Want To Know Yourself Better? Ask Yourself These Questions.

A key–perhaps the key–to a happy life is self-knowledge, because as the Fifth Splendid Truth holds, I can build a happy life only on the foundation of my own nature. In my own case, I’ve found that the more my life reflects my real interests, values, and temperament, the happier I become.

But it’s very hard to know ourselves; it’s easy to be distracted by the way we wish we were, or think we ought to be, or what others think we should be, until we lose sight of what is actually true.

As Christopher Alexander observed: “It is hard, so terribly hard, to please yourself. Far from being the easy thing that it sounds like, it is almost the hardest thing in the world, because we are not always comfortable with that true self that lies deep within us.”

Here is a list of questions meant to help you think about yourself, your daily habits, your nature, and your interests. There are no right or wrong answers; they’re fodder for reflection.

If something is forbidden, do you want it less or more?

Is there an area of your life where you feel out of control? Especially in control?

If you unexpectedly had a completely free afternoon, what would you do with that time?

Are you comfortable or uncomfortable in a disorderly environment?

How much time do you spend looking for things you can’t find?

Are you motivated by competition?

Do you find it easier to do things for other people than to do things for yourself?

Do you work constantly? or think you should be working?

Do you embrace rules or flout rules?

Do you work well under pressure?

What would your perfect day look like?

How much TV do you watch in a week (include computer time spent watching videos, movies, YouTube)?

Are you a morning person or a night person?

What’s more satisfying to you: saving time or saving money?

Do you like to be in the spotlight?

Is your life “on hold” in any aspect? Until you finish your thesis, get married, lose weight?

What would you do if you had more energy?

If you suddenly had an extra room in your house, what would you do with it?

What people and activities energize you? Make you feel depleted?

Is it hard for you to get rid of things that you no longer need or want?

Do you get frustrated easily?

On a typical night, what time do you go to bed? How many hours of sleep do you get?

If at the end of the year, you had accomplished one thing, what is the one accomplishment that would make the biggest difference to your happiness?

And here’s another question for you. What questions would you add to this list, to help other people know themselves better? It’s so important, and so elusive.

  • Margaret Graham

    Here’s one from Gregg Levoy, who wrote Callings:  “If I were to say to you, ‘Just go for it!’ what would ‘it’ be?”

  • Hedgehog

    What worries me is that ‘I don’t know’ is the answer to several of these questions and I don’t know how to find out.

    • Rae

      It’s taken me a long time to feel more confident about how I answer these questions. I think if you don’t know, just keep asking yourself and keep reminding yourself there’s no right answer. The exercise of thinking really intentionally about your ideal day was super helpful for me. I created a Pinterest board with all the things from sunrise to sunset I thought I would like to do on my average “perfect” day, and I realized I needed a lot more writing, nature, and chocolate in my life! 
      If you’re reading this blog, that shows you’re already thinking about this stuff, so just keep doing that!  Good luck! 

  • Michael F Melcher

    Another question is:  “What’s a lesson you keep on learning?”

    Imagine how much kids would get out of your reflection if they had a chance to think about it.  So much of youth is spent trying to fit into conceptions of how we think we should be.

  • Rae

    I’m being really intentional in my question to get location-independent, so I’ve been thinking about a lot of these. I’ve thought a lot about what my perfect day looks like, and how to make my every day a little bit closer to that vision. But I do feel like my life is on hold a little bit. I’m always telling myself to watch my budget so I can finally take that leap and start working for myself, but sometimes it just feels like I’m holding my breath. I’ve got to be really careful and keep my eyes open to make sure I value where I’m at right now and don’t overlook it in favor of the future. (BTW, I am *finally* reading The Happiness Project* and I am really enjoying it. My friends can’t wait to borrow it!)

  • Maria

    Wow, I like every single one of these! I found out about your site via an article about your redesign from a graphic design blog (yes, I am a design geek :). Glad I subscribed. This was a very thought-provoking article!

