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

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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…

Why You Hate Every Job You Get

  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 quitting without having another job lined up 4 months later…

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 grind 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
  • Your colleagues are going to be your friends
  • Everyone is going to agree with your ideas
  • You’ll be working at your own pace
  • No one is going to yell at you
  • Your boss/manager is going to be your mentor
  • Your hard work is going to be recognized, celebrated, and rewarded
  • You’ll keep receiving 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 harry@dearboss-iquit.com

All the best,


Written by:

Harry is the founder and creative director of Dear Boss I Quit. His mission is to inspire and help as many people as possible escape the 9-5 grind forever by building a passive income online just like he accomplished a few years back.

You can read more about Harry’s story right here.

24 Responses

  1. I have myself wondered if I was just broken to hate almost every job I have had. I grapple with going to school to fulfill my “dream” because what if I hate that too? I do struggle with ADHD and that has contributed greatly to my anxiety. I continue to get jobs in healthcare as all my work experience is there. I hate it. I want to be outside working in nature so being at a desk or caring for other people seems like torture after all these years. Going to school puts added pressure on my partner to pay all the bills which also affects my motivation to return to college. Your article at least makes me believe that there is hope I will find a job I love at the end of all this chaos. Thank you for that.

    1. Hi Christina, I’m glad that you found my article helpful.

      You’re definitely not broken. Statistics have shown that up to 85% of all full-time workers don’t like their jobs, so you’re part of the majority.

      I absolutely sympathize with the fear and anxiety you feel about going after your dream but what you have to understand here is that those are perfectly normal emotions when pursuing a new endeavor. The main thing separating those who go after and achieve their dreams from those who don’t is their ability to “ignore” their negative feelings and take action anyway.

      Talk to your husband about your dream and how going to college can help you achieve it. He might be able and willing to support your household for a while by himself. If not, you can always shift to part-time employment to free up some time and still have a steady monthly salary to cover a few of your bills.

      Your ADHD might add some difficulty to the process but it’s definitely not an insurmountable obstacle.

      There’s definitely hope. You can make your living doing a job you love.

      BUT, chances are it won’t happen by itself – you have to work for it.

      All the best, and stay safe,


  2. Hi Harry,

    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. 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,


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