I quit my job as a full-time engineer to be a freelance writer

And here’s how I did it

Kaylee Moser
Aug 27, 2019 · 7 min read
Photo by Christin Hume on Unsplash

If you are someone who has searched “quit my job” in hopes of finding stories of people who have quit their job to follow their passion, then this article is for you.

I can’t count the number of times I scoured the web looking for inspiration from people who moved from software engineering to freelance writing. I kept looking because I never found it.

I wanted to know that I wasn’t alone in feeling unhappy in my career. I was trying to find detailed stories so I could have a path to follow. I craved validation that I wasn’t completely loony to walk away from a high-salary tech job with full benefits to work for myself in a volatile field that pays much less.

I’m not here to tell you to copy exactly what I did, I’m just here to tell you is that it is possible.

I worked as a software engineer in the Bay Area for five years. While originally I went to college to study film, I decided to switch schools halfway through and change my major to computer science. I decided I needed to have a stable career that didn’t involve being on set all day, plus I wanted to move back home to the Bay Area (coincidentally where my boyfriend at the time lived too).

Upon graduating with a BS in Computer Science, I immediately entered the workforce. Over the next five years, I held a number of various engineering titles. I tried my hand as a Test Engineer, Back End Engineer, Front End Engineer, and even as a Sales Engineer. I worked at a giant corporation, a tiny 3-person startup, and a mid-size Series C startup. I coded in Tcl, PHP, Python, Go, and Javascript.

Some of it was better than others, but truthfully, I never really enjoyed any of it.

I never started out unhappy at any job that I tried. I was paid well, the work was interesting, and I liked working with engineers, they’re generally laid back and smart people.

But over time, the discomfort grew. I thought that it was just the particular job or company that wasn’t sitting right. That’s why I switched jobs so many times and tried so many different roles and companies. But no matter what I did, I felt like I had to force myself to code.

One time, my manager told me that I should be reading engineering blogs and listening to tech podcasts to stay up-to-date. I tried, but I hated reading about tech. It bored me.

I began to feel like I wasn’t a good programmer and never would be. I felt like I didn’t have the right brain for it and I wasn’t as smart as everyone else was. I even thought that I was only hired because they wanted to diversify the genders on the engineering team.

While so many of my peers were spending their free time contributing to open source projects on GitHub or creating their own apps, I was working on a blog about the Bay Area, crafting screenplays with my writing partner, and producing a comedy show in San Francisco. I didn’t view these as fun hobbies or side projects, I was doing them to try and gain enough success that I could switch careers.

I felt completely disconnected from the world I was immersed in. I could never understand why I should care about getting better at my craft. For me, it was a means to an end. I didn’t want to become a prolific coder or form my own tech company. I wanted to write.

My job as an engineer was merely a way to fund my attempts at breaking into writing.

In February of 2019, a rampant case of burnout caused me to pass out and hit my head on the sidewalk, resulting in a concussion. The recovery took about a month. Since I was unable to look at a computer screen, I had to take time away from work. It forced me to slow down and revaluate what I was doing with my life.

Although I was pretty bored a lot of the time, taking space from doing engineering work completely opened my eyes. I had been constantly working 60+ hours a week. I felt like my life completely revolved around my engineering job, and since that was not what I wanted to be doing, the feeling was suffocating.

I knew that I wanted to be a writer, but had never once in my life been paid to write something. What was going to make people start paying me now?

For longer than I am willing to admit, I stalled. After healing, I was back at my job again and just as miserable as I was before. I knew that I wanted to quit, but I was afraid to go out on my own.

I started saving up money so I would have three months of runway to get started. I began cutting back on frivolous expenses so that no longer having a steady paycheck wouldn’t feel like such a shock.

I spent exorbitant amounts of time on Medium reading articles about how you should definitely quit your job to follow your passion, and also how you should never quit your job to follow your passion. I read posts about writing, freelancing, and being an entrepreneur.

Slowly, I built a portfolio. I published my first article ever on Medium, My Anti-Sex Education, and woke up the next morning to find that it had been curated. That small sense of accomplishment gave me some validation.

Still, I scrolled for hours on job boards, trying to find another full-time role that felt like the right move for me. I applied to a few, but as I interviewed, I knew nothing was the right fit. Unfortunately, I rarely listen to my intuition.

A small startup in San Francisco offered me a job as their Customer Relations Lead and I verbally accepted. Finally, I had enough momentum to quit my full-tie engineering job. I set up a meeting with my manager and gave my two weeks. It was not a pleasant conversation, but it was done.

Immediately after putting in my two weeks, I had doubts about joining the startup. I was happy that it wasn’t an engineering role, but it still was far from the writing job I wanted. In a rush decision, I followed my gut and rescinded my verbal acceptance. I felt like trash, but knew what I needed was to try freelancing before going back into the world of full-time office work.

I’ve been doing it for three months now. It’s not easy by any means, but it’s also not the terrifying impossible challenge that many make it out to be.

I’ve been lucky to get a lot of writing projects from the company I used to work at full-time. Due to the amount of time I spent there, they trust me and were willing to let me write for them even though I used to be an engineer. The rest of my clients –– I have two that come to me with constant work and one with occasional work –– I found just by responding with care and detail to Craigslist writing gigs. No joke.

Other than obsessively worrying about my financial future, life is much better. I no longer have crippling panic attacks and run to the bathroom sobbing in the middle of the day. My life feels like I’m back in the drivers seat. I’m sure once I figure out where I’m going, things will start to settle into place.

As for writing work, I’m still trying to find my niche. I love writing about sex education and sexuality, but so far I’ve only been paid to write about technology, engineering, and startups. To be fair, it is what I know.

My plan is to build up my skills writing about things that interest me and hope that eventually I will be able to get paid to write about those things. Medium is a big part of that and I’m thankful to live in a time where making a living as a freelance writer is easier than ever.

The best thing you can do is prepare, prepare, and prepare some more! Good for you, you’ve already taken the first step by researching how other people got started.

Envision your future. What kind of work would you want to do? How would a day in your life go? Do you want to have a set schedule or work on your own whims? Do you want all of your work to be remote? How will you find clients?

Stay organized. Create a to-do list of all the things you need to do in order to start your freelancing business.

Save money. Having a few month’s runway is crucial in getting your business started.

Practice. Whatever you want to do for work, start before you quit your full-time job. Even if you don’t get paid for it, even if it’s just for 15 minutes a day, and even if it never brings you a client.

Spread the word. Talking to your friends and family is an important step in making big decisions. However, while hearing their opinions, remember that those who love you might caution you away from doing what they consider to be “risky moves.” Don’t let them tell you what to do or convince you that you should just stay in your job that you hate because it’s stable.

Take the leap. Quitting is the hardest part of this whole process. It feels just like that moment when you’re about to jump out of an airplane to skydive. You just have to commit to it and do it. Do you want to be that person who chickened out and never tried?

If it’s really what you want to do, you’ll make it work. I believe in you.

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Kaylee Moser

Written by

Kaylee is a freelance writer living in Oakland, CA. You can find out more at kayleemoser.com.

The Startup

Medium's largest active publication, followed by +564K people. Follow to join our community.

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