traditionally published authors may be able to count on advances, but a rare few get enough of one to cover living expenses through the full publishing cycle—especially with advances being split into increasing numbers of payments over more years. And until those books earn out, there are no royalties coming in.

Self-published authors have a two-fold consideration: first, how much do you anticipate earning on a monthly basis? And second, how much of that will have to be reinvested in the next book so you’re not paying out of pocket? Paying yourself as the author comes after any reinvestment needs.

Other writers will need to consider things like how many deliverables need to be written to hit an income target, how quickly invoices will be paid, and how many clients will be needed to ensure steady and reliable work.

For anyone who is self-employed, money coming in isn’t the only concern. There’s also the tax angle. That means:

Regardless, it’s money going out that needs to be accounted for in advance—and again, before paying yourself.

[Income Tax Management for a Freelancer]

Being self-employed can be a roller coaster of emotions. If you’ve only ever worked for other people or companies, being completely in control of your own time and effort can come with feelings ranging from exhilaration to panic.

There’s nobody to tell you what to do! You can set your own hours! But you also have to own the responsibility and accountability of setting your own schedule and managing your own deliverables.

Having systems and supports in place to manage both the highs and the lows is important. Creating mechanisms whereby you feel safe celebrating your wins is just as important as creating enough of a safety net that you can keep going during downturns.

While we don’t always have the luxury of planning ahead to exchange one income situation for another, taking advance steps can ease the transition regardless of where we are in the journey to do so.

Some questions to consider:

One last thing: pipeline. What are you planning to publish or submit next month, next quarter, and next year? For self-published authors in particular, a consistent publishing calendar will help with staying on track, better predicting income over time, and keeping readers satisfied.

Regardless of how you publish, keeping a notebook or Trello board of ideas helps ensure you’ve always got something for the next book or article, thereby keeping your pipeline full. Beyond ideas, also consider growth areas (i.e. different formats, genres, or topics), pitch markets, and income streams.

So with those realities covered, let’s get to the next part: how you really spend your time. Writing all day sounds amazing! But there’s more to being a self-employed writer than just writing—even if we set aside the mental and physical demands of spending hours writing every day.

Being self-employed is being a small business. That’s not just writing; it’s also accounting, legal, marketing, sales, IT, and production. That idea of writing all day needs to be balanced with the work that supports getting the words out into the world.

Additionally, many of us have become accustomed to an eight-hour day (or longer).

But how do we really spend that time? And is that how we want to spend time?

First of all, many of us don’t really spend all eight or nine hours of the working day working. “Work” time is likely also spent:

In other words, not on the work we’re meant to deliver.

There’s also Parkinson’s Law to consider, which says that work will fill the time allowed for it. Could you cut your productive working time to four highly focused hours over four days, and leave more time for the kinds of activities that refill your creative cup?

Furthermore, we’re surrounded by hustle and grind culture. But multiple studies show that after 50–55 hours of weekly work, productivity and effectiveness drop dramatically. Not taking at least one day off per week also spells trouble. But when we’re self-employed, it can feel like not putting in big hours seven days a week is taking money out of our own pockets.

This goes back to the emotional consideration discussed earlier, but it also connects to the money consideration: If you are continuing with a 40-hour week, is all that time spent in the best places?

There are tools and apps that can help with this. For example, if you’re writing books, freelancing, and consulting, you can track the different activities in Toggl. Apps like Forest keep you off your phone, while also allowing a granular breakdown of where time is spent. Others prefer methods like the Pomodoro Technique. Find one that works for you.

Also remember to check in monthly or quarterly to see where you’re spending the bulk of your time. If it’s not on the tasks that are making money, looking at ways to decline, delay, or delegate those tasks can help get back into balance.

These questions about time present another facet to consider: project management.

Regardless of what you end up doing when you quit your day job, there are ways to structure your newfound freedom. Having an understanding of project management can help conceptualize options for how to allocate the time and money which becomes entirely yours to manage.

Project managers typically break down the overall project into three components: scope, cost, and time.

At the core, of course, is balancing all of this in such a way that you don’t sacrifice quality. Determine which of these is most constrained, where you have more flexibility, and which has the greatest impact on quality.

When you’ve found the sweet spot, stay open to review and adjustment as your circumstances change. It’s easy to fall into a rhythm, but that rhythm can become a rut if you’re not careful—especially when you’re doing well and feeling comfortable.

Speaking of being comfortable, let’s talk about growth. Growth can be decidedly uncomfortable, but ongoing skills training is part of many jobs. Stepping out of your comfort zone to learn new skills, level up your writing, seek new opportunities, or make new connections is key to continuing success.

In waged or salaried employment, skills development often follows the needs of the business. For all the challenges of self-employment, one of the great benefits is the complete freedom to structure your own time, pursue what interests you, and develop in directions that excite you.

As you’re considering whether to quit your day job, think about what skills would benefit the direction you’d like to go in. You’ll need to market yourself as a writer—maybe a digital marketing course could be a good pre-quit investment. Or attending a conference to learn about different income stream opportunities and make connections. Take inventory of the skills you have now and those you might need to go it alone, then look for opportunities to develop those skills before you make the jump.

Personal development can be as important as professional (writing) development. At a day job, it’s easy to focus on (or blame) the external factors impacting mood, performance, and outcomes. When you’re self-employed, you’re your own boss and you choose your workplace.

So what are some areas you might work on, or at least take note of? This can be an empowering exercise—think of it as building your best life!

Last but not least, let’s talk about the larger human element to self-employment.

Part of many modern workplaces is the idea of the business as a “family” or an emphasis on social activities and team building. However you feel about that, the reality is that a day job is the focal point of socialization—good and bad—for many people.

Initially, making the transition to self-employment and full-time writing can be a relief. No more of the negative interactions! But without conscious effort to build the kind of meaningful connections that both refill our cups and provide new fodder for our writing, we can struggle mentally and emotionally.

Sometimes, being a hermit is a good thing. Having the space and freedom to completely close off and go hard on achieving a milestone or goal is great. But setting objectives and an endpoint for isolation can support a healthy management of personal time and social engagement.

This idea can apply to both physical interactions and virtual. Many writers and authors feel pressure to be on social media, constantly engaging and promoting themselves. Some are energized by it—but their work suffers from the distraction. Others feel drained and want to withdraw. Evaluating and making conscious decisions about how to engage is key to managing your energy effectively and in such a way that you stay visible to those with opportunities to offer.

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Healthy balance is key to so much about the choice and transition of quitting the day job and succeeding as a self-employed writer. Taking the time to plan out practical considerations like time, money, and a work plan can smooth the process and make the dream achievable.

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