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Should I quit my job? What are the top 7 questions we ask ourselves?

why should I quit my job
We all look gloomy when contemplating about quitting a job - Photo by Andrea Piacquadio from Pexels

This is a question people continuosly ask themselves.


It is a question that usually gets asked along with it’s derivatives in the form of:

  1. When should I quit my job?
  2. Should I quit my job before I have a new one?
  3. How do I quit my job?
  4. Should I quit my job and give 2 or 4 weeks notice?
  5. My boss hates me, should I quit my job?
  6. Should I quit my job if it makes me unhappy?
  7. Should I leave my job for more money?

These are all fair questions that people post, ask their friends, family, themselves…

…and google, which is where I found the questions and wanted to address them for how I see this matter.

Same as you reading this post might be asking yourself this question now (or one of the versions listed above), I have been asking this myself for the past half year more intensly then ever.

Why I decided in the end to quit my job, you can read in this looooong blog post here.

should I quit my job - top 7 questions

What went through my mind at the time, I will address by answering the questions above and see if you can identify or find an answer for yourself in those points.

Use the table of contents below or in the sidebar to navigate to specific questions or sections.

Table of Contents

1. When should I quit my job?

That is quite a common question for people that feel like they owe something to the company they work for or don’t like leaving while the company is in the middle of an important project or deadline.

I have a friend whom I worked with for half a year at a company and the pressure at work got a bit hard.

At first he was ok. 

He thought it was just a momentary thing.

But then, when he realized the pressure was going over his head not allowing him to function normally outside the job, the question arose Should I quit my job

And after some time the question in his mind changed from 

Shoud I quit my job?


When should I quit my job?

As said, the pressure was building high as he had other things in life not just the job.

The reason why he didn’t quit right away, even though he had another employment ready, was because he is the kind of person that won’t leave you behind when you strugle.

At the time he was considering to quit the job, our company, whom we were working for was going through some major new feature implementations and hard deadlines.

Being a nice person that he is, he stayed until things cooled off.

Short while after that, he gave a notice he will quit the job at the end of the month. 

Is that the same reason for you? 

Is that why you are thinking when to quit the job?

This was just a practical example from my friends’ experience, but I will give you mine too.

When I decided to quit my job

For me personally the reasoning was a bit different in all honesty.

I was working at the company for almost a year now.

From what I can tell from the praises I was getting, I was doing my job well.

When I started working at the company, I was stupid enough to sell myself short thinking to ask for a raise after proving my worth…


so…a friendly advice, if you know you are good, don’t sell yourself short.

don't sell yourself short when getting a job - when should I quit my job

Anyhow, after half year working at the company I asked for a raise thinking to myself:

“My work was well done, people say good things about me…

so lets do it!”

And so I did, I asked for a raise.

So what happened?

I ran into deaf ears, telling me to ask in about half year.

So what did I do?

Did I quit my job?


As a good boy, I went back to work and continued doing well, the same as I did up until now.

I worked for the next half-ish year as good as before if not better, even taking extra asignments, never refusing them.

So, after that 1 year milestone was closing in, I decided to ask for that raise once again, this time giving the company an ultimatum, that I will be leaving if I don’t get a better work position and a raise.

After speaking to the manager, must say he is a nice guy otherwise, he lead me to believe nothing was going to happen in regard to my raise at least until the end of the year.

Have you ever heard similar words? 

Telling you “Ask again later in 6 months, 1 year, 2 years” or whatever similar?

Well, for me that was the same as telling me:


…but in a nicer tone and words.

And that is when I realized that I should quit my job.

After that conversation I wrote my letter of resignation saying that I would be leaving at the end of the month.

The when in my situation is sort of complementary to “why” I wanted to leave. 

For me, there was a time frame/a date I gave to myself where if I wasn’t able to achieve that goal in that time frame I would go pursue other goals instead.

I don’t know what your situation is, but figure out why you want to leave and give your self some conditions that need to be fulfilled, “the when” will be easier to decide that way.

For the conditions, I believe the other points from the list above explain better which those could be, so read on to get a better idea about it.

2. Should I quit my job before I have a new one?

I didn’t.

That doesn’t at all mean you should follow in my foot steps!

Let me explain.

The way I see it, it depends on multiple factors if you should quit your job before getting a new job.

