55 Questions To Ask For A Better Life

I've developed an unexpected obsession with a set of questions.

I'm working on Sophia, a new HuffPost project to collect life lessons from fascinating people. I ask accomplished individuals to share practical wisdom about topics like happiness, relationships, aging, work, parenting, health, and daily routines, to name a few.

Often my interview guests are well-known (CEOs, artists, technologists, Nobel and Pulitzer Prize winners), but many times they aren't. All are thoughtful individuals with a lifetime of experiences and observations.

At the heart of the project is the set of questions I ask our guests. You'll find it below, divided into a few topics. The list is a constant work-in-progress, something we intend to grow and refine over time.

Already it's a mash-up of questions inspired by a myriad of sources, and I'd love your help to add to the list.

There are a few simple rules:

1) Every question should produce an answer that is practically useful to other people. We're not interested in trivia ("What's your favorite curse word?") or stories that are entertaining but not useful to others.

2) No questions that are better answered by science. We'll turn to experts with those questions ("What are the healthiest foods to eat?") rather than the collective wisdom of our guests.

3) No time-sensitive questions. We want our guests' answers to be relevant for years to come, so we don't ask questions tied to the news cycle, or about the gadgets they find useful, etc.

These are questions about living that have no right answers. Each person's responses are unique, and by reading the answers of others, we can find new insights and lessons that apply to our own circumstances.

Take a look at what we've assembled below, then suggest new questions. Add them as a comment or email us -- sophia [at] huffingtonpost.com -- we read every note.

  • What are some key beliefs you hold about living a fulfilling and successful life? / Have you had any recent realizations about living a rewarding life?
  • What is a great regret of your life?
  • How have your efforts to make yourself happy developed and changed? What has worked and what failed?
  • What is your greatest flaw?
  • As you look at your life so far, were there any turning points, any key events or experiences that changed the course of your life and set you on a different track? What happened and what did you learn?
  • Memories are an important part of happiness. Do you use any interesting techniques to keep track of your memories? I.e., Do you keep a type of journal or diary?
  • Many people have had deeply difficult or stressful experiences but learned valuable lessons from them. Is that true for you? What did you learn?
  • What is something minor or seemingly insignificant in your life that actually contributes greatly to your happiness?
  • What characterizes the periods of your life that you felt were most fulfilling, or least fulfilling? Are there any common threads?
  • Have you ever been screwed over? What happened and how did you respond?
  • Have you done anything recently for the first time, some unique experience or accomplishment?
  • What do you think about when you think about death?
  • Is there anything out of the ordinary you want to accomplish before you die?
  • What advice would you give your younger self about finding love and building lasting relationships?
  • Did you learn anything from your earliest relationships?
  • What's the best gift you've ever received from/given to a partner or close friend?
  • Do you have any lessons for best approaching love and relationships when you're single?
  • What advice would you have given yourself on the day you were married?
  • How did you/your spouse propose?
  • When did you decide that you were ready to marry your spouse?
  • What advice would you give to couples for keeping their relationship healthy after having children? [How did you adjust your marriage after having children?]
  • (If partner has died) Do you have any advice for dealing with the loss of your partner?
  • Do have any helpful habits or daily routines?
  • Do you have any tips or tricks regarding productivity or health?
  • What advice would you give those currently 10 years younger than you about how to make best use of the next decade?
  • Did you have a negative trait or habit that you overcame in a novel way, and if so, how’d you do it?
  • How is your sleep? What do you do to get your best sleep?
  • Do you have any unique hobbies or ways that you spend your downtime that are out of the ordinary?
  • What's the most memorable travel journey you've taken that you'd recommend to others?
  • What is the most beautiful place you’ve ever been?
  • What kinds of advice do you have for people raising young children?
  • What kinds of advice do you have for people raising teenagers?
  • Do you have any regrets regarding your own parenting?
  • What do you feel is the most helpful thing your parents did for you that many parents don’t do?
  • What did your parents get wrong that others can learn from?
  • Do you have any unique advice regarding disciplining children?
  • What are some parenting practices you tried with your kids that didn’t have the effect you intended?
  • Has parenthood changed you in any unexpected ways?
  • Do you have any advice about balancing parenthood with the demands of your career and your own personal development?
  • Are you content with the number of children that you had?
  • (If no children) Was that a deliberate choice? Are you happy with how that part of your life has unfolded?
  • Tell us about a book (or books) that had a profound impact on your life or intellectual development.
  • What advice would you give people so they get the most out of college?
  • How would you have handled your own education differently?
  • What advice would you give to young adults who are choosing a career path?
  • Who is the best teacher you had? What did they do that made such an impact?
  • In the course of your life, have you changed your mind about anything substantial?
  • What distinguishes the periods in your career when you felt most satisfied with your work from the times when you felt least satisfied?
  • Do you have any career-related regrets that would be educational for others?
  • Have you had a personal mentor and what did you learn from them?
  • Provide a snapshot of your industry/area of expertise. Explain the work that you do in lay terms. What about your work do you find most satisfying? Most challenging?
  • Tell us something about your profession that would otherwise take months or years to learn.
  • Do you have any overarching tips or unorthodox practical advice regarding money?
  • In your life, what has been the relationship between wealth and personal fulfillment?
  • Roughly speaking, what do you do with your money?

sophia project

Sophia is a project to collect life lessons from fascinating people. Learn more or sign up to receive lessons for living directly via Facebook or our email newsletter.