post written by: Angel Chernoff

40 Questions Everyone is Afraid to Ask

Questions We Are Too Afraid to Ask

Judge a man by his questions rather than his answers.

…because asking the right questions is the answer.


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Please share your thoughts with us in the comments section below. Also, check out our sister site, Thought Questions, for more photo-illustrated questions like these; and check out The Book of Questions if you’re interested in reading even more thought-provoking questions.
Title photo by: Colin Kinner
For all other photo credits please refer to

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  • Yikes… eye opener! (got sick at my stomach just thinking about some of these questions) I have changes to make.

  • All are such great questions. I love going through these.

    For one of them, the second one, the thing I’m most worried about my future is how it’ll turn out. I have plan’s to go to college and get a job and have a family, but what happens if I can’t get to college? I shouldn’t worry, but I do.

  • Quite a few things to think about here. Thanks for the wake-up call.

  • It definitely makes you re-examine your life and come to the realization that some changes are in order. An eye opener indeed!

  • I think it’s time to change some of the habits of mine and straighten my life again. Thanks for such awesome post!

  • Wow! A lot of my answers came immediately, some not so much. Definitely an eye opener. Takes a lot of courage to be able to answer these questions honestly (with yourself). Think it would be very beneficial to sit down with your partner and or good/great friend and go through these… would probably make for a great bonding exercise.

  • Very much a wake-up call that has reaffirmed much of what I already knew but wasn’t sure how to articulate. Now to find the courage to do something about it…

  • Wonderful post. I have pinned so many of these onto Pinterest. Thank you for sharing and challenging. I am really glad I have discovered your blog.

  • Thank you for putting into print that has been in my mind… time to contemplate a few things…

  • #11. Never thought of it from that perspective.

  • These questions are very inspiring. When I read these questions and think of my answers to them it makes me feel ready and energized to just get up and make some changes in my life that need to be made. I especially like the first question: If today were the last day of your life, would you want to do what you are about to do today?

  • question no. 11 really made me think! and thanks a lot for all the questions, they made me realize things that I didn’t realize about myself.

  • Sheesh! You’re killing me here. :) Great questions!

  • Guys, I love your blog!

    I can’t even remember where I came across you now, but but by bit, with fabulous, thought-provoking, challenging posts, you’ve reeled me in :-)

    Congratulations, this is excellent content, I really enjoy reading your stuff.

    Thanks for the time you put in, Paul

  • Great questions. The one I often wonder about is, what would you do if you knew it was your last day? I wonder if I could actually enjoy the day (regardless of the activities) if I knew it was my last. I imagine that no matter what, I would panicked at the thought of being separated from loved ones…

  • Angel

    Great questions that provoke thought. However, your position that everyone is afraid to ask these questions is somewhat of a generalization, and thus a lack of acknowledgement that there exists capacity in certain individuals to reflect on the same. Just my opinion.

    But I truly did enjoy this post, and I am a regular reader of your articles

    Kind Regards

  • Thank you so much, for your thought provoking questions today. They provide much food for thought….

  • I definitely know what it is I need to change in the next 12 months! The issue is - how on earth do I do it?!

  • I can’ relate to these excellent questions. I’ve been asking similar questions for the last 3 years, and wonder how to get unstuck. Just when I think I make some progress, something happens that puts me back into the black hole. I cry often, and ask that my prayers are answered, and keep hoping amidst my tears that something wonderful will happen today every morning that I still wake up.

  • What a wake up call for lots of us. Worry on so many fronts takes half of our time. At almost 3/4ths of a century I have answered a lot of the questions but there are others I need to work harder on. Thanks for keeping this blog. Dawn

  • These would all make excellent motivational-poster-esque pictures to have in your bedroom, office or other personal area.

    Personally, I’d love to have these kinds of pictures rolling in an electronic picture frame.

  • I am planning to use these questions at a future girls’ night - either for a journaling exercise or simply as one that allows the girls to share openly and freely for a few minutes before we move on to other activities.

    Thanks for always giving me food for thought, Marc and Angel.

  • Thanks Marc and Angel. You both continue to motivate me and positively push me to be my best self.

