5 questions to ask yourself before you leave your job

So many of the people I chat with about their careers wrestle with the same big question. It keeps them up at night, they talk about it with friends and family, and the answer is rarely clear.

How do I know when it’s time to quit my job?

If had a penny for everyone I’ve encountered who feels lukewarm about their job, I suppose I’d have lots of pennies. Finding a perfect job situation is rare and perhaps an unfair expectation. What you’re more likely to find is a job that you feel okay about, with good days and bad days, with nice people and some crappy people… this is just how it is.

While I don’t often encounter people who say “I freaking love my job!” with no caveats, if you’re one of them I am thrilled for you!

Knowing that most of us will be somewhere in the middle of the spectrum, how do we really know when it makes sense to stick it out and when it’s time to move on?

There aren’t clear cut answers… or a tried-and-true formula to figure this out, but you should ask yourself these 5 questions before you make any decisions.


Have I given it a fair shot?

This is really important, because change is really hard! And starting a new job is a BIG change. I think back to leaving J.P. Morgan and starting at Tory Burch (which was literally my dream job!) back in 2010. I’m not going to lie, the first few weeks were a shock to my system. I went from a large, structured team, to a tiny (2 people tiny!) unstructured team. I went from managing tasks I was 100% comfortable with to doing 15 brand new things a day.

It was easy to have a freak out moment, and I did… but once I gave it a fair shot, I loved it… and I stayed for 4 years.

Different people take different amounts of time to go through the change curve (topic for another day) but make sure if you give things a fair shot before you make up your mind. How long does that take? It depends… but most jobs go through cycles at different times in the year and while I don’t think you need to stay in a bad situation for a year just for the sake of it, a year is a good amount of time to really get a sense of things and make an educated decision.

If you’ve been having the “Sunday dreads” (aka: that pit in your stomach when 60 minutes comes on, promptly ending the weekend) for 52 Sundays, let’s talk… it’s may be time to move on.

Do I still have more to learn?

Jobs give you a number of benefits (even if you don’t love them). You get paid, you grow your network, you get stability, and you get experience. You also get to learn and grow.

So even if you find yourself in a less than ideal situation, ask yourself if you have more to learn. Maybe it’s a bit painful, but if you’re learning, growing, and stretching yourself, that’s a big benefit. Sometimes the things that cause you pain and discomfort can end up being really helpful you down the road.

Also, the better you get at doing something, the more fun it becomes… and the more opportunity you have to get creative, make an impact, and even get promoted.

Do I want to be my boss one day?

Especially with entry level roles, your job can feel boring and terrible, but there is a light at the end of the tunnel. Did I love printing 1000 name tags for campus events during my first year in the work world? Nope! But when I looked at what my boss was doing, recruiting talented people for the company, traveling around the country, hosting dinners and events, organizing and running a summer internship program… I was excited about it.

While I knew my first job was administrative and definitely not something I wanted to do forever, I knew there was an opportunity to grow. I wanted to be my boss, and maybe even my boss’s boss one day… and that’s a good indication that you should stick with something.

Do I like the people I’m working with?

Good people go a long way, and it’s not something you can take for granted. Even the greatest jobs “on paper” can be absolutely miserable if you don’t jive with the team. I’m not saying you should stick around in a job that isn’t right just for the people, but it should be something you weigh.

For me, a great team brought me a lot of happiness at work… even on the days that weren’t so great.

Am I trading out one set of problems, for a whole new set of problems?

It’s really easy to stand 1000 ft away and be jealous of how good someone else has it. It’s important to remember that every job out there has pros and cons, and it’s important to weigh them.

I was chatting with a friend the other day and she was saying that she wasn’t feeling challenged in her role (definitely a problem, I agree). However, she is getting amazing training and a great salary. Switching to a new role would probably come with more challenging work, but also a huge pay cut and much less training.

Always weigh pros and cons, and determine what’s a priority for you personally, but don’t make the mistake of thinking a new job is going to be perfect. Generally, it will just have different challenges.


This post originally appeared on The Prepary.

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