10 Powerful Questions to Ask Yourself

Leadership Newsletter #4

10 Powerful Questions to Ask Yourself

The University of Chicago offers students the opportunity to “major” in “Fundamental Questions.” A student will select one question of their own choosing, take courses, and undertake individual research projects to help them “answer,” or at least rigorously address, the one question they chose for their major. In addition, they will also take all of the “core courses” required to graduate. See the 2024 list of UChicago students and their questions here.

In this leadership newsletter, I offer ten questions, some of which you may have never asked yourself. These are not one-time questions; they are questions to revisit time and again in your life.

These might not be the best questions for you at this time in your life. I hope these questions do spur you on to create even better questions for yourself. I also hope you will recommend that those around you create 10 powerful questions for themselves and dive into answering them.

If you have a diary or write notes by hand or computer, you might want to date and save your answers to “your ten questions” and review them over time. I look forward to your comments. Since I will publish an updated and hopefully improved version of this newsletter every spring going forward, please send me powerful questions you develop for yourself. Please either reply to this email or add a comment below.

Question Number 1:  How can I improve? You can give both general and very specific answers to this question.

Question Number 2: How can I empower others to improve?

Question Number 3: What will I do today (or in the future) for the first time?

Question Number 4: What do I want to stop doing?

Question Number 5: What can I do to improve my country and the world?

Question Number 6: What frustrates me, and how can I overcome or successfully eliminate this frustration?

Question Number 7: Am I lucky, and if not, how can I become luckier?

Question Number 8: Do I have a “life plan?” If not, how can I develop one that might help guide my life, my next decade, my next year, or even my next week?

Question Number 9: What are the five most important values I live by?

Question Number 10: How do I make my most important personal relationships great?

Wishing you the best in addressing these questions. Feel free to email me at herb@herbrubenstein.com.