  • Julie: Keep staying strong and keep pushing forward. Not all the puzzle pieces of life will seem to fit together at first, but in time you’ll realize they do, perfectly. I promise, it gets better. And please, don’t hesitate to talk to a a friend, family member or professional coach about your pain and struggles. Oftentimes getting things off your chest is the first step to feeling better. Marc and I will keep you in our thoughts.

    @Jake: We’re so glad you enjoyed the questions. Sorry you didn’t like the title. The truth is, it wasn’t our intention to say, “most people are incapable of asking these questions.” We know most people are capable of this. But you must admit, they are difficult questions to ask yourself because they require self-examination - which is never easy. The choice in a title is often somewhat a matter of choosing something that is relevant and catchy. “40 Questions Everyone is Afraid to Ask” is certainly more catchy than “40 Difficult Questions to Answer”, don’t ya think? :) Anyway, hope that makes sense, and hope ya aren’t too upset.

    @All: As always, thanks so much for the positive feedback and personal insights. Thanks for keeping the conversation alive. We read every single one of your comments. Please keep them coming. And don’t hesitate to answer a few of your favorite questions right here in the comments.

  • Stop! Stop it! :) Stop making me look in the mirror… sometimes it’s TOO real.

  • Can’t say enough how much I LOVE this site. WOWZERS! Each and every time you open my eyes … and heart. thanks!

  • I have to say that it makes me think a lot … then I’ll turn off the internet and restart working on my project., To do is the secret, right? when you stop “doing” you start dying slowly… I just don’t want it. Have a grate weekend people :)

  • You folks are brilliant. I love what you do, and you keep doing it! Amazing. You make other people’s lives better. Thank you!

  • I worry sometimes that no matter all the hard work I’m doing and the attempts I’m making to actually acheive my goals that I might inevitably still fail. I’m so worried that I’ll potentially never find love again and that I’ll be alone–but deep down I know that I’m not alone.

    I have a great support system with family and friends and a lot of information on this site has been instrumental in helping me begin to focus on what’s important and not focus on the negatives in my life.

    I do think that I need to give myself some “me” time this weekend. I tend to be very hard on myself and close myself off and focus too much on the career I want to go into.

  • Wow…I have been in a horrible marriage for a long-long time and I can’t let go… for me a lot of these questions gave me a reality check…..specially the one about “when to start living”.

    Thanks so much for giving me the push I need to start making changes :(

  • Thought provoking list - but not something one can consider overnight. This one will take time to visit and re-visit… as with most matters of the heart.

  • Motivating and thought provoking! Thanks for sharing these questions.

  • This was beautiful - the questions and the photos. I don’t think it would have as much of an impact without the photos, so thank you for including them, it was worth it.

  • We all need to ask ourselves question every day. This are some of the the best questions.
    “What is one easy way to sum up life?” say it all.

    Life is a journey and looking on the positive side of that journey will make it a happy ending.
    Thanks for sharing and blessings to you both.

  • I love #8. I’ve been dreaming of starting a personal project for years and always came up with an excuse for not doing it (mostly because of financial limitations). Only recently did I start pushing myself to just take a step. Even a baby step, and see where it lands me. Well, I did that and have made progress that I never thought imaginable, just by reaching out to one person (and I have needed zero $ so far). So sometimes just pushing yourself a little bit and taking one small step can lead to great things. Or at least get you started on the right path. Thanks for posting!

  • I truly love your site, it’s almost like meeting with a great therapist!

    As an older person who has completed career and raising family , I still contemplate these questions. Especially with a recent diagnosis of cancer, I live with and have to mentally and positively believe I will conquer my fears and the disease itself. Living hopefully and positively in the face of facing your mortality is harder than I thought but I find living each day without worry or stress of any kind is the best way. I refuse to let anyone, children , spouse , or even a stranger make me feel bad about anything in my past present or future. It must to be our daily choice to feel good about ourselves and our life and not to allow even ourselves to negatively impact this. Thank you for reminding me of all of this with every post on your site. Only wish I’d realized some of it in my younger years, but still thankful I have now.