Here is a checklist to help you figure it out:

  1. What is your financial situation?
  2. Do you already have a secondary income, possibly a passive one? 
  3. Are you a family  guy? Having extra mouths to feed are generally extra expenses for the family guy
  4. What are your monthly expenses and will you have a problem covering them if you quit your job ahead of time?
  5. Do you have a home of your own?
  6. If you don’t have a home of your own, can you go live at your parents house?
  7. Is your job stressing you?
  8. What is your plan after you quit your job?

Depending on how you can answer the questions above for your own case, will determine if you can or should quit your job before you have a new one.

So lets elaborate a bit on those and maybe give you more food for the brain to help you make an easier decisions…

…after all, this is what this post is meant to do.

checklist -Should I quit my job before I have a new one
Should I quit my job before I have a new one - Checklist

The order of reasons listed above is sort of written in a priority order for you to check

And I am not saying other factors aren’t as important (some even more so like taking care of family), but let me elaborate and you will see that I have a point about it.

Should I quit my job before I have a new one? It sort of depends on your Financial situation

So financial situation is sort of the mother reason of them all, because if you have a good overall financial situation, quitting a job prematurly before you have found a new job is totally ok.

If you are financially secured, you either have a passive income or enough money that you can take care of your living expenses, housing and of course your family if you have one.

Having a good financial situation also makes it easier to quit a stressing job, but again this is a separate issue that has it’s own iterations, depending how stable you are financially…

…as some times finances aren’t the only factor, but having them in order aleviates some things.

Do you have a secondary income? A fair question to consider before quitting your job

should I quit my job without a secondary income

To answer to my own answer above why I quit my job without having another job, it’s simply because I already had a secondary income.

Now that I explained myself, I want to make clear that if your finances aren’t great, you probably should stay at your job until either you find a new full time job, find a secondary income or have a passive income (or generate one –> Check some good ideas for 2021 here ).

Why do I say so?

Well, it’s because I have been through it a few times already.

Having to strugle with money, god forbit having some debt on you or recurring payments you need to make…

…you are certainly in for some rough times.

If you plan to quit your job and want to do it before finding a new full time job, please do yourself a favor and at least find some gigs to do meanwhile.

Find some sort of complementary work to at least cover your basic expenses through the month until you find that next full time job.

Do you have extra mouths to feed and are thinking of quitting your job before finding a new one? WELL DON'T!

extra mouths to feed when considering to quit a job prematurely

Personally I don’t have a family of my own so maybe it’s not my place to talk


I grew in a pretty humble home, where most of the time only my mother worked and as much as she did her best, it wasn’t always marry times.

With that being said, if you created a family, make sure to take care of it.

Now, if I reference the above paragraph about a second income or a passive income…

…I would like to mention that if your case is such that the secondary or passive income covers yours and your family expenses, then feel free to quit your job before finding the next one, else clenche your teeth and endure it.

What Single Parents should do

For the single mother or single father also as this can be an issue for both genders, things can be a bit harder of course.

If you are a solo parent, try reaching to your close family, brothers, sisters, cousins, ants, uncles or parents and ask for  help.

I know from personal experience that doing a 8/5 plus trying to acomplish something along with it can be really tough not everyone can manage.

That’s why I say, you need some help.

Personally I quit my job, so I could focus on my other income stream more and do other things that fulfill me more.

So if you need to make a change in your life like a job change and need some help about it, if you have the option to ask, go ahead and DO IT.

Think of your monthly expenses before thinking on how to quit you job

This is how our society works, you need to have money in order to make a living .

Of course there are The Jobless Claims that many countries offer to their jobless citizens, but even with that money it’s not always easy.

ARE YOU thinking about YOUR monthly expenses?

I myself have been a recipient of jobless claims as well at some points of my life, while I was still living in debt and was looking for the right job.

Luckily for me, at least I was able to live at my parents home in order to save rent money, which helped me slowly recover and get to where I am at now.

My personal monthly expenses at the time weren’t big.

They still aren’t as I still live a pretty modest life style.

…but let us leave me aside for a moment and lets talk about you.

This is a rule anyone should pay attention to whether you come from humble origins or are used to living on a big foot.

If you are someone who was used to spend alot of money on a monthly basis, adjusting might be somewhat harder for you.

But you should do your best to work out your math and adjust to the situation.

Being able to shrink your expenses and live only on the bare minimum is a skill that will help you get through….

