“I Hate My Job. When Should I Quit?”

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A lot of the people I talk to and work with directly change careers, start businesses, or learn new skills because they hate their current jobs. They know they want to quit eventually but they don’t know when that is. If we work together, we eventually have the conversation about when it makes sense to say auf wiedersehen to the old job in the cubicle, with the overbearing boss, or doing the work you just plain don’t like.

Judging when to quit isn’t easy — especially when you make that judgement alone. People are hard-wired to overestimate risk and underestimate reward. If you’ve gone through the traditional K-12 system, landed a bachelor’s degree, and always put a reward on sticking through hard classes and awful professors, it feels weird to quit.

But there’s nothing inherently wrong with quitting. Sticking through sub-par situations shouldn’t be a virtue. If anything, training through K-12 and then higher ed conditions people for conformity and helps signal to employers those people who won’t explore better options in their careers and quit.

Quitting can be good for you, your career, and even your employer. When thinking about quitting, I encourage people to think about the trade-offs that exist between staying at your current job longer, like your social capital/reputation, your immediate earning potential, and your long-term earning potential.

What You Can Get When You Stick Around

There are benefits to sticking around at your job even if you don’t enjoy it. How you weigh these (see below) depends on your own values, the stage of your life, and why you want to work.

Immediate Pay

If you quit before you have another job lined up or you have deals in your own business pipeline, you sacrifice the immediate, predictable pay of a 9-5.

Some people are fine with this. They have savings, a spouse, some freelance opportunities, or just low enough overhead where they can go a short period without getting immediate pay.

Other people can’t go a single pay period without a paycheck. They’ll weigh this benefit of sticking around more heavily.

This is one reason why you should save part of your paycheck, if you aren’t already. Just because you enjoy your job now doesn’t mean you always will. Your company could downsize, management could change, your role could change, or you can change. Having a few months’ pay in the bank gives you the peace of mind to quit if you need to.


If you value stability, routine, and habit, a 9-5 job that you’re familiar with brings a benefit over working for yourself, freelancing, or starting a new job with different habits. Even if you stay in your industry and in your role and just switch companies, new companies come with new learning curves. Climbing the new learning curve introduces an element of instability that some people can’t deal with.

Like immediate pay, too, you know how much you earn in a few weeks, you know how much goes towards retirement, and you know where your health, dental, eye, and other medical benefits come from.

When you prepare to quit your job, have these stability elements ironed out. Will you use a spouse’s benefits? When will you be paid? How will you save for retirement?

Access to Connections

Your job comes with access to connections. These might be your boss’  connections, your colleagues’ or your own that you’ve developed through your role.

I encourage people I work with to give explicit attention to those business connections they value that they built as part of their 9-5 job. I tell them to then go and work on developing those relationships outside of their job title. This helps minimize the cost of quitting. These people, if they legitimately enjoy you as a person, will be open and receptive to continuing the relationship separate from your job title.

What You Can Lose When You Stick Around

Sticking around doesn’t just come with benefits. If you’re honest about your job, staying at a job you hate has costs outside of what your other options are.

Long-Term Earning Potential

Some roles and companies have natural limits to earning potential. Outside of sales roles, there’s a natural cap to your earning potential for a title and industry (and even then, some sales roles in direct sales tend to have de facto caps).

This is an area where self-employment really shines. While you might not have a stable paycheck (at first) or any idea where your future earning potential comes from, self-employment doesn’t necessarily have a cap to it. You can roll out new services, new products, new pricing, bring on new customers, attack new verticals, and, effectively, control how much you earn. That doesn’t make it easy, but this is a benefit of self-employment.

The CMO of a high growth, venture-backed startup probably earns more in the long run than the head of marketing for a small business with little to no year/year growth, too. Non-liquid earnings also play a bigger role in startup jobs, where employees earn stock options in exchange for lower immediate pay.


You shouldn’t ignore a toxic work environment, an evil boss, a terrible commute, and general drudgery, too.

These stresses wear down on people over time. A terrible day at work carries over into life after work. It carries over into your marriage, into your social life, into your life with your children, and into your ability to work on side projects and new employment opportunities.

I’m an advocate for spending considerable effort on bettering your job before throwing in the towel and going somewhere else. You shouldn’t ignore the cost of a bad work environment on your professional and personal success, though. Sometimes work elements outside of your control can outweigh all the professional and personal development you do to enjoy your job.

Free Time

My client Declan worked for Big Faceless Company Corp. As a young father, he wanted to spend his time with his son when they both had energy. This meant spending time together during the day instead of holding himself up in a cubicle and putting his son in daycare.

