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15 Questions to Ponder

Woman looking off into distance, pondering; Article: "15 Questions to Ponder" by Stacey Mason
May 18, 2023  |  By Stacey Mason

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“The unexamined life is not worth living” is a famous saying supposedly uttered by Socrates. Socrates believed that philosophy – the study of wisdom – was the most important (life) pursuit above all else.  Through questioning and logical argument, one could examine their own life.  

I think it’s not only about the questions we ponder, but also about the deep courage to embark on the journey that those questions take us on.  It’s about the process on the way to the answers. And so much of life is lived in this process.   

In this season of college graduation, I thought I would share 15 questions that you might want to ponder yourself as you start the next leg of your journey in life.   

1. Am I happy…?  Truly, deeply, and unabashedly happy.  Because happiness begets more happiness.  

2. What do I need…?  We are simply unable to be the best version of ourselves if our needs are not met.  What you need is not up for debate.  

3. What do I not need…?  An equally pressing question that has us eliminating some things and setting better boundaries.  

4. What’s not wrong…?  We spend so much time focusing on what’s wrong, when in fact most things are not wrong at all.  We can change the way we look at things – linguistically and figuratively.    

5. What matters most right now…?  Priority lists exist for a reason.  Get serious about your priorities and move forward with conviction.  

6. What do I know for sure…?  Core values.  True north.  Guiding principles.  Non-negotiables.  What we know for sure anchors us and gives us a framework to operate within while we ask the other questions.   

7. What do I not understand…? The universe is vast.  Knowledge is immense.  This question keeps us humble and curious.  

8. What if I’m wrong…?  You very well could be.  And you can’t possibly know until you’ve challenged yourself by asking this question.  

9. How are my relationships…?  Regrets are an enormous waste of time.  Tell someone you love them, issue an apology if you need to, reconnect if too much time has passed, clear the air if a misunderstanding took place.  It’s true what they say - relationships can make or break us.    

10. Does it make sense…?  Maybe yes, maybe no. You can’t possibly know until you ask the question.  

11. Why…?  Engineers are trained to repeatedly ask why.  Because eventually that line of thinking takes you to the root of the problem.  And solving the root is so much better than repeatedly addressing a myriad of symptoms.   

12. What is my legacy…?  We’re all leaving something behind – every single one of us.  The challenge is to leave behind something that will live in the hearts and minds of others.

13. What am I learning…? You never stop learning because life never stops teaching.  Everything you’re learning is preparing you for something else.  Stay teachable – and take good notes.  

14. Am I spending my time well…?  We all get 1,440 minutes a day. Yes, responsibilities and constraints eat into that total. But chances are we have at least some agency over how we spend them.

15. Where do I go from here…?  More questions, deeper introspection, greater courage.  Just keep going.  

Examining your life is an on-going process because life is an on-going journey.  We question, we reflect, we examine, we evolve.  And if we’re lucky, we eventually become the best version of ourselves.  And that is indeed a worthy endeavor.  

Ancora Imparo… (Still, I am learning)

Stacey MasonFounder of The Improv Lab, Stacey Mason has immersed herself in the field of Applied Improvisation for the last decade after co-founding several comedy improv troupes and training with various actor-teams including Second City in Chicago. Her corporate background includes nearly 20 years at Walmart in Logistics, Global Supply Chain and Merchandising/Replenishment before shifting towards culture coaching, stewarding the Walton Institute, Walmart’s flagship culture program. She partners with Walton College Executive Education on innovation programs and other initiatives