The Ten Hardest Questions

I‘m not a believer in self-help books, the value of leadership, gurus, transformation, twelve-step programs or, despite the title of this blog, saving the world. Pollard’s Law of Complexity states: Things (and people) are the way they are for a reason. If you want to change something (or someone), it helps to know that reason. If that reason is complex, success at changing it is unlikely, and adapting to it is probably a better strategy. Complex systems have self-reinforcing positive feedback loops that keep them the way they are, and which find ways to circumvent interventions intended to change or reverse them. If it helps you to believe that, under the right circumstances, you and the rest of our species can do anything we make our minds up to do, that’s fine, but this post is probably not for you.

I am a believer in asking “important” questions. An important question, as the word’s etymology implies, is one that “brings in” something new to your thought processes. That may be new information, a new perspective, or new ideas, something that sparks your creative or critical thinking in a novel way. My experience has been that enduring change generally follows revelation, not rhetoric. At any point in our lives we are ready to accept some new information, ideas or perspectives, and not ready to accept others.

The revelations and significant changes in my life that were not forced upon me by immediate circumstances, have come from three activities: (1) Studying/learning something new (the I didn’t know that! moment); (2) Being presented with a new synthesis or combination of information that I’d not put together myself (the aha! moment); and (3) Reflecting on important questions. This essay is about the third type of activity.

Most important questions, I have found, are hard. That is, there is no obvious or easy answer to them, and even understanding the question takes time and work. These questions often have dismissive answers that we use all the time to justify not thinking about them, or reassure ourselves that they don’t apply to us, or that there’s no point dwelling on them anyway since there’s nothing that can be done. We will dismiss them until we’re ready, until the pain or cognitive dissonance of our unquestioned lives or worldviews exceeds the difficulty of dwelling on and tackling the question.

What’s more, I don’t think there are all that many important, hard questions. What underlies them all is our personal happiness, or, more often, unhappiness, and our curiosity for answers, to know and understand. Each of these questions is dense and complex — hence the temptation to dismiss them when we’re not absolutely ready to explore them. Most of them are “how” (what process/practice can I use?) questions with underlying “why” (how did things get this way?) questions. The “answer” to each question is personal, elusive, inexact, and ephemeral. Here are the questions, first without context and then repeated with my own context and explanation of why I think they’re important and what they mean to me, which you may find either illuminating or limiting. I’ve posted them on my refrigerator, and often choose one to ponder when I’m out running or walking.

  1. How can I discover who I really am?
  2. How can I stop doing the things I hate doing?
  3. How can I live where and how I want?
  4. How can I set myself free?
  5. What can I (learn to) do to make the world a better place (doing something that I love)?
  6. How can I make love last?
  7. How can I find the right partners (to love/live with/work with)?
  8. How can I be ready for what the future holds?
  9. What comes next?
  10. What if…? (e.g. we lived in a world without property, or without growth)

OK, now some context (but no answers):

1. How can I discover who I really am? Self-knowledge, I think, is a prerequisite to self-awareness and self-love, and to knowing what we ‘should’ do, think and believe. It’s about discovering what brings us joy, what we’re ‘meant’ to do. Most of what I’ve learned about myself has come from understanding what my physical body and my ‘mind’ are, from studying human nature, and studying nature, and most of all from trying to do a lot of different things and seeing the result and what I came to know as a result.

2. How can I stop doing the things I hate doing? I keep telling myself I only have one life and my time is precious, yet I suspect I will be like so many who, at the end of their lives, lament wasting much of it in activities that brought them no joy. So why do so many of us persist doing things we hate, and putting off doing what we love? Duty? Responsibility? Fear? Lack of imagination? Addiction? Can’t help ourselves? Or is it because we come to believe the stories that others tell us, and that we tell ourselves, because it’s easier than changing?

3. How can I live where and how I want? About half of the average North American’s expenses relate to the place they live — home maintenance, commuting etc. Yet many of us dream about living elsewhere, living differently. We live a life style that’s unsustainable. And complain about the weather. So what’s holding us back? Can/should we just “learn” to be genuinely happy where we are?

4. How can I set myself free? In my last post I quoted Wolfi Landstreicher: “We want to live as wild, free beings in a world of wild, free beings. The humiliation of having to follow rules, of having to sell our lives away to buy survival, of seeing our usurped desires transformed into abstractions and images in order to sell us commodities fills us with rage. How long will we put up with this misery?” Yet I remain in this prison inside my head in the larger prison of my culture. I remain too attached to fears, to beliefs, to stuff. My goal of learning “presence” remains as elusive as ever. As I reduce the stress in my life, I get less practiced at coping with stress, so when it happens I get even more triggered, captured, cowed by it. How can I let it go, move past it?

5. What can I (learn to) do to make the world a better place (doing something that I love)? Like most, I am still looking to make a difference, to do something that I can take pride in, something that will outlast me and help many live better lives. I don’t want credit for it; I just want to know that I did something to mitigate the cruelty and suffering that this terrible culture inflicts on all of us, and which is getting worse. Or that I created something beautiful and memorable and enduring that many could enjoy. Not out of anger or struggle or feeling of responsibility, but as an act of joy and love.

6. How can I make love last? This is Tim Tom Robbins’ famous question. We all want it to last forever. Why is it so hard? Does our culture make it impossible, or is it not in our nature?

7. How can I find the right partners (to love/live with/work with)? This was never an issue when we lived in small, closed communities. In a community of 150, it’s a problem of collective self-organization. In a connected world of seven billion, it’s an impossibility. How can we at least make it easier, especially when (see question #1) so many don’t know who they are or what they’re looking for?