  • Peglud

    So – what do the answers to these questions mean?  Is there a scoring rubric for these questions that helps us better understand our true temperament?  What about the “yes/no but” answers – that need qualifying?  If this exercise is just an fyi for ourselves, what then?

  • Rachel

    So, If I feel like my life is “on hold” (until I finish my degree) – any suggestions for remedying this?

    • Lucy

       I felt exactly the same Rachel. I’ve now (at 26), moved back to my Mum’s, with Fiance and dog in tow so we can save for a house; I’ve been ‘on hold’ for nearly 10 years now!

      Sometimes you can’t (and don’t have to) be ‘there’ now, try to really enjoy being ‘here’.
      My big regret is that since leaving school, I’ve been so focused on getting to this ever shifting ‘there’, that I have few interests, hobbies, or casual friendships.

      If further study or career progression is what you want from your degree, finding other ways to expand your CV or field of knowledge may be enough to stop feeling stalled, or like you’re frittering away your time on the unimportant.
      I’m sorry that this isn’t a remedy really, but there isn’t just one. Good luck.

      • Jane B.

        Elena – so true. I would add one thing: spend time in nature. A Japanese acupuncturist I used to go to specified these three categories for increasing chi.

      • Jane B.

        Wise words, Lucy. “Now” is where we need to focus. That doesn’t mean that we forego goals, but that we need to try to enjoy every phase of the journey. Otherwise, we never fully experience the present.

    • Elena

       Rachel!! Try and do something every day that makes you smile a lot! Play iwth dogs and kids is especially fun to bring out the LIFE in you!!

  • S_ifat

    I have started to read and try to answer but after a few questions it didn’t feel right and I remembered a quote by Heraclitus ” no man ever steps in the same river twice”.

  • shobaday

    I actually found these questions quite straight forward, usually a contrast between one and the other.
    My only foddler for thought are questions that point towards a direction, which does help me now. Thanks!

  • Cbshughes

    Why does knowing and feeling comfortable with your true self seem so difficult?

  • 1 What are some secrets about you that you hope no one would find out?

    2 What’s the biggest regret of your life?

    3 If you were the king of the world what law would you change?

  • gs

    It could be very revealing to ask yourself this question (especially if you have lived long enough–in other words, if you are at least thirty years old and have had some years of life experience): What comes to mind when you think of something that you are ashamed of or feel guilty about? It’s important, I think, to focus on the first thing that pops up. Some people might feel ashamed of having lied or deceived someone; another person might feel guilty because they did something inconsiderate or even cruel. 

    What pops up for me is a time when a family member wanted to tell me about a medical problem they were going through, and I cut them off. I was afraid that they would ask me to help in some way, and I didn’t want to help. I felt like my plate was full already. I had no time to help one more person. Now I realize that all they wanted was for me to listen.

    It is interesting that I had a similar experience–coming from the other side–where I opened up spontaneously to a colleague. I was telling her about a family issue, and in the middle of it, at a crucial point in my story, she suddenly raised a finger, motioning me to stop,  and then leaned over to adjust the knob on the radio because she wanted to hear the results of a football game. I never felt the same way again about her. Worse, it reinforced my conviction that most people don’t care and won’t do even something as basic and simple as listening.

  • Linda

    Just wanted to let you know that I’m reading the Steve Job’s bio, and it mentions  “…a kooan-like phrase…’The journey is the reward’.” 

    Last night I was reading your book and you explained what a kooan was.  Thank you.  I would have never known & I love that I read these two things back to back.

    Keep up the good work.

  • guest

    I’m glad you posted this.  I just read your book and really appreciated it but one of my biggest sticking points was that I felt a happiness project along your lines would require throurough self knowledge, which it appears you have.  I was wondering how the happiness project would look different when you are early in your self knowledge journey.  It made me think that maybe happiness could come from searching for that self knowledge rather than actualizing it.

