Feeling Stuck in Your Career? 10 Questions to Help You Move Forward

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So you’re feeling stuck in your job or career; you’re unhappy and unsure what to do about it. To get unstuck, take the first crucial step and conduct a thoughtful self-assessment. Accurately diagnose the cause and identify the cure by reflecting on three areas: your life experiences, your current situation and your vision for the future.

One assessment approach I use with clients to gain the needed insight involves answering 10 questions that cover these three areas. Sometimes we’ll dive deeper into an individual question with a more detailed assessment exercise to get a clearer answer, but often that’s not necessary. Just a bit of thought about each question can provide you with the “aha” moment you need to see the path forward. Here are the questions for each of the three assessment areas.

Questions to identify patterns in your past experiences

  • When thinking about accomplishments that you enjoyed achieving the most, what patterns do you see? Come up with a few of your best anecdotes: accomplishments from work, education, or personal life that you’re most proud of and brought you the greatest sense of enjoyment/satisfaction while you were achieving them. Then analyze those to identify patterns. For example, one client noticed that almost all of the examples she chose contained the same two elements: persuading others and being innovative. She realized that when she didn’t have these elements in her work, she was less satisfied, so she weighted these two elements heavily when deciding on her next career move.
  • Do certain work situations consistently cause dissatisfaction (e.g. feelings of anxiety, resentment, frustration or anger)? Look back at your prior roles to see if there’s a pattern. If so, you may need to either a) fix yourself first before you can even know whether changing jobs will make you feel better, or b) find a job or career where that dissatisfaction trigger won’t be present. As the saying goes, “Wherever you go, there you are.” For example, one client realized that he had never been happy in any of his five jobs because in each role he felt that he was being treated unfairly. This was a big moment of clarity for him; he saw that prospective new jobs would not leave him feeling more satisfied unless he first changed his expectations regarding relationships with his colleagues.
  • When (if ever) were you happy in your career? What work (if any) did you truly enjoy? Why? With one of my clients, we had to go back 15 years to find a role that she enjoyed. Answering this question helped her to see the source of her dissatisfaction: that the market dynamics of her industry had shifted for the worse over the years. She decided to change industries while keeping the same job title, and was able to regain the sense of purpose and contentment she had missed for so long.

Questions to identify unique problems with your current situation

  • If you had “better” work colleagues, would you no longer feel stuck? For many of my clients, a poor relationship with a boss or colleague, or a feeling of being taken for granted, was the cause of dissatisfaction. In some cases those relationships could be improved. In others, changing jobs while staying on the same career track was the solution.
  • Does your work feel purposeful, meaningful, or important? If not, what can you do that would give you a sense of purpose? A lot of research has shown that purpose and meaning are key drivers of life satisfaction.
  • Does your work violate some key work-related value, something on which you really don’t want to compromise? Examples could be insufficient compensation, not enough authority, no time for family, lack of enjoyable colleagues, and so on.
  • If you know what’s holding you back but fear taking action, how reality-based is this fear? Ask yourself 1) What’s the worst-case outcome from taking action (being destitute, losing your home, losing your family, etc.)? 2) How truly likely is that worst case outcome? 3) What’s the worst case outcome for NOT taking action? 4) Is there a way to mitigate a well-founded fear of taking action? Once you answer these questions, the path forward may present itself. Sometimes that path isn’t a straight one. For example, one client feared losing income. To address this fear, he developed a two-year plan which included keeping his current dead-end job, enrolling in a six-month evening certification course and taking on consulting work part time to build experience in a new area. Yes, the path was a hard one; he had to work many more hours than he otherwise would prefer. But when he was able to switch into his dream career two years later, it all became worth it.

Questions to help you envision a better future

  • What regrets might you have in 20 years if you do/don’t make a move? When Jeff Bezos did this exercise, he realized he would always regret not quitting his lucrative investment banking job to take a chance on starting his own company. The rest is history.
  • What’s your vision for your life? What do you want your life to feel like five years from now? 15 years from now? Make sure that the career path you choose will help you reach that vision.
  • What career decision-making criteria can you develop from the prior nine questions? List the criteria in columns on a piece of paper or spreadsheet. Then brainstorm job or career options and place them in the rows. Score each row based on how well they fit the decision-making-criteria in the columns.

Once you’ve answered these questions thoughtfully, you’ll start to see the path forward. This path may involve anything from a major career change (I’ve made three of them in my life) to accepting and finding the good in, your current situation.

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