Dear Dan: When is it Time to Leave a Job?

Dear Dan,

This is my 10th year working at the same place. When is it time to leave a job? How will I know if I should stay or go?

I don’t want to leave my profession, just the current job.


Thinking about Leaving

PS I’m Albanian so I’m sorry if I do any misspelling.

Image of two ducks running on water.

It's better to run toward what you want than to run away from what you don't want.

Dear Thinking,

I assume you feel an itch to make a change.

You probably feel tension between the devil you know and the devil you don’t. In other words, we usually prefer the comfort of the status quo to the anxiety of stepping into the unknown.


Fear is useful.

Make a list of the top 5 things you’re afraid of losing if you don’t make a change. You might learn about yourself when you reflect on the items on your list. Use the following questions to examine your list of fears/concerns.

  1. Fear shows you what’s important. Look at your list. What’s important to you?
  2. How might you achieve what you’re afraid of losing without making a change?
  3. How likely is it that you will achieve what you want if you change jobs?


You might come at it from another angle. What do you wish was true at your current job? Perhaps you can craft a new place with your current employer. If you can’t, your wishes give you ideas about what you’re looking for.


If you stay at your current job, how will you feel about yourself?

If you make a change, how will you feel about yourself?


Talk over big decisions.

Find two or three disinterested people who can think through this decision with you. Don’t talk to friends or family. They all have some interest in telling you what you want to hear.


Another consideration is what opportunities are available?

Don’t leave your current job until you have something lined up.

A lateral move with more opportunity might be a viable consideration.


It’s better to run toward what you like than to run away from what you don’t like.

Final considerations:

Are you the type of person who tends to stay too long or leave too soon? What does your personal story tell you? Do you have too much grit or do you quit too soon? My feeling is you have plenty of grit.

People with grit tend to hang on to the same job too long.

You have my best,


What suggestions might you offer Thinking about Leaving?