Ask Yourself This

Image by Min An from Pexels, CC0

A couple of years ago, I wrote a post called May I Ask a Question?, which summarized my thoughts on what makes a great question, the benefits of such questions, and the types that can achieve each benefit. Here’s a quick re-cap:

The most important qualities of a great question:

  1. elicits honest, thoughtful answers rather than clever, safe, automatic or socially acceptable ones
  2. is not so personal, so complicated, or so distressing to think about that it makes people hesitant to answer, but is personal enough, challenging enough, and provocative enough to elicit sufficient consideration, focus and passion to produce interesting, revelatory and possibly ‘useful’ responses
  3. encourages follow-up questions and deeper explorations into the answers and reasons for them.
  4. achieves one or more of the following benefits:
    1. knowledge, ideas, perspectives, deeper understanding, and/or insights that otherwise wouldn’t have been achieved, that helps move things forward and provides a better understanding of the situation (Why are things this way and not that way; what’s actually happening here and why; who else should we talk with; what’s working and not working?)
    2. appreciation of what we don’t know, need to know, and/or can’t hope to know (What are we trying to achieve, and why, and why do we care; what do we need to find out?)
    3. surfacing novel ideas and alternatives (What if we…; how might we…; and imagine if..?)
    4. helping us learn important and/or interesting things about ourselves and others (How do you feel about…; what do you think/believe about…; what do you wish…; what would you do if…; what if you could…?)

Some specific questions to get to know someone better:

  • If you were getting a portrait taken, and the photographer asked you to hold something in your hand that told viewers something important about you, what would it be?
  • What do you believe that no one else does? (the famous Peter Thiel question)
  • What would you do if you knew you couldn’t fail?
  • What do you wish you’d learned earlier in life?
  • In a few sentences, summarize your worldview or philosophy of life. What do you think is life’s meaning or purpose?
  • What would you like to be renowned for?
  • What are you most grateful for?
  • What would you most like to know about your true self, or about your future?
  • What’s on your bucket list, and what’s holding you back?
  • What quality do you wish you had much more of?
  • Who inspires you the most?
  • When in your life were you happiest, and why? What was the biggest turning point, and how did it change you?
  • What do you most like about yourself? What are you a role model of?
  • What important thing have you changed your mind about?

I’ve added a few questions to the list above based on Life Changing Questions, a ‘game’ I had the chance to play recently.

Reviewing the previous post, I got thinking about the kinds of questions we ask ourselves, and the questions we often don’t ask ourselves when perhaps it might be helpful to do so.

Asking yourself a question is a quite different process from asking one of others. There is no onus or pressure to answer the question, so we might easily get distracted. We might not be motivated to put the effort into really thinking about it. It’s harder to be objective when there’s no critical ‘audience’ for our responses.

We can of course ask ourselves the questions in the ‘getting to know someone better’ list above. But what if we made a regular practice of asking ourselves questions every time we had the chance? What questions might help us know ourselves better, or help us become more self-aware? What questions might help us surface our blind spots, or help us bring more focus to things that are important to us, and not just urgent, or help us decide how to spend our spare time, our vacation time, or our disposable income?

Thinking about this can quickly get us into the murky area of free will (ie whether we have any). But let’s suppose we do, or believe we do. What questions might be most useful to ask ourselves as a regular practice?

My sense is that it depends on what you value, your worldview, what motivates you, how well you know yourself and a host of other issues that are different for each of us*. So I wouldn’t presume to produce such a list for others. But in my own case, limiting myself to five questions to contemplate, say, at the start or end of each day, or even more often than that, I might ask myself the following:

  1. How am I feeling right now? And what simple thing might make me feel better? This is about self-awareness, not self-judgement. And the ‘simple thing’ might be a special tea, a bath, making a list, a stretching exercise, or some nagging task that I could just get out of the way right now.
  2. If I had the last 24 hours to re-live, what might I choose to do differently? This is not about self-recrimination or blame, but about learning from experiences and mistakes.
  3. What do I really want? This is Denmark’s Katja Hunter’s “one question”, and I love its spaciousness.
  4. What if I really didn’t want [the answer to #3]? “Who would I be if that thing I’ve always desired was not desired any more?” Contrarian self-help author Mark Manson describes it as shifting your values or identity by ‘trying on’ a new one, and, if it ‘fits’, letting that value- or identity-shift drive changes in what you believe and do. This ties back to the classical self-examination question What does it mean to live a good life?
  5. Who am I, really? Yeah, I know. Don’t get me started.

To do any practice consistently, I have to give myself a prompt so I don’t forget it and can’t avoid it. Maybe I’ll put these questions on my bathroom mirror.

* Ironically, when I googled the title of this post, I was taken to the page for a book with this same title, whose first suggested question to ask oneself is “What do I know for sure?” The author, a minister, responded to her own question, saying essentially that there is a higher power and that everything happens for a reason, two things I don’t believe at all.  Joseph Deitch in Fast Company last month suggested a good question to ask whenever you encounter someone who says something you don’t agree with, or believe, or think is correct or fair: “Why don’t I understand why they believe that?” Another recent article suggests, when feeling an overwhelming emotion, asking “Is this feeling useful?” Another suggests the more generic “Is this the best use of my time?” And of course there is the compassionate question that David Foster Wallace recommends in his This is Water speech, which is (as Carl Richards paraphrased it in a NYT column a couple of years ago) “What is the burden each of these people around me is carrying?”


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3 Responses to Ask Yourself This

  1. Tree Bressen says:

    For more resources on this topic, check out Tom Atlee’s page on questions at Cheers!

  2. Ivor Tymchak says:

    “What do you believe that no one else does?”
    This question is garbage.
    To answer it I would need to know what everyone on the planet believes – clearly an impossibility.
    Belief is too close to opinion. There is no science in either so you might as well use the word ‘fantasy.’
    It’s designed to flatter the ego – ‘my belief is so special no one else has it.’ For every maverick outlier with solid evidence there were thousands of others who were simply deluded and spectacularly wrong.
    It encourages exceptionalism, which is a highly dangerous road to go down.
    I might just be having a bad day so apologies if I’ve misunderstood the intent of the question.

  3. Dave Pollard says:

    Hi Ivor: I think the Thiel question is meant innocently enough and I think it is more precisely “What do you believe that almost no one else does?”. Its purpose is to try to surface awareness of the experiences that separate us from each other, and hence help us better appreciate and bridge those differences. In his recent interview with Ezra Klein which I referenced in a previous post, Malcolm Gladwell says his answer is that “That all prisons should be immediately and permanently closed.”, while Ezra says “That eating meat is immoral.” I think those are fascinating answers. There are lots of people who are dubious about eating meat, for example, for various reasons, but not many would go as far as Ezra does. It’s not that he’s likely to convince any. But the reasons he believes this, the story that took him to that position, could serve as a basis for starting to know him a lot better, if one had just met him, and that’s what the Thiel questions is, I think, designed to do.

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