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

How I Knew I Couldn't Continue Working For Someone ElseAs 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…



  1. says

    Honestly, my side income has never been even close to (consistently) the same or more than my side income, nor is the side income work I’m doing something that I would want to ditch a career for. I’m really happy with the type of work I do at my full-time job and besides owning a small business that is much more scalable than my current side income, I haven’t found anything else I would want to do full-time instead. With all that being said, I would love to not have a boss – but only under the right conditions.

      • says

        I think it’s kind of a “relative” thing to. Don’t get me wrong, I would MUCH prefer to work for myself. The thing is, at this moment in time I simply haven’t found something that I could do on my own that I would prefer more than my current job/career. I have a number of requirements, though, such as ability to scale, must make equal or more than my current pay (including benefits which are a big part of it), etc. So yes I enjoy my job, but it’s relative to the other options available, which aren’t great imo (for me personally).

        • says

          I understand DC, that is nice that you have something that fits you right now. My day job at one point was good for me as well, until I realized I had other options that were better! :)

  2. says

    Great post. I knew I couldn’t work for someone else anymore when I realised that I was making the company a lot of money, but personally making *just* enough to get by. I also fell in love with travel and a 2 or 4 week holiday one a year wasn’t going to cut it.

    Actually, I require a 6 month vacation twice a year 😉

  3. says

    All great reasons to leave! I don’t have the sunday night dread because I don’t work mondays which is a huge help on my mind! Also, I enjoy my job. I would never continue to do something I hated. I enjoy being an employee and collecting a paycheque. I can’t see me ever surpassing my day job income. This month alone (in side income) I think I’ve only made like $100, which won’t go very far 😉 It’s been a baddddd month for me. You have a great thing going for yourself but to me self employment is more stressful! I also have a TON of independence and for the most part, control over my job. There are a lot of drawbacks but more positives so I can’t see me leaving for some time. Though I would eventually like to but back to 3 days per week when/if we have more kids.
    catherine recently posted..Our Frugal (Turned Not-So-Frugal) Long WeekendMy Profile

    • says

      It definitely helps if you enjoy your job. Mine was extremely boring and stressful work, and there were just no positives to it except for the pay.

  4. says

    Well, I’m headed there now as I just shared I quit my job. My first priority will be working for the family though and taking care of all things at the house. That decision came about after several years of feeling caught in the work-life rat race. Our weekends were brutal, trying to catch up with all our household tasks that we couldn’t do during the week.
    Brian @ Luke1428 recently posted..Why I’m Quitting My Job To Be A Stay At Home DadMy Profile

  5. says

    I was completely miserable at my job too, and I hated having a boss. Funnily enough, my boss was a really kind person and a good guy overall. But I was so stressed not to mess up, and with the idea that I had a boss that it was soon clear to me that I can’t work for someone else. Plus, I knew (and it seems I was right) that if I were to do the same thing I was doing for the company for myself, I’d earn a lot more. These two reasons are enough for me to keep on being self employed!

  6. says

    Making the switch to working for yourself sounds like the best decision you could have made! I’m so glad to hear that you left that horrible environment behind and that it’s working out so well. Seriously inspirational!

  7. says

    I actually have more stress as a freelancer. :( I think you hit the freelancing jackpot which not everyone has. I also made a lot more money working full time, which is why I’ve been looking to go back to that! The definite plus is a flexible schedule and working from home. I do love those two things, especially not having a commute in LA!
    Tonya@Budget and the Beach recently posted..Heat, TV, and the Neighbors, Oh My!My Profile

  8. says

    Sitting at a desk right now as I type- dreaming of the day where I don’t have to go to an office on a Monday. Starting to do some side hustle now, so hopefully in a year or two I can start a family and stay at home without losing all of my income.

  9. says

    I couldn’t do it either. I complained about my boss literally everday – it was getting pretty bad. I was miserable on Sundays and Mondays. Plus I had absolutely no benefits and very low pay. I really had nothing to lose by working for myself. Luckily everything has gone pretty well being self employed. And my income is gradually increasing so I’m pretty happy now!

  10. says

    IMO – Before you quit your day job, you should have ready replacement-job.
    Or else you’d be shooting your own foot.

    But since your side-job is earning your more, I think you’ll do fine. Assuming that the side-job has a constant income.

          • says

            Haha I had a little chuckle too. Reminds me of when I went in with my partner to his accountant. I had “taught” my boyfriend what I do and he was breaking away from personal training to doing online stuff. There were two accountants and both were dubious of my income. This was during my first year working online and I told them I expected to earn over $100,000 for the calendar year. They both told my partner to keep PTing “just incase” and seemed doubtful of my income. This year, I’m looking to earn double or triple and my partner’s done so much better with his online ventures than he was doing (financially) with his personal training.

