Should You Quit? Ask These 5 Questions
Recently, I was having lunch with someone earlier in his career. He was trying to decide whether it was worth staying at his current job or if it was time to make a change.
Knowing when to quit is really hard.
We grow up in a culture that rightfully teaches us to honor our commitments. “We don’t quit sports teams in the middle of the season” or something similar.
At the same time, overstaying your welcome is fraught with its own challenges and long-term implications.
So how should you think about when to stay and when to go?
Here are a few thoughts of when it might make sense to quit -
When something illegal and /or unethical is required of you. Obvious - If you have to violate your deepest principles, probably a good reason to bail
Your boss is a jerk. My summer internship after my junior year of college was at a large financial services firm in FL. The guy who ran our department would call me into his office and yell at me for an hour - as a summer intern. He would regularly bring in members of his team to mock and shame their performance. Just an all around bad person - life’s too short.
But please note - there is a difference between getting tough feedback and working for a jerk. Good bosses will push you and it may not feel great in the moment.When you are no longer learning and you are limited out. When you are earlier in your career, optimizing for learning is worthwhile. But you’ve got to give yourself at least 2 years in a job (generally), and longer as you get more senior.
The key here is that you may be at a developmental plateau and with some patience, a next layer of learning may open up.When your boss does not see what you are capable of. Just as a prophet may be despised in his home town, sometimes the fact that you started at a junior level will limit your ability to grow at a firm.
Knowing what you know now, you wouldn’t take the job / go down this path. Sometimes you go down a path, but what you learn tells you it’s the wrong one.
Here are a few indicators you may be on the right path - even with the normal ups and downs of a job?
Do you like/respect the people you work with? The people you spend time with matter deeply.
Do you get to spend the majority of your time in alignment with what you enjoy doing/are good at? Hopefully you can get as high as 75-80% within your zone of competence/enjoyment.
Is your compensation within a reasonable range of what is a market rate for the role? If you aren’t drastically underpaid, don’t be too quick to make a change.
Can what you feel is missing in your job be addressed in other ways? No job is going to bat 1,000 in leveraging everything you like doing, want to do, feel capable to do, etc. It can be exceptionally helpful to think of your career as a portfolio. Starting a side hustle. Volunteering. Finding a board to serve on.
Assuming your core job is not taking 100 percent of your waking hours - you have time to engage in other things in your life. The blend of everything you are involved in can be a powerful contributor to feelings of career alignment.


