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5 Questions to Discover Who You Are and What Will Make You Happy

Who I Am

“It takes courage to grow up and become who you really are.” ~E.E. Cummings

At twenty-five I was happily married and had a great career, many friends, and lots of money. During that time I also became deeply depressed, was put on medication for anxiety, and entered what would be a very long relationship with psychotherapy.

It was a real struggle for me to understand why I wasn’t happy when I had everything that I thought was important in life. Was I selfish? Were my expectations too high? I honestly couldn’t understand what was missing and how to fill this huge void that gnawed at me every day.

When I look back at my life, twenty years later, I realize that I really had no idea who I was or what made me happy. I kept expecting something or someone to answer this question for me.

The journey to find out who I was and what really mattered to me eventually involved divorce, the loss of my career and most of my possessions, and overcoming a serious illness.

It pretty much took the loss of everything I thought defined me and made me happy to admit to myself that I honestly didn’t know myself very well at all.

Who am I? What do I believe in? What is my purpose? What fills me with joy and wonder? These are questions that I am just beginning to understand after forty-five years of living my life, and I have to admit that getting there has been extremely difficult.

The hardest part for me was just knowing where to begin. After much therapy, meditation, self-reflection, and reading, I asked myself five big questions that served as a launch pad to begin my journey of self-discovery.

If you are ready to begin the process of truly understanding who you are meant to be, start here:

1. What or who would you be if you knew you couldn’t fail?

The risk of failure terrifies most people. How many times have you wanted to change jobs or careers, move to a new city, promote a cause that is important you, or become an expert in a certain area? Think about it. No risk of failure.

If you were 100 percent certain that you could be or do anything you wanted and not fail, do you know the answer?

2. What is your ninety-second personal elevator speech?

Probably the most important and poorly answered question in most job interviews, this is similar in nature. You can certainly include your career or career accomplishments in your personal speech, but think of this from the perspective of how you might answer this if you were making a new friend or going on a first date with someone.

How would you describe yourself so that the person asking the question would truly understand who you are and what is important to you?

3. What are your core personal values?

Personal values are the things that you believe are important in the way you live. They give you a reference for what is good, beneficial, important, useful, desirable, and constructive. Once you are able to determine exactly what values are most important to you, you can better determine your priorities.

In fact, having this information about yourself is the key to making sure your daily life is aligned with those values. If you need help defining your personal values, there is a great five-minute assessment tool here.

4. What makes you genuinely happy?

This one is closely related to your core personal values. However, ask yourself this question once you’ve really nailed down what those values are.

For example, if family is one of your core personal values, will taking a job that involves tons of travel make you happy? Take it a step further and really consider dreams you had when you were younger or currently have about what will make you truly happy.

5. If money were no object, how would you live your life differently?

Many people equate happiness and success directly to the amount of money they have. How many times have you heard someone say, “If I hit the lottery, I’d…”

But remember, this question isn’t really about money at all. It’s more about thinking outside the limits we tend to put on our aspirations and actions because things seem out of our reach financially.

You may not be able to do those exact things, but once you know what those true desires are, you expand your thinking and begin to develop a plan to work towards goals you may have never imagined possible.

These are tough questions and the answers may not come easily or quickly. In fact, I found myself having to think and re-think my answers several times. This work is hard but necessary in order to really understanding yourself on a deeper level.

While I can’t say that I now know everything about myself, answering these questions completely changed the negative internal dialogue that was limiting my ability to see myself as I exist today and the me that I can become in the future.

But the biggest change came from revisiting dreams and aspirations that I had long ago put on the back burner while I was stuck in the process of “getting things done.”

My dreams of writing about things that are truly meaningful to me, finding a fulfilling and passionate relationship, being more present with my children, and discovering a higher power are all coming true now that I am focusing my energy in the right direction—and that direction was to look within.

So, find a quiet place and allow yourself plenty of time to go through and really think about each question and then just go for it. Go ahead. Begin your journey. Change direction. Create new dreams or rediscover dreams you left behind. Now that I have started, I haven’t looked back since.

