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One Year of Self-Employment: The Past

This Friday marks one year since I walked away from my career to become self-employed. I can’t believe it – it seems like it’s only been a few months! I’m taking some time this week to reflect on where I came from, where I am now, and where I hope to go from here. 

I’ll never forget the day I decided to quit my job. Sure, I’d been thinking about it for months, but there was always some reason I stayed – the steady income, the need to be “successful” in my chosen career, the desire to make a difference, the fear of failure. Every time I thought I couldn’t take any more, I would convince myself to hold out just a little longer. And then one day I broke.

It was November 14, 2011. I spent the morning at a rural high school where I provided therapy to students, then drove to the clinic for an afternoon treating adults. As far as workdays go, it was pretty typical. But when I arrived at the clinic, one of my coworkers pulled me into her office.

“Did you see the memo from [main clinic]? They’re taking our benefits next May.”

“What? Why?”

“I guess they’re trying to get rid of some of us. You know how shitty revenue has been since the switch to managed care.”

I went to my office and shut the door. Took a deep breath and tried not to scream. Could this job be any worse? I had just started the position four months prior, leaving another role with the company for what I thought was a miracle job. In those four months, I had experienced a complete lack of guidance from my supervisor, the most messed up payroll system ever, problems with the staff at the high school (who seemed to think I was theirs to boss around instead of a contract worker), and a huge cut in the hours I could bill for therapy thanks to Kentucky’s change to privatized Medicaid. Oh, and let’s not forget the pressure I was under to commit fraud to cover someone else’s screwup. And now I was going to lose my benefits on top of it?

The Turning Point

My parents had grown used to my frantic phone calls about my misery at work. Lowering my voice so my coworkers wouldn’t hear, I filled my dad in on the latest development in the saga. I remember trying (unsuccessfully) to keep from crying as I told him, yet again, that I just couldn’t do it anymore.

“Get out of there,” Dad told me. “Just get the hell out. It’s not going to get any better.”

It was the first time he had openly encouraged me to quit my job. My parents are big on listening but not on giving advice; they don’t want to feel responsible if things don’t go well. So I knew it had to be pretty hopeless for him to say something like that. And I think a part of me was waiting for permission – I desperately needed someone to say it was okay.

I hung up the phone, then emailed my boss and her assistant to give my 30-day notice. The assistant called after she got the email, but she wasn’t calling to ask questions or wish me well. Instead, she barked out a list of things that would need to be taken care of before my last day. Listening to her drone on about closing charts and transferring my caseload, I never felt so insignificant (especially after working at the agency for 3 years). But I also never felt so relieved to be leaving a job.

The Plan

When I started this blog nearly two years ago, becoming self-employed was nowhere on my radar. I just wanted to improve my finances and hold myself accountable. I was shocked when I learned that people made money from blogging and that some of them even made enough to quit their jobs! It was totally different from the small blogging community that existed when I’d had my last website in 1998 or so.

Over time, I started making money here and there. I was recognized in some pretty cool ways, like the blog post that was published in Reader’s Digest. It was impossible not to have that thought in the back of my mind, Wow, maybe someday I could quit my job and work for myself!

During my employment crisis (with its insanely low paychecks), the money I earned from blogging and freelance writing paid my bills. Without that income, I guess I would have ended up mooching off my parents once my savings ran out. Throughout my notice period, I looked for jobs, but I also spent that time getting used to the idea of working for myself. Which turned out to be a good thing because there were no jobs to be found.

On December 14, 2011, I walked out of the mental health clinic for the last time. No one brought a cake or threw me a party or even looked up when I left – they were all too busy dealing with the same headaches I was escaping. Honestly, I think some of my coworkers were a little jealous of my ability to walk away, especially since I didn’t have a “real job” lined up.

I planned to earn money through blogging and freelancing, but I also had a bigger idea bouncing around in my brain. I had been creating and designing my own websites since I was 13 years old; maybe if money got tight I could offer some design services as well. Little did I know that writing would soon take a backseat as my self-employment experiment turned out to be NOTHING like I imagined…

About Andrea Whitmer

Andrea is a freelance web developer and mom trying to maintain a sense of humor in an otherwise chaotic world. She blogs in hopes of helping others avoid the same mistakes she made in the past. Join in the discussion here on So Over This, or connect on Twitter, Pinterest, Instagram, or Google Plus. You can also subscribe to new posts via RSS so you never miss out!


  1. moneybeagle says:

    Good for you. It's been awesome watching how things have gone. There was definite uncertainty but it seems that now you've found your groove and are much happier. Do you ever talk to people that you used to work with?

