Thinking About Quitting Your Job to Write Full-Time?

Ask These 12 Questions First

Years ago, when I was working for a corporate company and dreaming of being the next Carrie Bradshaw, my (now) husband set up an experiment asking me to take a day off work.

That morning, I went into the living room where he’d set up a writing desk with a notebook, pen, and my laptop with a screensaver showing: Karen - Freelance Writer. Basically, I’d been talking about leaving my job to become a writer full-time so much that my husband thought I should ‘test it out’ for a day. 

I can’t remember the exact details but I do remember the thrill of sitting down at that desk as my own boss, doing something I loved. If I’d had the option to quit my day job at that moment, I would have done so in a heartbeat. I was convinced being a writer was my one and only true calling.   

Several years later, after writing in my spare time, I left the corporate world to become a full-time writer and it was everything I imagined it would be. 

But, like anything, gradually reality hits… 

I missed working with a team and having a ‘work wife’ to gossip with. 

I missed having the (somewhat) certainty of a regular salary (I spent a lot of time chasing payments). 

But mainly, I missed the creativity because most of the work was copywriting for clients, writing to their tone-of-voice guidelines. 

I began to get bored and slowly, my Carrie Bradshaw dream was turning into another job, just without a regular paycheck, health insurance, and a team of people. 

It took a while but I eventually found a balance between creativity and commercialism. I found freedom in writing novels and handled the isolation by joining networking groups. (Unfortunately, I never escaped the soul-sucking task of chasing payments.) 

I was reminded of this experience when a fellow substacker Jana was asking for feedback on her potential plan to move to writing full-time. I know many people looking to do the same so I thought it would be helpful to share a few questions I asked myself (and many I didn’t!) before making the leap from writing around a day job to writing full-time.

Financial Stability

Do I have enough financial support for the first six to twelve months?

It’s a sad fact of life that writing isn’t the most lucrative of careers (especially in the beginning) so make sure you have financial support.

Whether it’s savings, a trust fund, or a very supportive partner, having this cushion will alleviate a huge amount of stress. When budgeting be sure to account for everything your job pays for such as health insurance but also the smaller things such as a food allowance, or gym memberships. 

Can I handle inconsistent income?

This might work if you’re a couple and your partner is working but add more responsibilities into the mix such as children or a mortgage and suddenly a regular paycheck may be more appealing.

I recommend creating a plan for income diversification (such as freelancing, consulting, coaching etc) so you’re not relying on one stream. I wrote about how I make money as a writer and included a visual of my different sources of income if you want to check it out. 

Writing Discipline & Routine

Am I disciplined enough to write consistently?

I consider myself fairly disciplined but there are definitely times when I procrastinate. Without the pressure of a manager and external deadlines, it can be hard to find the motivation. One tip is to work on changing your mind shift from writing as a side hustle to being a professional writer.

Do I have a realistic writing routine?

While your average corporate job is 9 - 5 (and then some), writing for a full day can be quite draining. Most likely, you’ll be able to write for a few hours and then do other tasks such as editing, pitching, emails and so on. Identify when you’re at your most creative and create a writing routine that maximizes productivity. 

Creative Resilience

Can I handle rejection and setbacks?

We writers can be sensitive souls but rejection and criticism are part of the job and when you’re writing full-time, you can expect more of it. If you’re working on a book, consider that most traditional publishers reject over 99% of submissions.

If you’re running your own writing platform, anticipate negative comments and if you’re penning articles for publications, an editor’s “constructive feedback” can hurt even the most stoic among us.  I say this, not to put you off, but to encourage self-evaluation on your emotional resilience and ability to stay motivated. 

Do I have a clear writing vision and a plan to get there?

Before writing novels, my vision was to write travel features for the likes of Condé Nast. To achieve this, I wrote travel articles for free (usually based on my vacations) to build up a portfolio of published work. When I finally did leave my job, I had a body of work that I could then use to get paid commissions.

My writing goal has changed a lot over the years but understanding what you want to achieve as a full-time writer will give you a sense of direction and purpose. 

Support System

Do I have a strong support network?

It’s not essential for a successful writing career but having the emotional, creative, and financial support from friends, family, or fellow writers makes the move to full-time a lot easier. I also recommend getting a mentor to help you avoid potential pitfalls and costly mistakes. 

Have I connected with a writing community?

A writing community can be a wonderful thing (as long as you don’t go down the compare and compete route) providing you with feedback, advice, and motivation. This could be online or in person (I do both) and are a great source for ideas and inspiration.

It can take time to find a tribe you connect with so experiment a little. A writing community can also help with the feelings of isolation. 

Career Strategy

Do I have a plan for growing my writing career?

Traditional publishers are more reliant than ever before on writers doing their own social media marketing. Today, you have to be a writer, a marketer, a social media expert and so on. Most successful writers I know have a newsletter or a podcast or a book club. All of this takes work and in some cases learning new skill sets.

If you plan to self-publish, you may have to learn about book software and platforms, cover design, and digital marketing. 

All this to say, that it’s not just about the writing but having a plan in place to grow your readership.

What will success look like for me? 

This is such a valuable question to ask as it’s not always about getting on the best-seller lists. Success comes in many forms - it could be about income levels, personal fulfillment, or simply being creative every day. 

Lifestyle Considerations

Am I prepared for the isolation of writing full-time? 

This was a particular challenge for me and there were whole days when I only spoke to the postman. I discovered I needed daily interaction to feel inspired. This might not be the case for you but it’s worth asking how comfortable you are with your own company for hours on end. 

How will this decision affect my family and relationships? 

Writing is hard enough without having support from loved ones. Discuss your decision with the people who will be impacted by leaving your job to move to writing full-time. Identify potential challenges and come up with ways to address them.

Once I left my full-time job, I ended up doing more of the household stuff simply, because, well, I was at home. It was distracting and gave me too many opportunities to procrastinate. To solve this, I created my own work space, took my profession seriously and had open communication with family.

While there were challenges, moving to writing full-time was the best decision for me. Ultimately, only you can know if such a major life change works for you but I hope by answering these questions, it makes your decision-making process a lot smoother. 

Have you made the move to writing full time? What was your experience? Share in the comments below.