Rather than try to say "here's how everyone should evaluate their career", I just compiled a list of questions you can choose from as you feel like to evaluate your career as it stands today.
The questions from this list were compiled from a fairly broad range of sources; they're roughly organized according to Maslow's hierarchy of needs.
Feel free to submit pull requests with your own questions!
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Am I, broadly speaking, optimistic about my future?
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Am I able to express myself fully?
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Am I focused on the right priorities?
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Am I fulfilling my dreams?
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Am I honoring my values?
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Am I making a difference?
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Am I exploring new territory?
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Am I promoting good ideas?
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Am I being challenged?
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Am I building something sustainable?
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Am I solving a hard problem?
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Am I allowed to be creative?
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Am I allowed to experiment?
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Am I allowed to fail?
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Am I confident in my abilities?
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Am I satisfying my curiosity?
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Am I leveraging all my talents?
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Am I headed in the right direction?
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What trajectory am I on?
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Am I growing?
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Am I opening new possibilities?
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Am I still learning?
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Am I encouraged to learn and share what I’ve learned?
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Am I respected by my colleagues?
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Am I working with colleagues I respect?
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Am I receiving useful feedback?
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Am I getting the recognition I desire?
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Do I have control over how I am judged?
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Am I admired?
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Am I feared?
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Am I beloved?
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Am I trusted?
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Am I inspiring others?
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Am I jealous of others’ careers?
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Am I mentoring and growing others?
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Am I excited about going to work?
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Am I excited to share my work with others?
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Am I surrounding myself with supportive people?
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Do my colleagues give me energy?
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Am I surrounding myself with curious people?
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Am I surrounding myself with brilliant people?
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Am I creating healthy relationships?
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Am I in a workplace with diversity of thought?
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Am I mentally in a good place?
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Am I physically in a good place?
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Am I emotionally in a good place?
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Am I able to shut off work?
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Do I have a good work-life balance?
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Am I able to handle stress due to work?
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Am I able to take meaningful personal time off work?
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Am I able to devote time to my relationships?
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Am I able to devote time to my passions?
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Am I financially independent?
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Am I able to buy the things I need when I need them?
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Am I able to buy the things I want when I want them?
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Do I have regrets?