by J. van der Gaag

Created on: February 22, 2010

The decision to quit your day job may be one of the most agonizing you will ever make.  We are not only tied to the money - often our very identities are wrapped up in what we do.  Finding yourself outside of the same comfortable box you have always had can be liberating or completely terrifying. 

You might want to leave your day job to return to school, launch a dream, or start your own business.  Maybe you simply hate what you are currently doing.  No matter why you are considering quitting your day job, you need to ask yourself a few basic questions.

Why do I want to quit?

You need to understand why you want to quit your current job.  Is it because you want to pursue a dream, or you feel unfulfilled?  Is it because a co-worker or your boss is a jerk?  Some problems will follow you from job to job; almost every workplace has something (or someone) wrong with it.  If you have ten jobs in a row and you quit each one because you cannot get along with your boss, the problem might not be the boss.  Less drastic measures, like changing teams or departments, an honest conversation, or a good vacation might be enough to resolve a problem.

Even if you originally loved your job you might discover that, over time, it does not bring you the happiness it used to.  Like any relationship, you and your job can change and grow apart.  Maybe it just took you ten years to get up the courage to follow your dream.  Before you leave your day job, you need to carry out an honest assessment of both your job and yourself.  Know how your job fit you and how it did not so you can avoid repeating the past.   

What will I do instead?

Some people just know that they need to quit and they need to do it immediately.  They do not necessarily have a “Plan B”.  Sometimes this works out and sometimes it does not.  In a bad economy, specialized industry or in a small town, finding another job might not be as easy as you think.  No matter why you decide to leave your day job, it is important to formulate a realistic plan for what you will do next.  Before you hand in that resignation letter, know the concrete steps that you will take on the first day of your new life.  Ideally, you should start the ball rolling on “Plan B” well before your resignation.

Am I financially secure?

You need to make a thorough assessment of how much money you need to survive while you

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