Photo by varun suresh

Profile photo of Dona Middleton

About Dona Middleton

Dona is a writer, reformed marketing workaholic, and single mother of two teenage boys. She is exploring who she is and what she loves one day at a time. Learn more at her personal blog, Becoming Dona,(, which is focused on her journey of self discovery, practicing mindfulness, and navigating life, love and relationships.

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  • I just wanted to say that I really enjoyed this article It’s funny cause all the things you mentioned having at age 25 were the things I thought I was missing at that age. In fact, I lived in the ‘if only I had…’ land that included marriage, money, career etc..instead I was just floating around feeling like I was missing out. I’ve come a long way since that time and now see that my life wouldn’t have been better with all those things, just more complicated than I could’ve handled at the time (I could barely get a grip being single, poor and with no goals ha..) thanks for the great article:-)

  • Dona Middleton

    Thank you, Michelle. It’s funny that the things we think will make us happy usually don’t. It’s taken me many years to come to that realization. Glad to hear you figured it out!

  • Jesssica

    Awesome article. It all rings so true. I believe that at 36 years old, I am just figuring out the things that truly make me happy and I am taking steps to make all my dreams come true.

  • Marta Bielak

    Hello Dona, this article really opened my eyes, thank you so much for writing it! 🙂 The one that was particularly powerful for me was the first tip, eliminating the idea of failure. As a university student, I tend to always fall into this type of fear where I find myself doubting my every decision and action, especially when it comes to my future career. I know that I’d like to work in Marketing/Advertising but am always second guessing or pushing myself to a limit. You’re absolutely right, these questions are hard but they are critical to understanding who you are as you walk through life. Thank you for this period of reflection. Like yourself, I will do my best not to look back. I wish you all the best!

  • Dona Middleton

    I’m so happy to hear that this article helped you! I struggled with the same doubts, especially around my career. I found by not taking action and questioning every step, I wasn’t just standing still, but falling behind. It’s really scary to take risks in every aspect of our lives, but if we don’t, we’ve already failed. Good luck and I know you’ll be a success…you’ve taken the first and most important step already!

  • Dona Middleton

    Thanks, Jessica. You’re 9 years ahead of me!!

  • StouneyCyril

    Thank you Donna, twas highly reflective and a great tool for realigned self discovery. It’s people like you whom God has established as affirmation and guidance. Thank You and praises to God

  • StouneyCyril

    Haha, I’m 24 and till recently thought I’d failed because I’ve no car, house, job, girlfriend etc. But thanks to being aware and awakened by such advices and advances in life. I’m about to tackle what I feared most. Haha, through God it shall be done

  • Kathleen

    I am going to share this with my 24 year old daughter and her 28 year old fiancé. I too had these concerns at 25-ish. As you said, these are not easy questions to answer but are so very important. I think we should write them in a journal and ask then answer them once a year. Or maybe twice a year. This way they are always rolling through our heads and stay in the forefront of our daily lives. Thank you for the article.

  • Jane

    Excellent, thank you for sharing.

  • 🙂 If it makes you feel better, I’m much older than 24 and don’t have any of that stuff right now either ha….I DID have a job but got laid off. I once had a car but sold it before moving to a larger city (I find NOT having one kind of freeing, actually…I never thought I would feel that way) I’m single and I’m currently move back ‘home’ with family (for the first time since I was 19) so we probably have a lot in common right now. But having had all that stuff and nothing right now gives me an opportunity to reevaluate my life. Don’t look at it as a failure, look at it as an opportunity! You can go anywhere, do anything, life is opened up for you. I have a friend right now (just to give you perspective) who is in a marriage that is lacking, has four kids, in debt, unstable career etc….he can absolutely change his life, but look at all the stuff that is sort he has to navigate at the same time. Focus on the positive, see no limits and all will fall into place:-)

  • Barbara Kolander

    Excellent, and my sweetheart and I were just talking about the expectations we are given and learn all throughout our lives, and how this shapes who we think we are and are supposed to be. Letting go of expectations and simply enjoying who we REALLY are is one of the hardest, but most rewarding things ever!

