(Quiz) Should I Quit My Job? 11 Things You Need to Know

“Should I quit my job?”

It’s something every sane person will ask themselves at least a dozen times at various points in their career.

The question is very complex and difficult to answer because it has so many moving parts: How terrible is your job? What’s the job market in your area like? What are your financial needs? How employable are you? Do you have a job lined up? Are you working on a side business you want to grow?

Depending on the circumstances you’re in, quitting your job may be the best you can do for yourself and your career. At other times, staying at your current company a little while longer may also be the absolute best approach for you now and in the future.

Should I quit my job without another job lined up?

Ideally, you should have another job lined up before quitting. Job seekers that are employed receive three times as many offers as unemployed ones, salary offers that are 23% higher plus more benefits. While it is unfair, companies and hiring managers discriminate against unemployed people and consider them to be less “confident” and “hireable” compared to employed job seekers.

Hiring managers heavily discriminate against unemployed candidates.

According to this study by the US Federal Reserve Bank of New York as well as another high profile study done by the UCLA (short version of study, long version of study), hiring managers overwhelmingly prefer employed candidates versus unemployed ones, and also give them higher wages.

To put it into numbers:

  • Employed job seekers have a response rate 4x times greater than unemployed job seekers, with the same number of sent applications.
  • Employed job seekers were invited to 2x as many interviews as unemployed job seekers, with the same number of applications.
  • Employed job seekers received 3x times as many job offers as unemployed job seekers, with the same number of applications.
  • Employed job seekers were offered, on average, hourly wages 23% higher than unemployed job seekers.
  • Employed job seekers received benefits in 60% of cases, while unemployed job seekers received benefits only in 37% of cases.

The reasons for this are unclear, but the 50 HR people interviewed in the UCLA experiment gave employed job seekers a much higher score for “confidence” and “hireability”.

Not only are unemployed people discriminated against when it comes to finding jobs, but they also have to navigate tough and pointed questions regarding their employment gap. Did they get fired? Were they unable to find a job? Why couldn’t they find a job? Etc.

And even if you are selected for the job, there’s a good chance you’ll receive a much lower salary offer and fewer benefits, simply because you’re unemployed.

Unemployment will greatly damage your self-esteem and mental health

Unemployment and being unable to meet your financial living without outside assistance is profoundly damaging to one’s confidence and mental wellbeing.

According to the previously mentioned study, the emotional strain is most pronounced when you still live by yourself, but receive money from friends or family. In these cases, you feel indebted and unable to reciprocate the kindness offered to you. This in turn encourages feelings of guilt which strengthens the downward spiral.

The emotional strain is less pronounced in situations where you move back in with parents or family. This gives you the opportunity to give back, either through “rent”, doing housework or other forms of contributions.

This study by Murphy & Athanasou in 1999 (direct link to PDF if you want to read it) is a much more in-depth study-of-studies on the subject of unemployment and mental well-being that comes to the same conclusion: as long as you’re unemployed, your mental well-being will suffer.

Another aspect of emotional well-being is how unemployment impacts your social life.

Most people view their colleagues as co-workers and not friends (although there are plenty of exceptions). Despite this, interaction with colleagues does actually go towards recharging your “social contact” batteries.  

If you have a good social life outside of work, this aspect will not impact you in any noticeable way (except if you can’t afford going out with friends anymore). However, if your social circle is very small, then the loss of social contact is something to take into consideration.

How long will it take to find a new job?

The main problem when quitting your job, is that at some point you’ll have to find a new one.

As such, the question becomes “can I find a job before I run out of savings?”

The most recent data shows that it takes between six weeks to six months to find another job.

However, that is the average. Within those numbers you have multiple extremes. Some fields are starved for qualified personnel, so hiring can take 2-3 weeks tops. Others are swarmed with applicants and it can take many months.

Consider your medical insurance

Do you need medical insurance? Give some thought to this one. Even if you’re in perfect shape and health, stupid accidents do happen. You could be cheerfully walking down the street, slip of a curb and break your foot. Next thing you know you’re 10,000$ into medical debt.

Small list of bridge jobs to navigate through unemployment

As part of your back-up / contingency plans, consider taking up a gig job here and there to plug in some of the revenue loss.

Here is a quick list of 20 gig jobs you can work as:

  1. Rideshare driver.
  2. Food delivery driver.
  3. Pet sitter.
  4. Freelancer.
  5. Personal shopper
  6. Courier delivery person.
  7. Mover.
  8. Tasker.
  9. Massage therapist.
  10. Crafts person.
  11. Virtual assistant.
  12. Renter.
  13. Survey-taker.
  14. Photographer.
  15. Child caretaker.
  16. Graphic designer.
  17. Cleaner.
  18. Consultant.
  19. Cook.
  20. Data collector.

Should I quit my job if it makes me unhappy or depressed?

83% of American workers suffer from work related stress. 16% of workers claim they have already quit a job because of stress related reasons.

Interpreting those two statistics through one another tells unhappy stories:

  • You’ll likely still experience stress if you switch jobs.
  • To be fair, some jobs will be “a little bit stressful” while others are “extremely stressful”
  • There’s a 20% chance your next job won’t be stressful at all.
  • Rather than quitting, most employees just develop coping mechanisms to deal with the stress.

