When is it time for you to end things … with your job?

No one takes a job with the expectation that it will turn into a disappointment, much like no one chooses to go into a new relationship thinking about how it may not work out. When you arrive at the realization that your job has become a source of anxiety, things may look grim indeed. If your relationship status with your job is “complicated,” that's just another way of saying “It's not working.” So how do you know when to end it?

Many professionals have a strong resistance to leaving a job that's not working out. Quitting is hard because it carries an implication that you gave up, did not try hard enough, or were not good enough to make it work. The reality, as Seth Godin so aptly puts it, is that the motivational quotes that tell you “Quitters never win and winners never quit” are wrong. Winners quit all the time — they just quit the right stuff at the right time.

That can be surprisingly difficult to do. How do you make sure you quit for the right reasons? How do you find a new job while employed? Here are five questions to ask yourself that can help you think through your “complicated” relationship with your job and make the best decision.

1: Where is the problem really coming from?

Before you plan your next career move, your first step should be to honestly look at the current situation and figure out what's happening. Sometimes, the issue has little to do with the job and everything to do with your personal life. Dissatisfaction or missing pieces in one part of your life can certainly spill elsewhere, so check your basics before you give up on a career. Health, sleep deprivation, relationships — figure out where exactly the problem is before you make any dramatic changes at work.

2: Is your discomfort temporary or permanent?

Professional growth does not come pain-free. If the discomfort you are experiencing is a temporary side effect of learning new things or stretching into new challenges, quitting your job will rob you of an opportunity to grow and advance professionally. If the discomfort is permanent or damaging, however, staying in the situation will cost you time from your career and not contribute much to your professional development.

3: What is your personal “point of no return?”

Everyone has a personal set of factors that are firm nonstarters. What are yours? An abusive boss, a job that has offered no opportunities for growth and career development, a commute to the new office that consumes two hours in one direction — you decide what would spell an absolute “no” for you.

4: What needs to change for you to feel great about staying?

This is the reverse of question three: Instead of thinking about what would make the decision to quit a no-brainer, consider what it would take to stay. Most situations can be salvaged, even if just in theory. Perhaps it might take reporting to a different person, finding a trusted mentor, or taking on a good career development opportunity or interesting side project.

5: Have you exhausted your options for making it better?

This may be the most challenging because it forces you to face the fact that the complicated and painful situation you are in was co-created with your active participation. Be brutally honest and ask yourself if you have really done everything you could to make this better. Own your part in the mess so that you can begin to dig your way out.

Related: It's OK to Quit (Your Job)

What if you have answered the five questions above and concluded that your work situation has moved beyond “It's complicated” and into “It's time to break up”? The best strategy to quit your job is by actively looking for other options and applying for jobs while still employed. This step is best done as quietly as possible, no matter how tempted you might be to make a scene. Here are five common job-quitting mistakes that could be detrimental to your long-term career. Avoid them at all costs!

Job-Quitting Mistake #1: Gossipping and complaining to co-workers

Sure, it may help you blow off some steam and bond over the shared misery. However, complaining and gossiping adds no constructive value beyond making you feel momentarily better. The relief will pass quickly, but the consequences may last longer than this job. Feeling frustrated and upset is completely normal in your situation, but try to channel those feelings into constructive next steps: Brush the dust off of that LinkedIn profile during the job search, get a professional to review your resume, or re-connect with professionals who can help you find a new opportunity.

Job-Quitting Mistake #2: Using the possibility of quitting as leverage

Here is the big secret: successful professionals either stay in a job and make the most of it or leave without making a fuss. They don't talk about quitting in hypothetical terms or use it as a negotiating leverage.

When you feel underappreciated or undercompensated, it's tempting to believe that the threat of leaving will make your boss realize how amazing you are and finally give you what you want. In your imagination, the company will pay you more, grant you the things you have been asking for, reassign you to a different job, and give you more flexibility — just to make you stay. Unfortunately, real life does not work that way. Instead of delivering on your requests, your boss is much more likely to begin searching for your replacement! Your outburst of “Well, I guess I will just start looking for other opportunities!” will lock you out of interesting new projects and make you look unprofessional and childish. Don't do it.

Job-Quitting Mistake #3: Not showing up

Checking out physically or mentally spells the death of good opportunities for professionals. It's difficult to remain engaged when your heart isn't in it (I'm not suggesting you become the company's biggest cheerleader!), but you think twice before you stop doing your work. Stay focused. References matter and today's business world is more connected than ever before. Do your best to leave with your performance reviews and professional integrity intact.

Job-Quitting Mistake #4: Making emotional decisions

Slamming a door in your boss's face will give you a few seconds of satisfaction. So will stomping out of a meeting or screaming at a difficult co-worker. In the end, though, all of those actions are more likely to sabotage your next career move than set you up for success. Keep your eye on the ball, take a deep breath, and do what's best for your career in the long run, which, in most cases, involves taking control of your emotional state.

Job-Quitting Mistake # 5: Quitting on a whim with no plan

Walking out of a job has its perks — a completely open day tomorrow, for instance. However, it also takes away one of your options without automatically creating others. Looking for a job while unemployed is definitely not an impossible task — plenty of professionals do it to great effect. However, searching for a new opportunity from the safety of a stable paycheck gives you the luxury of time. It lowers the pressure to find a position in two weeks or risk missing your rent or mortgage payment. That, in turn, improves the odds of finding a position that is a great fit instead of something to just tide you over.

When things get “complicated” at work, keep a cool head! Just as in romantic relationships, sudden, poorly-considered moves won't serve you in the workplace. Even if your situation at work leaves much to be desired, more options are always better. By continuing to show up and taking an honest look at your circumstances, you gain the perspective and the time to craft a plan and make your next career move a good one. After all, you deserve nothing less!

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