20 Questions That Can Change Your Life

I could ask you what your favourite cheese is or whether you prefer ballet or ham, but I don’t think the answers would be very productive.

Mildly interesting maybe, but hardly useful.

For useful answers—answers that give you real insights that you can take away and do cool shit with—you have to ask useful questions.

Here are 20 of them, and they just might change your life.

  1. What’s the real reason I’m doing this?
    A course of action can be started for any number of reasons (fitting in, avoiding pain, feeling sexy), all of which might seem perfectly fine at first. But there are layers to action, and the real reason you’re doing something might not be what you think it is. Don’t be scared of digging and seeing what’s really in it for you.
  2. How can this be easier?
    I’ll choose ease over struggle any day of the week. Don’t follow the urge to struggle, fight or suffer because you think that’s what needs to happen or how you become worthy; look at how you can make things easier.
  3. What can I let go of that isn’t serving me?
    Letting go is liberating. Letting go of something that drains you, frustrates you or otherwise takes away is just common sense.
  4. What’s my intention here?
    Is your intention in this moment to be at your best or just to coast? Is it to look for the bad or celebrate the good? Or maybe it’s to hurt rather than heal. Open that up and see what’s inside.
  5. What can I do to help?
    It’s often easier to look inward and have your own agenda dictate what happens. Nothing wrong with that, but beautiful things can happen just by opening up a little and seeing what you can do to help someone else, something else, somewhere else.
  6. If you did know, what would it be?
    If you don’t know the answer to something (which direction to take, what to say to someone, how to approach a challenge, etc) and are sitting in Stuckville, ask yourself if I did know the answer, what would it be? It sounds crazy, I know, but this is a bloody useful (and sometimes slightly mean) coaching trick that works like a charm.
  7. What is there that’s beautiful, just as it is?
    We’re all busy, we all judge and we all race through our days. But amazing changes can happen just by choosing to slow down and notice—really notice—what’s already beautiful and right there in front of you.
  8. What can I be grateful for in this moment?
    I kept a gratitude diary once, where every night before my head hit the pillow I’d write down 3 things I was grateful for that day. It wasn’t easy, in fact it was fucking crazy hard. But it helped to soften my hard, cynical side and to show me that expressing gratitude can be transformational.
  9. How am I getting in my own way?
    When things are hard or you’re just tired of trying all the time, take a look at where you might be getting in your own way. What are you doing that might be blocking something, or what are you doing that’s limiting results?
  10. How can I be at my best?
    Being at your best doesn’t mean pretending to be okay and it doesn’t mean forcing yourself to be a certain way. What it is, is honouring how you are when you’re at the top of your game, firing on all cylinders and flowing, and knowing that those things are woven through you in every single moment of every single day.
  11. What experiment could I run that would be fun?
    Change is hard and scary like an armoir full of spiders. Which is why making change less hard and less scary by simply running multiple, small experiments—without needing to commit and being able to pivot and adapt depending on the results—makes things a heap easier.
  12. Where am I pursuing validation or approval instead of trusting myself?
    You’re hardwired to fit in; wiring that sometimes has you seeking approval or trying to fly under the radar rather than trusting yourself to do what really matters. But you don’t need validation or approval. You just need self-trust.
  13. What am I tolerating that I don’t need to?
    Sometimes you think you need to put up with something because you don’t want to rock the boat or upset anyone. But your assumptions are worth challenging, especially if you discover you can remove something you’ve been putting up with all this time.
  14. What if I just laugh with it?
    Laughing’s my favourite, and I’m a firm believer that life is actually pretty ridiculous. So laugh with it rather than frown at it, and see what happens.
  15. What would [being a trapeze artist / loving myself / being successful / something else ] look like?
    Ideas come and go, and so does clarity. Asking yourself what something would look like (whether it’s a goal you think you might like to reach or a feeling you might like to have more of) helps you to cut through a lot of shit and look at how it could be. Insights follow.
  16. Am I more focused on being right than being happy?
    Sometimes you cling to an idea, a belief or a way of thinking just because it’s yours and it’s how you think. That’s just ego, posturing and bullshit. There’s freedom in not needing to be right all the time.
  17. If I could do something and know that I could deal with whatever happens, what would I do?
    You sometimes get hung up on what could happen as a result of your actions and have all that stuff dictate what you do. But what might change if you knew that you could deal with anything?
  18. What am I resisting, and what impact is that having?
    You know those things in life you wriggle and squirm at rather than engage with or settle into? What’s a better way?
  19. What’s my body trying to tell me?
    They say that your body is a mirror for your mind, so if there was something your body was trying to say to you, something it wanted you to notice or act on, what would it be? And how can you be more in touch with your body’s messages on a regular basis?
  20. Today, how can I connect with what matters to me?
    If you’re not spending some of your day connecting with the things that matter to you, just how are you spending your time?

What’s jumping out at you?

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