As for the primary causes of work stress, these are as follows:

  • Low pay: 14%
  • Unreasonable workload: 14%
  • Long commute: 11%
  • Annoying coworkers: 11%
  • Job is not in chosen career path: 8%
  • Poor work-life balance: 7%
  • No advancement opportunity: 6%
  • Fear of being fired / laid off: 4%

From a health and quality of life standpoint, working a stressful job is not worth it in the long term. Stress damage will accumulate and eventually outweigh any financial benefits you may receive. That being said, powering through short periods of stressful work can act as stepping stone to a more healthy future job.

Should you quit a well-paying, but stressful job?

The implicit meaning behind quitting a high-paying, but stressful job is that you will then look for a lower paying, but less stressful one.

Unless of course you love the stress and the high pay is the problem.

Jokes aside, it’s easier to make a decision if you look at the stress inducing elements of your job in terms of dollar value or health effects:

  • Adding 20 minutes to your commute makes you as miserable as getting a 19% pay cut. (Source)
  • A Swedish study of 3,122 employees, found that employees who continued to work for a stressful boss (with nonexistent interpersonal communication abilities) were 60% more likely to suffer a heart attack or stroke.
  • It can take up to 22 months for your stress levels to fully recover after a bad boss.
  • Women who worked 45 or more hours a week had a 63% higher risk of developing type 2 diabetes over a 12-year period. For some reason this does not apply to men.
  • Workers putting in 55 hours or more a week, compared with 35 or 40, had a 1.4 times greater chance of having a heart condition called atrial fibrillation, according to a study of more than 85,000 men and women in Europe. This increases chances of a stroke.
  • Working 55 or more hours per week increases chances of a stroke by 33% and the chance of heart disease by 13% over a 7-year span.
  • Source for the 3 previous bullet points.

That being said, there’s one more thing you should consider before quitting your high-paying but stressful job:

There’s a chance the new job will just as stressful, and on top of that come with a pay cut.

This Medium article describes such a situation. Here are a few excerpts from it:

The job I landed in was less stressful on paper […]. But soon I realized that the work I was meant to do simply didn’t motivate me in any way. The massive mental exertion required just to force myself to do work that I had no interest in doing sapped all the energy from me. […] The personal stress and unhappiness caused by this lack of motivation outweighed all the other luxuries of my “less stressful” job.

Work stress can lead to self-destructive coping mechanisms

Negative and damaging habits you can’t seem to stop are often caused by stress:

Stress can drive people to seek release in alcohol.

This may be an effective strategy for a few hours or a day. However, once the effect wears off, alcohol (through the neurochemical changes it produces) can actually increase the feelings of stress and anxiety. In the worst case scenario, a moderate drinking habit can spiral into full blown alcoholism.

Stress eating is another common coping mechanism. It is generally more common in women (men prefer alcohol and tobacco). Fat and sugar heavy foods act on our brains in such a way that it can release tension and stress.

Stress causes anger issues.  Other people release their stress through a habit of emotional spending.

Quitting a stressful job can allow you the mental space required to get the rest of your life back on track.

Is the job itself stressful, or the career stressful

A more uncomfortable situation can arise if your chosen career path is stressful by its nature, in which case the question is if you should consider a career change.

List of most and least stressful jobs in the USA.

Coping with stress to pad out your resume or CV

One occasion you should seriously consider staying at your current job is if you’re actively working on a high-profile project, one that recruiters would find appealing.

This could be the launch of a new product, signing up a big client, reducing costs for a given department etc.

The only condition is that the project end soon. Very few jobs and achievements are worth one year or more of working in a toxic and stressful workplace.

As an example, visual artists that work in the gaming industry are under strict NDA not to show anything about the game they are working on until it is released. As a result, they are not allowed to include images from the game into their portfolio.

To pad out their resume, visual artists in the gaming industry usually quit their jobs soon after release of a video game, so that they can update their resume and portfolio with what they worked on the past few years.

Should I quit my job and start my own business?

As a rule of thumb, consider quitting your job after validating your business idea, either by generating revenue or proving there is demand for what you want to sell. Next, consider if your business can grow faster by investing your income from the job, or by resigning and putting in an extra 40 hours a week.

How many businesses fail in their first year (fewer than you think)

One of the things that holds people back from starting a business is the fear that their venture will likely fail.

Well, statistically, that will likely happen. However, it’s not quite as bad you’ve been led to believe.

According to the Bureau of Labor Statistics, here are the following failure rates of businesses, at different time intervals.

  • About 80% of businesses with employees will survive their first year in business.
  • About 70% of businesses with employees will survive their second year in business.
  • About 50% of businesses with employees will survive their fifth year in business.
  • About 30% of businesses will survive their 10th year in business.

There are a few different ways to interpret this statistic.

Most businesses do fail, however the failure rate will be stretched out over a fairly long period of time.

In other words, even if your business does fail, you’ll likely have made a pretty good run with it and generated some money you wouldn’t have as only an employee.

