Is Now the Time to Quit Your Job? How to Know When to Go

Rosie Allabarton, contributor to the CareerFoundry blog

Do you dread going into the office on Monday morning, and spend your week counting down to Friday? This is a sign of more than the Monday blues – it’s a sign that you dread going to work as much as you dread going to the dentist. Quitting your job may seem impossible, but no one needs that kind of dread messing with their work/life balance.

After all, work takes up a huge portion of your life; you can’t afford to spend that time feeling unexcited and unfulfilled. Now might be the time to quit, or even to change careers.

Here at CareerFoundry, many students have told us they felt like they had reached a dead end in their careers, but they didn’t know if now was the right time to quit. They worried: – What should they do once they quit their job?- Would they truly be happier if they left their company?- What would it take to learn web development and start a new career?- How could they tell if becoming a freelancer was right for them?

Below we cover 8 reasons your job might not be right for you, and what to do about it.

Signs now might be the time to quit

Whether you spend more of your workday in front of the coffee machine than in front of your desk or are just plain irritable while you’re in the office, there are certain telltale signs that you should start considering a career change, or at least a change in role.

1) You could do your work in your sleep.

When was the last time accomplishing a task gave you the urge to jump up and down, call your mom about the good news, or hang your work on the fridge as a measure of your talent? If you can’t remember, chances are you are no longer challenged by your work, and it gives you no reason to feel proud of what you do.

Feeling proud of what you accomplish at work is a key motivator for you to show up to work in the first place. If working no longer makes you feel accomplished, your role is not satisfying your creative needs.

2) You are not learning anything new.

Along the same lines, feeling unchallenged at work means you are not learning anything new. If you are a software engineer, for example, your job might not be pushing you to learn new languages or adopt new tools. Since you are not being challenged, you probably feel like your brain has turned to mush. And I don’t blame you.

Have you seen your time at your company grow, but your skill set become stagnant? It’s no wonder you find work boring. Whatever the reason, a number of causes might be preventing you from gaining new skills at work, including:

  • Your company isn’t growing fast enough to create open leadership positions or upward mobility
  • Bureaucracy is blocking you from putting new ideas into action, taking on new projects or switching teams
  • A lack of transparency prevents you from understanding your company’s growth strategy and decision-making process
  • Your team is not growing as fast as your product, creating an undesired time lapse in the implementation of testing and designing
  • Your happy-go-lucky manager is always satisfied by your work – even when you feel your work is mediocre

Just one of these factors would be enough to make anyone want to quit!

3) You feel underpaid and undervalued.

While pay is not necessarily the only thing motivating you to work, let’s be honest: you see your pay and benefits package as a measure of how much your boss values your work. So if you are not making much more now, years into your career, than you were as a doe-eyed, inexperienced graduate fresh out of college, chances are you feel undervalued.

Even worse, being constantly overlooked by your manager for new responsibility and praise, despite how hard you work, can be really discouraging. If your salary and responsibility do not reflect your experience level, I hear you: it’s no wonder you are growing tired of your job.

4) Your life circumstances have changed.

If you recently married, brought a new life into this world, or saw another major aspect of your life change, you might find that the work-life balance that suited you before is now out of whack. You might need a role that lets you spend more time with your family or, in other cases, take on more responsibility – or even start your own venture!

5) You do not want your boss’s job.

When you’re daydreaming at work (admit it, we all do it at times), do you ever imagine being in your boss’s shoes? “If you can’t stand the idea of having your manager’s job, you need to think hard about what’s next,” writes Amy Gallo of the Harvard Business Review. Not aiming for your boss’s role is a sign that you might not be in the right place to ensure your longterm happiness. Because if you can’t look up to your boss, who else are you aspiring to be?

6) You have grown irritable and uncharacteristically stressed over the past few months.

Last week you heard your co-workers comparing you to Ebenezer Scrooge in low voices. In a way it was funny, because last night at karaoke your best friend said the same thing. While many life circumstances, such as watching your favorite character bite the dust on Game of Thrones, can turn you into a cold-hearted miser, there is a good chance that any long-term irritability is being caused by dissatisfaction or discomfort in your work environment. A number of things in the workplace could be poisoning your mood, including:

  • Gossipy coworkers
  • A disagreement with your manager
  • A company mission or strategy you don’t believe in
  • Company culture or values you don’t agree with, such as its hierarchy or mandatory stand-up meetings
  • Company ethics that clash with your own; for example you might disagree with the way your company handles its clients

Whatever the case, your negative work environment has bled into your personal life in a very bad way.

7) You unconsciously roll your eyes when someone asks what you do.

“So, what do you do?”

