Awkward questions


Question mark made of puzzle pieces

Building a bigger picture from questions


Recently on Twitter, I’ve been tweeting about ‘Questions people don’t ask often enough’. (The most recent questions have their very own hash tag #questionyourself – wish I’d thought of it sooner.)

These questions have arisen in my work with clients. Quite often they are the questions the client should have been asking themselves. Sometimes, finding the right question for a particular client will stop them in their tracks. You can see their perspective changing as they start to think in new ways about their situation.

Most of the questions relate to career decision making, but some of them are broader and could apply to many aspects of life.

Because Twitter has long-term memory problems, I thought it might be useful to keep a list of the questions here on the blog.

I was going to try to link these questions to career theory in some way but Bill Law has saved me the effort by using some of them in a new article on Career Learning Theory (PDF).

I will add to the list as I tweet new questions.

Some of these questions have been suggested by other people or have arisen from discussions with thought-provoking individuals. Where this is the case, I’ve tried to give due credit.

I’m happy to take suggestions for other questions here or via Twitter.

Questions people don’t ask often enough

  • Am I asking the wrong question?
  • Am I missing something?
  • Is there a pattern?
  • Who do I need to be in the future?
  • How would it look from your perspective?
  • What if I’m wrong?
  • Will today’s easy option become tomorrow’s dead end?
  • What evidence is that opinion based on? (via @SimonK_Cascaid)
  • How representative was that experience?
  • Is there an alternative explanation?
  • What might happen if I stepped out of my comfort zone? (via @Ninianna)
  • Is the answer that I want too simplistic?
  • What do I owe it to myself to attempt?
  • Who can help me to look at this in a different way? (via @targetjobsUK)
  • What can I give to the world?
  • Am I the problem?
  • Rather than trying to change my situation, do I need to change myself?
  • Am I looking for the wrong thing in the wrong place?
  • Will this always be as important to me as it seems to be now?
  • Do I have a constructive suggestion to go with my complaint?
  • Then what?
  • Why don’t I like the answer I’ve already got?
  • How have I edited my memories of the past to be consistent with my current self image?
  • What am I running away from and am I running towards anything?
  • What do I get out of staying the way I am that stops me making necessary changes? (via @jillelswick)
  • Is what I’d gain by changing worth more than what I’d keep by staying the same? (via @jillelswick)
  • Who am I trying to satisfy?
  • Why am I doing this…again? (via @SimonK_Cascaid)
  • Whose story am I trying to live?
  • How much fun am I going to have today? (via @imofo)
  • Is that just the palatable explanation?
  • What am I responsible for? (via @Ninianna)
  • Why have I put these restrictions on myself?
  • Could I surprise myself?
  • What aspects of myself have I yet to discover?
  • Is that just how I would like things to be?
  • What could I lose if I don’t take the gamble?
  • If I risk and lose, could I still gain something? Does that change the risk?
  • Why don’t I just forgive myself for making a mistake and move on?
  • Where’s the guarantee that says I can have everything?
  • How can I improve what I’ve got right here, right now? (via @Ninianna)
  • Am I living my values? (via @jillelswick)
  • Am I trying to justify a decision I’ve already made?
  • Why am I so sure about that?
  • How could I make this simpler? (via @targetjobsUK)
  • Do I really want this? (via @jillelswick)
  • Do I still want what I thought I did?
  • How could I be more useful? (via @TheFactoryPod)
  • How can I make this moment one I will look back on with delight?

More questions

  • What impact do I want to have?
  • Are my expectations for the future spoiling my enjoyment of the present?
  • Is my enjoyment of the present spoiling my expectations for the future?
  • What’s the question I don’t want people to ask me? (via @SimonK_Cascaid)
  • Am I just reacting against other people’s expectations?
  • Are there more important things in life than being right all the time?
  • What are my beliefs about how the world should work?
  • Do I ignore evidence which contradicts my beliefs?
  • Do I really know what success means?
  • How could I change the plot of the story I am telling about myself? (via @TheFactoryPod)
  • Have I bought into an idea of success which is unsustainable?
  • How am I different from my past self, and how would I like my future self to be different?
  • Why do I think I need permission? (via @Ninianna)
  • How do I know that what I want actually exists?
  • If what I want doesn’t exist, could I create it?
  • Should I be worried that no-one is contradicting me? (via @SimonK_Cascaid)
  • What important lessons can I learn about myself from my critics? (via @TheFactoryPod)
  • Should I stop asking myself pointless questions and just get on with something? (via @jonfish)
  • Who can I listen to today?
  • Does it matter that I can’t answer these questions? (via @jonfish)
  • What question am I avoiding asking myself? (via @helencurry)
  • If I never change my mind about anything, do I really have free will?
  • Could I entertain an alternative viewpoint, even for a moment?
  • Are my beliefs based on things I’ve experienced myself or dogma I’ve inherited from others?
  • What do my heroes tell me about my aspirations? (via @TheFactoryPod)
  • What communities do I need to be part of?
  • Is an unfulfilled dream holding me back from getting on with life?
  • Is one dominating factor leading me into lop-sided thinking?
  • How do you know that the bad things you imagine will happen if you act will be that bad? (via @SimonK_Cascaid)
  • Why do I think it’s selfish to think about myself?
  • Why do I think there has to be a definite answer?
  • Why am I in such a hurry? (via @helenbuz)
  • When did I last do something to enrich the lives of others?
  • If what I’ve been doing isn’t working why don’t I try something different?
  • What’s the most powerful force in my life: ‘should’ or ‘can’?
  • What really matters?
  • Have I set my expectations such that I’m guaranteeing disappointment?
  • Why do I assume happiness will come from something external?
  • Do I realise that I am on a journey and have I got any idea of the destination?
  • Am I focusing too much on what I can’t control (the outcome) than what I can (the process)?
  • Am I excluding a whole range of possibilities because the most obvious path looks too difficult?

See my article on questioning from the Resources section (PDF).

Related post: Questions about guidance

Photo credit: Horia Varlan
  1. #1 by Ian on 31 August 2010 - 14:23

    These should be re-asked every couple of months, and the responses evaluated and monitored. The simple fact that these questions make us think hard about the responses and their consequences is enough reason to keep them close and use them to help us grow. Nice job, David. Thanks very much.

  2. #2 by Jill Elswick on 6 September 2010 - 23:45

    Great to have these questions all in one place, David. I love this list. I’ll keep it handy. Thanks for including the questions I sent and the ones we brainstormed together (marked with a “via”).

  3. #3 by John king on 13 September 2010 - 09:57

    Am I asking so many questions of myself that I am failing to take action?


    • #4 by David Winter on 13 September 2010 - 10:32

      Considering some of the actions you take, John, that might be a good thing! 😉

  4. #5 by Andrea H on 19 April 2011 - 09:22

    Just gone back through some older posts of yours David as I often use your blog as a resource for generating new ideas or making me stop and think about theories and their application to my work. Thanks for this list, really useful 🙂

  5. #6 by David Winter on 20 October 2012 - 06:39

    Steven Handel (@stevenhandel) has posted on the power of asking yourself questions

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