- At the end of 2019, Wendy Fox left her six-figure job in senior leadership at a tech company.
- She decided to take the plunge to become a full-time freelancer and author, having already published three books while she held a day job.
- To make it work, she timed the choice carefully and met with a financial planner to see what her needs would be.
- She treats her writing like a startup, currently seeing herself as well-positioned but bootstrapped – and she’s realistic about what she needs to make it work.
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I always wanted to be a writer, but, for much of my working life, I didn’t want to try and make a living as a writer. Even a decade and a half ago, when I was finishing graduate school – I have a Master of Fine Arts in writing – earning money in the writing life was bleak. These days, most freelancers can only expect to earn about $10,000 to $20,000 a year. One 2018 survey of 1,300 freelance writers found that almost 60% of them made less than $20,000 in gross revenue.
Book publishing is not necessarily more lucrative. The average advance for an author is somewhere in the $15,000 range for a fiction book, and more like $20,000 for a nonfiction book.
Even if you’re a fast writer and crank out a book every two years, that still means every advance has to be amortized over at least 24 months. You don’t see another dime until the advance is “earned out” – an advance is a loan against your royalties, and you earn it back about a buck a book at a time. In my final months of grad school I was not planning my move to New York City; I was teaching myself to touch-type, relatively sure I would end up at an office job.
I did land a teaching gig just out of school, but I didn't see a way forward in higher education without a doctoral degree (more debt) and a book (I hadn't written one yet). After almost two years, I found a tech company who was willing to take a chance on me. Over the next decade and a half, I climbed the corporate ladder to an SVP of marketing position.
Yet, despite being very aware of what I was getting into, near the end of 2019 I left a six-figure, senior leadership role at a growing tech company to take the plunge as a freelancer and author.
While I'm at the beginning of this journey, here's how I planned for it and what I've learned so far.
I did some real soul searching
Meaningful work - and we are all allowed to define this in a way that makes sense to us individually - is very important. I had to think about and reconcile what it meant to leave a career that I had worked so hard to achieve, and that had so much of my identity wrapped in it.
I had to come to terms with how my identity as a writer was coming in second to my life as a VP, even though writing felt more significant to me. While I left the company I was working at for seven years on good terms, the truth was that I was ready to move on. The brand I helped build was ready for a fresh eye, and I also increasingly felt that I was not aligned with senior leadership.
What I had to figure out for myself was if I finally wanted to pivot away from a tech gig or go out on the market and find something new in professional or cloud services.
Over time, I found a way to manage both my day job and writing on the side. I said no to everything that was non-essential. I built a barrier around my personal time that was impenetrable by family events, the need to exercise, household chores, and friends.
I'm embarrassed to admit that, at the peak, I was spending $800 a month on outsourcing things like house cleaning and laundry, and that does not even include my Instacart, GrubHub, and Drizly bills. My husband, who also works in tech, traveled over 130,000 miles last year on close to 100 flights, so he was not available to help out much with these chores.
Money was something that had become easy for us, at a certain point.
What I need was time to pursue my writing. There was the time I protected, and there was time I could buy. In a way, it worked: I did get those three books done and landed a promotion to SVP. Yet, I also had to force myself to ask if the status quo of balancing all of this - and hanging on by a thread emotionally - was really worth it in the long term.
I understood that timing is everything
It took me years to build my career in technology marketing; it was a path I went down because I had debt and student loans. Being in tech removed much of the financial pressure I had been feeling, and it was the right choice at that moment. I was able to afford a starter home in my late 20s.
I stayed because I liked the actual work, which is both creative and analytical; evidence shows that liberal arts grads are excellent workers. I not only learned a great deal about the physical, virtual, and application infrastructure powering the modern economy, I was also exposed to business at large in a way that I would not have had if I stayed in education.
