10 Surprising Reasons You Hate Every Job You’ve Ever Had

10 Surprising Reasons You Hate Every Job You’ve Ever Had

Hating your job is absolutely normal!

Most people who have been active in the workforce for a few years, including me, have worked at least one job they hated for some reason.

However, hating every single job you get, is a whole other story…

Nowadays, work occupies at least 50% of our waking hours.

Spending such huge chunks of our days doing something that makes us miserable for years could have a very negative impact not just on our out-of-work life but also on our physical health and emotional well-being.

Having said that, the purpose of this article is to help you break the endless cycle of going from jobs you hate to other jobs you hate by outlining 10 Reasons That You Hate Every Job You’ve Ever Had, as well as how to counter them.

Let’s start digging deeper…

10 Reasons You Hate Every Job You've Ever Had

  1. You Pick Jobs Using the Wrong Criteria
  2. You don’t Know What Makes You happy
  3. You Haven’t Experimented enough
  4. You’re in the Wrong Field
  5. The 9-5 Rat Race Is Not for You
  6. You Are Prejudiced
  7. You Have Bigger Dreams
  8. You Keep Blaming Others
  9. You Have Unrealistic Expectations
  10. You Suffer From a Mental Illness

1. You Pick Jobs Using the Wrong Criteria

So, Why Am I Still So Unhappy

The first reason that might be keeping you stuck in a pattern of constantly landing jobs you hate, could be that you keep picking them using the wrong criteria.

For instance, you might be going after only jobs that pay exceptionally well, based on the assumption that a larger salary will make you happier.

Maybe, you’re considering only jobs approved by your parents because you don’t want to disappoint them.

Or, you might be putting all your focus on getting jobs that’ll make you look prestigious and important in order to gain the acceptance of your peers.

Whichever the case, picking jobs solely based on superficial gains such as money, prestige, approval, or whatever, is a surefire recipe for hating them.

And I’m talking from personal experience here…

A while back, I took a job I knew I’d hate just because its paycheck would allow me to live a “better lifestyle”.

However, despite attaining that better lifestyle, during the 2 years that I stayed at that job, I was the most miserable I’ve ever been in my life

If can relate, I strongly suggest that you start focusing on getting a job that you could potentially enjoy even if it’s not as high-paying, prestigious, or approved by your parents.

Chances are that enjoying what you do for a living is going to make you a lot happier than having money to buy the latest crap, or gaining the acceptance of your peers, or not disappointing your parents ever will…

2. You Don't Know What Makes You Happy

I Have No Idea

If you don’t know what would make you happy in a job, it’ll be nearly impossible to end up in a job that makes you happy.

During the 2 years that I was “stuck” in that job I hated, I was constantly job hunting.

However, since I didn’t have the slightest clue about what kind of job I’d actually enjoy, I kept applying to any job that came with an adequate salary and a relatively reasonable working schedule.

Eventually, I got offered a position that looked pretty decent, I accepted it, and left the job I hated.

At first, I was really ecstatic!

But unfortunately, it didn’t last long

A couple of weeks into that new job I started hating it so much that I actually ended up jumping ship just 4 months later without even having anything else lined up

My point here is that if you keep aimlessly applying to any job under the sun without being aware of what kind of job you could potentially enjoy, the chances of landing a job you won’t hate are practically zero.

One of my favorite philosophers, Alan Watts, claims that to find what makes you happy you have to get to know yourself better.

To do so, you can start by answering the following questions:

  • What makes you lose track of time?
  • What do you like spending your money on?
  • What kind of activities would you engage in daily if you didn’t have to work?
  • Have you ever lost sleep due to being excited about something that would take place the next day?
  • What do you love doing in your free time?

In addition, you could list every single thing you’ve hated about each of your past jobs and try and avoid all the jobs that come with similar characteristics.

Likewise, you could make a list of all the things you liked about your past jobs and try to locate jobs that display similar ones.

Consulting a career counselor and/or a life coach could also help you out immensely.

Once you start uncovering what truly matters to you and what you couldn’t give less sh*ts about, figuring out your desired profession(s) will be a piece of cake.

3. You Haven't Experimented Enough


Another course of action that could help you construct a clearer image of your “ideal” job, is to start strategically experimenting with as many diverse opportunities as possible.