…in case you desperatelly need to get out of your job before getting a new one.

I am not suggesting you should quit your job before getting a new one.

But in case you are seriously considering it, let this be your guide whether you do it or not.

Calculate your monthly expenses

Do your math properly

Monthly expenses are one of the first calculations you need to make before considering if you should quit your job before finding a new one.


Take your pen and paper, a calculator and do some additions and subtractions to see how much is your reserve and how much you will likely be spending in the next months or however much will take you to get a new job.

Btw, making a living expenses calculations is a smart life approach regardless of thinking about quitting your job.

Knowing how much you make and how much you spend will also help you understand how much money you can potentially put aside or even invest for a better future.

Conclusion…DO YOUR MATH!

Do you have a home of your own or can you "rent for free" for a while?

These are basically point 5 and 6 united and explained together.

Having your own home or a rent free place to stay at will significantly reduce your monthly expenses, at least for an average person. 

I mentioned parent’s home as that is usually where most people run to when they have money or housing problems.

home sweet home

But, of course if you have some other family member or a close friend you can ask for the favor, the better for you.

Just as a btw remark, it pays to be a nice person, because in these critical situations it’s good to have a good reputation and people willing to help you.

Another important factor of having a place to stay is that you won’t be pressured about having the rent money or face eviction…

…and those who have been though that know what I am talking about.

I realize if you don’t have a home going to live to your parents, especially if you have already a family of your own might be troublesome for varoius reasons, but look at the bigger picture and think of it as a temporary solution until you get your life together.

In conclusion, this section is sort of a subsection of the expenses section where having a place to stay for free or very cheap can in fact help you make the decision if you should quit your job before finding a new job much easier. 

Is your job stressing you

is your job stressing you and you are thinking to quit your job

Job stress is a factor that leads to many people quitting their jobs.

Having a stressing job in addition to thinking of “Should I quit my job before I have a new one?” can lead to to many unhappy feelings.

In fact a stressing job is probably one of the leading factors why people decide to quit their jobs before finding a new one.


I know it’s hard to hear these words….

But please do not quit if the other points aren’t fulfilled as it will make you regret the decision and resent yourself for it very soon, when you find yourself pondering where to find the money for the monthly expenses.

Instead, if your job is stressing you, figure out why it is stressing you and if you can, try and fix it.

If that isn’t an option still, then make a plan on how to get out of it without you paying the consequences on the long run.

In case you need more Information or Useful Tips...

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Hold strong in stressful situations and try to cover the other checklist items first

I know stress can be a horrible thing as I experienced it myself too with my neigbours renting next to us and having to deal with that for 2 years before actually doing something about it.

But even so, unless you have a way to get by financially during the “no job time”, don’t just quit the job because of stress before finding the next one, make that be the last reason why you quit…

…go through the checklist above and if the financial part checks out, then you have my blessing too, run as fast as you can.

To conclude this paragraph.

Even though I say check your financials first, I am fully aware that a toxic work place can be heavily detremental to you and your mental health on the long run so if you can, I absolutelly support getting away from it. 

What is your plan after you quit your job?

Not the best example of a PLAN

This question would probably be more suitable for the end of this article, but the answer I am giving to it is:


Don’t just quit your job. 

Whenever you make an important decision in your life, have a plan for the future.

It doesn’t have to be a big long term plan…if you have one, more power to you of course.

But just having an intermediate plan on how to handle the situation after you make that important decision like leaving a job, can make a difference where you will land in the end.

Whether you want to leave jour job before getting a new one or wait to leave it until you get one, make a plan how to handle things…

…it will make it easier on yourself.

Planing things and following a plan is easier then wondering around without a plan!!

But that is a subject I will cover in another blog post.

3. How do I quit my job?  Step by step guide.

This is another one of those questions that opens more questions.

