Sad girl with head down sitting on benchCareer stagnation, second guessing, and playing the career-comparisons game are the seeds of job discontent, decreased self-esteem, and career regret; especially as the year is beginning its inevitable winding down, job boards are filling up with new jobs, and your friends and professional acquaintances may be moving on to bigger and better careers or going back to school. If you aren’t progressing alongside of your peers you are probably beginning to feel the unavoidable feelings of regret that accompany career dissatisfaction. Your mind may be filled with thoughts of the “should haves” that would have (in your mind) made your life more fulfilling and successful.

Especially if you are comparing your progress with that of others, thoughts such as, “I should have climbed up the ladder by now,” “I should have picked a different career,” and “I should have ditched this job already,” can nag at you and force you to conclude that your attempts at career progression are pointless thus planting the seeds of anger and resentment that may lead to indifference and resignation. Not only do these feelings affect how you feel about yourself but your loss of motivation and ambition become obvious to others who will become more likely to overlook you for big projects and less likely to approach you in social situations. There is only one way out of this rut, and that is to revolutionize your ways of thinking.

The best approach to changing your thinking is to transform the depressing and demotivating “should have” thoughts into the more inspiring and productive thoughts of “what ifs.” And you can’t do this alone. You’ll first need some good friends or trusted colleagues to help you brainstorm, and the added perspectives of people other than yourself can help you see your regrets in a different light. Don’t allow your own negative thinking to affect the people you choose to help in this endeavor as the more positive and creative your team is the better the end result will be.

Once you’ve assembled your group of positive thinkers, come up with as many “what if” questions as you can that are directly related to the cause(s) of your feelings of regret. Examples may include: “What if I used my skills to work for a cause I feel strongly about?” “What if I taught others the basics of my field?” “What if I coached others to improve their own skills?”

Finally, turn those what-ifs into actionable items. Figure out which of them are worth exploring and considering as potential replacement career paths. The more excited and energized you feel over a particular possibility, the more you should work on it to make it real. You should find that by simply working towards a goal that you find promising will reinvigorate you and give you a more positive attitude and outlook.

No matter when they hit, career regrets can have a devastating effect on your outlook and can create the conditions of a self-fulfilling prophecy where your fears are confirmed by the world’s reaction to your own negativity and sense of futility. But by seeking out some support from the positive people in your life and working to put your career in perspective, you can change your “should haves” to “what ifs” and discover new ways to find fulfillment in your career.



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