  • porterman

    great article. your 5 questions are good fodder for me to journal about over the coming days. I’m trying to sort it all out myself – am 35, emerged from a wicked divorce, but am now with someone who loves me a ton, but I’m not sure this is what I want either. hopefully some of these questions will help me figure out how to press on.
    cool blog – post more!

  • Dona Middleton

    Great idea about reviewing these questions every year!

  • Dona Middleton

    Thanks for reading!

  • Dona Middleton

    Thank you so much for such an amazing compliment. I’m happy to share my struggles and insight if it helps even one person out there. 🙂

  • Barrett Values Centre

    Thank you, Dona, for including our free Personal Values Assessment in your article! We hope that people find it meaningful to explore what’s important to them and what makes them happy. The response has been overwhelming, and our server needs a little time to catch up. If you have taken your Personal Values Assessment and haven’t received a response yet, please be patient. You should get it within the next 48 hours. If not, please email

  • Fiona

    Very helpful and inspiring advice – thank you so much!

  • Dona Middleton

    Both your site and your assessment tool have been a great resource to me. I’m glad others are finding it helpful too!

  • Dona Middleton

    Thank you! Sounds like your experience has been similar to mine. The most important thing that happened in my current and very happy relationship was my ability to focus more on making myself happy, rather than on his ability to make me happy. Once the pressure was off and my expectations were realistic, everything fell into place.

    Hope to see you over at my blog!

  • Dona Middleton

    Thanks for reading!

  • Dona Middleton

    That is so true, Barbara. Glad you enjoyed the article!

  • Savannah833

    I wanted to respond and say that I relate to your post so much– those were all things I thought I wanted to but the truth is, back then, those things would have made my life more complicated than I could handle as well. I was working on becoming an adult throughout most of my 30’s (I’m 38 now), so much energy went into discovering who I was and what I needed to do to become more “complete”–and adding a child(ren) to that would have not been healthy for anyone. Thank you for the perspective

  • Savannah833

    Wonderful article, thank you for sharing these five questions and for providing a link to the personal values quiz. I took it! I also shared your article with a few of my best girlfriends as I think they too would appreciate reflecting on the questions (we’re “introspecters” I’m at a crossroads in my life in many ways– ended a long journey in therapy because I finally felt ready to let go and use the amazing tools my unbelievable therapist gave me, I’m looking for a new job, for the first time I don’t feel like being in a relationship and I’m wondering what that’s all about, and I’ve made my health my priority– watching my caloric intake using My Fitness Pal, and exercising regularly. I feel happy…yet untethered. Not a bad place to be but I seek answers and know they will come in time either from myself or the universe.

  • Judy Crawford

    I agree wholeheartedly that your writing here is both true & awesome! I absolutely love these questions!! And the thing is, keep them handy, because if you’re lucky enough to live a long life, you will repeat this process a few times… with slightly different answers or outcomes.

  • Dona Middleton

    Great! So glad you found it helpful and shared with your friends. Do the things that make you happy and everything else will fall into place. Good luck!

  • Sonia

    This! I’m currently going through all of this (24, recently separated after identifying that I was prevented from being myself and therefore was depressed) and its both extremely difficult and liberating at the same time! Thank you so much for this post.

  • I’m same age (and experience) as you, Savannah833! I didn’t even start to get it together until my 30s and actually, I’ve done the vast majority of my growth in just the last year. I’ve been fortunate to read a lot of amazing books, discover some great writers and experts that helped me along the way. Currently I am reading a great book by Gabrielle Bernstein that I wish I had got my hands on even a years sooner than I did….oh well, the point is that we are moving forward on our journey. Good luck to you and thanks for the great article, Dona:-)

  • Savannah833

    I am so glad you found things that have brought a lot of knowledge your way! Would you mind passing along the book you mentioned by Gabrielle Bernstein? I would love to read it!