I suppose the first question I will ask you is:


There are graceful ways and less gracefull ways of leaving.

do you want to quit your job gracefully or in a hurry
Do you want to leave greacefully or in a hurry? - Photo by Wellington Cunha from Pexels

As a general rule of thumb, same as many suggest, the best way is to leave gracefully and this is how you should do it to achieve that:

  1. Figure out if that is really what you want to do and the reasons why you want to quit.
    If there are reasons that would make you stay, discuss them with your manager or your boss and try to find a way if possible.
    Because changing jobs can be difficult, if that is what you are looking to do.
  2. Are you looking to leave with grace? 
    If so, then tell just your manager/boss about it and don’t make a fuss at the work place or other coworkers. 
  3. After you told them that you are leaving, give them a resignation notice of 2 weeks or more with a formal letter.
    In case there is a longer resignation period in your work contract act accordingly.
  4. Act normal and do your job as ussual until the last week or few days of work and then write a goodbye letter to your co-workers.
  5. You will probably get asked by some of them the reasons why you are leaving.
    Keep it cool and whatever your reasons for leaving are whether you tell them or not, don’t trash the company or the people, mention it in a composed manner.
    You never know when a good reference might come in handy. 

Should you ever quit your job and leave ungracefully?

There is another version of this story though.

What if the employer wasn’t really great, do you still exit gracefully?

I suppose it depends on the situation at hand and if you can try to be the bigger person.

But that is not always the case as sometimes the work conditions can be hard and tough on you…

…and in those scenarios prioritize yourself.

For example if you just found a new hot job that really wants you all hands on deck asap and you can’t wait to start working there, then for a shitty employer I honestly wouldn’t bother too much being gracefull and with all the resignation period stuff.

If I got my new hot job and would have to start next week, I would simply call them up or go to them in person if that is an option and tell them I am leaving…

followed up by a written resignation letter as there needs to be an official document.

Chances are, if the boss or the company wasn’t nice to you, that they will not be really upset that you are leaving.

In fact there is also a chance they wanted you to leave on your own terms as some laws state that you can not hire a new emplyee for the same position unless you fired the previous one for a justified reason or they left on their own.

Disclaimer: that is how it works in my country, but I am not a lawyer or know enough to say if that is how it works everywhere in the world.

There are also plenty other scenarios which I will not be listing here beacause my posts tend to get very lengthy, but ask me in comments and I may write a separate post addressing your specific questions and queries.

4. Should I quit my job and give 2 or 4 weeks notice?

2week notice or 4 week notice when quitting your job

Giving a 2 weeks or 4 weeks notice I guess it depends on the urgency and a little bit on the contract with the company.

Another factor is of course the reason and urgency of why you are leaving.

If you are trying to leave gracefully and you know in advance that you will leave in a month or more, you can easily give them a longer period of notice therefore 4 weeks.

On the other hand if the situation at work isn’t the greatest and you found something better so you want to leave in a week or two, two weeks is fine in my opinion.

There is also the factor of how quietly you want to go of course.

Sometimes giving a 4 week notice of leave will somehow get the information leaked out and your co workers will learn about it before you wanted them to know and maybe cause some weird interactions in the office.

If those are your concerns, consult with your manager or someone you trust in the company and act accordingly, potentially even limiting the leave notice to 2 weeks only.

There are likely other scenarios which you may know more about…even I don’t know them all 🙂

So if you have something to add to this, please leave a comment below.

5. My boss hates me should I quit my job?

my boss hates me, should I quit my job

Are you sure?

I am going to be a bit mean here and ask…are you sure he hates you and not the other way around?

Jokes apart, sometimes we people think that others hate us just because we don’t get the attention we think we deserve.

Another option is that the guy is bussy with so much stuff on his back, that he simply appears to be mean or hatefull.

Does that necessarily mean that your boss hates your guts and you should quit your job because of it?

Probably not.

In many cases you should probably first look yourself in the mirror and figure out if you are the one getting the wrong impression of him.

If you can make a conclusive assertion that your boss hates you, it still doesn’t mean you should quit your job, you still got some options.

Lets discuss those options now.

Boss problems in a bigger company - how to act? Should you quit your job?

I mean, if the company is big and has many divisions, your boss might be just a pawn in the whole story and has anger issues by being played by higher ups.

As first thing maybe try talking to him/her and see if you can find a solution and you can make peace with him.

Some times that will work and sometimes not.

It’s another one of those situation where it kind of depends on many factors to list them all.

But as a general rule, you should try talking to the superior and be willing to make some compromises, if that is what will help you “achieve peace” and continue working there.

In case that backfires, maybe try reaching to some one up the chain and maybe try to get moved to another division…

…or have that boss moved away…

…or perhapse just get yourself assigned another supervisor that you can work with.

What if none of that works?

Well, in that case, you are probably better off and you should be looking to get another job and move away from there.