Quitting his job (and freelancing, then turning his freelancing into a full-fledged business) allows him to spend time with his son. Now, while everybody else fills out TPS reports, he makes goofy videos with his son on YouTube.

What You Can Get When You Quit

Quitting isn’t just throwing off the shackles of a job you hate. It also brings new opportunities and flexibility.

New Earning Opportunities

The biggest and most-missed bonus of quitting is new earning opportunities. If you have any marketable skill — and if you don’t, you can develop marketable skills — you can freelance, consult, or run a business on the side. As you spend more time on your business and better your business development efforts, eventually you can earn more working on your business than you can at work.

A simple example here is a freelance copywriter.

An experienced and skilled copywriter can easily earn $100,000+. If you do copywriting gigs on the side while you work in marketing during the day, you can earn your salary plus whatever you earn from freelancing. Copywriting is a time-intensive skill, though. Eventually, you have to either decline new assignments, raise your prices, or cut back your day-job to buy you the time to work on your lucrative new projects.

Even if you aren’t yet skilled enough to earn a lot freelancing, the time you spend at your day job could be spent developing your portfolio.

Freedom to Choose Your Time

Some people don’t work well in an office environment or with managers. Some work shouldn’t be interrupted with meetings and phone calls.

Controlling your time has a premium value to it. If you work better in the evening, rolling into the office at 9 AM might be hurting you more than helping you. If you work well with long, uninterrupted chunks of time, working with a manager who blows up your Slack every day undermines your long-term ability to create.

Quitting brings with it the added cost of figuring out how to spend your time (not easy for a lot of people), but once you get through the Time Freedom Learning Curve, you can get a lot more done in less time.

Diverse New Connections

Chances are most of your connections fall into a few different and distinct work-related buckets.

If you’re an insurance agent, you probably know mostly insurance agents, adjusters, and clients.

If you’re an airline pilot, you probably know mostly airline pilots and flight attendants.

If you’re a marketer, you probably know mostly marketers and ad men.

Changing industries, companies, jobs, or launching your own business gives you the opportunity to go out there and meet new people you otherwise wouldn’t interact with. If you have to spend Thursday evening at a networking event (hint: don’t) for your company, that’s an evening you could spend meeting different people at a different event.

Social Capital With Your Boss (When Done Right)

Quitting can actually make your boss like you if you do it right. Most people get so focused on their next opportunity that they neglect their old job on the way out. This creates more work for your colleagues and your boss and puts you in a position of lower social capital with them.

Here are some steps you can take to resign the right way:

  • Make sure your entire job is checklisted-out and all of your records are up to date. You should be able to get hit by a bus without your company losing valuable information. Update your CRM, update your training manual, make notes of any important information you have like passwords, information on clients (put that in the CRM), and any other tacit knowledge.
  • Give your boss sufficient notice. Two weeks is the standard.
  • Volunteer to help with the replacement search. They’ll probably say no — but volunteering doesn’t hurt.
  • Let them know in person (or on the phone if you work remotely).
  • Don’t be a jerk in your exit interview.

What You Can Lose When You Quit

The downsides of quitting are probably already at the front of your mind (or else you would have already quit).


Some people really like the predictability of a paycheck, of knowing where to work, and of being told what to do. If this describes you and you still hate your job, line up another job that brings the benefits of security and predictability before quitting.

Identify what characteristics you hate about your current job so that you don’t end up in the same position at a different job. What, exactly, do you hate about your current job that can’t be fixed? What, exactly, would you change that would allow you to get a new job without giving up the security and predictability you value so much?

Social Capital With Your Boss (When Done Wrong)

Obviously if you walk into your boss’ office and tell him to shove it while throwing a chair out the window you will lose social capital and reputation with him. You’ll also lose social capital if you leave in a messy fashion, if you ghost your colleagues needlessly, and if you engage in any drama while quitting.

Be calm, cool, and collected while quitting and remember that you don’t need to burn bridges to leave your job.

Your Social Network

Most American adults can count only a handful of friends who are not colleagues.

Don’t be one of these people.

Don’t let yourself be isolated and atomized if you choose to quit and your colleagues stop talking to you. They probably will stop talking to you. Don’t take it personally. “Out of sight, out of mind” is a cliche because there’s truth to it.

How to Balance the Trade-Offs

With these trade-offs in mind, start thinking about how you balance them against each other. Each one roughly falls into one of three categories: opportunity cost, psychic costs and benefits, and social capital.

