50 Deep Questions You Should Ask Yourself

deep questions you should ask yourselfEveryone needs periods of self-reflection and evaluation.

Asking some deep questions, that too to yourself helps in understanding better who you are, where you want to be, what you want to do, etc.

You take the time to think things over and as a result understand yourself better and see things more clearly. I’ve seen that this is the best way forward to your personal growth.

I have tendency to overdo this though, don’t know why.

Ok, coming back to our discussion, below are some deep questions worth asking yourself. They are though provoking and often lead to additional questions.

1. What’s your passion?

2. What would you do in life if you did not need to work for money?

3. Where do you want to be in 5, 10, 20 or 40 years?

4. What are your fundamental life values?

5. Who are the 3 most important people in your life?

6. What is your biggest dream?

7. How much are you ready to sacrifice for your dream to come true?

8. What are the 3 things in your life that you would like to change?

9. When was the last time you laughed out loud?

10. What are you grateful for?

11. When was the last time you tried something new?

12. When was the last time you did something spontaneously?

13. Which are the most memorable moments from your past?

14. Are you making the same mistakes over and over again?

15. Forget your real age for a second – now tell yourself how old are you?

16. How important is social approval for you?

17. Do you live for others or for yourself?

18. What was the last life lesson you learned?

19. When was the last time you helped someone?

20. Did you ever help a complete stranger?

21. What is your greatest fear?

22. Which word describes your personality best?

23. What inspires you?

24. What was the biggest change initiated by you in the past 5 years?

25. What’s your life’s biggest achievement?

26. When was the last time you were proud of yourself?

27. If you could choose any place, where would you live?

28. What stops you from making the first step towards your dream?

29. When was the last time you took a risk?

30. Who are the 3 people who had the most powerful influence on you?

31. What’s your deepest secret?

32. What is happiness for you?

33. What habits would you like to quit? Why don’t you start today?

34. How much are you ready to sacrifice for a successful career?

35. What will you never forget?

36. Which were the most emotional moments of your life?

37. If you wrote about your life and only mentioned most colorful, vivid, strong and impressive periods how many pages would the book be?

38. How many times have you fallen in love?

39. How many times has your heart been broken?

40. What makes you keep motivated and carry on?

41. Do you give up too soon?

42. Do you know how it feels to wake up with a smile?

43. When was the last time you cried?

44. Do you like your birthdays?

45. Are you at peace with yourself?

46. If not the financial matters, would you work where you are working now?

47. How much time do you spend on social networks?

48. Is the cup half empty or half full for you?

49. Did you experience a paradigm shift?

50. Usually do you listen to your heart or to your brain?

Maybe these self reflection questions will not bring solutions to your problems but they will at least help you see what those problems are. In my opinion, self reflection is the best way to boost your personal development.

Ask some deep questions, be honest with yourself and you will find out things about yourself that even you did not know!


By the way, if you are interested in knowing more about yourself, your partner or your friends through questions, I suggest you take a look at “The Book Of Questions” by Gregory Stock Ph.D.

Photo by M0THart

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75 Responses

  1. Bobbi Emel says:

    Ani, these are good questions. Perhaps you should continue to save up more like this and do a Question-A-Day calendar. Might be very popular!

  2. Priska says:

    Great questions. I might use them as writing prompts. By the time I reach the end I am sure to have gained a lot of new insights.

    • Ani says:

      Actually depending on the angle you look at the questions (not too agocentric) each one may eventually become potential blog post on the subject.

  3. Kaylee says:

    Great questions, Ani. This one particularly jumped out at me: 42. Do you know how it feels to wake up with a smile?

    I haven’t woken up with a smile lately, and this question made me realize how much I miss that. I think it’s my goal for tomorrow to wake up with a smile. =)

  4. Ciara says:

    Great list of questions, I love Bobbi’s idea a thought provoking question a day would do wonders for a person’s personal development over the year.

  5. These are wonderful questions and can spur reflective dialogue on so many different issues in our lives! Thanks!

  6. Jason Harvey says:

    I think “What would you do in life if you did not need to work for money?” is one of the more popular questions that I think a lot of people have thought about at one time or another. Especially lotto players! It also relates to a lot of the other questions on your list in some way.

