Why I Quit My Job to be Self Employed

self employed

Hey everyone! If you saw today’s post title and thought to yourself, “What the heck? I thought Kim just said she quit being self employed to go back to a traditional job?!” rest assured you are not going crazy. (At least no crazier than the rest of us!) 🙂

Kim did indeed decide to go back to a more traditional job, and thus she also decided to give up blogging here at Eyes On the Dollar on a regular basis. I’m still hopeful that we’ll hear from her on occasion so she can fill us in on her life happenings.

In the mean time, I’ve got some pretty big shoes to fill.

Who am I?

Yes, I suppose it is time for an introduction of sorts.

I’m Kayla and I blog over at ShoeaholicNoMore.com. When I heard of Kim’s decision to take a backseat role over her at Eyes on the Dollar, I was honored to be offered a chance to add my voice to the site to continue sharing knowledge of money and personal finance with all of Kim’s readers.

To start things off this week, I just wanted to give you a bit of a backstory on me, my personal finance journey, and a taste of what’s to come. Then next week, we’ll be ready to jump right back in with our regular Monday post. 🙂

The Beginning of My Personal Finance Journey

Clear back in the fall of 2014, I started reading personal finance blogs. Honestly, I stumbled across the first one during a panic-stricken Google search marathon when I couldn’t sleep in the middle of the night because I was so stressed about the lack of money in my bank account.

I’m pretty sure I searched something along the lines of “how to pay off debt” or “how to make ends meet” or something like that.

This lead me to a personal finance blog which I devoured every post of before moving on the next and devouring it too.

I read nearly 20 personal finance blogs, mostly ones focused on paying off debt, from beginning to “current” between September 2013 and December 2013 before starting my own site.

I started my blog as a way to track my financial progress as I worked to simplify my life, pay off debt, and build my savings. But somewhere along the way I got a bit de-railed.

Changing Directions

Part of the problem and the reason behind my lack of financial progress was that my monthly bills and minimum debt payments took every cent of the paycheck I earned at my full-time job. I wasn’t earning enough to get ahead very quickly and I had cut everything that I was willing to cut from my budget already.

One thing I’ve learned about myself since this time is that I am definitely not naturally inclined to be frugal and I’ve grown very accustomed to my lifestyle. Thus, I had to find ways to earn more money instead.

This us up to July 2014 when I started freelance writing and blogging, and working as a VA and blog manager.

I originally started this side hustle to help earn extra money to put toward my debt and savings goals, but after just a few months I realized this was something that could be a viable way to become self employed. Plus, I enjoyed it quite a bit more than my day job as a credit analyst at an agricultural lending institution.

Becoming Self Employed

Almost 1 year to the day after I started freelancing as a side hustle, I was earning enough to quit my full-time job to become self employed. My last day at my full-time job was July 31, 2015.

At that point, I still had about $16,000 of consumer debt, about $116,000 of mortgage debt, and not much in savings. I also went from getting a steady, predictable paycheck every 2 weeks to getting paid whenever I complete a project, or on a somewhat regular basis for on-going projects. Instead of freaking out about my lack of financial security, I used it as fuel to motivate myself to work harder at growing my business.

Fast forward just a few more months and I’m not earning almost 3 times what I was at my full-time job, plus I feel content and satisfied with my life a much higher percentage of the time.

As Kim has pointed out, self employment is definitely not all rainbows and butterflies. There’s good and bad in every employment situation no matter if you are self employed like me, or if you are going to work in a traditional job like Kim.

The bottom line is that you have to decide what is right for you. Just because many people in the personal finance niche have made the switch from traditional employment to self employment doesn’t mean it’s the right choice for everyone. In fact, I know there are several people, not just Kim, who’ve recently made the decision to switch back to traditional jobs instead of continuing to be self employed. There are definitely pros and cons to both avenues of employment.

That said, I hope you’ll all wish Kim good luck in her new job and allow me to try and fill her shoes here at Eyes on the Dollar, although I know it’ll be a tough act to follow!

Written By
Sydney White is a Texas-born stay at home mom who enjoys spending time with her family, bargain hunting and, of course, writing. She is currently the editor-in-chief of Snipon.com.


  1. Thanks for your kind words. Great to have you taking over.

    I think self employment is a wonderful way to increase income and make the life you want. Heck, I did it for over a decade! I’d still be there if the once in a career job hadn’t come along.

  2. Welcome to EOTD Kayla. What a nice and inspirational introduciton.
    It’s wonderful that self-employment worked out so well for you.
    Best of luck to you, and Kim!

  3. Congrats on the move! Just wondering your thoughts on engineering your layoff to negotiate a severance package? I’ve been trying to encourage people to do this ever since I did this and published my book on how to negotiate a severance in 2012. But, I think I’m failing badly.

    Why do you think more people don’t try to negotiate a severance? Entrepreneurship is hard. I would be much more stressed if I didn’t receive a financial runway.

    Thanks for your perspective!


    1. Hey Sam, I don’t think that’s applicable to me as I wasn’t laid off. I quit my job specifically because I wasn’t happy there and I wanted to be self-employed. My business is a little bit unique in the fact that I have many clients who pay every 2 weeks on the dot, so even though the amount I earn is sometimes variable, I get paid nearly the same way (every 2 weeks) as I was at my job before.

    1. Hey George, thanks! That’s a good question. Is there anything in particular that you are itching to read about? I’d love to get some feedback from EOTD readers. 🙂

      1. Similar to you, I quit my job to pursue my own business about a year ago. However I quit before I had any revenue coming in. There are times when I wonder if I left too early.

        I’d love to hear your thoughts on how people can evaluate what the right time is to leave the full-time job. How did you know when it was right for you? Was it when you had enough side income to cover your daily expenses? Were there other non-monetary factors? Would you quit without an idea of what you want to pursue (like people who travel the world while trying to figure something out).

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