101 Thought-Provoking Questions

So, clearly, I like questions.  This time of year, I tend to ask myself a lot of questions and seek out tools to build my self-knowledge so I can enter a new year with new insights and plan appropriately.

I’ve been sick as a dog for the last few days.  Literally spent all weekend in bed and took today off.  I got up a few minutes ago, and it was approaching 9 pm.  Seriously.  My liver actually aches.  That’s how sick I am. Add to that, a cracked wisdom tooth that is making its presence abundantly know, and I could use some distraction.

I don’t remember how I found these questions, but they’re appropriate for the work I’m doing on myself this month–when I’m not sleeping or feeling like crap.  (This may be an installment blog, depending on how tired I get).


(source: https://www.pickthebrain.com/blog/101-thought-provoking-questions-ask-late/)

1. Do you like who you are?

Yes.  Finally, yes.  It’s a little bit intimidating to admit that because I spent so long not really liking the person I was…eternally beating myself up.  I think I’m a pretty awesome person, though.  I’m interesting, resilient, smart, and funny.  I fought for this life, and I like the person who evolved from it.  Does that mean I stopped beating myself up?  Not at all!  Hah.  I’m far from perfect and struggle, hard-core, with that some days.  The past is still very painful for me at times, but I’m proud of how I constantly confront my own bullshit. That takes guts.  I’d want to be my friend.

2. What would people say about you at your funeral?

Oh, God.  I don’t know.  I really hate even thinking about that, or giving it any kind of energy…partially because my own death sort of scares me.  I think it’s the one thing left to be scared of for me.  I still have at least 1/2 life to live, and I have so much to learn and do still.  So, I don’t even want to answer that.  But–if I died tomorrow–I’d be pretty sad just because I haven’t gotten to do a lot of the people sort of work I need to do.  I haven’t found a life partner or had kids.  I haven’t really found a tribe to call mine.  I think, by and large, many people would say they never really knew me.  Or people would say they thought I was one thing, but learned in our later interactions that I am so much more.  I think I really surprise people.  I think the people who have gotten to know me know my heart.  They know how loyal I am and that I’m a very forgiving person who really always tried to do the right thing–even with limited tools.

3. What would you regret not doing in your life?

I actually have lots of regrets.  I know people like to say they have no regrets.  But I absolutely do.  And I don’t think that means I don’t appreciate the life I have.  I never would have chosen the paths I’ve taken, and thankfully, they led to great surprises and things I never would have expected.

But–yea–regrets.  Um…I would have given my Daddy a break.  I was a kid, I know, but man–I was hard on him.  He was hard on me, too.  We’re a lot alike.  I’d also have been less concerned with being perfect or achieving…but, then, without that mindset–I’d be stuck in Westwood.  I would have said goodbye to my mother on the morning of her surgery.  I would have gotten therapy sooner.  I would have leaned on people more.  I would have taken more time to tell people exactly how I felt in moments–good, bad, indifferent.  Especially people I loved.  I wouldn’t have gotten so many undergrad degrees.  I would have saved money sooner.  I would have gotten out of bad jobs as soon as I felt they were bad.  Oh, and I would have embraced boundaries. Hard core.

4. What’s the wisest thing you have ever heard someone say?

Maya Angelou said once, “When someone shows you who they are, believe them.”  Oh, man: preach.

5. What lessons in life did you learn to hard way?

Hahaha!  I learned all my lessons the hard way.  Let’s see…sometimes, it’s not about you.  You can always be more patient and kind.  We are all capable of absolutely anything.  People are good, at their cores, but they are also imperfect.  Actions say more than intentions.  It’s easy to get caught up in your wishbone when you need a backbone.  It’s better to be respected than loved, sometimes.  I worry about shit that will never happen, most of the time.  And the shit that does happen is never as bad, in reality, as it was in my head.  But then, some things are EXACTLY what I think they’ll be.  There is no escaping yourself.

6. How often do your biggest worries and fears come true?

Maybe 1% of the time, and then it’s so much worse than I could ever fathom.  But the mind and the heart are resilient creatures.

7. If you had one year left to live, what would you try to achieve?

I think I’d do mostly the same things, but with more intensity.  I try not to do things I don’t love, usually.  Try being the operative word.

8. Do you serve money or does money serve you?

I serve money.  Man, I hate it.

9. Are you afraid of being your true self around others? Why?

No.  I’m absolutely me most of the time, even at work.  I just have filters.  Building walls is not worth it and limits your soul.

10. What are you grateful for?

Absolutely everything.  Especially, often, all of the shit.

11. Have you done anything you are proud of lately?

I’ve chosen self-care nearly every day.  A big accomplishment for me.

12. Have you made any recent acts of kindness?

Did dishes for roommates even though I had a fever.

13. If you knew that you would die tomorrow, what questions would you ask yourself?

How do you want to feel today?  Who do you look forward to seeing?  What kind of ice cream do you want tonight? Do you have clean underwear?