8. How can I be ready for what the future holds? We are heading into what James Kunstler calls The Long Emergency, decades of waves of turbulence, discontinuous change, challenge and unpredictable Black Swan events. But we don’t know when, where or how crises will unfold, or how severe they will be. Humans (and other creatures) are not designed or equipped to think about or prepare for high levels of uncertainty, volatility, or unpredictability, especially when they’re chronic and long-term. How can I learn to be resilient no matter what happens, less dependent on distant, centralized, fragile systems and infrastructure, and on other people to tell me, in the moment, what to do?

9. What comes next? What will I do next? Not what I should do next or could do next or am scheduled to do next, but what do I choose to do (or not do) next? Or do I really have any choice? Will I procrastinate, or do something easy or fun instead of that huge and/or unpleasant task waiting to get done, because that’s just who I am (in which case why not accept that and stop setting myself up for disappointment and failure)? If I choose to do something I like instead of something that is expected of me, could that change everything? Or if I just get started on that huge project I’ve been putting off, perhaps a project I’ve always wanted to do but just seemed too daunting, could that change everything? And looking at the question another way, in the context of collaborative activities with others, or a conversation I just had, what comes next to move forward, or to move in a different direction, or to act on a challenge or obstacle or need? What needs to happen next? What wants to happen next? What comes next if we all just keep doing what we’re doing, and can I live with that? Also, we live in an age of just-in-time learning and actions, that does not leave room for practice, and therefore perhaps eaves no room for excellence. Does whatever “comes next” allow me time and space to practice what I must to be competent to handle “what comes next” after that?

10. What if…? (e.g. we lived in a world without property, or without growth) The purpose of asking “what if” questions, in my opinion, is not to lead to the subsequent question So how do we make that a reality? That’s loading the questions in a way that is sure to lead to discouragement. Things are the way they are for a reason. The purpose of “what if” questions, I believe, is to open our minds and imaginations to what might have been, or might one day be, or might be possible on a small scale or as an experiment. It’s creating another model of the world to mine it for ideas and insights. If we lived in a world with no growth (no population or economic growth), for example, would it be sensible to make new building and automobile construction illegal? What would that mean for dealing with urban sprawl, brownfield redevelopment, forest destruction, the redefinition of community, recycling, renovation, craftsmanship? What can we learn from that that we might apply to the world we have? What could we be doing therefore that would be sensible even if that “what if” wasn’t even a possibility? If we lived in a world without (private) property, how would we make zoning and development decisions? How would we negotiate what gets built and manufactured, and who gets to use it? What can we learn from this that might be useful and bold, even in a “private property” world? What if… we lived in a world without money? What if…?


I’ve tried in this post (it’s hard) to avoid proffering advice. If you choose to reply to this post, please tell me, and other readers, what you have tried doing to answer these questions, rather than suggesting what others “should” do. Or add to the list — I stopped at ten, but there are undoubtedly other important, hard questions that merit consideration and thoughtful reflection. I’ve asked a hundred questions in this post. The purpose isn’t to solicit answers, but to challenge you, if you’re so inclined, to ask them of yourself (actually I wrote this post to challenge myself to ask them of myself more often).

So, what is the reward for the hard work of asking and thinking about these questions? For me, there are two rewards. The first is that I feel a little more in control of my life, and of myself, a little more conscious of and self-directed in the choices I make. It helps me in my striving to be nobody-but-myself.

And secondly, even when my mind doesn’t want to ask these questions, my body is asking them all the time. It is telling me in a thousand ways (stress-related illness, the embodiment of my anger, sadness and fear) that the decisions I make and the way I lead my life often don’t make sense. My body’s been good to me, and I believe it is in my best interest to listen to it, and think about these questions, and even let it have its say in my reflections on them. Doing so helps me cope with and make a tentative peace with this terrible world, far more effectively than the popular alternatives of escapism and inurement. The questions may be hard, but the alternatives of an unexamined, unquestioning life are, I think, harder still.

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5 Responses to The Ten Hardest Questions

  1. claude says:

    You can tell a man is SMART by his answers
    You can tell a man is WISE by his questions


    Is there life before death? — that is the question!


    “I seek the meaning of existence.” said the stranger.
    “You are of course, assuming.” said the Master, “that existence has a meaning.”
    “Doesn’t it?”
    “When you experience existence as it is — not as you think it is — you will discover that your question has no meaning.”

    and last

    Q.- “why did the chicken cross the road?”

    A.- Albert Einstein — Whether the chicken crossed the road or the road crossed the chicken depends upon your frame of reference.

    A.- Buddha — If you ask this question, you deny your own chicken-nature.

    A.- etc…

    Thank you for a most inspirational post !

  2. Jon Thorne says:

    What works for me … Is to focus on how I choose to socialise.

    How I socialise effects how I think … What I say and do. So the biggest choice I have is how I choose to socialise

    The choice I took was to socialise in approval seeker mode or self motivated mode …

    More on my website …

    Hope this adds :)

    Cheers Jon

  3. jj says:

    One of my own philosophical questions is: “how can I learn to be content with what I already have?” It is something I am still working on, but I find that taking a few moments every day to reflect on the things I have to be grateful for helps a lot.

  4. Bill Martin says:

    Thank you for the hard work of writing the hard questions. Based on your closing comments and on my own experience I would add question #11 – “What is my body telling me to do?”

    I find the practice of Qigong helps me focus on that question. When I allow the rigidity and resistance in my physical frame to dissipate, I find the mental resistance softening as well.

    You do good work, difficult work. Keep it up and enjoy it.


  5. Anonymous says:

    On the #6 question… I believe it’s Tom Robbins :) He’s my favorite writer.

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