  • My question would be: “What are three values you have?” Only by truly identifying my true values I was able to focus on what really matters for me. Haven’t I asked myself that, I wouldn’t have started a blog (www.smilestep.pl), I wouldn’t have pushed for more in core aspects of my life…

    I have a comment to the questions altogether though, because I believe that they have their unique power. By asking right questions we can put ourselves in right state of mind, focus on whatever we want and take from what is happening the best.

    When I wake up I try to ask myself few questions:

    What will I do to develop myself today?
    What will I do to work on my body today?
    What am I grateful for today?
    What is great today?
    What do I feel passionate about today?
    What am I proud of?By asking those questions I am ensuring that my day starts great and that it will be even better!

  • I like that this is just a way of becoming more familiar with yourself. It is not about judging or changing as much as just being simply more aware. Great!

  • MyPeaceOfFood

    I think other good questions can be simple, like What’s your favorite color, book, movie, etc. As kids we proclaim our favorite things all the time, but as adults it’s a fun game we stop playing.

    • gretchenrubin

      Excellent point.

  • Dawn Herring


    Wow, you have quite the list that covers so many territories and dimensions of life. These are worth exploring, dissecting and discovering in our journals and then some! The energy focused questions resonate, since I have come to appreciate those activities that add to my energy. What we would do with extra time if we had it: I love the open-endedness to that possibility. When we answer these questions, we can truly delve deep into our personality, our preferences and even our purpose in life. Know yourself!

    I have chosen your post, Want to Know Yourself Better? Ask Yourself These Questions, for the #JournalChat Pick of the
    Day on 10/30/12 for all things journaling on Twitter;
    I will post a link on Twitter, Facebook, LinkedIn, my blog
    and website Refresh with Dawn Herring, and in Refresh Journal, my weekly
    e-journal: http://tinyurl.com/9q4ubhc.

    #JournalChat Live is every Thursday, 5 EST/2 PST, for all
    things journaling on Twitter; our topic this week is Your Journaling: Your Appreciation Appointment.

    Dawn Herring
    Host of
    #JournalChat Live and Links Edition on Twitter
    Author of
    The Birthday Wall: Create a Collage to Celebrate Your Child

  • Sue D

    Some questions that I have found to be important to ask yourself :

    Am I an introvert or an extrovert (i.e., does being around people drain or energize me)? While I am not shy, once I accepted that I am an introvert and need my “alone time,” I am much more comfortable with myself.
    Am I an optimist or a pessamist? Which am I and how do my demeanor, attitude and comments affect me and those around me? We need to look at our role in relationships. Are we the negative person others want to avoid or the cheerful one they want to be around?

  • Kitty

    A huge question for me to allow was, “Is is possible that you have a handicap, an injury, a mental challenge?” At 54 years old, I have final answered some tough internal questions about childhood abuse. Survivors are very good at outrunning our pasts and if you’ve always been running you may not even know it. Once I looked at my past in a new, open, adult way, I was able to stop and begin to look at what was chasing me. I can see my emotional damage now and how logical it is that I get tripped up more than others. I most likely will always carry scars and unhealed places. But I’m much happier and much less fearful. I don’t stumble nearly as often and if I do, I recover quicker. It’s like someone pointed out to me that I am missing an arm and I look down to see for the first time that in fact this is truth. And now it makes so much sense that I never was able to excel at mountain climbing. But the knowledge frees me up to pursue the thousands of other things I want to do in my life.

    • Jane B.

      Kitty, your comment moved and humbled me. Your insight and bravery are inspiring. May you speed along the path of healing that you are on.

  • joyi

    Nice article. I was amazed to know the answers to some of the questions. I guess I am putting too much pressure on myself since a long time, to be somebody that other people expect of me. I’m trying to let go of that pressure. I’ve become bitter and frustrated, and feel I’m not good enough for anything. Really need to work on that. Any help is welcome.
    Thank you 🙂

  • aisf

    i had really liked it but will u please help me with answer thanks

  • Ann

    ‘If you could go back to one time in your earlier life, and do a ‘do-over’, when would it be, and what would you do?’