    I really like this question because in one way it can get your excited and hopeful; dreaming about what you would do everyday. I would just like people that really do think about this question to also think about what they can do right now to make it happen. What steps can they start to take for this to be a reality at some point in the future.

    • Ani says:

      Agree Jason. From “What would you do in life if you did not need to work for money?” derive many other important questions. And yes, without taking steps and acting nothing will move forward.

  7. Amit Amin says:

    Oh… these are some tough questions. Perhaps I should use some of them as a journaling prompt….

    “Do you know how it feels to wake up with a smile?” No – I wake up with headaches :)

  8. Good…and deep questions. I have asked myself most of these questions but there were a few I had to really think about. I think I might use this list as art journal prompts. By the end of the journal I will probably understand the excavation process of self reflection and “fruedian” examination. Thanks.

  9. Frunze says:

    Great questions, they are so important! It seems like God can ask everyone this questions, especially the ones who complain about their life and problems :) .

    • Ani says:

      I am glad you enjoyed them. Very soon I will be launching an e book with one question per day for the upcoming year. It will be available for free to all subscribers :)

  10. Hasan says:

    Great list of question. Thanks.

    This is my first time visit of your blog – nice blog.

  11. Excellent questions, I’m still going through them. Good job!

    • Ani says:

      Thanx for the comment Stefan. There are many more in “the Year in Questions” free e book, which you can get by subscribing :)

  12. Fabian says:

    Thanks so much!

  13. Life says:

    “Only he who attempts the absurd can achieve the impossible.”

  14. AJ Walton says:

    Excellent questions – difficult to digest all at once.

    “What’s your deepest secret”? There’s one to pause and really think about…so many interesting implications of the answer.

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  17. sex says:

    Post très fascinant

  18. XxBrookiexX says:

    I’m gonna answer these in my next comment :-)

  19. XxBrookiexX says:

    1) My passion is shopping until I drop :-)

    2) Good question… I’d probably go on endless vacations

    3) In 10 years, I’ll be 26, so I want to live somewhere nice with one child and a husband.

    5) My parents, my siblings and my boyfriend.

    8) My procrastination is the only thing I’d like to change… :-/

    9) Last night I was watching an hour of PewDiePie’s scary moments montage, and I laughed so much 😀

    10) I guess I’m grateful for the stuff I have even though I can be spoiled, because my dad’s sorta rich… (I don’t like to brag)

    11) When we went on a field trip on Friday, we went to a museum and for the lunch there was sushi and some other stuff I can’t remember. So, yeah, I tried sushi. It’s okay :-/

    13) When I pushed my brother into the pool, lol, and when I nearly broke my arm in gymnastics.

    15) Right, I feel like I’m 9 even though seven years older then that xD

    19) There was an old woman in the store, and she couldn’t reach something from the tippy-top shelf, so I got it for her :-)

    20) This man walking down the street needed directions.

    21) Vermiphobia , fear of parasitic worms and normal worms. Ugh… :-(

    22) Wow, there’s a lot of words to describe me but I’d describe myself as loud and outgoing :-)

    25) Being a gymnast.

    26) When I won a gymnastics competition in Brooklyn. Lol, Brooklynn is my name 😀 (with two n’s)

    27) In Brighton because PewDiePie lives there 😀

    29) Hoho, I take a lotta risks… 😉 The most recent one was jumping over a flight of stairs on a skateboard, by the way, I can’t skateboard. Long story short.

    30) Mom, Dad, Principal 😮

    32) Always being right. Ahhh, I love the feeling :-)

    33) Talking waaay too much.

    35) When my sister was born… Lol!

    36) My grandmother’s death. :-(

    37) About the size of Harry Potter books.

    38) Three times. I’m dating my third crush now. <3

    39) Once.

    41) Heeeeeell no.

    43) When my frickin brother tickled me until I nearly peed myself!

    44) Yup. My Sweet 16 was on March 29 😀

    47) I have instagram, facebook, twitter, and I text a LOT!

    50) My heart <3

    Thanks for reading my long comment xD, it's okay if you didn't though. :-)

    -Brooklynn xoxox

  20. Nicest and life changing list. Thanks for sharing.

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  22. Titus oneil says:

    Fantastic questions bro!!! I think u r a creative thinker,and i like the q.no.3 and q.no.42 very much…..

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