But then, there’s also those 30% of businesses that are still alive at the 10 year mark. Those are the businesses that are strong enough to last, and also offer a comfortable financial situation.

So overall, there’s a 3 in 10 chance that your business will be very successful and reach the 10 year point.

Hiring managers look favorably on ex-entrepreneurs

If there’s one advantage to quitting a job, it’s that hiring managers generally have a good opinion about taking on ex-entrepreneurs as employees, but there is a catch.

According to this article by Harvard Business Review (which uses this study as a starting point), would-be entrepreneurs do end up making more money thanks to entrepreneurship.

However, most of those gains actually occur after the entrepreneur returns to the workforce as an employee.

In other words, while you may not have success starting your own company, you will make up for it by becoming a more attractive employee that commands higher wages – at least 10% higher wages, to be more precise.

And now for the catch: the 10% pay bump only kicks in if you managed to be on your own for a period of at least 2 years.

As the lead researcher of the study says: “It seems that the labor market values the experience of being self-employed [….]. Maybe the skills developed during a self-employment spell are useful as a salaried worker.”

Decide if your business needs time, or money

Before quitting your job, find an answer to the following questions:

Will your business grow faster if you quit your job, and invest 40 extra hours a week?


Will your business grow faster if you stay employed, but invest all of your wages into the business?

When weighing up these two questions, it’s worth noting that there are some things only you, as the entrepreneur, can do. If you don’t have the physical time to do actual business activity, then your company can’t take off the ground.

In some situations however, It’s possible for you to outsource a lot of your daily activity. For instance, you can:

  • Outsource your social media presence to a freelancer or small agency.
  • Outsource inbox management, scheduling and other admin tasks to a virtual assistant.
  • Outsource some of your marketing strategy to an agency.
  • Etc.

Depending on the deals you will strike, you can outsource most of your mechanical, time consuming tasks on the cheap, and allow you to focus on the real important aspects of your business – all without quitting your source of income.

Product market fit and validating your business idea

42% of start-ups fail because they don’t manage to fill in a market need and is the number 1 reason for business failure, according to CB Insights.

In business jargon, this is called “finding product market fit” and failing this step will in many cases bring down the company, as mentioned above.

The best way to prevent this fate is to validate your business idea before you quit your job and work on it full time.

As an example, let’s say you want to sell a particular kind of marketing services to local businesses. A good way to test if you can attract clients is to gather a list of 10-100 local businesses, email them with an offer to improve their services and see how many you can then turn into paying clients.

If you get 1-2 clients – that’s great, it means there’s a demand for what you’re selling and quitting your job could allow you to scale up your fledgling business.

A neat example of validating a business idea is that of Zappos, the online shoe retailer bought by Amazon.

Way back in 1999, the founder of Zappos wanted to buy some shoes online, but found out there was no place he could do so.

As a result, he wanted to see if an online store selling shoes was a good business model. To test this, he set up his online shop and whenever a customer ordered a product, he would physically go to the store, purchase the shoes and then ship them to the customer.

During the test, he came out at a loss. But he wasn’t looking to make money. He wanted to see if his idea was valid, and if it could be turned into a business.

Should I quit my job to focus on school?

Quitting your job to focus or go back to school is one of the best possible choices you can make. Higher education levels are very strongly correlated to increased earnings, lower risks of divorce, increased marital happiness, general life satisfaction and lower chances of unemployment.

These trends go back decades, and are just as true in 2020 as they were in 1980, maybe even more so.

Higher education levels lead to increased earnings

Study after study has shown that the more educated you are, the more earning power you will have.

If you don’t believe in studies however, then you might believe the US Government’s Bureau of Labor Statistics. As a government institution it has by far the most accurate and in-depth data on the labor market.

Here’s what the Bureau of Labor Statistics has to say about the correlation between unemployment, income and unemployment as of May 2020:

Chart for median weekly income.
Chart for unemployment rate

College degrees are rapidly becoming “must haves”

The previous two charts show that there is a significant gap in earnings between education levels.

What it doesn’t say is that the income gap is growing year after year and shows no signs of stopping.

In recent years there has been an explosion in the number of people with a college degree. You would think that since so many graduates are entering the workforce, that it would push down on wages since there’s a “degree inflation”.

But as the chart above shows, that’s not the case. College grads earnings are still increasing every year compared to non-grads. This means that a college degree adds real value, and is not just for show.

The downside however is that nowadays you really need one in order to be on a level playing field in the job market.

30-40 years ago it used to be that having a degree made you stand out and be easier to hire. Nowadays, having a degree is the default. If an employer has to choose between two candidates with identical resumes, but one has a degree and the other doesn’t, they will nearly always choose the one with the degree.

College degrees are strongly correlated with life satisfaction

Many studies have shown that a college degree is strongly associated with increased life satisfaction.

Part of the explanations is of course money. As mentioned previously, college grads still earn more than non-grads.

The other part of the explanation however is that a college education imprints a sense of purpose that cannot be easily learned otherwise. 

Finally, there is also a strong correlation between college degree and divorce rates.

In conclusion, a college education brings far benefits to a person, and not just financial ones. In many cases, these non-financial benefits can sometimes even be a greater source of comfort.