Boss problems in a Smaller company and what to do about it

In smaller companies the issue is a bit different as likely your boss is also the owner of the company.

What to do in that case?

There aren’t many options really.

Go to talk with the man, or boss woman and see if you can sort things out.

I worked in a few smaller companies myself and remember at some point in one of these companies I discovered I wasn’t happy with my co-worker, so I went to speak to the boss.

Actually, this was pilling up for a while, it was just me hoping the co worker would change, which he didn’t…so I went to the boss.

Long story short, he wasn’t willing to let the guy go, so I left instead.

The story is actually pretty similar if you have issues with your boss directly.

Talk to him and see if there is a potential solution to whatever the issue might be.

If there is not, start looking for a different job.

In case you are hard to hire, my suggestion is to clench your teeth, stick to the job and start playing the lotery 🙂

Jokes apart, what you should do if you aren’t a person who is very hireable, maybe start thinking of starting your own company, maybe that suits you more.

6. Should I quit my job if it makes me unhappy?

Should you quit your job if it makes you unhappy…?

Is that a trick question?

Personally if something makes me unhappy, I try to avoid like the plague…


Well, except if you need your job for the reasons explained in point 2:

Should I quit my job before I have a new one?” <–Click here to scroll back up

Go read that first if you skipped to this part, maybe it will clear some thoughts.

Being unhappy with a job is similar to what I explain in the section about being stressed at your job or because of it.

If something causes negative feelings in you and makes you disfunctional, you should try and see if there is a solution for it otherwise abandon ship if there isn’t.

Being happy with your job given that it is something that you do everyday should at least have neutral feelings.

Bad feelings about something on the long run don’t work.

It will either cause you to become socially disfunctional or implode.

…likely both.

Staying at a job for a greater good even if unhappy, yes?

Even if you are unhappy at a job, but you are staying there for a greater good, I do not condemn that.

Actually, what that means, is that you likely have a plan and if you are willing to stay at a job that doesn’t make you feel good in order to achieve that, more praise to you.

Striving for a higher goal and looking past your short term obstacles on the way is probably what will likely get you there.

So if you can do that, hang in there, I know it ain’t easy…

…but it will be worth your while in time.

7. Should I leave my job for more money?

Should I leave my job for more money

I would love to give an absolute yesssss!! to this one, but again, it’s not an absolute answer for everyone.

So what do I mean by that?

Well, Iam sure some of you at least have friends with high paycheck jobs, or maybe you are that person.

When your social security isn’t as much at risk, the other benefits like the chill work environment, the easy going colleagues, maybe some free gym pass in the building or free snacks provided…

…and many other little things that make your day better, will matter more then a few extra bucks in the pocket.

If your pacheck isn’t the main issue, you will start considering those benefits as maybe more valuable then I don’t know 300-500$ extra on your paycheck.

So you see, it’s not an absolute answer and it depends on whom you ask.

For example a friend of mine joined a company based on my suggestion as he is good in his field and got a good paycheck there.

The problem was that the work environment made him feel pressure and he did actually the opposite then the the question at hand: 

“Should I leave my job for more money” 

…he actually started considering to get a job even for a lesser paycheck, just to get out of the mess and the pressure he felt.

And that is an example that demonstrates that bigger paycheck is not always the obvious move.

What if I need the money?

i need the money

The answer to that question is a bit self answering.

If you need the money, I guess you will have to take the job and whatever comes with it.

But, from personal experience and what I have been told by some friends, in the end when the pressure on the job is too hard or the working environment unbearable, there is a high likelihood that you won’t stay at that job for too long.

Even if the paycheck is better and you changed the job just beacause of that.

But then again…I guess it also depends a bit on your character and what you can endure…

…we are not all built in the same way and some have harder skin then others.


As you see quitting a job isn’t always the easiest thing to do and there are always various options to each of the questions we ask ourselves.

I realize that there is more to be said on this matter and the questions could be explored even deeper.

But yet I hope I have given you some directions or ideas on how I see these matters and hopefully they will come in handy.

If there is something you didn’t understand from my explanations, ask in the comments and I will do my best to answer.

Also check in one of my next blog posts about how to write a resignation letter.

I am not a big pro in the field, but I am sure you will find it usefull 😉

And for the end as usual if you enjoyed the article, like subscribe and share.

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