            I guess doubt is what separates those of us who do it, from those of us who would kind-of, maybe like to do it.

  11. says

    You are part of a growing trend, the reverse of the industrial revolution. Big picture: until the industrial revolution, for all recorded history, mankind lived where they worked. That was the norm. The notion of commuting to a job with a big organization is very recent. Technology created “jobs” and technology is, again, creating the return to home.

  12. Candice says

    Once again inspiring me Michelle. I knew I had to quit when everyone said they were tired of hearing me complain about my boss lol.

  13. says

    I would love to be self-employed for so many of the reasons that you’ve mentioned – control being the biggest one. Being able to decide (to a certain extent) how much work I want to take on, when I want to take time off, who I work with, etc. is pretty much every one’s dream, I’d imagine! And it’s so refreshing and inspiring (as always!) to know that it can be done.
    Debt and the Girl recently posted..A College Student on CompromiseMy Profile

  14. says

    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!

  15. Dave Lalonde says

    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.

    • says

      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.

  16. says

    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.
    Christine Rosko recently posted..By: AndreaMy Profile

  17. says

    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.
    Jason B recently posted..Ebay Update 5/13My Profile

  18. says

    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!
    Clarisse @ Make Money Your Way recently posted..Carnival of retirementMy Profile

  19. says

    You really are setting the example on how it’s done Michelle! It’s been over two years since I turned an 8 year full-time position with a company I truly respect into an amazing self-employment opportunity. It takes time and effort to create the change you want in life and I do not regret that decision one bit. The freedom I feel is priceless to me. I am planning to leverage my skills more this year and bring in more SE income. I feel really blessed to enjoy what I do and get paid well for it from the comfort of pretty much anywhere!

  20. Adam says

    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.

  21. says

    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.
    EL @ Moneywatch101 recently posted..Why People Spend Out of ControlMy Profile

  22. says

    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! :)
    John @ Wise Dollar recently posted..Four Money Saving Tips for Your Vegetable GardenMy Profile

    • says

      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.

  23. says

    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!

  24. says

    I was thinking today how I haven’t read your blog in ages (sorry!), and wondered what you were up to. I also seriously dislike my day job, and while I am NO where near making the kind of money I would need to quit, things are slowly happening. I don’t know if I ever could financially blog full time, but the dream and desire are definitely there! So imagine me coming to “visit” and reading this post. I totally can relate to how you felt in your last job (well, minus the track to VP status, lol), so thanks for this :) Hope all is well!
    Nichole C recently posted..Monday 5.19.14My Profile

  25. says

    Totally agree Michelle, I’m not a big fan of my job either. Sundays and Mondays are a dread and most of the people I work with have nothing in common with me other than the fact that we all work at the same place. But more than that I think it’s just the fact that I’m not fulfilled with what I do and that I know I am capable of so much more. I currently run my own website and I’m looking to ditch my job in the next few years as well.

    Thanks for the inspiring article Michelle.

  26. says

    Oh I totally hear you on so many of these. Vacation is never a vacation because you have so much work before and so much work after. It’s also really hard to be surrounded by other people who hate their jobs. Even if you’re happy and positive it’s easy to get “sucked” into the misery.

  27. says

    Pretty awesome that your side income made you more than your regular job. If I was able to pull that off, I’d definitely consider leaving. Great point about vacation…all it really means is that you have to get things done before leaving and working harder when you return…the work still piles up. One thing that would be great if I could leave my job is the commute (1 hour each way). I’d save 2 hours a day. 10 hours a week!
    Andrew@LivingRichCheaply recently posted..Price of the American Dream: Are your costs escalating?My Profile

    • says

      Wow that commute sounds horrible! My commute wasn’t too bad when I had my day job. It was usually around 15 minutes. However, there were several days each month where it would take 3 to 4 hours just to get to work or just to get home because of an accident. UGH!

  28. says

    I don’t remember if you have said before what industry you were in but this 100% describes my situation as well and what I left to freelance!

    “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.”

  29. says

    After 36 + years working in a supermarket I know I can no longer continue working for someone else because I am exhausted physically and have missed much of life due to the working hours. I began a blog a few years ago and have been told by many people that I highly respect that I have a gift for writing though I have backed off I may begin another with a new direction. I am not sure where everything is headed but your posts are definitely helping my focus. Having married 2 years ago, we are looking into a side business also. Thank you for the helpful info.
    Amber recently posted..Fantasy Dinner Party, Who Made the CutMy Profile


  1. […] How I Knew I couldn’t Continue Working for Someone Else. Michelle at color me frugal shared the reasons she knew she had to become self […]

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