Nightmare or dream job? A checklist to stay or go

Is your job a nightmare or a dream?

I suspect every job is a blend of both. Some days are more dreamy; others more like a nightmare, making you dread going to work. Even as self-employed entrepreneur designing my own work, I’ve had my fair share of disgruntlement. On occasion, I even fired myself for a time.

Nightmare or dream job? A checklist to stay or go


However, if you find yourself persistently wondering if you should stay or go, it may be a sign that it’s the start of a new chapter in your life. You may also be suffering from treadmill fatigue. You’ve been doing the same thing for a Very. Long. Time.

When I was in my thirties, I ran the international support organization for Cray Research, a supercomputer manufacturer. We were responsible to make sure the multimillion dollar computer systems our customer purchased continued to operate as expected. The job was exciting, challenging, and, yes, fatiguing. After seven years of constant crisis management, I was—to put it mildly—toast.

One night, in a plume of distress and a collapse of reason, I phoned my division VP at home and told him I couldn’t go on. I asked him to assign me to a new role. It felt good to get it off my chest, but I knew that decision was made from acute emotional distress not acute mental faculty. Fortunately, he knew it too and gave me some time to reevaluate my request.

If you’re facing a similar quandary, a checklist of whether you should stay or go may help. Ask yourself the following:

  • Am I experiencing an unusual level of fatigue? Job satisfaction is often related to the stress you’re trying to manage and you may find that your outlook quickly improves following a vacation, or even the completion of a taxing assignment. The good news is that, even in the most demanding jobs, you can increase your ability to manage stress to make it more enjoyable.
  • Do I enjoy the company I work for and do I embrace its mission? If not, there’s not likely to be any position within the firm that will be meaningfully rewarding. Yes, you might find one that will compensate you nicely, but without alignment to a mission you’ll remain conflicted and that tension will sap your joy in challenging times.
  • Are there other positions within the firm that might be more meaningful to me? If you’ve been in your position for awhile, as I had, you probably need a change. If so, have you taken the time to evaluate what kinds of jobs would be appealing? And have you asked your boss to help you develop the skills to get there? Don’t assume he or she can read your mind. Even more importantly, don’t wait like I did until you’ve experienced burnout to start thinking about it.
  • Can you champion a new position that would better suit you? Perhaps you don’t see another position in the firm that looks like a dream job to you. Why not champion a new one? Imagine your dream job and why the company should put you in it. Do your homework and create a business case that articulates why it would be beneficial for the business to have you do it. You’re the best person to design a perfect job for you. And if it benefits the company then it’s a double win.

If your answer is ‘no’ to all four questions, it may be time to move on. The sooner the better because even a nightmare can become reality. As someone once put it to me, “It’s better to move while you’re unhappy than stay and make others unhappy with you.”

What other questions have you asked to know whether you should stay or go?

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