When to quit your job

The biggest factors you should weigh out when considering changing jobs.

Recently I was at a coffee shop with a friend who was unsettled at his job. As he was talking about the pros and cons, my mind went to a simple 2x2 chart that I learned from Jason Calicanis. I took out my notebook, drew the above image, and flipped it around so he could see it.

On one axis there is growth and on the other is compensation. When both are strong, it’s a great place to stay. When both are low, it’s likely time to start interviewing. And when one is high and one is low, it’s important to know your goals.

High Growth & High Compensation

This is what most people dream of. A workplace that they both are growing at professionally and where they are being compensated well. A workplace like this not only is deeply satisfying but also opens doors both through increasing one’s skill and having more financial options. Unless you have a really good reason, this is a place to stay.

Low Growth & Low Compensation

If you feel like you’re stagnating in your career and you know you’re being underpaid, it’s likely time to look elsewhere. It’s possible that “elsewhere” can be in the same company (if it’s a larger company) by switching managers or asking for a raise. However if the growth and financial stagnation you’re feeling is embedded into the company’s culture, this likely won’t move you out of the bottom left quadrant. If that’s the case, you’d do well to begin polishing up the resume.

High Growth & Low Compensation

If you’re growing by leaps and bounds but you’re being compensated poorly, it may or may not be time to say goodbye. If you’re early in your career, it’s usually worth the financial sacrifice in order to grow under a great leader (internships are the extreme version of this where compensation is typically very low while learning is very high).

If you’re further along in your career and/or have a family, mortgage, and other significant expenses, you may owe it to those around you to begin looking at other options. An open and honest conversation with your manager is likely a helpful step here as well - if you’re an A player, companies will fight to keep you and there may be more flexibility in your compensation than you’re aware of.

Low Growth & High Compensation

If you’re stagnant in your growth but raking in the money, it again may or may not be time to look over the cubicle wall to find other options. Most of us have a fear of running out of money. This fear drives us to stay in unproductive or unhealthy situations too long.

In reality, time is nearly always more valuable than money. Think about it - the vast majority of us will run out of time before we run out of money (i.e. on our deathbed, our bank accounts will still be in the black).

That said, money is a powerful tool and has its place. You may have some specific financial goals (buying an engagement ring, paying off the house, getting your kids through college, etc). If you have specific financial goals and this job can help you get there, it may be appropriate to stay - but ensure you know why you’re staying. Don’t simply stay for “more money”.

Other Factors

Some readers might call this chart overly simplistic. They’re probably right. There’s a few additional factors that don’t fit as well into this chart which have their place.


It’s possible to have high compensation and high growth but to be incredibly stressed, leaving little left in the tank for family, friends, or self care.

Your ability to take on this level of stress can vary with your stage of life (a single 20-something is likely able to take on a heavier load than an older worker who is bringing their kids on college visits while simultaneously caring for aging parents).

Ultimately, you are responsible for putting boundaries in place to protect what’s important for you. Do you stay at work after 5pm? Do you take work home? Do you work on the weekends? If you’re unable to perform the job while keeping your boundaries and your manager isn’t willing to work to find a solution that works for everyone, it may be time for a career switch. Your career is important, but it’s not the only important thing.


Most things worth doing aren’t easy. If you’re deeply in love with the mission of the organization, you may find the compensation or tedious work worth it because you know the impact it’s creating. However, don’t let this be an excuse to not have boundaries. Ask any burned-out pastor and they’ll tell you from learning the hard way that if you really want to make an impact, you need to have boundaries so that you can stay in the game long-term (and ultimately have even greater impact).

Toxic Culture

If the culture is truly toxic, you’re likely not growing in helpful and constructive ways and it’s almost certainly contributing to higher stress.

Do your best to change the culture around you. (When I interview someone who claims their previous workplace was toxic, I ask them what they did to try to fix it regardless of their role in the organization - I want to hire people who take ownership of their situations.)

If the organization won’t change despite your best efforts, it’s likely time to move on. Life is too short to live in this type of environment.


Occasionally, if you’re working at a company that is very well known in your industry (for tech workers think Google, Apple, Tesla etc), having that company on your resume will open doors.

If you’re fortunate enough to be at one of those types of companies, hopefully they are compensating you well and helping you grow. But if they aren’t, it may still be worth sticking around for a bit to learn everything you can and build the resume. I would want to see someone at a company like this for 2 years in order to mentally give them the credibility of having “spent time at that company”.

Most of the items on this list are scales that need to be weighed in order to determine if you should leave or stay. If there’s something ethical or legal however, this is a bit more black and white. If something is across the line, bring it up to your manager. Ask them in a non-judgmental way to help you understand why a certain practice exists. Make sure it’s not just your inexperience that’s misperceiving the situation. If the responses to your questions don’t sit well however, move on.

Something else is calling you

Sometimes a new opportunity is calling so loudly it’s impossible to ignore. Perhaps it’s a dream job, maybe it’s a career switch, or it might even be the entrepreneurial call to start something new.

My best advice: don’t do anything for 6 months. I can’t keep track of how many times I’ve gotten excited about an initiative only to have my passion fizzle a few weeks or months later. If the passion is still there after half a year however, it’s time to consider a change. It has staying power.

When I interview people, I love hearing them describe their career journey as running toward something rather than running away from something. And if that new thing you’re chasing is a startup - be sure to do your homework. There’s a lot of steps you can take before you quit your day job that will increase your odds of success. If possible you should work through the first three levels of the startup journey and be getting strong positive signals on your MVP before taking the leap. And whatever you do, be sure you’ve truly fallen in love with the problem, not the solution.

Leaving Well

Unless its the most extreme of circumstances, you should have another job lined up when you exit. And when you do have that conversation with your boss, it’s a significant moment in life.

And with it can come with some significant negative feelings toward your soon-to-be past employer. No matter how you feel, do your very best to leave well. Give them two weeks. Be candid but respectful in your exit interview. Don’t badmouth them to the community. Not only does this show decency to fellow humans, you’d be amazed at how many times that company or people from it will intersect your future path.