While it was tempting to quit my corporate gig when my first book went under contract, I was only 18 months into a new job that felt like it had some promise. Good thing I didn't leave: I ended up not earning out my advance. My second book, two years later, sold somewhat better, but by then I was committed to waiting to really get serious about making the switch until I became what is called a "mid-career author," someone with three or more published books. My most recent novel and third book, "If the Ice Had Held," has sold audio and translation rights, and the book, somewhat ironically, has a corporate setting.
I'm in a far better place at this point both financially and artistically, with a fourth book under contract and early interest in a manuscript that would be my fifth full-length one. I'm glad I delayed leaving my day job, and I'm glad that I went that route in the first place. Getting the timing right has ultimately been an onramp to a dedicated writing career.
I worked with a financial planner
Only 17% of Americans work with a professional when it comes to their finances. The rest are winging it.
Earlier in my career, I did some very dumb things, like leaving a job four months before I would have fully vested in a retirement plan (I could have just stayed, but I was in a hurry and it cost me) and using the default options in company-sponsored savings plans. Working with a financial planner who cared about what I ultimately wanted out of life helped me create an actionable program with concrete numbers. This made the prospect of leaving my day job for a freelance career much more tenable, because I had a clear idea of what I was working toward. Now, I have a more appropriate idea of how much I need to earn in order to stay on track.
Budgets, while a relatively simple concept, can actually be pretty challenging in practice. People who earn more money are often much less disciplined than those who are making less. A reputable certified planner who listens to what you want can go a long way in ensuring you are making smart money decisions concurrent with a large change.
Frankly, I thought my planner was overestimating what I would truly need on a monthly basis because I was not looking at my finances as closely when I was receiving a paycheck every two weeks (see above, $800 a month for household services). Sure enough, in week one without my regular paycheck, a rabbit started living in our garage and chewed through the wiring in my car. Unexpected repair cost: $384.
I treated my career like a startup
As a writer, I care about language, and the words we use to describe what we are doing matter. I find myself constantly correcting people who ask about my "retirement."
I am not retired - I am a 40-something woman who is taking a big risk on a career change by being self-employed. This could easily blow up in my face if I do not protect my time.
Though the stigma of being away from work is changing, it has not totally gone away. Every day that I do not return to a corporate gig makes it less likely that I will be able to, should I want or need to, so the stakes feel necessarily high.
Yet, it's helpful to think about my new career in terms of being a well-positioned but still bootstrapped startup. I'm in a cash burn right now, but it's not as bad as it would be if I didn't make some adjustments to in-source instead of outsource. As a knowledge worker, my biggest and most valuable commodity was time, and that still holds, but I do have more time to reclaim tasks that I was farming out.
In that same vein, Parkinson's Law - the idea that work expands in order to fill the time available for its completion - is very real. I still have to set deadlines for myself. I have to meet daily word count goals, and I have to apply the same pressure to perform that a boss might put on a worker. While my daily work schedule is not as regimented as it was when I was going into an office, I still find myself saying "no" to non-writing-related activities almost as often as I used to while I work toward getting myself to break even and then be profitable.
But doing this work just for me is more engaging and rewarding than doing it for someone else.
I was realistic about what I needed
It's worth noting here that I do not have children (by choice), I am not in a single-income household, and I have health insurance through my husband's employer. That said, I was never comfortable fully hitching my financial life to a spouse, and I've had to be realistic about what taking a huge step back from a high-earning career in order to write for freelance wages means.
An article like this nets between $200 and $400 in many national publications. Rates can slide up (or down!) depending on the topic, the brand of the writer, and the publication's distribution, but freelance pay obviously is not a cash cow. Each story assignment, in a way, is like getting a new job.
The choice to write freelance probably wouldn't work for me as a sole mortgage holder, like I was a decade ago. It also probably would not work if I didn't live in a relatively mid-priced city.
But it does help me in healing from the grind, and using the time I have now to write articles like this one. I suppose at some point, I also need to vacuum, but that, for now, can wait until I meet my next deadline.