February 09, 2014, 11:04 AM — I've been a Unix systems administration and information security specialist for a lot of years and have made my fair share of stay and go decisions. In general, they are always hard decisions to make, but there a number of decision criteria to keep in mind when you're wondering whether or not it's time to move on.
The most obvious is whether you're relatively happy or downright miserable in your current position. I say "relatively happy" because, if you're deliriously happy, you're probably not reading this post. Of course, your happiness level may not be all that easy to pin down. You might like your boss, get along with most of your coworkers, and think your work is interesting -- but feel stagnated and ignored when promotions are announced. You might feel appreciated and well rewarded for your work, but also acknowledge that the work you are doing doesn't align very well with your priorities or your values.
If you are downright miserable in your current position, the decision to look for another job is pretty much a no brainer, except -- and this is a big exception -- when there's really no place to go. I'm not much of a "grin and bear it" kind of gal, but there are times when staying put makes sense even when you'd rather be anywhere else. Other jobs are not necessarily better just because they're different. It's always OK to look but, when the market seems bereft of opportunity, it might be time to carefully assess what is and isn't working in your current position and honestly ask yourself (and maybe even your boss) what you do to can change some of the things you don't like. Without an honest, carefully considered view of why you're so unhappy, trading one job for another could land you in an even worse position -- and one without the benefit of the connections and time on the job you've just left behind.
Another key indicator that it's time to move on is when you don't feel valued or don't feel that your work is valued. If yours could be the next head on the chopping block, you owe it to yourself to be on the lookout for something new and different. If you're not feeling valued, however, this might be the right time to start a "What can I do to be more helpful and productive" discussion with your boss. You might get some feedback that opens doors or changes your viewpoint.
Another question to ask yourself is whether you are picking up new skills. If there's one hard earned insight that you should take to heart, it's this: if you're not learning, you're losing ground. This field that we work in is constantly changing. If you're stuck in a job where you do the same thing year after year, you might find yourself seriously lacking in skills and insights when you have to go looking for that next job. To the extent you are able, always insist that some part of your work expose you to new tools and applications, even if they're above and beyond what you get credit for.
flickr / markhillary