What Questions Never Leave You?

[Each Tuesday I take the top voted question from readers and answer it (submit yours here).  With 119 votes, this week’s winner was submitted by Max]

To answer the question about what questions never leave me I skimmed through my journal. Few people keep them anymore and I don’t understand why: it’s a secret weapon for sell discovery. A diary is a time travel device anyone can make. It lets you jump back in time and see what you truly thought in the past, which is very different than what you believe you thought. Human memory is terrible and reading a journal you discover hidden patterns in your thoughts and feelings you might never discover any other way. Writing in a diary today is a gift to the future version of ourselves.

I didn’t find many questions in my journal. There were certainly some, on average one per entry, but is that a lot? Since I have no basis for comparison I don’t know if the number I found was low, high or average. And of course most of my thoughts stay in my head, never making it into my journal which means at best my list below is a guess. I considered the questions I believe I ask myself often, but since I wrote it knowing it would be published it might be biased towards ones that sound impressive, rather than ones I truly ask myself often.

Death is a powerful motivator and is often on my mind. It’s no surprise many of my questions center on time and how I use it, as do the rules I live by. Since I ask these questions often I have answers to them that rarely change, which suggests I need to ask myself why they haven’t changed in a long time.

  • Is there any point to existence, or the universe, at all?
  • What is the best way to live given what I know, what I don’t know and what I can’t know?
  • What are the meanings of my life that I have chosen?
  • Is my time aligned with my goals?
  • Am I giving time to the people I care about most?
  • Am I giving time to the ideas and beliefs I care about most?
  • Are my actions aligned with my beliefs?
  • Am I taking my life seriously enough?
  • Am I enjoying life and not taking life too seriously?
  • How am I not myself?
  • What am I hiding from?
  • Am I pushing myself and loving myself?
  • What assumptions am I making that I don’t realize?
  • What blind spots do I have that are hurting me or others?
  • What questions have I forgot to ask myself?
  • Should my answers to these questions change?

What questions do you find yourself asking often over your life?


8 Responses to “What Questions Never Leave You?”

  1. Maximilian

    Hey Scott!
    Thanks for answering my question. I enjoy a happy feeling right now thanks to you!
    I have a “random thought” journal as well as a question journal. I realized that making the questions explicit allows me refine them, choose between them and see whether my answers change over time (which it does a lot, as I am 19).
    I do have questions without final answers such as:
    What makes me unique? What do I like? What makes me feel alive?
    What aspects of my personality do I under or overexpress?

    And progress questions:
    How can I expand my perspective?
    What stages of personal development can I identify and which are relevant to me?
    How can I find out ideas that are relevant to life? Where and how? Are there really relevant or do I overintellectualize?
    Why do I ask this question?
    How do other people grow and choose in life? What is it that they are burning for with passion?

    To relationahip questions:
    What makes me happy in RLs and what makes others happy? Who are people I enjoy?

    I realized that I like to contemplate good questions as much as good ideas. And I wonder which questions someone asked and why.

    Yours, Maximilian.

    1. Scott Berkun

      Thanks Maximilian for the question and the comment. You are very wise for 19, or any age for that matter. Cheers to questions!

  2. Sean Crawford

    The asking of questions is a powerful thing: Like having goals. I can say that because I too keep a journal. I could consider answering just one Scott question per day, keeping it going like a background process as I wrote about everyday things. For me that would be an optimal amount of focus, rather than grazing all Qs all at once.

    In my middle age I no longer have bad days of swimming in a dark blue sea, but if I did then that “truth” is not what I would expend any time writing about. Because such truth would not serve me. Better to have a semi-permeable membrane where only brighter stuff is worth writing about, even if that means writing little, and leaving my desk and doing non-journal things instead.

    Today I use my journal not only for satisfying philosophy questions—so much fun!—but also as a means to approach the self-discipline of Scott, by writing in the morning what I intend to do in the day, seeing what happens, and then writing what I did. This is because I have a crazy fear of becoming a couch potato. But too much couching won’t happen, of course, not if I stay accountable and positive.

    1. Scott Berkun

      As I’ve aged I add to my journal less and less. When I was younger I had more thoughts that need a home. Now it seems I find other people and places for those thoughts to go. But I do think returning to a regular practice would be a good thing in many ways. Perhaps I’m hiding from certain questions and thoughts more than I realize. Only one way to find out!

  3. Dan Szuc

    Comfort in the idea that we only get one chance at this life.

    So enjoying as much as we can from this chance experience and also to do as little harm on others as possible.

    One recurring question is why do humans have such capacity to inflict pain on each other and not learn from it?

  4. Dave Gordon

    The worst questions are those that make you wish for a do-over. I’ll be 60 years old this fall. Lately, the question that keeps recurring to me is: “If I die tomorrow, will someone have to clean up a mess?”

    There are two kinds of people in this world: those who can walk past a mess, and those who can’t. If you’re the sort who rounds up two or three shopping carts as you cross the parking lot, you’re in group two, with me. My project management training and experience has me making checklists and going over them with both my colleagues and my wife, designating successors and delegating authority, and generally preparing to leave this world, suddenly. And the funny thing is, it’s been a release. A week before my birthday, I’ll become the longest-lived male in my lineage. That thought has been weighing on me for a while now, and now I realize that I’ll probably make it. And I’m grinning.

    The best questions are those where our answer influences our behavior, and our outlook on life. We don’t need a do-over – we need to figure out what to do next.

    1. Max

      Hey Dave,
      belated congratulation to your 60th birthday!
      I like your statement:
      “The best questions are those where our answer influences our behavior”
      You highlight the instrumental nature of questions. I think this is very important, given that asking so many questions makes you prone to overthinking.

  5. Teknik Komputer

    How has Scott Berkun’s writing and public speaking impacted the way people approach creativity and innovation?


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