  • I enjoyed answering every one of the questions and even teared up at my answers on a few of them. Also shared this post with friends who reflected on the questions as well, which and got us discussing and sharing a few inner fears and secrets.

  • Thank you for this thought-provoking post. It’s always the deeper questions in life that have the most significance and lead to living more consciously.

  • Thanks for everything! You both are awesome!

  • Wow… I am in such a rut, and these questions I know I should have asked of myself ages ago.

  • I LOVE these questions… they each make great journaling prompts!

  • Thanks for this thought-provoking exercise. I answered all the questions and, although a bit tough, thoroughly enjoyed it.

  • #20 is the key for me. We in the process of creating our future right now. Life does not just happen to us.

  • Thanks for making me think about how to get back on track.

  • Wow… for better or worse, some of these questions questioned my entire existence. Eye opener!

  • Julie, know that you’re not alone. Every day is a gift as it can be the start of something beautiful - just reach out and you may grab a hold of it!

  • Awesome questions! Some are hard to answer, but worth it.

  • Great questions!

    I live in a house with lots of visitors and parties. We always have a couple of pieces of butcher paper up with questions on them so people can answer the questions, or express themselves in some way. I will definitely use some of these questions for that! Can’t wait to see the responses! Thank you!!

  • What great, thought-provoking questions… I tend to just stare at my journal blankly every night lately, might stick these in there.

  • These are truly awesome questions. A question that I often ask my life coaching clients is, “What one action will you take today to move closer to your goal.” This really helps people to see the disconnect between what they say they want what they’re committed to having.

  • Thank you for bringing these questions to my attention. I will try to answer them all :D

  • Francisco Pedro
    April 15th, 2012 at 5:16 pm

    All these lead us to reflect on our lives, and how short it is. For me it was a good reflection!

  • One easy way to waste a life: not doing what you love and not loving who you do. :P

  • Marc and Angel,

    This has got to be one of your best posts ever. The reason I listed my comment as I did was because I think I’ve broken all of your questions and what they stand for at one time or another. I’m 75 years young and a recovering Alcoholic also was doing uppers and downers drugs but I’ve enjoyed 30 years of sobriety—-I found God when I was 50, had a very loving and supportive family and the rest is history! These 40 questions have been most refreshing! I hope everyone loved your post as much as I did! Thank you for coming into my life! Sorry to ramble on.

  • Wow, number 10… what a powerful sentence.

    Such simple questions have such different perspective. Thanks for everything, I come to this blog every time I need a new angle on life.

  • I love all your posts. I hope there are really two people here named Marc and Angel, because knowing positive people like you exist helps me. Mahalo for your generosity and positivity… I share your posts with a lot with others.

  • Lots of food for thought! Thank you.

  • These are awakening questions. They tend to trigger some things that have been kind of dormant in our minds for some time now. Thumbs up guys.

  • reply to 21. I want him to be happy, and I like him the way he is. I wouldn’t change a thing. But if I have to choose, I choose intelligence.

    Thank you for your posts.

  • Ouch. Tears. Piercing right to the heart of the matter. Thanks for the wake-up call.

  • What an exceptional post, I love this!

  • What is worse than death?
    Being misunderstood/misinterpreted.

  • Awesome questions! These would make great postcards.

  • Wow, I can relate to a lot these questions. They make me think. I guess that’s good and sad.

  • These are questions I/we can ask ourselves everyday. This is the first step and we can only take one step at a time. Read and take action constantly. That is life.

  • What brilliant questions I,ll have to go through them all again. Deep, and a bit frightening.

  • Interesting! Great Questions…

  • Thanks for posting all these great questions!
    Keep on making more.

  • i stumbled upon your website today and what i found out is truly a treasure worth every second of my time. spent the whole day going through your articles. thanks for sharing all those wonderful stories, questions and much needed write-ups that not only provide inspiration but could turn a life around.

  • A few years ago I would’ve not been able to answer these questions or I probably would’ve given some vague answer. Today, though, I have answered them very genuinely and I understand that I’m in a time dedicated to study, self discovery and spiritual development. Answering these questions helped me to understand that my life’s journey will take me to where I need it to and I’m ready…

  • A wonderful collection of superb questions and photos :)

  • Good questions… it’s time to stop living an unconscious life.