My general rule of thumb is that your opportunity cost is lower at the beginning of your career. Use this time to take bigger risks and invest your time in learning new skills. As you get older and become more skilled, your time is worth more. Psychic costs that used to be marginal to you (like commuting) start to feel bigger. Your reputation gets more entrenched. Keep the time element in mind while weighing these categories against each other.

Opportunity Cost vs. Psychic Cost & Benefit vs. Social Capital

Your earning potential, new earning opportunities, new networking opportunities, and social capital with bosses who respect a timely and graceful exit are all captured in the concept of opportunity cost. The cost of staying at your job longer is the opportunity cost of staying at that job. This is a combination of real, dollars-and-cents — captured in freelance invoices, consulting projects, and time you could spend building and launching a product — and intangibles like the people you could meet if you didn’t have to stay at the office late for a project.

Understanding Opportunity Cost

You want to get as good an idea of what this opportunity cost looks like as possible. One of the best ways of doing this is getting real, tangible opportunities that you could jump on.

If this means working on your business on the side, line up clients, interview potential customers, and implement business development and marketing plans (these are all the types of work I do with people who want to turn freelancing into a full-time business).

If this means changing jobs, develop a list of companies you’d like to work at and roles you’d like to fill. Build a personal website, a portfolio, a blog, and/or a pitch deck. Research these companies. Understand their revenue models and their growth challenges. Brainstorm ideas on how you can help them. Reach out to decision-makers and set up meetings or calls (my email scripts work for this).

Get tangible opportunities before quitting.

The more tangible the opportunities, the better you can understand your opportunity cost.

If you’re starting a business where you consult with data science companies in the healthcare space, for example, and you have an offer from a client to work on a $7,000 project that requires your full-time attention for 2 weeks, you know that the cost of staying at your job two more weeks roughly looks like this:

(Two weeks’ pay + benefits +(psychic benefits-psychic costs)) – ($7,000 + other business opportunities + (psychic benefits-psychic costs))

Some elements captured in opportunity cost:

  • Opportunities for advancement
  • Job opportunities
  • Freelance opportunities
  • Learning opportunities
  • Travel opportunities
  • Networking opportunities
  • Consumptive/leisure opportunities

Understanding Psychic Costs & Benefits


Psychic costs and benefits are essentially those elements that define your quality of life that aren’t captured by opportunity costs and the reputation you have with others.

One of my favorite examples of a psychic cost is commuting. Most people don’t enjoy commuting but rarely factor it into their quality of life. This is so much the case that when people move to the suburbs to buy a larger house the trade-off they accept is a longer commute. But people get used to living in smaller houses in exchange for shorter commutes. They don’t get used to longer commutes.

Commuting isn’t captured in opportunity cost (though, I guess you could think of all the enjoyable activities you could do while commuting and capture it there). Nor is answering to a boss, having unlikable coworkers, or general toxicity in your work environment.

Some people really, really hate commuting (I am one of them). For them, the chance to not commute might be worth more than what they currently earn.

This idea is captured in Tim Ferriss’ new rich, a concept he introduced in The Four-Hour Work Week. The new rich may earn less than the old rich, but they have better control over their time and efforts.

Get a sense of your psychic costs of staying at work and your psychic benefits. 

This is one of the reasons my Ambition Mapping workshops start with via negativa — making clear what you hate. (You can download the workbook here.) Psychic costs and benefits are largely subjective. You have to take the time to figure out what they are for yourself.

If you don’t enjoy the idea of tracking down and closing deals for your own business, quitting your job to become a freelancer imposes great psychic costs on you. The stability and security of a normal, 9-5 job has its benefits. If you don’t mind tracking down deals, then the trade-off of staying at your job might be higher than its worth.

Some elements captured by psychic costs and benefits:

  • Commuting
  • Work environment
  • Coworkers
  • An automatic social network
  • Flexibility & Freedom
  • Security & Stability
  • Responsibility
  • Clear opportunities for advancement

Understanding Social Capital

“What if I quit my job and my friends and coworkers hate me?”

This is a big fear looming large in a lot of people’s minds, whether they hate their jobs or just want to move onto new opportunities. This fear kept me in jobs longer than I should have been.

This is social capital. Social capital captures your reputation that you have with friends, coworkers, connections, partners, and bosses. When you have strong social capital, you can make requests of people and they don’t blink in fulfilling them. When you have weak or no social capital, they refuse, wait, or ignore your requests.

