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Probing Questions You Should Ask Yourself

Your honest answers to these self-appraisal questions could change your life.

Pixabay, CC0 Public Domain
Source: Pixabay, CC0 Public Domain

Over the past quarter-century, I've kept improving the list of questions I often ask clients to tease out their essence and help them develop goals.

Here is the current list of those questions, divided into four categories: relationships, work, health, and overall life questions.

Don’t struggle with the questions. If something is important, an answer will generally pop into mind. If not, go on to the next question.

Your relationships

Is there someone you should spend more time with?

Is there someone you should spend less time with?

How do you really feel about your mom? Your dad? Your stepmom? Your stepdad? Each of your children?

Should you have a child?

Is there anything you should change about your sex life? Accept about your sex life?

Now, look into your crystal ball. Will you achieve what you’ve been striving for in relationships?

Your work

Should you try to find better work? If so, do you need to quit your job to make that likely?

Should you devote more or less effort at work? At home? On your volunteer work? On your creative outlet?

Should you change how you behave at work: Toward your boss? Your coworker(s)? Your supervisee(s)? The work itself?

Should you try to make money from your creative outlet? As your main source of income?

Do you want to work for some cause? If so, what cause?

When, if ever, should you retire?

Now, look into your crystal ball. Will you achieve what you’ve been striving for careerwise?

Your health

What’s your best guess as to how old you’ll be when you’re no longer capable of doing professional-level work? Does that suggest anything you want to do now?

Do you want to lose weight or accept yourself as-is? If you want to lose weight, what, if anything, do you think will help you defy the odds and lose the weight and keep it off?

Should you exercise more? Less? Differently?

Do you believe you’re using mind-altering substances too much, too little, or just right? If too much, is there anything you want to commit to doing about it?

Now, look into your crystal ball. Will you achieve what you’ve been striving for healthwise?

Your overall life

What’s the question you’re most afraid to be asked?

In what way(s) would you like your next decade to be different from your previous one? Is there anything you want to do now to help make that happen?

What would give your life more meaning?

If you didn't care what anyone thought, what’s your most deeply held aspiration?

What's an unusual even weird value you hold? Does that suggest anything careerwise? Otherwise?

Imagine that everyone who knows you well is in a room. You aren’t there and they know you’ll never find out what they said. What’s the most important positive thing they’d agree was true about you? How might you build on that strength?

What’s the most important negative thing those people would agree is true about you? Can you and do you want to improve on that? Do you want to change your environment to minimize that negative aspect’s impact?

Do you want to accept your personality as-is or do you want to change something, for example, become more or less social, more or less friendly, more or less aggressive? Something else? If you want to change, what will help you do it? If you want to accept yourself, what will help you do that?

What’s something you’re afraid is true about yourself?

  • You’re not that smart
  • You’re lazy
  • You’re annoying
  • You’re physically unattractive
  • You’re malevolent
  • Other (specify)

In light of that, is there anything you want to do?

Have you accomplished as much as you’d hoped to? If not, is there anything you want to change to improve?

Do you think you’ll ever care enough to get much more done?

This final question was suggested by a reader, Irina Popa-Erwin: Who are you? Answer in one sentence.

Your action plan

Now, look back on or think about all your answers. Is there at least one thing you want to commit to doing? Starting now?

Dr. Nemko’s nine books are available. You can reach career and personal coach Marty Nemko at

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