14. If your biggest fears came true, would it matter in five years from now?

Yes–because it all matters.

15. How would you describe yourself?

Sometimes enigmatic.  My parents’ daughter. Restless.  Seeking.  INFP.  Lifelong learner.  writer.  Oceans.

16. Do you take people’s advice?

Not really.  I seek it out, often, but only so I can ramble my way through what I already know.

17. Do you get quickly offended?

Depends on if it’s a value.  See also: INFP.

18. Do you consider yourself to be a likable person?

Superficially, yes.  When you get to know me, I can be a terrible brat. But maybe that makes me more likable.  Who knows?

19. ‘We make a living by what we get, we make a life by what we give’ – What does this mean to you?

I think it speaks to a whole lot of martyrdom.  I think life is about the give and take.  Valuing one over the other is a recipe for burnout.

20. Are you enriching the lives of others?

I don’t know that I actually think about that.  I feel like I almost always contribute something positive to anything I’m part of.  I can be negative at times, but that’s usually a sign that I’m not getting what I need.

21. Are you living a meaningful life?

Yes.  I seek meaning in absolutely everything I do.

22. What makes a meaningful life?

Intention + action, aka integrity.

23. Would you ever give up your life to save another?

Of course. In a heartbeat.

24. How much would you be willing to sacrifice for people in poverty?

I think that’s a kind of dumb question.  Nothing I could monetarily sacrifice would really help “people” in poverty simply because I’m not far enough out of it to make that kind of impact–unless you’re talking social justice movements.  I’ve protested, spoken out, marched in the streets, risked arrest.  So, in those terms–quite a lot.

25. If you could live one day over and over again, what would you choose to do?

Oh, God no.  I’d hate that.  I have often said I’d like to go back to the day of my Mama’s surgery, just to say goodbye, but honestly–she knew.

26. Do you think you are important and worthy of affection and love?

I don’t know that I am any more important or worthy than anyone else.  There are plenty of people who go without love and affection.  I think the better question is–am I worthy of my own love?  And that’s a yes.

27. What would make you feel more worthy? What do you believe needs to be different about you?

Oh, the worthy thing.  Honestly, that’s the focus of therapy and isn’t something for this medium.

28. What brings you down the most often?

People.  When they ignore me, forget me, are mean to others, act like bullies…don’t admit the truth.  Avoid vulnerability.  People routinely break my heart.  Even those I loved and thought I knew often were nothing like they seemed.

29. Would you rather work less (and do the things you enjoy) and have less money?

I don’t make a lot now.  I’d like to make more money and work a lot less.

30. Where do you find peace?

Water. Any kind of water, basically. Nature, at night, too.

31. What is the most important quality you look for in another person?

Sense of humor.  You’ve got to laugh at this nonsense. Especially the dark stuff.  A dark sense of humor wins me over, every time.

32. What is your biggest dream in life?

To have fun and be known.

33. What is your biggest fear?

Dying like my Mama.

34. How would the world be different if you had never been born?

I don’t think it would be very different on a large scale.  I certainly don’t think my exes would have noticed.  My cats would miss me, though.  🙂

35. What life lessons do you wish you knew 10 years ago?

You’ll be happy again.  And it will be because you did the work.  No one saved you.

36. If you could tell your younger self one thing, what would it be?

You are stronger when you are weak. Say the shit in your head.

37. If your life was a movie, what would the title be?

Oh, I can’t share that.  I’m writing it–so…

38. If your life was a movie, would you enjoy watching it?

Yes.  I like the stuff I create, usually–though I wince when others read/watch it.

39. What does success mean to you?

Being me. Having enough.

40. If you could be a different person, who would you be?

No. I don’t like most other people.  🙂

41. What was the best day of your life? Why?

No best days.  Still got too many left.

42. What do you look forward to most in life?


43. What bad habits do you want to ditch?

I don’t like to call any habits “bad” because it creates a meaning I don’t want.  I’d like to isolate myself less.  I’d like to eat less meat.  Drink more water and less soda.  Sleep better and more often.

44. Who do you look up to and why?

Paul Auster.  I just love his work.

45. Do you know your partners love language?

I have no partner.

46. Do the people you love most know how much you love them?

Probably not.  I don’t think you can ever fully know anyone or their heart.  Expression always falls short.  Our ability to say and their ability to receive.

47. Are you satisfied with the depth of your relationships?

No.  But then, I like my relationships to be as deep as oceans.  Most feel very superficial to me.

48. What do you owe yourself?


49. Based on your current day-to-day life, what do you expect to achieve in 5 years from now?

If I just did what I’m doing now, I could climb my company’s ladder.  But I don’t want that.

50. Do you say ‘yes’ too often when you really want to say ‘no’? Why?

No.  I am proud to say I say no a whole heckuva lot.  I need to say yes more often, though.