Strategical experimentation can consist of voluntary work, side projects, internships, part-time occupations, or full-time employment in various industries, fields, and settings, such as:

  • large companies
  • small family businesses
  • office jobs
  • outdoor jobs
  • solo jobs
  • team-based jobs
  • etc

Exposing yourself to such a vast variety of different environments will broaden your perspective and provide you with valuable insights and feedback that could help you better identify jobs that match your preferences.

Each individual experiment should last for at least 6 months unless you’re 100% sure that sticking it out for that long would be a complete waste of time and no more than 1 year unless you come across something that could be worth trying more seriously for a longer period of time.

Lastly, make sure to carefully reflect on and write down as much as possible about each experiment, such as how it made you feel, what you loved about it, what you hated, what you didn’t quite like but could tolerate, etc.

Strategical experimentation is no walk in the park…

The process of adjusting to different work environments, learning new skills, practices, and procedures, meeting new people, and constantly changing bosses is going to be extremely challenging.

However, this could prove to be one of the best, fastest, and most effective ways towards breaking that endless cycle of working jobs that make you miserable once and for all.

4. You're in the Wrong Field

What is that which you hated the most about each of your past jobs?

Was it your boss, your manager, the environment, the company’s culture, the coworkers, the long commute?

Or was it your daily duties?

If it’s the latter, chances are that the reason you hate every job you get is due to being in the wrong field.

A few years ago I landed a job at the customer complaints department of a large international company.

Most aspects of that job, from the boss and the working environment to the paycheck and the benefits, were pretty satisfactory.

However, my daily work consisted of listening to people whining and bitching about gaps and failures in the company’s services for 8 hours straight.

I truly hated it

Eventually, I left that job for a very similar one in a much smaller firm thinking that my work there would be a lot more manageable and tolerable.

I was wrong…

Within a couple of weeks, I started hating that new job too.

My point here is that if the aspect you’ve hated the most in your past jobs is the work itself, then it’s probably time to start considering a career shift.

There’s practically no reason to spend the rest of your life doing work you hate.

5. The 9-5 Rat Race Is Not for You

Go to school. Get a college degree. Land a desk job that pays well. Live happily ever after…

Most people are conditioned to believe from a very young age that this is the only path to success, career fulfillment, and being a constructive member of society.

However, this couldn’t be further from reality.

Truth is that fitting every single person in the exact same box is impossible.

While there are definitely tons of people who are pretty content with leading this kind of mainstream lifestyle, for some, including me, being part of the 9-5 rat race feels like a nightmare.


The good news is that there are dozens of ways towards making a living other than working a regular 9-5 job, such as:

  • Freelancing
  • Consulting
  • Dropshipping
  • Affiliate marketing
  • Print on Demand
  • Selling courses
  • & more

The way that I personally managed to escape the 9-5 rat race was by utilizing affiliate marketing.

If you’re not cut out for being a 9-5 corporate drone, try to figure out a way to build a source of income by doing something that really fulfills you.

As you’ve seen for yourself, you definitely have options

Life’s way too short to be settling for a profession you despise.

6. You Are Prejudiced

Being prejudiced towards all jobs just because you happened to stumble upon a few “bad” ones could fuel confirmation bias.

Confirmation bias is the tendency of favoring information that confirms already existing beliefs while rejecting or ignoring all conflicting evidence.

This basically means that if you’ve convinced yourself that all jobs suck, you might end up hating decent opportunities just because you’re predisposed to highlighting only their negative aspects.

What you need to realize here is that 99.99% of the time, assumptions derived from prejudice are wrong.

Every job is different, no job is perfect, and all jobs have their pros & cons.

Just try to keep an open mind and avoid being negatively biased towards anything before you even get a taste of it.

7. You Have Bigger Dreams

Bigger Dreams

If your dreams are bigger than being an average employee until you retire, working a regular job will not only never fulfill you, but chances are that it’ll also hold you back from achieving your dreams

This is one of the main reasons that I hated my last 2 jobs – I had a dream of building a successful online business and they were both standing in my way of fulfilling it.

Eventually, in an attempt to give my dream a chance of coming alive, I ditched the 9-5 rat race altogether.

At first, I was scared as f*ck

I was scared of the unknown, running out of money, failing, being unable to find another job if needed, etc, etc.

