28 Powerful Questions for a Happy Life

Silhouette of a Man

“Keep your head clear. It doesn’t matter how bright the path is if your head is always cloudy.” ~Unknown

Have you ever noticed that your biggest “aha” moment comes from someone asking a powerful question? Suddenly everything seems to make a little more sense, and you know what you need to do from that point forward, right?

That’s exactly how it is for me. Someone will ask me a seemingly trivial question and bam! I’m suddenly overflowing with answers, emotions, solutions—I’m practically made of clarity!

I remember a friend of mine asking me over coffee one rainy afternoon a few years ago, “What are you avoiding, Blake?”

“What? Nothing. I mean, I guess I don’t want it to fail.” I eventually replied.

“Yeah, and…” She quips back. “What happens then?”

I came to her because her willingness to face challenges head-on amazes me, and I needed her to face my challenge and give me that sage advice I knew she could. I wanted to leave corporate America and venture out on my own, and I wanted her to somehow make that sounds less crazy.

I wanted to throw caution to the wind and follow what I most passionately believed in.

I wanted to be my own success story.

I also wanted someone else to tell me it was going to work.

Calculating, weighing, analyzing—these things can only take you so far. I subconsciously needed something to get me out of my head and into some clarity. I needed that push.

We bounced back and forth for what seemed like eternity. When most people have conversations like this, one party inevitably snaps out of the pattern and either says something oddly profound, or simply gets frustrated and tells the other to bugger off.

I was lucky enough to receive the former rather than the latter.

“When do you stop calculating risk and rewards and just do it?” she asked. “Because it feels like you’re building a magnificent ship you’re too much of a baby to ever sail. What are more committed to, dreaming it or doing it?”

Holy cow, I was stunned. She was right. What was I more committed to? What a brilliant question.

As a coach (yes, I made the leap and ventured out on my own), I make my living asking these questions to help clients get out of their own way.

The beauty of these questions is there are no right or wrong answers. They are just meant to get your wheels turning, and maybe help you see the decisions you’ve been making, and the ones you’d like to make from now on.

These are 28 of my favorite questions:

1. We learn from our mistakes, yet we’re always so afraid to make one. Where is this true for you?

2. What risk would you take if you knew you could not fail?

3. What is your greatest strength? Have any of your recent actions demonstrated this strength?

4. What are the top five things you cherish in your life?

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

6. When do you stop calculating risk and rewards, and just do it?

7. At what time in your recent past have you felt most passionate and alive?

8. What do you most connect with? Why?

9. What one piece of advice would you offer a newborn child?

10. Which is worse—failing or never trying?

11. Why do we do things we dislike and like the things we never seem to do?

12. What are you avoiding?

13. What is the one job/cause/activity that could get you out of bed happily for the rest of your life? Are you doing it now?

14. When it’s all said and done, will you have said more than you’ve done?

15. What are you most grateful for?

16. What would you say is one thing you’d like to change in the world?

17. Do you find yourself influencing your world, or it influencing you?

18. Are you doing what you believe in or settling for what you’re doing?

19. What are you committed to?

20. Which worries you more – doing things right or doing the right things?

21. If joy became the national currency, what kind of work would make you wealthy?

22. Have you been the kind of friend you’d want as one?

23. Do any of the things that used to upset you a few years ago matter at all today? What’s changed?

24. Would you rather have less work to do or more work you enjoy doing?

25. What permission do you need/want to move forward?

26. Really, what do you have to lose if you go for it?

27. How different would your life be if there weren’t any criticism in the world?

28. We’re always making choices. Are you choosing for your story or for someone else’s?

Powerful questions can change the very fiber of our construction. They give us a chance to challenge our own ideals and perhaps shed some light on what we are and are not committed to.

It’s important to understand that we’re always committed to something. If it’s not success out on our own, it’s staying safe in the comfortable success of someone else. If we’re not committed to creating our opportunities, we’re committed to floating around, hoping, waiting, and wishing for circumstance.

Are you more committed to dreaming it or doing it?

Ask yourself some of these questions when you feel stuck. What comes up just might surprise you!

Peace, love, and a million successes to you, my friends!

Photo by Tobias Mandt

About Blake Alexander Hammerton

Blake Alexander Hammerton helps professional 30-somethings gain clarity and confidence to move through their "oh crap, what now" moments and create the extraordinary life they deserve. He believes in adventurous love, laughing until your sides hurt, and going boldly into challenges.

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  • Dochy

    Awesome post! 🙂 I recently got hooked onto this idea of questioning myself when in trouble/or just a bit down… Here’s one site I usually go to for this… I’d add some of your questions to my list now! 🙂 And I have to add, you have an awesome friend! 🙂

  • allison

    Beautifully written. Thank you Blake. It is because of writers like yourself that I look foward to Little Buddha emails everyday.

