How I Knew I Couldn’t Continue Working For Someone Else

As most of you know, I left my day job last year and I now work for myself in my home. I quit in September of 2013 and my last day was in October, and not once have I looked back and regretted the decision I made to leave my day job. Below are reasons for…

Michelle Schroeder-Gardner

Last Updated: August 26, 2024

Disclosure: This post may contain affiliate links, meaning if you decide to make a purchase via my links, I may earn a commission at no additional cost to you. See my disclosure for more info.

As most of you know, I left my day job last year and I now work for myself in my home.

I quit in September of 2013 and my last day was in October, and not once have I looked back and regretted the decision I made to leave my day job.

Below are reasons for why I knew I could not continue working for someone else. My day job was not fun at all, but I understand that it paid the bills. Just like how freelancing isn’t for everyone, my day job was definitely not for me…

I absolutely dreaded Sundays and Mondays.

Sundays were horrible because I knew that I had work the next day. Mondays were horrible because I actually had to go to a job that was so incredibly boring, but also stressful, that I didn’t know what to even do with myself.

I also had no one to talk to because I worked independently, and even when I met with clients they were all older businessmen. So not only was the work horrible, but there was no social life at the company or in the industry as well.

Since switching to my freelancing business full-time, I actually look forward to each and every single day. I look forward to any new leads, and to also work for my current clients. I also enjoy everything I do! And, even though I work from home, I have a much better social life than I did when I had my day job – I talk to other freelancers, friends and family pretty much all day long.

 

My vacations were okay, but I knew they could be better and longer.

At my day job, I did receive a fair amount of vacation time. I can’t remember the exact amount (I have a horrible memory), but I believe I received around 3 weeks each year.

However, just because I was on vacation it did not mean that I didn’t have to work.

The work would just pile up on my desk until the day I came back, and I would have to work outside of my normal 8a.m. to 5:30p.m. hours to catch up after a vacation. Also, the days leading up to a vacation were just as stressful because all of the work that had to be done before I left.

I was on track to be Vice President of the company, and I knew with that came even more responsibilities. I would have to be on-call 24/7, and being on-call 24/7 with the boring/stressful work kind of made me want to cry.

Those 3 weeks above also included any sicknesses, family emergencies and more, so you can easily see how quickly it all added up whenever things came up in life.

 

My side income was higher than my day job income.

Once my side income was higher than my day job, it was very hard to stay motivated at my day job. I knew that if my side income grew any further, that sacrificing my happiness was not worth it any longer to be working in an industry that I did not enjoy.

 

I saw others around me hating their jobs.

After landing my first “professional” job after college, I started noticing more and more about how others perceived their jobs. I saw how much others genuinely hated their jobs and what they did, and I could see it controlling them completely.

I knew I did not want that. I saw the opportunity that my side hustles gave me, and I jumped on that. I wanted to do something different, with the hope/dream that it would all work out, because anything was better than my current situation.

 

I wasn’t in control.

With my day job, I did not feel in control at all. Even though I was a good worker (I was great!), I still felt like I was constantly tiptoeing around.

I knew I would never lose my job, but I also didn’t know what was in store for my future.

Now, I feel way more in control since I am my own boss. I can dictate what I want to do, what I don’t want to do, and when I want to do it all. I can create a flexible schedule that works best for me, and I can grow my business in the ways that I desire to.

 

I knew I couldn’t continue wasting their time and mine.

My heart just wasn’t in the work that I did.

The job I had may be for some, but I still can’t believe I got myself into that mess.

I knew I couldn’t waste any more of their time since I knew I wasn’t in it for the long haul. I was wasting both their time and mine by continuing to work there.

 

Do you ever want to work for yourself? Why or why not?

 

P.S. I received my inspiration for this post from Holly. Last month, Holly at Club Thrifty published the article Why I Would Rather Be Poor Than Work for Someone Else. It was an awesome article, and I knew I wanted to do a followup article to hers…

 


Michelle Schroeder-Gardner

Author: Michelle Schroeder-Gardner

Hey! I’m Michelle Schroeder-Gardner and I am the founder of Making Sense of Cents. I’m passionate about all things personal finance, side hustles, making extra money, and online businesses. I have been featured in major publications such as Forbes, CNBC, Time, and Business Insider. Learn more here.

