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If you’re reading my twitter you know that I have finally decided to set the goal of finding another job within the next six months. It’s something I’ve considered for months but making the final decision was tough. There were signs along the way that I ignored.
Everyone goes through a period in which they question their job and/or the company their with. It’s difficult to know when to stick it out and when to leave. If you watch out for the warning signs you can figure out when to begin a serious job search before it gets to the point where you blow up or put in your notice without a backup plan.
Your Displeasure Lasts for Months
As I said, everyone goes through periods in which they question their decision to stick it out. But, they are short periods and should not last for a long time. If you find yourself displeased continually for more than three months or more than it’s time to look at moving on.
You’ve Tried to Fix Things but It Doesn’t Improve
Maybe you are in a hostile environment or maybe you are not as challenged as you would like to be. You should always try and fix things before you resign yourself to leaving. If you’ve tried to fix these things in several different ways then they’re probably never going to change.
Your Mentors and Trusted Advisers are Telling You to Leave
Don’t listen to your friends that will tell you to quit your job every time you complain. Listen to the trusted advisers who tell you when it’s in your best interest for your career for you to leave. If you don’t have someone like this in your life right now get one!
There’s Nothing Left to Stay For
If at some point in weighing the options you realize that there’s nothing left to stay for or that the reasons for staying are superficial then you should start looking for another job. The grass isn’t always greener on the other side but if the grass is brown on your side of the fence it’s worth a shot. You should always have solid reasons for staying at a job.
Having just one of these warning signs does not necessarily mean you should leave your job. Many times they go hand in hand. For example, of course you may be unhappy for months if you’re not being challenged but if you haven’t attempted to do anything about it then you’re equally at fault.
Use these warning signs as a trigger to start seriously looking for another job. Who knows what may happen in the time that it takes to find another position. You can always change your mind before you give your notice.

I am in worker's hell. My friends/co-workers tell me to leave (they are looking as well). becuase they see the dirty politics that are being played and it is making them sick! I trust almost no one at work except those few. Upper management has been discribed by others outside our division as snakes. A few fellow employees have gotten lawyers (just in case) while a some have had to bring their lawyers into their meetings with upper management. Then there are some who ended up sueing our employer for discrimination, harrassment, or other illegal incidents. And then there is the open use of pirated software by the computer techs (and they pass it around like candy) ... Every where I look there is moral decay and back-stabbing. Some of my co-worker friends mentioned that they would want to work for me if I get into a hiring position outside.

I had three of the four signs when I decided to quit my first job. I was young and unaware then, so I didn't have an adviser! I would maybe add a fifth sign. You should leave if you can think of something you always wanted to do and your current job is not in that field.

What about a change in "Culture" (or ethics)? There are times there you out-grow the company or organization and they no longer provide the challenges that you seek.

I am definitely in this boat now. I recently realized that I may not want to be in an office environment anymore. My current job is boring and I have way too much time to blog more than work and I take any and everything that anyone requests or needs. My boss is good and my coworkers are cool. One of the main reasons why I am staying is becasue I like my boss and coworkers.
There is no challenge and the ladder up is not where I would like to be. I'm looking as well but not as actively. The stigmatism of job hopping always slows me down.

@Scott - The problem is that those kind of things happen everywhere. You make a great point about a change in culture. My organization will soon be going through a huge change in culture which many people seem to be holding onto as a last hope.
@Vanessa - I didn't even think of that! I think that describes my first 10 jobs or so :)
@Tiffany - You sound like me a month ago. The only thing that's changed for me now is that the people aren't enough to keep me.

@Rachel - Granted that many are unhappy about their current employment situation, employers are taking advantage of the situation as well. When the time comes where the economy turns for the better, the employer will be looking fro new employees - not becuase they are growing but the good ones will jump ship to better opportunities.
We are sometimes told by management that "If you don't like it - there's the door!" (actual quote) It has gotten to the point where contractors are refusing to work with our organization. Apperentlly we are gaining an unpopular reputation amoung contractors ...

How funny that I just found this...I actually just quit my job today because I have been experienced three of those four things. The things I would consider staying for are the benefits -- stock options, health insurance, 401(k) matching, etc. I have decided to leave for a nearly full-time contract job that will allow me to work from home and have more time for freelancing. I haven't been happy for many months at my current job, asked for more flexibility and barely got any, and was told by my mentors there that they knew I probably wouldn't be around too much longer in the future -- they knew I had more interests and talents than this job allowed. It was hard to get the courage to take this step, but now that I've put in my two weeks, I feel a huge sense of relief and know I made the right decision.

@Scott - You certainly don't want to stay with an organization that is developing a bad reputation. The perception of the organization will follow you around on your resume.
@Emily - I'm glad you found something that worked for you. It's also great that you have mentors that can help you along the way.

Great post, Rachel. I've been seeing and ignoring sign posts for several months now, and it's amazing what happens when you see them listed out one by one- it's almost as if everying becomes more clear. I've been working on my back-up plan for a couple of months and I'm really looking forward to breathing that sigh of relief and embarking on a new adventure.