Our last post looked at how to quit with grace. But how do you know when it’s time to quit versus when you should stick it out a little longer?

There are a number of reasons you may want to consider leaving your current position and moving on to something else. In our experience, people who manage their careers well have the patience to see through the normal bumpiness in the world. They usually stay with a company for about five years. They have a solid network and are cautious about when they switch positions. But there does come a time to leave.

One caveat: if you work in startups, when to quit might be out of your control if there are acquisitions or mergers. When it is under your control, though, how do you know when to go?

Our founder, Mark Phillips, gives us his take:

1. Everybody else is leaving.

Mass layoffs happen, especially in an environment where there are a lot of acquisitions, such as in the startup world. If you’re not included in the mass layoff but other people are, it might be a wise idea to ask yourself if it’s time to leave or not. It might be better for you to stay, but give it a closer look and make sure you do the right thing for yourself and your career.

2. Your company is offering advantageous terms to leave.

Sometimes, if a company is failing, they will offer a severance package for people to leave voluntarily. We’ve seen it happen where those who stayed got nothing when the company ultimately failed, but you’ll have to make the call of whether to stay or go. Severance packages can be quite attractive and give you time to find your next position.

If you opt to take the severance package and the company really wants you to stay, they may offer something like a retention bonus or extra stock to keep you around.

Realize, though, that even if you’re one of the lucky ones who is offered a retention bonus and decides to stay, the company will look and feel very different after a mass layoff. Your co-workers will be different, people may feel shaken, and leadership could be different. Make sure you’re prepared for that.

3. You’re bored.

You’ve been in the same position with the same responsibilities for so long that work has become tiresome and your workplace isn’t giving you opportunities to advance or take on new responsibilities. Before you decide to walk away, talk to your boss and see if anything can be done to change the situation. All they can do is say no.

4. You feel undervalued.

If you’re being passed over for promotions or feel your compensation isn’t up to market standards it can be frustrating and make you want to quit. Again, before you do, take action first. Explicitly ask for a promotion or set out a growth plan with your boss. Ask for a raise. Talk to an advisor or mentor. Sometimes just articulating a problem can shed some light on it. Don’t passively wait for them to come to you with an offer, take the initiative and go to them. Set a timeline for things to improve, say six months to a year. If things have not changed for the better in that time, perhaps it’s time to leave.

5. There’s a lot of management change.

It can be exhausting if you’ve had four different managers in the last six months (or even four in four years!). If there’s a lot of leadership turnover in an organization it can also indicate a larger institutional or upper-level issue with the company.

When you see turnover at the middle level, it usually means there’s turnover at the executive level. For example, a new CEO might start and bring in their own cabinet, so to speak. Make sure to examine your specific situation carefully before deciding to leave.

6. Your company fails to live up to its commitments.

This can be to its clients/customers and employees, or even in terms of releasing products or new features as promised. We’ve seen companies not give their salespeople a sales goal until 8 months into the year or not follow through with commission payments. If there’s a pattern of such behaviors in an organization, it’s a valid reason to leave.

7. There are big changes coming to the marketplace.

If new legislation or policies are coming it can result in a significant shift in the marketplace, which can negatively affect a company. We’ve seen companies lose 40% or more of their revenue as the market shifts, which can lead to mass layoffs (see #1). Don’t be paranoid about this, but do keep an eye on the market in your industry.

8. Toxic company culture.

“Toxic” as it relates to company culture is overused; we usually find that most negative work environments result from inexperienced leadership. Before labeling the culture as truly toxic, try giving people the benefit of the doubt. Take some steps to be intentional about improving the relationship. If your efforts hit a brick wall, it’s probably an indicator of actual toxic culture. Again, set a timeline for this to improve and act with agency. If things have not improved in your set time frame, perhaps it’s time to go.

9. Anything illegal is happening.

If anything illegal is occurring, you most likely want to leave and do so quickly. This could include discrimination on any level or any shady business practices. If these things are happening at your company you may want to take additional steps in terms of filing legal action, but you’ll have to decide that on a personal level.

10. After your stock vests.

Sometimes benefits are tied to tenure, and it’s a good time to exit once those benefits mature. From what we’ve seen, all the good people leave money on the table (year-end bonuses, 401Ks, matching donations, paid vacation time, and so on). If you’re in a toxic situation, can you last three more months until you get your $30,000 bonus, or do you really need to leave immediately? If you do need to leave immediately, you might be able to use it as a compensation bargaining chip with another company.

11. You have a better offer elsewhere.

If you’re working your network properly, you should have a pretty regular flow of opportunities coming your way. It’s good to take calls and maybe even interviews from headhunters to gather more information, but if you’re still in the early days at your current position, you might want to think twice about leaving unless your current situation isn’t panning out as planned or the offer is just too good to pass up. Be open to new opportunities, but don’t jump on everything. You want to be strategic and judicious and not be known as a job hopper. As we said, most people with successful careers don’t change jobs more frequently than every five years.

While we’re not saying you should remain in a bad position, there are times you may want to think twice before leaving.

For example:

1. You’ve only been at a company for a short time.

Historically, job tenure was an important requirement when looking at candidates for jobs. Leaving a position after three years carried a stigma. While this has altered a bit with the pandemic, it’s still not great to job-hop too much. If you’ve been with three companies for just one year each, people will hesitate to hire you.

2. You haven’t yet taken action to improve the situation.

As we mentioned above, make sure to do your due diligence before leaving. Ask for the promotion and/or the raise. Ask for the additional responsibility or new project. See if you can make things better, and give it at least six months to improve. If it doesn’t, take another look at walking away.

3. You don’t have another job secured.

If you’re in a toxic, illegal, or undervalued situation, you might feel bad enough about it to move on without having another job first, but if you can, make sure you have your next position in place before walking away from your current position. Make sure the new job is 100% before giving your two weeks’ notice.

4. You’re acting from a place of emotion.

Leaving your job is a huge decision. Don’t make this decision when you’re angry or emotional; wait until you can look at it from a mindful, regulated state and take some of the steps in #2 above first. Make sure you’re not taking an action you will regret.

Leaving your job should be the final action in a longer process. Make sure you’re taking a number of initial steps before taking that last big step.

Have you decided it’s time to move on? We would love to help you find your next big thing! Check us out on hireedu.com or give us a call at 877-HIRE-EDU.