Making The Decision To Leave Your Job

Making The Decision To Leave Your JobHey everyone! I hope all of you had a great weekend. Lately, I have been answering questions that readers have been asking me. The other day I published Financial Changes When You Work For Yourself because many people have asked me how self-employment is financially different from working for someone else.

Surprisingly, many people I have talked to in person think that self-employment means that you are retired. Oh boy are they wrong!

I have been asked by several people whether I am happy with my decision to leave my job, and how I even knew that I should leave it. I definitely think that people should either go for their passion, or go for a job that allows them to pursue their passion in some form.

I’m not saying that everyone should go into work this week and quit their jobs. However, most of us have had a job though that we were not in love with. I recently read that around 30% of workers do not like their job. Also, around 75% of workers would actually LEAVE their job if they received a better offer from another company. That seems like a lot of people!

There are some things that you should ask yourself if you think that you may want to leave your job.

Why do you want to leave your job?

Almost everyone at one point in their life has dreaded Monday morning (or whenever the first day of the work week is for you). No matter how much you love your job, I’m sure there has been at least one point where you would rather be doing something else (such as sleeping in).

Do you actually want to leave your job, or are you just going through what most people go through after they work somewhere for a long time?


Do you see a future with your current job?

Not everyone wants to become CEO of a company when they are older, but do you see your job/company giving you the future that you want? Whatever your dream is, will your job allow for that?

Maybe you want a dream position at a certain company. Can you eventually reach this position or is that impossible at your current company? This is a case where you might want to look for a company where you may be able to reach your dream position.

Maybe you want to start a family, and your current job means that you won’t be able to have a good work-life balance.

Maybe you want to travel the world, but your job doesn’t allow for any vacation time.


Do you have realistic expectations of what you plan on switching to?

When you first think about leaving your job, you may have hopes for something better. However, that may not always be the case. What will you be switching to? How will you make an income? How do you not know that your next company/job/boss/colleagues may not be just as worse?


If you weren’t afraid, what would you want to be doing?

One of the top reasons for why a person doesn’t leave the job they hate to pursue what they want to do is because they are afraid.

They are afraid to fail, afraid to not love it, afraid to let others down, afraid to not make enough money and so on.

Fact is, you will probably be scared leaving your job. You will be scared to do whatever is next in your life. However, create as solid of a plan as you can, and believe in yourself.


Do you have another job lined up?

If you want to leave your job, then you might want to have another job lined up if you don’t have a well-funded emergency fund. Yes, there may be some instances where leaving your job cannot wait another day, but you should be as prepared as you can before you leave your job.


If you want to start your own business, could you start it and keep the job you have?

If you can, try to pursue your next position or business on the side to see if it is even possible. This can give you a good taste as to whether or not you think your “passion” is actually your passion. You might find out that you actually hate it and you might want to just stay at your day job.

This way you don’t lose out on any income, and you get to keep your job.


Have you made an action plan to leave your job and pursue your passion? Why or why not?

What would you do if you could leave your job?



  1. says

    I’ve got to agree with that last point the most. Starting a business is HARD! The uncertainty of whether it will work or not, whether you’ll ever make any money, etc. A good way to “test run” if you’re ready for it or not is to take on a project at work where you’d simulate being on your own. It might be a new division or a new product launch. But if you have trouble doing it (or don’t like it), then you may want to re-consider the self-employment route.
    My Money Design recently posted..Using a 72t Distribution to Get Early Access to My Retirement SavingsMy Profile

  2. says

    Great post! I have been thinking about this a lot, as I am one of those people who is not wild about their job but keeps at it because I presently have no other source of income. But I am working on that big time and trying to grow my blog! Yes, it is scary to think about leaving the world of working for an employer but I think probably anything worth doing is always a little scary, right?
    Dee @ Color Me Frugal recently posted..Start 2014 With Cash GiveawayMy Profile

  3. says

    This is exactly where I am right now Michelle! I’ve been offered a great amount to be an IT consultant (basically half my salary to work 1.5 days a week for them), but I don’t think it’s time to leave my current job just yet. It’s hard to say! If I can do both for 6-12 months that would work out the best for sure, but I don’t know if that will work for the consulting gig.
    FI Journey recently posted..Avoid Overspending When Throwing A Pity PartyMy Profile

  4. says

    I blogged about this a few weeks ago and I honestly have no intention of leaving my job. While I would love to make a full-time income on my side hustles, it’s just not there yet. Even if it was there it would take me a long, long time to leave, mainly because I am learning so much at work and I really do think I have a good setup as far as the company I work for. This is so important -> “If you want to start your own business, could you start it and keep the job you have?” My marketing prof and I discussed entrepreneurship often and this was his biggest question/advice. Start it while you still have your current job, if at all possible! It eliminates a lot of the risk of starting a new biz.

  5. says

    I left my job in April/May to freelance/blog full-time. I haven’t regretted it. I have a lot more responsibility now but I’m also able to make a lot more money. I do miss some of the people I worked with occasionally…but I don’t miss my job! =)
    Holly@ClubThrifty recently posted..Squashing Vacation EnvyMy Profile

  6. says

    “If you weren’t afraid, what would you want to be doing”. That is one of the most important questions we can ask, I think, Michelle. So many times we make decisions out of fear. Fear of not having enough money, fear of being solely responsible for our employment, etc., etc. Great post, Michelle!