  • Onder

    This post came out at the perfect time as its the perfect way to start off the new year. Many people face challenges due to not believing that they can achieve what they want from life. And the beginning of each year is a reminder that time is precious. I write about this in my blog post which i ironically posted this afternoon
    The lesson is simple. Find what you’re really passionate about and do it. Setting off on your journey serves as a catalyst for facing challenges and hardships that you will inevitably be faced with. 2013 will be a great year for all of us!

  • kari

    Big love for this post! <3 thank you !!

  • The ship building analogy that your friend made is spot on! Also, the question “What are more committed to, dreaming it or doing it?” is of most importance to me among many, if not all of the rest.

  • Anonymous

    I absolutely love this post!!!! Before reading today’s posts on Tiny Buddha, I wondered what type of posts would have the “honor” of starting off 2013, and I think this is a PERFECT article for today, right now, where I am as an individual, and where we are as a nation. Thank you so much for these powerful questions! I had to stop and think for quite a few of them!!

  • Great post!

  • Dawn Maynor

    Very good! Love the questions at the end. I want them all in my back pocket all day! LOL!

  • Thank you for your kind words! We’re standing at the threshold of a brand new year and a little reflection goes a long way, I say. I’m glad it resonates with you.


  • Nicole,

    I’m glad you liked the analogy. Truth is, I adopted them from that point on! Now I’M the one talking about being the “captain of your own ship” – it just fit so well, I couldn’t let it go! I’m a dreamer and can often find myself dreaming a lot more than doing. This question still hits me in the face from time to time, and springs me back into action. I’m so glad you connected with it!


  • Thanks Kari!

  • Thank you Dawn! I really like the last one, myself. I want to be in charge of my own prosperity, not someone else’s. I’m glad this sparked a little fire in you!

  • Thank you very much, Allison. It’s because of feedback like yours that I continue to work, write, and inspire others everyday. Your words make a big difference. Stay brilliant, Allison!


  • Onder, I’m glad it resonates with you! I agree completely. Your article is spot-on as well. It’s about gathering a little perspective and clarity on what you’re doing… and who you’re becoming. When you’re able to see clearly into the reasons WHY you do what you do, and feel what you feel, you’re suddenly granted the confidence and permission to change. Once you know it and own it, you can change it.

    Breathe deep, and shine on, Onder!


  • Dochy, I completely agree. She still amazes me. Fearless. Simply fearless.

    And I love the site you mentioned too! I’m so glad some of these questions hit home with you. Keep asking yourself great questions, Dochy!


  • Fabiola

    Awesome Post, Blake!

  • Suzan Bafford

    Great content, wisdom enriching!

  • Jasen Aura

    WOWza! I am going totally take note Blake, thank you for providing amazing content!

  • I’m so glad you share my philosophy on this. I actually created an app based on this concept — QuestionUp for iPhone. It’s about helping people brainstorm by answering tough questions — and sending their answers to Evernote if they’d like to store it. I can send you a promo code if you’re interested in trying it? Sounds like it would be right up your alley 🙂

  • Fantastic insight! Powerful questions snap me out of a fog too and BAM, the answers that were there all the time become crystal clear. Love this post!

  • Dena-Lynn, It’s such a funny thing that a powerful question or two can change so much, isn’t it? Sometimes, when I’m really stuck or want to dig deeper, I try to stay IN the question. It’s more of a “collect data” mode for me. I stay inside the curiosity and explore what comes up. I’m glad this resonates with you!


  • Marcella, I’d love to check out your app! I don’t have an iPhone, but the iPad should be able to work that out. I love that you connected it to Evernote so the questions and answers become part of a real game plan for change. What a brilliant idea. We definitely share the same philosophy, Marcella. Keep up the good work!


  • Thanks Jasen!

  • Thanks Suzan!

  • Thanks Fabiola!

  • Thanks Brian!

  • Venessa

    Profound, genuine and helpful. Thanking you Blake

  • You’re very welcome Vanessa. Thank YOU for your kind words. I’m glad this resonates with you, and I hope you find yourself discovering new avenues through these questions.


  • Winnie

    Great article, great questions. What I have discovered is that if I sit quietly, removed from all distractions, and think about something that’s bothering me, I gradually start hearing a voice inside me asking me questions like these. This voice never answers or tells me things, only ever asks questions. I believe we each carry around our own best counselor. The trick is to create time and space to be able to hear the quiet questioner. And these questions are a good place to start the process, until we can hear the questions coming from within.

  • Julie

    Great questions and I Love the conversation with your friend! :O)

  • Jen

    Great post and great questions Blake!

  • Thanks Jen!

  • Thanks Julie!

  • Winnie, I could not agree more. In my line of work, we call that inner voice your “captain” – the loving, supportive, curious, confident, trusting voice we have, but often have trouble hearing. I LOVE that you can reach a peaceful stillness and access this powerful voice. It’s such a gift to know you can challenge your beliefs with your inner “questioner” anytime you get still. I’m so glad this resonates with you, Winnie.