Like this article?

Join the Conversation

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. E.M.

    When taking a vacation is so stressful you can barely enjoy it, how is it a vacation anymore? I’m glad you were able to earn more from your side hustles and leave. I have tiptoed around jobs before, mostly because my bosses tended to be moody. You never knew what you were in for!

    1. Michelle S.

      Thank you! 🙂

  2. Dave Lalonde

    It must have taken a lot of consideration to have gone self-employed full time! If your side income was more than your day-job, then something’s not right with that! But seriously, I admire the fact that you chased after what you enjoyed most.

    1. Michelle S.

      Thank you Dave! I did make a good amount from my day job, but there was just so much stress that went along with that job that it just wasn’t worth it.

  3. Will Lipovsky, First Quarter Finance

    Your freelance/blog income was surpassing your day job income?! You must have been working like crazy while pulling double-duty! How many hours total per week were you working?!

    1. Michelle S.

      I was working a ton. Anywhere between 80 to 100 hours each week!

      1. Will Lipovsky, First Quarter Finance

        Dang, that’s awesome! Powered by passion.

        1. Michelle S.

          Yup! Thanks Will!

  4. Christine Rosko

    I don’t think there are words that can describe exactly how much I want to be my own boss. I think about it while I’m at my day job. I’m trying to get my out of work income to a level where I would feel comfortable quitting my regular job. Until that day, I’m stuck.

    1. Michelle S.

      I’m sorry Christine that you feel stuck. I hope you find something great for you one day 🙂

  5. Michelle S.

    The reverse industrial revolution sounds good to me! 🙂

  6. Michelle S.

    Good luck building your side hustles. You can do it!

  7. Michelle S.

    Yup! I hated Sundays.

  8. Jason B

    My side income is nowhere near what I used to make with my previous full time job but I haven’t looked back since I quit last year as well. I am looking for another full time but it will only be temporary. I agree with a lot of the points you made in this post. I want to be 100% in charge of my time and also my vacation time.

    1. Michelle S.

      Thank you Jason! 🙂

  9. Clarisse @ Make Money Your Way

    I was working in a company too before, that was 6 years ago. After I gave birth to my daughter, I decided to continue my work, but every time I’m at the office, I can’t help to feel guilty because I’m not taking good care of her. So I resigned from my work and luckily after a few months I started working as a VA and my clients are really good too!

    1. Michelle S.

      That’s awesome! 🙂

  10. Michelle S.

    That’s awesome. Good job!

  11. Adam

    Wow! It sounds like you are describing my job there. I dread Monday’s right now too, and work almost by myself (I’m the only employee left just the owner and some independent contractors). Unfortunately, I don’t have a side income yet that would surpass my current income. Someday hopefully I’ll get there.

    1. Michelle S.

      Yup, we sound a lot alike Adam. Do you do anything for side income currently?

  12. EL @ Moneywatch101

    All valid reasons to leave a career. Wow Michele you were going to be a VEEP, LOL. Funny show on HBO. Well if you side income is more than your full time income, because the tiping of the libra scale , you made the right decision. Plus you can always get another job in the future if things change.

    1. Michelle S.

      Thanks!

  13. John @ Wise Dollar

    Great post Michelle! I was the very similar in a lot of these areas myself. The kicker for me was when I started to become physically ill when I walked into the building. Add that to no real control over what I could do and it was evident that I needed to leave. I’m hitting the two year mark in a few weeks and there’s no looking back – I think I’ve been spoiled for the corporate world! 🙂

    1. Michelle S.

      Congrats on almost two years John! 🙂

  14. Allison

    Very interesting Michelle!
    One question I have for you….what do you do for health insurance?

    1. Michelle S.

      We have a “catastrophic” plan right now. It’s about $200 a month for the both of us but it doesn’t kick in until we spend about $12,000 out of pocket. It’s a sucky plan but we plan on improving it once we are more serious about having children.

  15. Deacon

    I can definitely relate to you as far as not wanting to work for someone else. I hated the limitations that came from not being my own boss. Having limited vacation time, having little-to-no control over my hours, and I didn’t really enjoy the work that I was doing. Now that I am my own boss, I don’t think I could ever go back!

    1. Michelle S.

      I could never go back. Gah, I can’t even imagine!