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Should I Stay or Should I Go? 7 Questions to Ask Yourself When Deciding About Quitting Your Job

02/21/2014 02:45 pm ET | Updated Apr 23, 2014

"Should I Stay or Should I Go?" is not just a song by the English punk band The Clash. It's also a question many people ask themselves when it comes to demanding or unhappy work situations.

Recently, I received the following question from a LYJ (Love Your Job) Search alumna: "I'm contemplating quitting without having another job. It's for a number of reasons, but I was wondering what you think about that."

I believe there is no easy or right answer to the stay or go question. I've seen people do both. Even in this economy, I'm not one to definitively say you'd be crazy to quit your job. At the same time, it's not a decision to be made in a rash moment or after a bad day at work. Here are some questions to ask yourself when sitting with this decision, which I hope will allow you to confidently choose what's right for you:

1. One of the biggest questions is, of course, a financial one. Plain and simple -- what is your financial situation? How long would you be prepared to be without a job? Could you handle six months or one year+ if your next opportunity or freelancing is not coming easily?

If the answer is no to the latter, then you'll need to think long and hard about whether it's wise to quit your job without having a new one in place. You may be better off hustling and focusing on getting a new job first before giving notice. If you have enough saved, can cut back on expenses, or are confident you can line up freelance or consulting work, then this will not be as strong a consideration.

2. Can you handle the psychological toll of not having a job?

Finances are not the only consideration: There is also a psychological adjustment. If you are burnt out from your current non-stop job, or from a bad boss, chances are you'll need a break after you quit. Once you've recharged and adjusted to your newfound freedom, the reality of not having a fixed schedule and structure to your day will set in. You also will no longer have the "identity" that went with that particular job. This may be a huge relief but it can also involve an adjustment to your new blank slate. Are you someone who can cope with this type of change? Make sure you think it through and perhaps talk to those who have gone through it and come out the other side. This question is not to be taken lightly. Explore your other options first if the psychological toll of being unemployed will be too great.

3. How will you create structure during this period? What is your support system and accountability?

Setting up structure and a support system before you leap into the unknown can help you be more confident with your decision. Remember that jobseekers often have to fight off a "desperate" vibe after awhile of being unemployed. It's part of why it's easier to get a job when you have a job. That said, plenty of jobseekers with the right qualifications and ability to market themselves get jobs without being currently employed. Figure out how you will create weekly structure for yourself and who or what you'll need to help you through this period.

4. How long have you been in your last few positions?

If you've been in the same role for some time, any resume gap would not come into play as much plus you can potentially take on consulting to fill in a gap if that becomes an issue. If, however, in your past two jobs you stayed an average of six months and are ready to leave again, you may want to think about staying until at least the one year mark because future employers will surely start to question your job-hopping, even when there are good reasons for it. Not everyone agrees on this point so ask neutral parties in your field of choice how your resume reads and for ideas on avoiding a gap. You can also make sure to use only years on your resume and skip the months.

5. Are you staying in your field or trying to make a career change?

It may be easier to bounce back if you have already established yourself in your field and have a broad network to rely on to open doors for you. An established professional brand will be helpful. Career changes can take longer than expected so if you quit your current job hoping to transition to an entirely new area without having already put in the legwork involved, be sure you're realistic about your expectations.

6. What does the current market look like for your field and skill sets? How in demand are you?

While you're deciding, it could be good to reach out to a few recruiters in your field, just to understand the market better. If recruiters are not an option for you, then talking to professionals in your field of interest will help you understand the market for your skill sets better.

7. What would make your current position tolerable in the short-term?

There may be things to negotiate for before you take any giant leap. Is there anything at all that would make a difference? More money? Better title? Change of responsibilities? Flexibility with time/hours/less time for the next six months, etc.? Would you want to be in a PT or consulting role? We are at our most powerful when we're truly willing to walk away, assuming you are valued by your employer. If you make the decision to leave, the sky's the limit in terms of what you could potentially ask for. Worst case -- your employer says no, and it's no big loss since you were planning to leave anyway. And if the answer is still no in terms of what you're looking for (there's nothing that could change in terms of the job, it's simply time for a change), then that's good information.

There's no right or wrong. I once quit a job after nine months and, looking back, I wish I had stuck it out and made it better, since it took me awhile to land on my feet -- I did land though.

Give yourself some time to think this decision through. Ironically, an earlier post, "How to Decide If a Job Offer is Right for You" offers an approach and questions that are also useful with this process.