    Good luck to you on your journey as well! I can’t tell you how much your comment has lifted me.

  • Absolutely! She has three, but the one I’m reading now is Add more ING to your life. I know it’s a weird title but it is really good and an easy to read. Very easy to relate to as well. I also signed up for her newsletter and another great site is The Daily Love – lots of inspiring articles and it’s really directed at young people (cause we are still young;-) trying to figure out life. I’m so happy to have helped you. Feel free to keep in touch –

  • Jesse

    To figure out how to be happy, just answer this simple question:

    1) What would make you happy?

    … gee, thanks. Really helpful.

  • Savannah833

    Thank you so much! I look forward to looking into that book. Will send you an email as well. =)

  • I loved this article Dona, it really fine tuned some ideas I’d already been discovering about myself. Interestingly I found my elevator pitch was all about my beliefs – I wrote them down before I read point number 3.

  • Chris

    Number 5 hit me hard. I just want to not have to rely on money to live. It’s the most restricting element in life for me. I have to work everyday, but I just want to travel and experience the world, experience different cultures, build meaningful relationships. I want to rejoice in life, but I’m anchored by the need for money. I loath it.

  • Nina Camara

    I was never really ina personal crisis. However I started to change my behaviour a bit after I left my very stressful job and found another, more peaceful one and had more time for myself.
    I became a lot happier when I accepted that there always will be people who have achieved more than me and that’s OK. Having said that I also started to focus on development of my skills because at some point I’d like to move on career-wise.
    What helps me is being laid-back about things, not taking myself too seriously.

  • Jerkin Jared

    Once again

  • ananth rao

    Good Suggestion…But do we get what we aspire..Don’t you think that we need to be deserving those “WANTS” . Unless that is there what is the point is just writing down , “This makes me happy” . For me, I think . I should have one Building complex which fetches me regular income and I have no loans to pay and just enjoy the amounts receive on regular basis. Just spend that and be peaceful being the saintly persons and discussing spiritual matters which gives us peace and make our future lives also better… but how does dream come true?

  • pravin

    Hi Friends..

  • John

    This is so close too home it hurts. I’m 25, in a really good 7 year relationship, making lots of money, about to be promoted as a leader, and I have good friends. I also am facing inner turmoil over who I am, and sometimes even hate myself. Anxiety and depression have both become a big issue very recently. I think those are great questions to ask myself. You found yourself heading in the right direction by looking inward. I’ve been putting off facing who I am for years and lying to myself about what matters. Thanks for this. I can say it has played an inspirational role in my path of self discovery…. I hope I can face those inner demons soon.

  • John

    Thanks dona. I’m 25 and ostensibly doing very well. My life sounds exactly like your did – this is hitting so close to home it hurts. This scares me but also gives me hope. Wish your website was working, because I’d love to hear more. I’m at a cross-roads in life and I need to learn who I am and what actually makes me happy. It’s so hard to stop lying to myself. Thanks again – this really was a great article.

  • Paul

    I’m Paul and I am married to an amazing woman..I have to great kids who I truly love.i recently was injured while serving for the British armed forces and have now found myself in a state of depression this is the first time I have openly spoke about this tho it has been demon I have thought against and losing the fight for a very long time.And can’t remember the last time I was truly happy.its a horrible thing depression not sure where to go next thank you for listening

  • eleni

    I’m nearly 21 and I’ve been suffering with depression for 3 years. These questions have ignited a fire to discover who I am and how to overcome. I know it’s not that easy, but it’s a start.
    Thank you very much

  • Trish Chasity

    God bless you Paul

  • Nick popageorgeo

    Bunch of shit!!!