This Inevitable Party Question will always find its way to you in social gatherings. If you loved what you do, the Question would be no problem. But if you dread answering it, there’s a pretty strong chance that you flat out hate your job.

Whether you dread the Inevitable Party Question because you’re unchallenged or the company culture just doesn’t suit you, it is time for you to make a change.

8) You’ve asked yourself if you should quit for some time now but haven’t made a move.

Of all the signs that it’s time to leave your job, this is perhaps the most obvious. If you have been asking yourself whether you should quit your job, you are clearly unhappy with your work. There’s no question about it: it’s time to move on.

How to be sure

So you’ve recognized one (or more) of these signs in yourself. How can you be sure you’d be happier doing something different?

First, test that there truly is no way to make your job better

Are you unhappy with your assignments, or feel like you have stopped learning? Try to take on new or more challenging assignments, or switch teams to see if the change suits you. Take the time to talk with your boss to assure yourself that there really is no room for growth. You can even take courses to gain new skills to make you more eligible for a promotion (more on that later).

Search for new opportunities

Have you tried to make things better at work, but to no avail? Now is the time to think about other possibilities.

If you work at a large, established company, browse job openings at small startups. Or look into jobs in industries you have never worked in before. Do these new opportunities excite you? Take note of what appeals to you most, and keep track of any further skills you might need to obtain before applying to jobs like those.

Consider the risks

So you want to move on to bigger and better things. Great! Before you do anything, though, consider the immediate downsides to your actions. At first, when you quit your job, you will lose income – paychecks don’t grow on trees, after all! Depending on the situation, quitting might even damage your relationship with your boss or your professional reputation. Plan ways to mitigate any negative effects, such as helping your manager train your replacement, and putting a little extra into your savings account before you call it quits.

It’s time to move on – now what do you do?

You recognized the signs, you tried to make things better, but you still aren’t feeling so hot about your job. The time has come: you must move on.

There are a number of actions you can take now, like further training , starting down a new career path, or even freelancing to reignite your creative spark. Before you take the final jump into new territory though prepare yourself for what’s to come.

Below are a few steps you can take to help you transition:

Upgrade your skillset

Before you apply to other positions or ask for a promotion , prepare yourself to handle a broader range of tasks and take on a different kind of responsibility. Our offerings, of course, can help you gain new skills in web development and UX design at your own pace. Other programs, both online and in-person like those at General Assembly, can help you become a more attractive applicant in a variety of fields.

In addition to taking classes, volunteering is another great way to gain new skills. For example, offer to create a mobile app for a non-profit you admire, pro bono, to gain new development experience. Or offer to help manage a fundraising campaign in order to gain leadership skills. Idealist runs a frequently updated list of non-profits seeking volunteers.


Are you looking to enter a new field or even change careers? Most likely this means you will have to undergo more training. Many local colleges can help you prepare for a big change by offering night classes at affordable rates. If you’re looking to make a big change, you might even consider enrolling at a university to earn a higher degree. Finally, if you seek to enter a rapidly growing field like tech, look into training programs like ours, that get your trained up in web development or UX Design skills in just a few months.

Go freelance

Feel that being your own boss and choosing your own projects would be a welcome change at this point in your career? Think hard about the skills you have to offer as an individual, and begin drawing up lists of potential clients. Start promoting yourself and taking on projects while still at your day job and, if you work hard at it, you should have enough work coming in to sustain yourself as a freelancer before long.

Start your own business

Similar to going freelance, being successful at starting your own business takes a lot of time and hard work – and a lot of risk. Consider what services you would like to offer, and make sure they are targeted to a specific niche. For example, maybe you would like to start a boutique web design firm that specializes in servicing small businesses.

Next, consider taking a business course at your local library or college in order train in things like creating a business plan, human resources, payroll, taxes, and investor relations, which can be especially helpful if you have not had much experience leading a company. Once you know more about the legality of starting your own business, you can go about applying for the investment and/or loans you might need to start up and search for people you would like to work with. You might even consider finding a co-founder whose skills complement yours, which should make the day-to-day of running a business much easier.

Start loving your job

Work is a huge part of our lives; few things are more important than enjoying what we do for a living. If your job has you feeling bored, unaccomplished and undervalued, consider building the skill set to start at a different company – or even to start a company of your own.

Need some more advice? Still not sure what to do? Check out our video by Emil Lamprecht on what he did when decided to change careers.

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Looking to start a career in tech? CareerFoundry offers custom-designed courses to help you gain the training and expertise you need to become a UX designer or learn web development.


Lauren Mobertz is a New York-based freelance writer and editor who specializes in startups, labor, and digital nomadism. When she’s not writing about the career moves of gutsy millennials, Lauren is usually running in strange places or trying to dance Brazilian zouk. You can find more of her work at

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