  • This is awesome! What hit me the most is “Are you holding on to something that you need to let go of?”

    It hit home because I have been holding on to my relationship that has since ended, and I just realized that it’s time for new experiences!

    Thanks so much for sharing!

  • These are really great questions we need to constantly remind ourselves.

    Thank you for creating this website and sharing all the quotes, questions, and stories, really enjoy and love it~ =D

  • What a great list of questions.

  • Love It!

  • Wonderful questions all. How to get to the answers is quite hard and what to do when you get there is fraught with difficulties. How many people are trapped no matter the dream. It is an awful feeling, and wishing does not pay the rent.

  • All of these questions are so nerve wracking. I have wanted to travel to so many places for so long… and I’ve wanted to live for myself and love myself. But all of that requires a lot of money, and I need money for “stability” in today’s society… I feel so stuck.

  • Many are hard to answer, but a very good list for Self-Improvement. Everyone should write the answers to these questions every year to assess and notice the change.

  • Live life to the fullest and focus on the present, the not past or future. Live in the moment and make the best of what you have or don’t have. If you live inside your mind all the time you will miss out on life. Get out and live, work, play and be among people who enjoy your company. Optimism, is just as contagious and pessimism. Be careful!

  • Wow… what fabulous thought provoking pics. Amazing. This should be a book… Or a poster series on my wall. A fabulous recipe and balance of life activities.

  • These are all really great, but the fourth question was a big revelation for me. We constantly put ourselves down or have a negative outlook on ourselves, but we see that as okay because that’s just how we are. However, if another person treated us that exact same way, we would hate them and think of them as one of the worst people that we know. It’s really strange to think of what we will take from ourselves, but not put up with from others.

  • Too good! That’s a lot of good questions to work through…work through everyday. Thanks for the blog!

  • On question 21, I would rather my child be less attractive and more intelligent. In the end, it only matters what’s on the inside, not the outside.

  • Worst than death?

    To live a full life doing what you do not want to do.

  • #27…. if it had come first, I would’ve stopped reading then.

    As it is, I stopped reading at #27.

  • Interesting questions. I think I’ll store this for a journaling resource. In going through the comments I can definitely see that where I am in my life has made my answers different than some of these folks at different points. I remember worrying about college and getting a job. Now I worry about doing right by my kids and helping them be successful adults. And worse than death: losing a child. I would definitely rather my children be less attractive and more intelligent. I’m not beauty queen, but I have a loving husband who is as attracted to my brain as my face.

    Oddly, going through these questions made me feel very good about where I am in my life and the choices I’ve been making. That is a nice change from some past me’s.

  • Makes you want to be a better person, asap. Kind of a reality check, it helped me remember not to stress about many things in this world. Good questions all around.

  • Here’s a great saying that I begin my day with:
    “Yesterday is but a memory, Tomorrow is a vision,
    But, Today well lived, will make every Yesterday
    A memory of happiness and
    Every Tomorrow a vision of hope -
    Look well, therefore, to this day!
    Kobo Daishi, Buddhist Master

  • These are very provocative - twingy feelings in the solar-plexus kind of provocative. It is good to check in against the dark forces of denial!! Thank you Marc and Angel for being in my life, it is always refreshing and interesting reading your blog.

  • Some of those questions - well, lots of them were kind of a slap in the face saying, “Get it together man!” Although I’ve had those thoughts in the back of my mind for a very long time, I’ve always just pushed them out of the way…

  • Wow! This gives me some great fodder for my blog on ‘Helping Fathers Become Dads’, not to mention great incentive to think about things and ourselves, which we often do not take the time to do.

  • No. 36, keeps bothering me every night. I want to speak it out. I want to quit my job. I just don’t know how and when is the right time. :/

  • This is such a beautiful list. Thank you.

  • I am just speechless, because this post really touches every area of my life.

  • All of these questions are so great…I am reading them again, again, and again….and finally I have started changing from who I was. Thanks so much for posting this!

  • Thank you for your thought provoking questions, and wonderful pictures.

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