The Self Reflection Edition

Some key questions on your past, present, and future

Jenni Dawes (JD) is a friend of WITI and a Paris based writer and strategist. Check our her MMD here.

Jenni here. I have a business of asking deep questions (truly), and a ritual of deploying them presently, bridging the psychological abyss that we insert between one year and the next.

There’s a certain levity that comes with carving out a sacred pause, of turning our errant curiosity inward to bestow the precious gift of attention - “the rarest and purest form of generosity”, according to Simone Weil - upon ourselves.

It’s a process of marking what matters; forging meaning in actions past, taking stock of the current situation, closing chapters, stretching a beckoning hand to the future self.

Why is this interesting?

As Churchill stated, “Those that fail to learn from history are doomed to repeat it.” There’s a science to contemplation, the efficacy of the examined self. A certain prescience also, as the maxim goes: “If you want to know your future, look at yourself in the present...”

I am what I choose to become (so says Jung), and inaction is a decision in itself; I can abdicate the captain’s responsibilities, leave the course to external forces, but there’s still no getting off the ship. Agency, as such, has always been more appealing, consciously charting a path, following (self) knowledge like the sinking star sought by Tennyson’s king.

Here, 25 favourite questions to guide your exploration. Concentrate on the most evocative, or set aside a couple of hours to cover them all. If you’d like a co-pilot, or are keen to dive deeper still, grab a bite-sized inquisition.

Past

1. How have you changed over the past year?

2. What have you done/ become in the last year that makes you proud?

3. If you could go back and relive one day, which would it be, and why?

4. What’s the most adventurous thing you did?

5. What, if anything, do you wish you’d done differently?

6. What do you wish to leave behind?

Present

7. What are your most important rituals?

8. What makes you feel most alive?

9. What currently feels at the edge of your comfort zone?

10. What do you need more of in your life? Less of?

11. Who / what is most important to you?

12. What are you currently concerned about?

13. How would you describe your relationship with yourself?

14. Where in your life are you most avoidant?

15. Where do you find peace?

16. What’s holding you back from your fullest potential?

17. What are the common characteristics of the people you most admire?

18. Does your current environment support you in who and how you wish to be? If so, how? If not, what can you change?

Future

19. What does success look and feel like for you?

20. What do you still want to discover in the world?

21. What’s the number one change you need to make in the next year?

22. What part of yourself do you wish to give more time/energy/space to?

23. What are your three biggest priorities?

24. If you were braver, what would you do differently?

25. What will your future self wish you had done?