I like to think that every work place and every job is redeemable, to test this, I ran the following thought experiment:

Can I think of a list of 10 things that would tell me that it is time to stop trying and give up on a job or a workplace?

It turned out that I could:

10. You Can’t Stop Dreading Monday Mornings

It crept up on me slowly, but eventually something subliminal started telling me “you aren’t doing what you should be doing”. It manifested itself mid-day every Sunday, when I started thinking about the coming week, and a feeling of dread washed over me. By every measure I could think of, I had a great job; but I couldn’t shake the feeling of dread, no matter how hard I tried. All rational efforts I took to sculpt my job, and its responsibilities, to better fit my (identified) motivations and talents, were undermined by a sense of dread driven by my subconscious. I suspect many of the elements that follow contributed in a big way, but the dread was the warning sign. If you get this feeling about your job, start preparing now for your eventual exit.

9. You Aren’t Learning Anything New

If someone paid you to fall behind the rest of the world in your skills and knowledge, would you take the money? You are being paid to trade your time and energy to advance someone else’s goals, but this shouldn’t mean that you are trading that money for a decrease in your own value to the market. Repetitive jobs that don’t allow you to build relationships with people, learn new skills, or become better at existing skills are a slow ticket to the bone pile. Good jobs provide you with money, increased talent and knowledge, as the reward for contributing to business success. The typical recruiters writes job descriptions that don’t bother to explain what you are going to gain by working for the organization (aside from –on occasion– the salary). Instead, they specify the education, experience and duties of the job as if they will find the perfect cog to replace one they have that is wearing out. Ask yourself, are you going to get 5 more years of experience if you stay 5 more years, or 5 x 1 year doing the same thing? If it is the latter, and your discussions with management on the topic are going nowhere, don’t let yourself be that cog wearing away in the machine. [And yes, here is Dan Pink’s ‘Mastery’ concept again. -ed.]

8. You are Working for a Narcissist / Sociopath

Narcissists are purpose-built to become bosses. They have all the self-promotional tools, grandiosity, and motivation to move up the ladder, without any of that pesky baggage that comes with caring for other people. They build fantasy worlds, with themselves as the reining monarch, and make sure that they take credit for anything good that happens within their kingdom. If your boss is a first-line manager, you may be able to manoeuvre out from under them to a better boss (unless you are really really good, then they will undermine your efforts to move out of the group). If your boss is higher up in the organization, you’re screwed. When narcissists move up in an organization, the organization itself becomes narcissistic and it’s time to move on.

7. You Don’t Fit, and That is a Bad Thing

Pure breeds aren’t healthy breeds. Most companies proclaim that they want to embrace ‘diversity’. Unfortunately, they think that true diversity comes from having people of different coloured skin, religion, language, etc. Those are symptoms, not the cause of diversity. The bridge crew of the Enterprise wasn’t effective because Uhura was a black woman, Spock was a male Vulcan or Kirk a male human, it was that they had diverse mental abilities, experiences, and very different ways of looking at the world. Often companies forget this, and personality types get marginalized to the detriment of diversity. It is very hard to put into words how you know when this is happening, but one clue is that the same problems appear again and again, based on issues that nobody else thinks are important. This problem –called ‘group-think’– indicates that there is a lack of true diversity, and when your contrary ideas (offered with good intent) are constantly met with emotional resistance, it’s time to find another group to think in.

6. Your Industry or Job is Dying

It is easier to see these trends in hindsight, but I think a lot of people saw the writing on the wall in the following industries: record labels, photographic film, whale oil, and typewriter manufacturers. You might feel it disloyal to jump ship, but large organizations have the corresponding momentum and –to extend the analogy– it is often hard to change their course. Here is the list of their corresponding icebergs: iTunes, digital photography, oil wells, and the PC. It is a lot more fun to take the useful skills that you have developed, and take part in the next wave as an active participant, than watch a company wither and shrink around you due to market pressures. The same goes for individual jobs: if your job can be easily turned into a process, digitized and/or done overseas, seek out opportunities to make your value proposition more unique, because the writing is on the wall, and its says ‘China & India’.