  • Emily webster

    Someone call me i need a friend 4402518172

  • Ahmed jaber

    Great article Donna Midelton ,it really touched me deep inside .
    Unlike many articles on the web it’s deep short and profound .
    I’m still thinking about question number 1 and 5 and till now I couldn’t find the right answer!!!
    Ahmed Jaber

  • John Owed

    1. What or who would you be if you knew you couldn’t fail?
    I would be the best version of myself. Health,
    wealth, mental. I would put in the small efforts each day that I know would
    lead to massive shifts in the future as sometime I tend to question if the small
    things are worth it. Knowing I would not fail would give more purpose to each

    2. What is your Ninety-Second Personal Elevator Speech?
    I am in control of my actions and my response
    to the outside world. I am a problem solver who looks for the most efficient
    way to go from point a to point b. If there is not a clear way to make it from
    point a to point b and if it is worth it, I will find a way. I learn quickly
    and can emulate others while creatively designing my own way of doing things.

    3. What are your core personal values?
    I value healthy progress both personally and in other people. I
    value health and happiness of the physical body and mind. Honest and integrity
    are necessities.

    4. What makes you genuinely happy?
    Progress followed by reward – enjoying the
    fruits of my labor. Like a farmer tending to his crop and then celebrating the

    5. If money were no object, how would you live your life differently?
    I would go with the flow and help people along the way. I would do the things I needed to
    do personally but then I would dedicate the other part of my life to others. I
    would not be tied to any physical location and could be anywhere when needed. I
    would enjoy the best food when I wanted with great people.

  • Rysby

    now what if i don’t know the answers to these questions?

  • Mostafa Ahmed Mohammed

    Where I can find more about the writer of this one of a kind article “Dona Middleton” ?? please

  • Mostafa Ahmed Mohammed

    I mean FB page or a twitter account .. I hope she sees my comment

  • Jomer Cenes

    This is very appropriate for me … thank you Donna.

  • Sophia33

    What makes me truly happy is staying home with my husband and cats and occasionally traveling to new places. Unfortunately I have to work all the time which is slowly killing my spirit for life. I am exhausted and unhappy all the time because of work. I don’t like to work and if money were no object I would never work again and I would just stay home all the time. I have changed jobs multiple times and hated every one of them. I’ve been working for 20 years in many different fields and I have given up on ever having a job that I can even tolerate. I really wish I could just stay home and be a homemaker.

  • meoww

    I’m afraid my bf won’t want to mary me. I’m 25. Been with him for 5 years. Don’t know how to bring it up..

  • Holly

    I was just wondering, what’s next? Once you have figured out who you are and what you want – what do you do with it?

    I feel that answering these questions is great but perhaps my answers are unrealistic, in the sense that I will never be 100% certain that I will never fail at anything or that money not be an obstacle.

  • David

    Good article but wow people just shock me. Marriage vows seem to mean nothing these days. There are people at age 25 who have been througn real hardships…like cancer or car crashes where they are paralyzed..and you had it all you have your looks and couldnt be happy.

    Thats the problem people grew up having relatively easy lives in a first world country have no clue what real hardships are..and then complain they arent happy its sad and funny that thats what this world has come to.
    Try visiting a poor country where kids dont have enougn food to eat and then come back and complain.

  • Lilipod

    I’m 18 and I did enjoy this article too

  • samuel

    lame post.

  • yolo

    hmm interesting article, but do whatever you want , We all have responsibilities and i think that is what makes us as a human being stressed and when we are stressed are we happy? no I don’t think so, so crude as it may be you are getting to question bigger than this like, why are we here, what is our purpose, society has grown so much. At the end of time we’re human beings and honestly I think the most happy anyone will be is by pursuing greatness. Like you said if you given up for multiple reason just try to make the best of it we are not all meant to do great things and you should be happy with that, their are 7 billion people on this earth. Deal with it dont stay feed the pig

  • s0nicfreak

    That’s the exact difference between depression and sadness, though. Sadness is caused by external factors – you’re sad because you’re poor and hungry. Depression is caused by chemical imbalances and faulty mood regulators in the brain – you have everything you need/want and still feel sad. Depression is not something you can get over by looking at people who have more right to be sad than you do.