“Why do I keep quitting jobs?”

If you switch jobs every couple of months, this won’t go over so well. People will think you lazy or unwilling to commit.

Don’t let that bother you.

Compulsive job quitting is actually a good thing. It means you haven’t made peace with the status quo yet. You refuse to do work that is meaningless.

Learn to embrace job hopping, why you should start your own passion business, and how can quit the rat race altogether.

Reasons for Quitting

If you are wondering, “Why do I keep quitting jobs?”, it might be for one of these reasons.

You Dislike Hierarchies

Many people quit their jobs because they struggle with hierarchies. They don’t like dealing with superiors, especially if their bosses are on a power trip.

You Feel Undervalued

We want to feel appreciated for doing a good job. If that never happens, we will eventually walk.

You Feel Disconnected From the Organization

Often, management loses touch with the people on the ground; the larger an organization grows, the more of a problem this becomes. If this goes on for too long, you might quit.

You Hate the Office Gossip

The 9-to-5 existence is dull. So, people gossip to entertain themselves. If you are on the receiving end of this, you’ll eventually want to leave.

You Lack Purpose

Most jobs are pointless. What difference does it make if you fill out that Excel table or attend that meeting? None. Once that realization sinks in, many people throw in the towel.

You Are Not Getting Promoted

We want to feel like we are making progress. If you have been in the same role for too long, you might start thinking about switching.

You Are Not Learning Anything

Many employers hire you to do one thing. But this gets old. You want to expand your expertise. If your employer doesn’t support that, you might try somewhere else.

You Received a Write-up

Your boss doesn’t like how you do things, and now you have received a write-up. You feel affronted and start looking for a new gig.

You Have Personal Reasons

Many people keep quitting their jobs for personal reasons:

  • Health issues. Maybe you are suffering from a mental or physical condition, like depression or chronic back pain.
  • Family issues. Maybe you have a sick family member you need to care for or are going through a tough divorce.
  • Work-life imbalance. Maybe you have difficulty balancing your personal life with your professional life.

You Are Seeking Better Opportunities

In a strong labor market, job hopping is a way to improve your financial situation and increase your job satisfaction, as it allows you to explore new roles.

Don’t Feel Bad About Yourself

Mainstream society views habitual quitting as a failure on your part. If you can’t keep a job, something must be wrong with you. You must be lazy or afraid to commit.

Don’t let this kind of shaming get to you.

First, it is your life. You have no obligation to make the people around you happy. If you want to quit every six months and try something new, that is your choice.

Second, you might earnestly be looking. But some employers you click with, and some you don’t. There is nothing wrong with shopping around until you find the “right” fit.

Finally, when other people call you lazy or afraid to commit, a big part of that is projecting. It is them who are afraid to try something new. They are holding on to a crappy job for dear life.

So, stop beating yourself up about, “Why do I keep quitting jobs?”

The Real Reason Why You Keep Quitting

The real reason why people keep quitting their 9 to 5s is that employment is fundamentally flawed.

As an employee, you are essentially a slave. You must now …

  • … follow orders
  • … work on projects that bore you to death
  • … live life on your employer’s schedule
  • … stay put in the same city

Nobody enjoys that. We want to roam freely, not be locked in a cage.

Then there is the lack of purpose. As humans, we were meant to realize our unique potential. That is the meaning of happiness — to create yourself. But when you are working for somebody else, you are working to make their vision happen, not yours.

On a more practical level, employment has become less attractive over time. 20–30 years ago, the social contract between an employer and an employee was stronger than it is today. If you gave your life to the company, you were at least rewarded with stability. You would keep your job, get some health insurance benefits, and receive a modest pension. Don’t get me wrong — it was still a prison, even back then. But it was a somewhat more comfortable prison.

No matter how you look at it — employment is a lost cause.

What’s the Solution?

If you are a habitual job quitter, you have three options:

  1. Embrace it
  2. Start a passion business
  3. Exit the system

1. Embrace It

Here is how “normal” people go about quitting their jobs.

Person A is tired of their current job. They do mundane work, their boss is being a jerk, and the pay is crappy. As a result, person A keeps fantasizing about finding a new job — one that is interesting, treats them well, and comes with a bigger paycheck.

But due to inertia, they keep putting off applying. Only when things really escalate will they finally make the switch. And for the first six months, it’s great. Just being in a new environment induces them with energy.

But then, inevitably, the whole cycle starts over. The work starts to become routine. Their boss is not as laid-back as they originally thought. The office politics are driving them crazy. Person A is back to where they started. And now it will take them half an age again to do something about it.

The strategic job quitter looks through all of this. They understand that every job ultimately sucks. It’s only those first few months that make you feel excited. That’s why they keep switching — they get all the positive stimulation they can out of a particular job. But once the routine kicks in, they are off to the next gig. They are gaming the system.

There are a few things to keep in mind to make this work.

