My mom tries her damndest to get me to stay at every job I land for at least two years. But the truth is, the longest I’ve stayed at a company (since I was 19) is about 45 months, and 4 of those months I was on maternity leave.
“No one is going to take the risk of hiring you. You move around too much,” she tells me. So far, she hasn’t been correct.
I don’t take the decision to leave a company (or a relationship, or bad environment) lightly. Here’s the checklist I go through before I make the decision to start looking for a new job (or apartment, or car, or whatever…)
Is this a bad second, a bad season, or a bad situation?

Think of a bad second as an insignificant amount of time compared to the big picture. Did you have 20 minutes of severe stress over a project that you let ruin your mood for a whole week? Did that email from your boss rub you the wrong way, but not actually contain any harmful or offensive content? Does your landlord take his time making sure the grass gets cut, but is actually pretty great in serious circumstances? Maybe this is just a bad second, and you can just chill out.
By contrast, a bad season might light a fire under you to get out of whatever you’re stuck in. Think of the last season of Game of Thrones. Terrible, but did not, in any way, ruin the entire show. I mean, remember the Red Wedding? Ned Stark? For the love of God, Jason Momoa?! That show is still the greatest, and, come to think of it, maybe we should re-watch it? (*buys HBO*) Seriously, a bad season may be you saying “wait, I’m having a series of bad seconds.” Watch for patterns in this time. Maybe your department is understaffed and you have to pick up a ton of extra work right now. There’s a light at the end of the tunnel, but for the foreseeable future, it sucks. Or maybe you are due a promotion, but you know the company just does not have the money to pay you what your worth right now. If you have the vision, sticking it out during a bad season can reap great benefits. Choose wisely.
For a lot of people, COVID-19 has been a bad season. Working from home with our families has been almost unbearable. If your company has been patient and lenient with you, try to give them the benefit of the doubt.
Bad situations are clear environmental or personnel issues that have no clear path of recourse. Here’s a real world example: At my first “big girl job,” I would come into work at 530am and leave around 3pm. (I never got manager approval on this, I just started doing it. Probably part of the reason I got fired.) When I would come in early, I’d hear other departments chatting amongst each other. One morning I heard particularly racist conversations happening. An employee was making fun of one of her children’s black friends. [Insert lots of stereotypes and racial slurs, and laughter amongst the other employees. Yeah. It was that bad.] I reported the incident to HR and I got in trouble. That’s right. They told me to stop “policing” other people and to focus on my work. Ouch. I was too young and immature to realize it at the time, but this is a clear example of a bad situation. The company was telling me that I wasn’t entitled to a safe, equal work environment.
Your bad situation may not be this cut and dry. Maybe you are continually unsupported by your boss, or there is truly just no path to advancement in the position you’re in. This is the time to take a deep breath, take inventory of the pros and cons of your current position, and decide if it’s time to look elsewhere.
If you leave for the right reasons, you’ll have no problem explaining clearly, and diplomatically, the reasons for your spotty resume.
Good Luck Out There!