You build up social capital by doing well over different opportunities. Somebody who delivers under-budget, ahead of schedule, and above expectations accrues social capital as somebody who can be trusted with increasingly complex roles and responsibilities. Somebody who continuously flakes on meetings, delivers projects late, or is full of excuses develops negative social capital and a reputation as somebody not to be trusted with new responsibilities.

Gauging the social capital effects of quitting can be particularly hard in American companies. Most of your friends are probably coworkers. Your boss may be a long-time mentor.

Here are some ways to think about re-framing the fear that you will lose social capital if you quit.

Reframing Fear of Quitting in Case You Want to Go Back: Reversibility 

(h/t Josh Fischer for raising this point to me, which he credits to Tim Ferriss.)

If your fear is that you may want to return to your job someday, stop and ask yourself, “how reversible is this decision?”

Chances are it’s actually reversible.

Some employers won’t re-hire somebody who quit but if you leave in an orderly fashion and make clear that you’re leaving not because you hate the company (even if you feel like you do right now) but because you have better opportunities, you can leave the door open to return someday. If you’re in-demand elsewhere, your employer may perceive you as having even greater value.

You can gauge this by asking your manager or employer why they enjoy working with you. They’ll then give you reasons why they like having you around — reasons they will remind themselves (and you can play up) should you return and ask for your job again.

Reframing Fear of Quitting in Terms of New Growth: “Your Greatest Growth Is Ahead Of You”

I take this mental reframe from Ramit Sethi’s Mental Mastery course (I recommend the course if you like reframes and personal development).

Instead of looking backwards and asking yourself, “what might I miss out on if my coworkers or boss don’t like me anymore?” think about the growth that is ahead of you by cashing in that social capital. Regardless of whether your colleagues like you, by sticking around at your job, you’re missing out on some of the greatest growth that’s ahead of you.

This helps you move from thinking about social capital, relationships, and reputation in the weeds to thinking about it relative to the other costs of trying to preserve it. Sometimes growth comes at a cost to your old relationships and that’s okay. There’s nothing inherently valuable about these relationships. They are only valuable to the extent that you mutually enjoy them.

If you start working out and you have friends who judge you for taking care of your fitness, would you stop working out or think about the cost to your health and fitness that comes with listening to them?

The same can be applied to your professional growth.

Reframing Fear of Quitting to HELP Your Employer: “I Want People Who Want to Be Here”

I have an old business partner who would fire employees he discovered weren’t planning on being at the company for more than a few years. This seemed harsh when I first found out about it so I asked him about it.

“I want people who want to be here,” he told me. “I want people who I can invest in and who can invest in our company. If they’re already planning on leaving when just starting out, there are probably better growth opportunities for them at other companies. It doesn’t make sense for my company or for them to stay around and put off the inevitable.”

If you stress about letting your employer down or looking bad when quitting, you can reframe with this example. Quitting does them a favor. It opens up a spot in the company for somebody who might consider your job a dream job and want to stick around for a few years.

Free up that spot. Help your employer find somebody who wants it more than you. Help yourself move onto something better.

Reframing Fear of Quitting in Terms of COST of Staying: Be Careful What You Wish For

Sometimes people put off quitting longer than they should because they fear what their colleagues will think of them. While they do this, they resent the job more and more, become more exhausted with it, and their performance starts to slip.

After weeks or months of putting off quitting, their performance at work has deteriorated so much that they end up generating resentment from their colleagues anyway. Their desire to make their colleagues happy results in lower performance in the long run and resentful or frustrated colleagues.

If you truly hate your job (or even if you think you should really just move on), sticking around longer because you don’t want to rock the boat might just rock the boat more than leaving early.

Put together a solid exit plan, make sure you have documented everything you can, and give your employer sufficient notice to find a replacement.

Suggested Action: Just Reduce the Relative Costs

I actually think the social capital/reputation concern is overblown in most people’s minds. Evolutionarily, we’re designed to make and preserve relationships for survival.

Humans are not atomistic creatures. Humans are tribal. Companies try to capitalize on this instinct and turn the business or the business unit into a tribe. The more your social life is invested in the company, the more time you’ll spend in the company and the harder you’ll work to preserve your relationship with the company.

But you can counter this by having more than one tribe. You can, and should, make friends outside of work.

You should network outside of work.

You should build relationships outside of work.

You should gain opportunities outside of work.

You should invest in your skills outside of work.

You shouldn’t allow your job to be a single point of failure in any aspect of your life.

If you do this, you reduce the relative cost of quitting. No matter what happens with your new job, your new career, or your new business, you know you’ll be fine because you’ve set your life up in such a way that it doesn’t entirely depend on a single job title or organization.

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