    • I keep in touch with quite a few of my former coworkers. A lot of them were laid off shortly after I left – the agency cut 50% of its outpatient staff, starting with the newest employees. So I was incredibly lucky that things happened the way they did; I would have been laid off anyway. Anyway, we still try to get together every few months for dinner. It's a little weird since I'm not in the field anymore, but it's so great to be away from that place I don't mind much.

  2. Andrea, I think I've known you almost the entire time I've been part of the PF blogging community. It's truly been a pleasure and and honor to follow your story and watch you find a successful direction in life. You're a great role model. 🙂 I think you should make WWAD (What Would Andrea Do) bracelets and sell them at #fincon13 for people struggling to find their way. LOL. Seriously though – congrats, friend – I'm really happy for you!

    • I first read that as "a pleasure and horror" – hahahahahaha!

      The thought of WWAD bracelets scares me to death, because normally the answer to that would be, "The opposite of what a sensible human being would do." 😀

  3. I can't believe it's already been 1 year! It really does not seem like that long at all. And you're doing great! 🙂

  4. So awesome! I had just started reading your blog around this time last year, it is great to see how far you have come and how strong you have been through all the ups and downs of self-employment. Congratulations on all the things you have accomplished this last year!!

    • Thank you! I feel very privileged to have made it this long. I hoped I would, but I honestly didn't think it was possible. Here's to one more! 🙂

  5. Budget & the Beach says:

    You know it's the right job to leave when they react that way instead of saying, "what can we do to keep you here?" I didn't know you then, but you have seem to come so far. It's amazing how one idea turns into another on things you probably never dreamed of. You "sound" so much happier. Hope that's true! Very inspirational!

  6. Congrats on one year of taking the plunge! As tough as your clients can be, I imagine they aren't as hard as your previous management, am I right?

    • The clients definitely aren't as challenging, but my new boss is a total slave driver! She never lets me take time off or relax between projects. Honestly, I'm way harder on myself than any boss I've ever worked for, but it's in a way that works.

  7. It takes guts to leave a job no matter how miserable when you don't have another job lined up. Especially when you're a single parent.

    But good for you – you did it and not only survived, but seem to have thrived too.

    • That's such a nice way of saying I was an idiot. LOL 🙂

      Seriously, it was a huge risk. Had I not had an emergency fund in place, I never would have made it (nor would I have ever considered something so drastic). But I also had the comfort of knowing my parents would have helped if necessary – I'm very proud to say that I haven't had to borrow money from them at all since I left my job. I just assume it was the right thing to do because things have always fallen into place at exactly the right time. Thanks for stopping by!!!

  8. I just kick myself for not thinking of this sooner. Then again, I really didn't have my act together financially before last year, so it would have been a disaster. I will always remember that sick feeling I used to get on Sunday nights – now I'm always excited for Mondays instead! It's so different; I'm definitely a much happier person.

  9. I remember starting to read your blog when you had just quit you previous job. I remember you were nervous and concerned but now look at you! Its good to see that you have only flourished since that time. Hopefully this new year will be even better for you.

  10. Anne_UGifter says:

    I also remember when you first quit. So glad to see things are humming along and that you are much happier! Keep on looking up 🙂

  11. It's been so crazy watching your journey, but I think you ended up where you're supposed to be. You're very talented at what you do… so it looks like life just had to force you into it.

    I know you'll see your business grow in 2013. I have a lot of faith that you could take over the interwebs. I would support that.

  12. therandompath says:

    I am glad that everything has worked out for you Andrea! I remember stumbling across your blog last year and reading everything you were going through: the ups and downs of that job and finally taking that leap into self-employment. Good for you, for following your goals and dreams 🙂

  13. Congrats on your continuing success, Andrea! You are an inspiration, to say the least. YOU GO GIRL!!!

  14. I didn't know you a year ago but I can say you definitely made the right decision in hind sight 🙂 Can't wait to read the rest of the series!

  15. Frugal Portland says:

    I just started reading you around then — it seems like yesterday and ten years ago — seriously congratulations — you're inspiring!

  16. plantingourpennies says:

    Congrats on the anniversary of such a big event. =) Making it as self employed for a year is definitely a huge accomplishment!

  17. Canadianbudgetbinder says:

    Way to go Andrea! Great story and you will succeed with determination!!! Good Luck and happy Anniversary with the blog! Mr.CBB

  18. Wow! i can't believe it's been a year either thanks for taking us along the journey hopefully i learn something along the way !

  19. @blondeonabudget says:

    No one did anything special for you on your last day!? I hated my last job and was still sent off with gifts. I'm so happy you got out of there when you did, lady!

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