However, not only nothing of what I was afraid of ever happened but in the hindsight, quitting 9-5 was one of the best decisions I could have made.

That’s because going after what you dream of, even if all the odds are stacked against you, is inexplicably more fulfilling than the “security” and “steadiness” of any regular job.

No amount of security is worth the suffering of a mediocre life chained to a routine that has killed your dreams. – Maya Mendoza

At the end of the day, even if everything goes wrong, the regret of failing while trying will be much more bearable than the regret of failing to try.

8. You Keep Blaming Others

I Blame You!

People love blaming others for everything that’s going wrong in their lives…

That’s because shifting the blame for any given unfavorable situation onto someone/something else is the perfect way to avoid spending time and energy taking the necessary steps to fix it.

Don’t get me wrong…

Hating your job because your boss is a psychopath or a colleague offends you, or the workload is unmanageable, or whatever else, is absolutely justified.

However, having someone else to blame for every single job you’ve hated indicates that you’re probably the one doing something wrong.

Maybe you don’t have a solid job-screening process. Or maybe your boss feels like a psychopath because you’re overly sensitive.

Your colleague might have offended you because you unknowingly offended them too. Or you might just be easily offended.

Maybe your workload seems unmanageable because you’re kinda disorganized.

That being said, if you sincerely want to break that endless stream of bad jobs, you must start holding yourself accountable.

Even if you’re truly not at fault, reflecting on where you went wrong and improving your situation is still YOUR responsibility.

Every single mistake we make teaches us life lessons and allows us to grow.

Next time you mess up, fight the urge to blame others for your failures by thinking about what you could learn if you owned up and accepted responsibility.

You can then reflect on why things happened the way they did, and figure out ways to prevent them from happening again. – A Conscious Rethink

9. You Have Unrealistic Expectations

Your disappointment towards all the jobs you’ve ever had could also be the result of having unrealistic expectations about them.

For instance, according to acas.org, over 50% of Generation Y graduates expect to become managers within three years of working for a company.

Out of those, 13% expected a managerial promotion within just one year.

However, according to The Balance Careers, most companies won’t promote someone to a manager unless they have 5-10 years of experience and/or a proven track record of effectively managing a team.

For some, this inability to achieve the expected career advancement within a company could fuel frustration and hatred towards their job.

However, this could be easily avoided by becoming better-informed regarding exactly what it takes to become a manager.

Other common unrealistic expectations people have about their jobs include:

  • Expecting that everyone is going to play nice with you
  • Expecting that your boss/manager is your friend
  • Expecting that everyone is going to agree with your ideas
  • Expecting that you’ll be working at your own pace
  • Expecting that no one is going to yell at you
  • Expecting that your boss/manager is going to be your mentor
  • Expecting that your hard work is going to be recognized, celebrated, and rewarded
  • Expecting frequent salary boosts

If your disappointment towards your past jobs is indeed the result of thwarted expectations, simply gaining some perspective could immensely improve your situation.

10. You Suffer From a Mental Illness

I Think I Need Help

Many studies have shown that working a job you hate could adversely affect your health, both physical and mental…

However, apparently, this could also work the other way around…

A few days ago, I came across an article in Frugality Magazine, according to which, a discussion on Reddit involved dozens of people complaining about hating their jobs.

One day, a person joined the discussion and claimed that his doctor pointed out that the reason he hated his job was due to having depression.

Symptoms of depression include reduced feelings of pleasure and increased negative thoughts…

So, what was causing that guy to hate his job wasn’t the job itself, or his boss, or his duties, or whatever, but rather his depression.

According to him, once he started receiving treatment, he actually started finding his job much more tolerable.

While I’m no doctor, if you’ve hated every job you’ve ever had, I suggest that you consider consulting with a therapist to figure out if your dissatisfaction could stem from some kind of undiagnosed mental condition.

Bonus: Infographic

Reasons You Hate Every Job You've Ever Had Infographic

If you’d like to embed this infographic on your website, just copy and paste the code right below to your HTML editor:

<img class=aligncenter src=https://dearboss-iquit.com/wp-content/uploads/2021/01/Reasons-You-Hate-Every-Job-Youve-Ever-Had-Infographic.png alt=10 Reasons You Hate Every Job You’ve Ever Had Infographic width=600 />
<p style=text-align: center;><strong>Created by <a href=https://dearboss-iquit.com>Dear Boss I Quit</a></strong></p>


Hating every job you’ve ever had is nature’s way of telling you that you’re doing something wrong

Maybe you keep going after things that don’t have to potential to fulfill you, such as money, title, prestige, or approval.

