Author Ryan Holiday originally published a list of 12 Questions That Will Change Your Life in 2014, then followed up with 13 additional questions for reflection in 2019. In the original posts, Ryan includes amplifying context to engage each question, and it is worthy of reading. Sources span the ages, from Stoics and philosophers to contemporary authors. Links: 12 Questions; Additional Questions.

12 Questions That Will Change Your Life

1. Who Do You Spend Time With?

2. Is This In My Control?

3. What Does Your Ideal Day Look Like?

4. To Be Or To Do?

5. If I Am Not For Me, Who Is? If I Am Only For Me, Who Am I?

6. What Am I Missing By Choosing To Worry or Be Afraid?

7. Am I Doing My Job?

8. What Is The Most Important Thing?

9. Who Is This For?

10. Does This Actually Matter?

11. Will This Be Alive Time or Dead Time?

12. Is This Who I Want To Be?

13. Bonus Question Sort Of: How do your actions and decisions answer the question, “What is the meaning of life?”

What If I Said No? (And Other Questions To Consider Daily)

1. How can I be stronger for this?

2. What books changed your life?

3. Does anger make this better?

4. Am I being kind or clever?

5. Is this getting me closer to my ideal life?

6. Does this stop me from acting with justice, temperance, courage, or wisdom?

7. Why do I care what they think?

8. What if I said no?

9. Is this something only I can do?

10. Who owns who?

11. Where does this person fit into the world?

12. What am I working to get better at?

13. What can I let go of?