Overworked, Underpaid, And Fed Up: How I Dumped The Grind To Be My Own Boss
May

This is a guest submission by Kristin from KristinOffiler.com
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.
Yuck.
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.

Randy Cantrell
Good for you! Burn the boats.
Kristin Offiler
Thanks Randy!
Cordelia
I am so feeling you on this one! My job isn’t quite as overwhelming as yours was, but I do work in a small office, and over the years I’ve held a number of positions. So everything from high-end client crises to burnt out light bulbs is usually thrown my way. Stressful enough if you’re passionate about your work, but if you only have it because it’s a paycheck?
I’ve always resented this job (which I’m in the process of escaping) because it’s been a sidetrack from the real career I always wanted to pursue (also writing). But more and more lately, I’m coming to agree with your philosophy that “it’s helpful to at least briefly hold a job you hate.” My having been in the grind has made me even *more* passionate about following my dreams, and it’s also helped me find a subject to write about that’s led to a blog of my own.
Sometimes you’ve gotta experience the bad to really appreciate the good. Kudos to you for embracing your passion and following it!
Kristin Offiler
Thank you for the comment! If nothing else, crappy jobs definitely help us become more passionate about what we really want to do. Best of luck to you on your journey!
Marlon @ productivity bits
Kristin,
I just wonder if you approached your boss and negotiate your terms. It appears to me that you were in a good negotiating position because you were doing everything.
Kristin Offiler
I did. I had to ask for a raise after about 10 months because if I didn’t suggest a performance review, he’d never offer one. In all fairness, my boss did have many good things to say in my review and did give me a raise, but even then it wasn’t cutting it with the amount of stress I was under. He replaced me pretty quickly, so I doubt he would have given me the pay I deserved if I had suggested it before leaving the job. Plus, it just wasn’t what I wanted to do with my career.
Harriet`
You know I wish I had your guts and could just start being self employed! I’m still in university at the moment but I’d love to just becaome self employed as soon as I get out of here!
Kristin Offiler
Harriet, it might be more possible than you think. There are a lot of resources for people who go into business for themselves and if it’s something you really want to do, I know you can do it! Part of it is guts, sure, but more of it is knowing what you want to do, figuring out how to do it, and just going for it. Good luck to you!!
Benny
That sounded like a painful experience!
Glad you got out. I know a year feels like ten years for sure.
Kristin Offiler
Absolutely! Every month felt like an eternity. That’s an unpleasant way to live.
Susana
Very inspiring story indeed Kirstin. I just managed to gather up the courage to start blogging, hoping one day I can do the same as you.
I dream of being a full time writer in the near future and freelance writing would be a perfect way to support myself.
Let’s see what the future holds.
I wish you all the success in the world.
Susana*
Kristin Offiler
Thank you for the kind words, Susana. You can absolutely make a great living freelance writing, I know it. Check out resources like MakeALivingwriting.com (Carol Tice manages that blog and she’s very good at what she does). Also check out Linda Formichelli’s TheRenegadeWriter.com. Both are successful freelance writers who share their know-how of the business with newer writers. I’ve found both of their sites to be extremely valuable. Marie Forleo is another one to check out for business info in general.
Best of luck to you! You can totally do this.
Anthony
Following your dreams is what it is all about. I believe anything is possible if you do so and you made some calculated decisions to become a freelance writer. Well done!
Kristin Offiler
Thank you! I agree; it really is all about following your dreams, as cliche and cheesy as that sounds.
Susana
Thanks for the tips Kirstin! I’ve been reading a lot on the subject of course. I’m in the middle of the wonderful and pretty realist Ariel Gore’s book “how to become a famous writer before you’re dead” – great stuff too!
Best of luck to you too 😉
keep smiling,
Susana*
Justin | Mazzastick
Hi Kristin,
Being an employee means being parasited from. The energy that you were putting out was not being matched by what you were receiving. Good for you for quitting that job and doing something that inspires you.
Kristin Offiler
Thanks, Justin! You’re right… I felt really taken advantage of so many times. I’m much happier putting my energy towards my own business (even if it means putting in more hours than my previous job. It’s worth every second!)
Kristin Offiler
Ha, if you ask me an insurance questions, I might break out in hives 😉
Good luck when the train slows down!
Keshav
This was a great post Kristin. Very inspiring for me. Thanks!
Jimmy johanes
well, demand and supply never lies.
🙂