Maybe you have a bunch of character traits that hold you back, such as being unable to hold yourself accountable, or being prejudiced, or being too afraid to go after your dreams.

You might be in the wrong field…

Or you might just not be cut out for the 9-5 rat race, but rather for launching a startup and being the boss of yourself.

Whatever the case, if you’d like to stop jumping out of a falling airplane right into another falling airplane and end up making your living by doing something that truly satisfies you, you have to step back and start doing some work with yourself!

  • How many jobs you’ve ended up hating so far?
  • What were the main reasons that you hated them?

Leave a comment below and let us know all about your story…

Or just vent and get it all out of your chest!

If you have any questions or need any further help or guidance, I encourage you to reach out to me at xaric@dearboss-iquit.com

All the best,


This Post Has 22 Comments

  1. Mel

    Hi Xaric,

    I find myself in this situation as well. I have had 5 jobs in the span of 10 years. I have hated all of them. I started my current job in March, with extremely high hopes, only to now search the internet and see if I am the only one who is a chronic job hopper.

    I believe numbers 1, 5, and 6 pertain the most to me. I realized last month, I am the problem, not the jobs. I now realize like many in the comments I have to take accountability and work on myself and for myself. I am interviewing life coaches, to see if they can help me pin down the best solution for me.

    Great article, thank you.


    1. Xaric

      Hi Mel, I’m so sorry to hear that you’ve hated all the jobs you’ve ever had. I know from my own personal experience that this is a very tough spot to be.

      However, the good news is that you now seem to have put yourself in a position that only a few people dare to put themselves in – you’ve admitted that there’s a problem that needs to be solved and you’ve started taking action to actually solve it.

      Good for you!

      If you need any additional help and/or advice, please don’t hesitate to reach out to me…

      I’ll be more than happy to help you out!

      Best regards,


  2. Sue

    I am 40 and have been working for 24 years with at least 20 jobs and I have hated ALL of them.

    For years, I have known the problem was not the jobs, but me.

    Ten years ago, I did a lot of soul-searching, went to graduate school and got my master’s degree and started working in the mental health field. Turns out, I hate working in that field too!

    I am angry at myself for putting all that time and money (student loan debt) to end up back where I started: hating every job.

    I don’t know what to do (yes, I have been to career counseling.)

    I have been blessed with good coworkers and bosses at most of my jobs; the problem is that I always hate the work itself. I want to find work that I actually enjoy and that doesn’t give me health issues (most of my jobs literally make me sick and I have to quit because of health issues.)

    I was so stressed from one job that I had shingles on my eyelid and almost went blind.

    What is it like to have work that gives you life and energy rather than depletes you and makes you ill?

    1. Xaric

      Hello Sue!

      First of all, thanks a lot for sharing your story with us!

      The key here is to not beat yourself up.

      Yes, you’ve made mistakes… Okay, everybody does! This is how people learn. Don’t dwell on the mistakes you’ve made because you can’t change them… But you can leverage the lessons derived from them towards changing your future for the better.

      I assume that you might also be feeling too old for changes now, right?

      I understand that you are probably not a carefree 20-year-old anymore but you are not 60 either.

      I know people who have completely turned around their lives during their 50s or 60s. And if they could do it, you can do it too!

      Now, if I were you, I’d start experimenting with as many different activities and hobbies as possible for 1 – 2 years. Don’t stuff 6 different activities in just one day or you might get overwhelmed and end up burned out.

      Go for 1 – 2 different activities for a month. Next month, choose 2 different activities and stick with them for another month.

      For instance, from January 1st to February 1st, you can go dancing on each Monday, Wednesday, and Friday, and Yoga on each Tuesday, Thursday, and Saturday.

      From February 1st to March 1st you can attend skydiving classes each Saturday and maybe take a cooking class every Monday and Wednesday.

      I think you got the point!

      All the feedback that you’ll gather through attending such a vast amount of activities will help you construct a better image of what your “dream job” or maybe even your life’s purpose is.