First, this is much easier to pull off in certain industries than in others. For example, in the marketing world, it is common for people to change jobs a lot. So, pick an industry that accommodates these tendencies.

Second, constant switching will be more acceptable in a metropolis like New York, Paris, or Berlin. Life is faster here, and this also applies to the professional world. So, consider moving to an urban center.

Third, you can omit prior positions on your CV, to make it look like you switch less often than you do. Few employers bother to check. To be clear — that is lying. But then again, you are dealing with a system that just wants to exploit your workforce. Should you really feel bad about exploiting it back?

On an emotional level, it can help to let someone in on your switcher mindset. When you can share your rationale with a confidante, it will strengthen your resolve. The opinions of others will less affect you.

Finally, don’t make excuses. When you want to quit, tell your boss how it is — you dislike the work. This is not about doing the “right” thing; it is to desensitize yourself. If you practice being direct, you will become better at it. You will stop caring.

2. Start a Passion Business

If you keep switching jobs because your work feels meaningless, maybe it’s time to start your own passion business.

The idea behind a passion business — you monetize an activity that you are truly excited about. This way, work stops feeling like work. For example, if you love yoga more than anything else in the world, consider becoming a yoga instructor. If you practice your shredding every free minute, maybe your calling is being a studio musician.

There are a few limitations with passion businesses that you need to be aware of.

Passion businesses take longer to monetize. If you offer copywriting or app development, you will have almost instant cash flow; that’s how sought-after these services are. But if you want to make a living from self-publishing your space operas, be prepared to not make much if any money for the first few years.

Overall, passion businesses are not as profitable as “regular” businesses. You can make a living from them, but you probably won’t get rich. I call this the “boring vs. exciting spectrum.” As a rule of thumb, the “drier” your job feels, the easier it is to earn. That’s why B2B entrepreneurs tend to do well. But the more “inspiring” your job feels, the harder it will be to earn. There are not that many millionaire SciFi writers.

Notwithstanding these limitations, starting a passion business might be the best thing you ever do in your life. I have done it several times and never regretted it. Yes, the initial two to three years are hard. But once you start to get some cash flow, you are now part of an incredibly fortunate elite — you get to do what you love most in life. At this point, there is no reason for compulsive job quitting anymore.

3. Exit the System

The third option is to exit the system altogether.

Some people simply don’t want to work, at least not in the traditional sense. And if you are okay with the consequences — missing out on consumerism, no financial security — then that’s perfectly okay. It’s your life. You can do whatever you want with it.

One way to pull this off is to cut your expenses to the bare minimum. Think $700–800 per month. With that little money required to survive, you can get by working the occasional odd job. Once you finish a stint, you can go several months before you have to take up another odd job. For most of the year, your days will be wide open. You will be free to idle.

How do you cut your expenses to $700–800 per month? Here are some tips:

  • Move apartments. This could mean moving in with roommates, moving cities, or even moving countries. For example, long-term rentals in SEA can be as low as $100–200 per month. Certain countries in Latin America and Africa come close.
  • Cook at home. Buy all your groceries at discounters like Aldi. Pay attention to items on sale. Then cook all of your meals at home. This way, you can spend as little as $100–200 per month on food while also eating healthy.
  • Get rid of your car. Sell your SUV and get a used bike. Better yet, walk everywhere. If you need to travel somewhere further, use public transportation. Not only will this save you lots of money, but it will also take care of your exercise needs.

If you are set on getting by on $700–800 per month, it can be done. The more difficult part is to withstand the social pushback. Your family and friends will let you feel their disapproval. They will think you a dropout and a loser.

Ultimately, you need to ask yourself what is more important to you. Do you want to please the people around you? Or would you rather live your life in a way that makes you happy? I would argue it’s not a difficult choice.

There are people who take this even further. In 2000, American Daniel Suelo decided to quit money. He moved to a cave near Moab, Utah, and started foraging for food as well as dumpster diving. Later, he traveled the country by hitchhiking, making it as far as Alaska, where he survived on catching wild salmon. If you are interested, the writer Mark Sundeen chronicled Suelo’s adventures in, “The Man Who Quit Money.” Great read.

Of course, when we hear a story like this, our first reaction is, “What a weirdo.” But what is so weird about going off-grid? What is so unthinkable about getting a plot of land, building a hut, and growing your own produce? Humans lived like this for thousands of years — and many still do.

It’s easy for us to turn up our noses at somebody like Suelo. But when life comes to an end, who do you think will feel more at peace with themselves? The outcast who had all the adventures? Or the corporate slave, who worked 40 hours a week for 40 years? There is something to be said for quitting it all. Don’t outright reject this option.

1 thought on ““Why do I keep quitting jobs?””

  1. Niel thank you. I’m 22 and I feel like it’s time I work for myself. I’ve always had a problem with others being in charge of my life. I’m currently a regional assistant director and at the time it was cool being in meetings with top executives, but I realize working for others is not for me. I needed to hear this.


Leave a Comment