  • lv2terp

    Fantastic post!!! Thank you for sharing your wisdom and these wonderful questions!!! 🙂

  • Thank you so much! I’m glad it had an impact for you!

  • I had a friend in my earlier years who always threw these sorts of challenge-questions at me, and I appreciated it (and miss it). It’s an unusual but wonderful friend who will do this. I’m glad to have your list in front of me! So many problems and issues can get reframed when we’re challenged with a different way of thinking about them or a different approach in looking at resolution. Given this new view in the form of a question, especially one that feels difficult to answer, we are encouraged to dig deeper to find an honest response from within.

    Thank you, Blake. This isn’t a read-once post. I’m definitely bookmarking it for repeated playback. 🙂

  • Daria

    Such a wonderful and inspiring post!
    Thank you so much!

  • Guest

    Such a wonderful and inspiring post!
    Thank you so much!

  • What would I do if I knew I could not fail? Everything. (That bright light you just saw was the Blinding Flash of the Obvious.) Thanks, Blake, for this article.

  • Karla

    I would love to share this with others. Thank you very much for this inspiring post.

  • Nasimeh Bahrayni

    Man. That question – “what would you do if you knew you could not fail?” – that hit me DEEP. I started writing it everywhere. I really hope to meditate on that one and let it guide me in more decisions this year. Thanks. :}

  • Well acutally these questions gave answers to some of questions about what next I’m going to do in my life.. Thanks for sharing these questions with us Blake.. 🙂

  • I’m so glad they helped give you a little clarity, Chetan. I hope they spark the creativity inside you to go out and tackle something big, and leave you feeling bold and satisfied!

  • That sounds like an excellent plan to me, Nasimeh. When you meditate and get to your creative plane, play with that question. Let the images of possibility come to life, and connect to the emotional response within you when you experience them in meditation. When you awaken, who knows what amazing steps you’ll take!

  • Thank you Karla! Please share and share and share. You might just help someone else get “un-stuck” in his or her journey!

  • I totally agree, Karen. I wrestle with the “yes, but I do fail, so let’s be realistic, Blake” thought immediately after I ask myself that question. The answer is, of course, obvious. The way I push through that second, negative voice is by questioning what I truly have to lose by taking a step in the direction I choose.

    Being realistic is such a waste of talent, innovation, and creativity. It’s the equivalent of putting a hair dryer on an airplane wing. Sure, it has thrust (a nearly infinitesimal amount), and it’s manageable and safe (nobody ever hurt themselves from the pressure coming out of a hair dryer), but it will never, ever lift a plane.

    If you feel the thrust and power of a jet engine inside you, explore how often you only let your “inner hair dryer” do the work. It sucks to never get off the ground.

    You got this. Buckle up! Thrusters to full! Let’s get this bird in the air!

  • Thank you Daria! I’m glad it resonates with you!

  • I’m so glad these touch something for you, Kate. Sometimes the simplest questions can churn our insides enough to let the real, right, and true answers come out. A couple of nights ago, as a social experiment, I asked the same two questions to a group of people all struggling with something different individually. After about 7 rounds of the same two questions, nearly all of them had an “aha” moment.

    Explore the question. Stay curious in the question. Let the answers come to you, and when one of them suddenly feels real, right, and true for you, you can stop asking… for now. Play with them and see where they take you!

  • Happened to come across this when i was browsing for something related.
    You have shared such a wonderful list of questions that helps one to unwind the “ME” in myself.
    Thank you for sharing this 🙂

    Marrilyn S.H.Tong

  • Blake Alexander Hammerton

    You’re very welcome Marrilyn. I’m not surprised you happened to find this post and it opened you up to something else. Sometimes it’s all about synchronicity and listening to the Universe flirt. I’m so glad you enjoyed it!

    Have a beautiful day!


  • marlyn

    “How different would your life be if there weren’t any criticism in the world?” hit me deep. I wouldn’t be as anxious and might actually leave my house. Also, “what would you do if you knew you could not fail?”

  • EverSubtle

    Lovely Article. The questions are not just Powerful, but also your words.

    Question now is will the power of the questions be realized and acted upon.

    I know when I asked myself these questions, right away I knew what I thought should be the Right answer to many of them … so to be honest to myself, I had to answer it wrong based on what I had just perceived Right when I first read the question. It also forced me to look and admit that there are times I and dare I say ‘we’ struggle to get it Right.

    (ofcourse this is all based on my personal perception of what I consider Right & Wrong. to ‘Questions’ that may not really have Right & Wrong answers.)

  • Mary

    Lol i Love THose Question i asked my guy and now we’er both in love and we will get amrried soon..

  • Hannah McGillivray

    I LOVE the first question! So powerful. And so true. I am going to really ponder this. I know one area where this is true for me that straight away comes to mind! Thank you.