      Also, consider that you might not be meant to work a normal, 9-5 job. I don’t really think that any person is made to work a 9-5 job but most of them just settle.

      But then there are the ones like you and me, who just can’t take it.

      If this is the case with you, make sure to check out Wealthy Affiliate and/or Project 24.

      Those 2 platforms teach people how to make their living from home by building profitable online businesses around their interests and passions.

      Wealthy Affiliate and Project 24 helped me quit 9-5 forever (hopefully) and gave my life a purpose.

      I will always be grateful to both of them and I believe that one of them or both could potentially help you out as well.

      Lastly, consider studying a little philosophy. Chances are that your problem might not be physical but mental and philosophy could help you solve it without having to actually change any of your external circumstances.

      Allan Watts is my favorite philosopher.

      He talks a lot about happiness and fulfillment through an alternative point of view that could help you counter your problem.

      There are tons of videos of his speeches on Youtube.

      Meditation could also help a lot in the longterm.

      I really hope my advice helps you out!

      If you have more questions or require clarifications, I would be more than happy to help you out.

      My best regards,


  3. Carol5162

    I always get excited when I get into a new job. The prospects of a new salary, new friends and a different environment altogether. But after a few weeks, I’ve come to the realization that employment is not something I want to do for the long haul.

    Basically, 9-5 is not for me. I am grateful for the things I have been able to accomplish because of my 9-5, but that is not my all. I want the freedom and the potential to earn as much as I can, outside the traditional office.

    And your point is so true…GO FOR PROGRESS. This is where I am at the moment with my online business. Progressing, one step at a time.

    Thank you for this great post.

    1. Xaric

      Thank you for sharing your story with us Carol.

      My best wishes to you and your online business!


  4. water life

    All the reasons you mentioned explain exactly why most people today hate their jobs. Doing a job that you don’t really like is bad but maybe, as you said, the problem is not the job but you.

    In my opinion, the right professional orientation plays a decisive role in the life course of the individual, since he essentially determines his professional future. A mistaken decision will lead the person to dangerous and difficult paths while the right decision leads the individual to professional success. 

    Confucius said, “Choose a profession you like and you will not have to work in your life again”. It’s in our hands to experiment and look for the right job in order to become happy. 

    Thankfully, I chose the right job for me and I’m proud of that. 

    1. Xaric

      Unfortunately, if someone doesn’t know exactly the kind of job they’d love to do, they will inevitably make mistakes and work jobs they won’t like. I don’t consider such mistakes dangerous as they are part of the whole process of gaining the required experience to finally find out what kinds of jobs satisfy you and whatnot.

      By the way, this is actually one of my favorite quotes!


  5. Tohin

    This is such a thought-provoking article, I must say.

    While growing up, most of us have been brainwashed to think that in order to find happiness we should follow the norm, especially when it comes to jobs and studies…

    It is only after experiencing somethings the hard way, like being unhappy with a career choice we made simply because our parents wanted that, that we come to realize no one and nothing can define our happiness besides ourselves.

    Also, I didn’t know that being unhappy with every single job one has worked so far has something to do with oneself.

    A friend of mine complains about her job(s) almost all the time. I have to send her this article, so she could take a step back and reflect on herself as to what her true problems are.

    1. Xaric

      I couldn’t agree more with you!

      Since I was young, my family kept telling me that the way to happiness is going to college, finding a good office job, settling down, getting married, have children, wait to die…

      It took me a long time to realize that this was their ideal way of life but not mine… Nobody told me about businesses, freelancing, being creative, questioning everything, and being happy with your profession.

      I had to find out everything for myself after wasting 2 years of my life working 2 jobs I absolutely hated which according to my parents were ideal for me!

      So basically yes, if you’ve hated most jobs you’ve worked, chances are there’s something you need to correct within yourself…

      In my case, it was the belief that having an office job was the key to my happiness…

  6. Paul

    Dear Xaric,

    This is a great article as you speak on behalf of so many people on the planet. 

    I’m one of the lucky ones who always feels like every job is just a game and I just have the best time (not all the time but most of the time). Most people just go through the motions and think it’s acceptable because everyone else is doing the same. 

    We are brainwashed into being sheep and the government is the sheepdog pushing us to do want we don’t necessarily want to do.

