This is a guest submission by Kristin from

It was out of necessity that I looked for and found my miserable office job in early 2009. I had just started graduate school and was no longer working as a peer tutor at my undergraduate college (a job I adored, but had to leave when I left that school).

Needing some kind of income while I was working on my MFA, I took a part time job at a doctor’s office. I expected it to be easy, light clerical work, like answering the phone, doing patient intake paperwork, and scheduling appointments. And to be honest, the job might have been tolerable if my duties were as simple as I originally expected.

In reality, my responsibilities were that of someone single-handedly running an office. In addition to making appointments and handling patient files, I was doing medical billing, a complicated process that most people go to school for.

But it didn’t stop there—I was also responsible for cleaning the office, processing insurance explanations of benefits, calling and battling with insurance companies over issues I didn’t even fully understand (because my background was in English and writing, not insurance), filling out and mailing birthday cards to patients each month, handling issues with patients as they came up, running errands for my boss, making personal phone calls for him, babysitting his child in the office on a few occasions, fending off romantic advances from a really creepy patient, and even watering a potted palm tree. For real.

Getting Worn Down

The job itself was stressful, draining, and complex. I went home in a bad mood every night, and I saw no way out. In my mind, I had to keep the job because the economy was tanking and I was lucky to have work, even if the work was turning me into a bundle of anxiety.

And to make matters worse, I was getting paid a pathetic hourly wage that was almost insulting considering how much I did as the doctor’s only employee; I should have been full-time, salaried, and receiving benefits.

After a year of being absolutely miserable, I quit. I’d hit my wall and needed out.

Making The Switch To Freelancing– Slowly

Before I threw in the towel though, I figured out what kind of work did I want to do. I knew I wanted to write (and that if I never saw another explanation of insurance benefits form again, I could die happy).

I started freelancing for local newspapers on the side and did some math and realized I only had to write a few articles a week to match what I was making in the office. But I also had to figure out if switching to a freelance life would suck up more or less time than the office job because after all, I needed time to do my schoolwork, too.

Once I felt confident that I could handle freelancing, I quit my job. I gave my two weeks notice and let my boss know that I couldn’t focus on the office and grad school at the same time anymore.

It was true; the job left me so drained that I had no energy in the evenings to write, and my boss often asked me to come in on my days off to catch up on all the work I had. But in addition to not wanting to balance the job and school anymore, I really wanted to earn money writing and I wanted to do it on my own terms.

Don’t Look Back

It’s been over a year since I left the office life for a career in freelance writing, and while I’m still feeling my way through self-employment, I’m much happier overall.

I get to write for a number of different websites and I’m even learning how to create killer copy and put together winning resumes and cover letters so my writing business will cover a range of services.

I just have too many interests and passions to narrowly follow one path as a writer, and since I’m the boss now, I don’t have to limit myself.

And even when I stress out and feel like I should try to find office work that’s steady and reliable, I have to just think back to what it was like being in that office. Of course it wasn’t awful every second of every day, but I spent a good portion of a year being really unhappy with my job. And that kind of unhappiness tricks you into believing that you can’t find a better job, and then you can get stuck in a holding pattern of being miserable, denying your passion, and blindly accepting your fate at a job that doesn’t fulfill you.


If you sit with that unhappiness long enough, you’ll start to dream about all the other things you’d like to do with the time you spend being miserable. That can lead to change, to a new path that will actually fill you with joy and a sense of purpose.

It’s not easy to leave the comfort of a regular paycheck, believe me. But when you know you’re meant do something, you have go after it with everything you’ve got, even if you take baby steps at first.

It’s also so important to have support; I was lucky that my husband encouraged me to make the leap to freelance and was there to carry us financially if it didn’t work out as planned. There’s a myth in this country that if you’re not working 40 hours a week in an office, you’re not really working.

Don’t fall for that garbage—if your passion is leading you to a career that doesn’t fit the mold, do it anyway. Do the work that fulfills you, makes you proud, and puts money in the bank your way. It’s not impossible to do and right now, tons of people are striking out on their own.

Freelance writing is less steady than an office job and it can be scary since it’s on me to make it work, but it’s a career that is filled with a million possibilities, and all of those possibilities involve stringing words and ideas together and getting paid for it. And to top it all off, I never have to waste half my day calling insurance companies again unless it’s for me.

Kristin Offiler is a freelance writer who lives in the northeast with her husband and dog. She has an MFA from Lesley University and does a wide range of writing as a freelancer.

Her work includes blogs—both personal and for businesses, articles, advertising copy and resumes/cover letters and is currently working on a novel. She thinks it’s helpful to at least briefly hold a job you hate because, if nothing else, it will point you in the direction you want to be moving.

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