15 Questions for Self-Exploration

Written by: Jennifer Schidlow

There’s nothing like a little contemplation and self-awareness to deepen our authenticity and support us in the pursuit of living fuller lives. Now seems like a great time to pause and ask some questions.
Take some time to reflect, and then answer these questions at a pace that works best for you; all at once or one per year – no need to push yourself. To maximize the depth of your inquiry, find a cozy, quiet space for reflection. Let yourself relax, and be gentle with yourself especially when difficult emotions arise.
It’s important to recognize that not everyone has the ability to shelter in place safely and/or with financial security. May we understand that it’s a privilege to have the physical and mental space to ask these questions.

  1. What am I grateful for?
  2. What are my most important values? How am I living to honor these values?
  3. How am I censoring what I really think and feel?
  4. What are my gifts?
  5. In what areas of my life am I trading authenticity for safety (or what appears to be safety)?
  6. What makes me feel motivated and excited?
  7. Am I holding on to something that is no longer serving me? What’s holding me back from letting go?
  8. What would I like to be remembered for?
  9. How am I benefiting from privilege?
  10. How do I feel about my last mistake and what did I learn from it?
  11. What’s one thing I would like to do more of and why? How can I make that happen?
  12. What does my inner critic tell me? How does it stop me from moving forward?
  13. Do I feel supported by my family or friends? Who supports me?
  14. What makes me feel most like myself? Why?
  15. What’s my biggest dream?

Asking deep questions can be both challenging and profoundly rewarding. Allow this inquiry to light up your curiosity and lead to growth, appreciation, and compassion. What questions would you add to this list?