    1. Xaric

      Considering every job as a game is a way to go for sure. Sometimes I just wish that I could do that as well. It would be so easier than quitting and then going for another job and then quitting that job again…

      In my opinion, everything is acceptable for oneself as long as it doesn’t hurt others. If somebody wants to keep wasting his life working jobs he hates because everybody else is doing the exact same thing, then, by all means!

      We are definitely being brainwashed by the government, television, fashion, other people, the internet, etc. But at the end of the day, nobody pushes you to do anything. That’s why they are brainwashing us… In order to make us do what they want us to do without pushing us.

      We still have a choice over our actions. And in order to be able to control them better, all we have to do is become more conscious of them.


  7. Queen

    Oh my Gosh! This is so me!

    After reading your article and looking back now, I believe I must have hated every one of the four different jobs I ventured into because I wasn’t cut out for a 9-5.

    I went into the jobs being happy, I thought they were what I love to do, but in the end, they all just sucked for various reasons.

    In the end, I do believe I am cut out to be my own boss and that is why I am exploring the world of affiliate marketing right now.

    We will see how it pans out, hopefully, like you, it will be the right choice for me.


    1. Xaric

      Hi Queen,

      I totally feel you, although I haven’t really hated every single job I’ve worked. Just the last 2! However, becoming my own boss and earning my living online is my dream as well and so I believe that no normal job is going to really fulfill me.

      I hope that everything works out fine for you and your affiliate marketing business!

      To becoming our own bosses,


  8. Rahye

    No 3 speaks to me the most.

    Growing up and based on my past experiences with several jobs, I have come to realize that this 9-5 thingy is not for me…

    Not that I’m introverted but I enjoyed being an entrepreneur, my own boss.

    Working in a job was just a means to raise capital for my own business and during my internship. 

    Thank you for sharing!

    1. Xaric

      That’s exactly how I feel about all jobs… They are just a means to make some money to pay the bills until I am making a full-time income through my online business…

      Hopefully, it’ll happen soon!

      Thank you for sharing your point of view with us.

      My best regards to you,


  9. gr8megawinner

    Those are some valid reasons why some people hate all the jobs they get. 

    I have a theory that those who never fit in in an employee world is because they need to be an employer themselves. Instead of looking for new employment why not look for a way to start something of your own around your passion?

    1. Xaric

      That’s an awesome theory and I would believe that it is true.

      However, we have to accept that sometimes those who don’t make good employees and tend to hate all their jobs are just people who are lazy, unmotivated, and are looking for ways to slack off.

      I didn’t mention this in my article because I believe that such people would never bother to go online and actually make research towards improving their situation…

  10. Katya

    Hi Xaric, I’ll be honest with you, I started to read your article very reluctantly, like ” ok, let’s hear Mr. Smartass” and then, with every reason you counted, I could see the raw and inconvenient truth that it’s me, not the job. And it’s hard to hear that I should work on myself and not bitch about it. But you’re right, I should figure out what I want and stick to it.

    I shall put my big girl pants on and do some radical changes.

    Thanks a lot, I’m looking forward reading more from you,


    1. Xaric

      I feel the exact same way when I read other people’s articles providing advice about quitting a job 😛

      But some of them contain pretty solid advice…

      I am glad that you found this valuable and I hope that you find your way!


  11. Marios Tofarides

    Hey there Xaric,

    All of the reasons you mention are legitimate. If I’d pick 2 or 3 of them, these would be the 9-5, picking the wrong job and having other dreams. And, to add to that I’d say, fear of leaving a steady, secure, high paying job. Which, in my opinion, is the biggest reason. You might hate your job or not have experimented enough, or even have other dreams, but you are afraid of leaving the security and the salary.

    How would you deal with that?



    1. Xaric

      Dear Marios, 

      Making money isn’t tied to working a job you hate… All jobs pay a salary so you could earn your living just as easily by not working a job you hate…

      In addition, there are other ways to make your living without you needing to work a normal 9-5 job.

      Also, you can work on your dreams on the side of your job… This is what most people do… And when their dreams bring in enough money for them, then they go ahead and quit.

      Lastly, no job is safe and secure. It might seem that way right now but it’s really not. The only way to be truly secure financially is to work for yourself

      Hope this helps!

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