5. Your Job is Killing You

Part of getting older and wiser is gaining a level of self-knowledge. What situations will put you in the worst frame of mind, or at the greatest physical peril? You only have so much mental and physical energy, and some has to be left to enjoy your private life. Situations that particularly drain you should be minimized. For example, if you are an introvert, accepting a customer-facing role will take a heavy toll on the energy you have left over for your family. If you are an extrovert, solitude may be what will drive you mad. If you are prone to overeat, you may want to reconsider that job that requires you to travel all the time. If your head is constantly filled with creative ideas, a repetitive process-driven job will be soul-crushing. Keep in mind that work shouldn’t be your only outlet for your inner drivers, but if you are left drained (in a bad way) at the end of the day, you may not have the energy to do the things you need to do to stay mentally and physically healthy.

4. Your Job and Your Inner Compass Don’t Align

I won’t be the first person to compare a corporation to a psychopath, but as I have seen it put very succinctly, “they have no soul to save, and they have no body to incarcerate”, yet they have all the rights of an individual; how do you think that is going to turn out? Maybe this is the fertile soil that the narcissists from #8 thrive in… but I digress. Some companies have a culture of ethical behaviour, others so not, but what matters is: how important is it to you? If you don’t give much though to the environment, child labour, giving your customers cancer, wasting taxpayer money, or filling the Gulf of Mexico with crude, you can safely skip to #3. If you do, and you aren’t in a position to help guide your organization’s moral compass, you might want to find another role, because it will eat at you, slowly but surely.

3. You Can’t Avoid Being Micromanaged

If you continue to pull tighter and tighter on the reigns of leadership, you’re going to end up looking a gift horse in the mouth… and you know what they say about gift horses… yes, you don’t look them in the mouth. [I just made that up, I am so proud of myself, I just combined two metaphors instead of splitting one! -ed.] If you are reading this, I can safely (?) assume you are getting paid to use your brain. If so, continuous micromanagement (beyond new job training) is a sure sign of one of two things: your boss doesn’t know how to manage people, or your boss thinks you suck at what you do, and aren’t getting any better. Do either of those two reasons make it sound like you should stick around? Smart people are paid to use their brains, smart leaders let them use them. [You can clearly see Dan Pink’s ‘Autonomy’ in #3.]

2. You Need a Bigger Pot

Steve Jobs used to work at Atari because he saw the potential of the personal computer, and Robert Noyce left Fairchild to form Intel when he wanted to create a better management culture. These guys had good jobs, but better ideas. It’s hard to know when your ideas are better than those of your boss, or if your boss just has a better grasp on reality. But, if you are pretty sure it is the prior, get yourself set up financially and emotionally to take the big leap. If you are capable of much more, and feel like you are leaving a lot on the table every day, you should seek out opportunities that will offer more responsibility and/or a greater opportunity to grow.

1. You Can’t Seem to Find Your Purpose

Do you need a sense of purpose at work, or is it just a job? This is a personal question, but for me, if I go way back to #10, I think it was the source of my dread feeling. Your work doesn’t have to define you, it can simply be a vehicle that supports you in fulfilling your sense of purpose in your non-work time; with your family, your hobbies, or volunteer work filling that role. Increasingly though, the concept of finding purpose in your work seems to be gaining importance as a means to boost personal performance, and that of the organization. This can simply (but not easily) be a good leader making it clear how your job relates to the organization’s success, or finding a cause that will be clear, tangible and meaningful to the whole organization (hopefully both). The latter can be a real challenge for the companies detailed in #4. A critical step is figuring our what really motivates you, and what goals you have in life. [You can clearly see Dan Pink’s ‘Purpose’ in #1. -ed.]

Your own take on what is important in your job is very personal, that is why building highly motivated work environments is so tricky, but I am sure you can certainly find some on that list you can resonate with! What would you add? [We are talking about previous jobs of course, not the one you have now –wink, wink– ed.]

My lawyers tell me to remind you that I am not actually recommending that you quit your job, and instead suggest you hire me to help ‘redeem’ your organization, so they can get paid.