  7. says

    This is a great post Michelle! People simply do not think these issues through. Instead they get ticked off at their job and leave without thinking about the future consequences. Then when the future arrives and becomes the now, they find themselves in a financial mess. Have to plan your exit better so the transition to a new life doesn’t become disastrous.
    Brian @ Luke1428 recently posted..My 8 Step Method for Writing a Blog PostMy Profile

  8. says

    I’d say insurance is the #1 reason I’m still with my current job. Having to sign up for Obamacare would bleed me dry right now, but I’m also not confident enough to live without any form of insurance. So, I figure stick with insurance and income while I continue to freelance for extra money and find a new job. I have been developing an action plan while admiring you and so many others who quit their day jobs.
    Broke Millennial recently posted..Loosening My Purse StringsMy Profile

  9. says

    In my case the job vanished and I had to find my footing as a freelancer. Wasn’t too happy back then, but it really worked out well.

  10. says

    Very solid advice Michelle! I love that I now look forward to Monday morning instead of dreading it. I use to get so stressed out on Sunday evening thinking about going to work the next day. It’s such an amazing feeling to wake up and start working on something you enjoy doing.

    I would add to save up a bunch of money if you’re thinking of going out on your own. I know I certainly wouldn’t have been comfortable taking the risk without having money to fall back on.

  11. says

    I like my day job as a real estate agent, but there are definitely some drawbacks such as working weekends sometimes or never feeling like you’re off the clock. I think of living off of side income activities, but I like the social interaction I have with this job so I’m looking for a balance of the two to appeal to the different sides of my personalities but also for more stable income.

  12. Candice says

    I’m quitting my job this month! I have no reason to stay. I’m so excited!! I know working for myself is hard and it won’t be fun all the time but I’m doing it now because I’m young with nothing to lose.

  13. says

    I quit my job once. On the spot too. I was in a position at the time were my husband was making enough to support us both and I wasn’t too worried about the money part of it. It was a reatail job and the boss just seemed to have something against me and made working there impossible. I was lucky though and found a new job the very next week.

  14. says

    I’ve made a few bad career decisions out of fear. I went from one unhappy job to another because of my fear of being unemployed, not having a stable paycheck, what other people would think, etc. I’m trying to remind myself that money isn’t everything, happiness is.

  15. says

    I don’t hate what I do, I just don’t want to do it 5+ days per week in an office. My solution is to work harder on the days I’m there so I don’t have to work everyday. At this point in my life, there really isn’t much I know how to do that could make more money, so until our real estate empire is complete, I’ll be checking eyeballs!
    Kim recently posted..Pros and Cons of Being a CaregiverMy Profile

  16. says

    These are great questions to ask yourself if you’re contemplating leaving your job. For me, I haven’t found something I’m truly passionate about. I would love to wake up and actually look forward to going to work. Being in an admin position isn’t very exciting/motivating. I think it will come in time, as I know I have to build up experience first, but it can be a painful wait.
    E.M. recently posted..Holiday TraditionsMy Profile

  17. says

    Quitting your job is the best thing you could do to live the lifestyle you want and control the money you earn.

    It’s really hard to commute monday to friday, spend 8 hours at an office and just follow directions.

    I have been working for two years now, and decided I wanted to be a freelance writer and blogger.

    Best decision ever.

  18. says

    I am satisfied with my new job. I don’t love it but I enjoy being around others and learning. I would like to leave corporate america to run my own business but that is more long-term for me at this point. My dream full-time job is to be a blogger. I love all things personal finance. I also have an idea for a niche site that I would like to put together. Blogging is so time consuming though! Not sure I could handle both websites at once with a full-time job.

  19. says

    My feeling about my job ebbs and flows.. I love the work, but the corporate red tape just wears me down.
    I love writing and the blog world even more than doing IT work.. but I am nowhere close to the point to where I could switch.

    My goal is to find opportunities with my current employer that increase my job satisfaction. Leaving is just too risky when you have mouths to feed.
    jefferson @SeeDebtRun recently posted..Finding a Kids Cell Phone PlanMy Profile

  20. says

    The best thing to do is to start a side income right now. You don’t have time to waste. Use that one hour in the evenings to get things done. Find a client ASAP. Stop messing around!

  21. says

    I’ve tried to leave my job 3 times. Each time I try, they give me an offer I can’t refuse. The last time, Friday of last week, I explained to my employer that it was costing me more to be at work than he paid me…I’m doing a lot of writing and making pretty good money at it. Anyway, he said he’d be willing to pay me my full time salary if I stayed here and did my work from his office in my 3 to 4 hours of spare time a day….hmmm…I don’t think I’ll ever be able to leave this place! Thanks for the great read!
    Joshua from recently posted..Is It Time To Start Investing?My Profile

  22. says

    I really enjoyed this post. Thanks for the great advice Michelle. I’m a definitely in a transition stage and unlike most people am very happy about the Affordable Health Care act. I’ve created a budget that includes the cost of the insurance and it has made my visions of working for myself a lot more realistic.

  23. Adam says

    I like the people I work for and with and even though the company I work for is a very small business but I still feel “out of place” if you will. I have the drive and initiative to want to work for myself and have had the drive for many years but the process of getting to that level and being able to survive it at the same time has been very drawn out it seems. Year after year though I keep trying so maybe one day it’ll pay off. =)
    Adam recently posted..December 2013 Starts A New ChapterMy Profile


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