30 Must-Ask Questions for Meaningful Connections

Because answers are born from asking the right questions.

Sydney Chiu
The Post-Grad Survival Guide

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Photo by Duy Pham on Unsplash

Here are a list of questions I’ve concocted or borrowed, tried and tested over the past two years, and ultimately compiled here. For you to better understand others and yourself. It’s okay, you can thank me later:

  1. Life-changing habits?
  2. Earth-shattering moments?
  3. What keeps you grounded even when everything else is chaotic and out of your control?
  4. Best non-monetary investment that has give you the highest return of happiness?
  5. Whose voice pops into your head during certain circumstances and what do they say to you?
  6. Memory you can recall as if it happened yesterday?
  7. Situations where you behave most differently than your true, genuine self?
  8. When do you feel most empowered?
  9. Turning points and season you’ve weathered in your life?
  10. Greatest self-discovery moment?
  11. If you could have one reminder super-glued to your mind, what would it be?
  12. Favorite metaphor or anecdote?
  13. What memories provide you with the most profound nostalgia?

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Sydney Chiu
The Post-Grad Survival Guide

keeping the promise to my eager-eyed, journal-obsessed 9-year-old self who dreamed of becoming a writer