51. What did you learn yesterday?

Meryl Streep can make me cry.

52. What do you like about yourself?

Eyes, hair, how flexible my body is, sense of humor, optimism, stubbornness.

53. Would you consider yourself to be a generous person?

Yes–at times, to a fault.

54. Do you really listen when people talk to you?

Yes.  And I listen to all the things they don’t say too.

55. What is the number one change you need to make in your life this year?

Really putting my health first and working on the soul needs.

56. How many hours per week do you spend on the internet?

Fucking too much.

57. What are your most common negative thoughts? Are they logical?

It’s your fault.  You’re crazy.  You’re too lazy.  Nope.

58. Do you think it’s too late to do certain things in your life? Why?

No.  I’m delusional enough to think it’s never too late.

59. If you could be the most influential person in the world, what would you change?

People’s bullshit toward one another.  Just stop with the nonsense.

60. How much time do you spend with your family and friends?

Depends on what “spending time” means to you. Depends on who is friend and who is family.

61. Where do you want to be in 5 years from now?


62. Is your life complicated by unnecessary things?

Sure, it is.

63. How can you simplify your life and focus on the most important things to you?

Well, if I knew that…  I think being very self-aware, but also having a plan and several plan Bs.

64. What stresses you out?

Oh God, everything.  Usually shit I can’t control.

65. What makes life easier?

When people get out of my way.  🙂

66. How often do you give without expecting anything in return?

Always. I never expect anything.  The only time I really have pain is when I do.  So I’ve learned to just never expect anything from anyone.  It’s kind of sad, but a better way to live.

67. What is your greatest challenge?

Choosing vulnerability and connection.  It is a daily choice.  Sometimes a moment-by-moment choice for me.  Mostly because my brain wants to shut all people out.

68. What is most important to you in life? Are you giving it the time it deserves?

Survival. I give it way too much time.

69. If you could send a message to the world, what would you say in 30 seconds?

Stop being assholes.

70. What do you most regret never telling someone?

Goodbye.  We’ve been through this.

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


72. Are you afraid to speak your own opinion?

Haha.  No.

73. Do you give into others too often and feel resentful because of it?

Sometimes. Yes.

74. Are you holding onto something that you need to put behind you?

Sure. But it’s not just mine.

75. How often do you let your fears hold you back?


76. Do the people in your life bring the best out of you?

Some of them.  The rest, I’m trying to release.

77. How often do you make excuses?

We all make excuses.  I usually own that they’re excuses though.

78. What is one mistake that you will never do again?

I can’t answer that. I will probably do it again.

79. Which is worse, failing or never giving it a shot?

Depends. It’s not black and white.

80. What has grown you the most as a person – your challenges and trials or the comfortable yet enjoyable moments in life?

Challenges. Specifically my mother’s death.

81. If you could choose to have no more challenges or obstacles in life, would you?

hahah. No. What fun would that be?

82. In one word, what is standing between you and your biggest goal?


83. How often do you go to bed feeling angry?

Never. I have a no anger at bedtime rule. Sometimes, that means I just don’t go to bed.

84. Would it be wrong to steal in order to feed a starving child?


85. If you paid more attention to the sad things in this world, would you feel more conflicted about it?

I pay a shit ton of attention to the sad things and believe me I have the appropriate amount of angst about it.

86. If we learn from our failures, then why is it so bad to fail?

Because Americans are dumb and think winning is some bragging right.

87. What could you pay more attention to in life?

Not being a hermit.

88. Why do we think of others the most when they’re no longer around?

I don’t.  🙂

89. What does it look like to make the most of your life?

I dunno.  I never filmed myself making the most of my life.

90. What have you given up on?

Perfectionism.  The idea that I will ever have any kind of friendship with exes.  The idea that I will ever really fully know anyone.  The idea that I control anyone or that what they do is some reflection of who I am.

91. How many people do you truly love and what are you doing for them?

Right now–not sure how to answer that based on the “truly love” qualifier.

92. Do you ask enough questions, or are you happy to settle for what you already know?

Clearly, I’ve been asking too many questions my whole life.  And getting in trouble for that.

93. What were you doing when you last lost track of time?


94. Do you think you would be happy if you never had to work again?

I’d get bored.

95. How old would you be if you didn’t know how old you are?

People think I’m about 28. I feel about 28.  So, 28.

96. If you could ask for one wish, what would it be?

Courage. And like go-go-gadget energy packs.

97. What inspires you in life?

Almost everything.

98. What can you not live without the most?

Cheese. Kitty face hugs.

99. What do you enjoy doing over and over again?

Eating cheese. Hugging my cats’ faces.

100. When did you last laugh so much it hurt?

It’s been a while.  Been a really rough few months.  It was something I did, though.

101. What is stopping you from living the life you want to live?

Nothing really.  Just a matter of figuring it out.


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