I feel the desire arise to write an essay. It might be the coffee, or the Bonnie Dobson, or the morning light coming into my office. It might be the book I am reading (Creative Selection), or the last Tweet I sent, or the Podcast I heard last. It could be all of these things, but it is a familiar feeling that I listen to. I open up the word editor and start typing.
But of course the question comes urgently as it always does: what will I write about? Isn’t it weird that the desire to write precedes the “about what?” part? It doesn’t always happen this way, but it often does. Could I go back and point out which of my writing started with pure desire and which started with an idea of what I wanted to write? I probably could. I distinctly remember my essay Digital Infants starting on a whim one night in Greenpoint, Brooklyn. It was closer to how a poem starts than an essay. I had no idea where it would go but out came the phrase “I’m not sure. We like Persian rugs and odd coffee mugs”.
I have a few things on my mind right now. Things like creativity and sources of inspiration, playing “the long game” in your career and life, creative programming, the power of giving yourself creative mandates, the benefit of having multiple projects going on at once, the lessons I’ve internalized, friendship and partnership, documenting your work well, building interest in your work and finding likeminded people, collaboration, how to learn things well, The Beach Boys’ harmonies, the magic of demos (in engineering, design, and music), batching your life, Archimedes questions, and more. I think all of these could be interesting explorations, but can only choose one for now.
The most surprising item to show up in that last paragraph was Archimedes Questions. I have never heard that phrase in my life yet I typed it. I combined the idea of Archimedes’ Lever with my recent wondering about why asking yourself (and others) thoughtful questions seem to solve almost any issue. These high-leverage questions hold a strange power to disarm, cut through the mud, and get the brain exploring rather than staying on script.
I’ve been fond of good questions for a long time. What is the earliest example of this I can think of? I am not sure right now, but I do remember introducing questions into my poetry and writing very early. I saw how much personality a good question has.
“Do I dare Disturb the universe?”
“Wouldn’t it be nice?”
“What sphinx of cement and aluminum bashed open their skulls and ate up their brains and imagination?”
“To be or not to be?”
“So what?”
“Do you realize?”
“Do I contradict myself”
“Where’d all the time go?”
But style aside, aren’t questions at the root of countless prescriptions for working through problems? Therapy: meet with someone skilled at asking questions and answer them honestly over time. Journaling: ask yourself what’s on your mind and answer honestly on the page. Relationships: ask each other questions and examine the answers together. Inventing: framing the question simply so that it can be answered elegantly. Startups: “what if…?”
Of course I am forcing these somewhat, but not entirely, they sort of work.
Aren’t questions the antidote to an unexamined life too? Is it that we associate questions, linguistically, with another entity existing to ask them? So that when we ask ourselves questions, we are more objective, imagining some other “self” asking them? They also immediately signal that an answer should be given in reply. So we must search for an answer and most of us don’t want to be wrong, so tend to actually look for the real answer. I think this might be why the common advice of stacking three questions (why? why? why?) is given. The first answer may be partially true, but it also might be the more polite or convenient answer. Stacking questions is like refining a LLM prompt to get higher fidelity results.
Here is a current guess at what makes a question good: A good question simply tricks the person being asked it into answering a staler version of itself which the person has had practice answering falsely. Instead of asking “how are you today?” for instance, what if I asked you “what was the best part of your morning so far?”? That isn’t a great question by any means, but it is a unique path into the central idea of “how has your day been? what’s your current mood?” The answer someone gives to that modified question will quickly cue you into their mood and state of mind.
I wrote this Tweet about questions that sneak past the stale (but important) question “what do I want?” in response to this Tweet from Visa Veerasamy. Notice how these make you think about things you enjoy or don’t enjoy without actually prompting you with that concept?
I am fond of the idea of collecting questions (I am fond of collecting things in general). Here are some of the current questions I am asking myself.
- If I couldn't tell anyone about this, would I still do it?
This is a clever way of asking yourself what your true motivations for doing something are. It helps detangle the tricky bundle of wanting to do something and wanting to be known as someone who does something. Picked this up from a recent Tim Ferriss interview.
- If I only had half the time in the day to work, what would I work on?
A question for prioritizing.
- What do writing, inventing, and music have in common?
A question that hopes for a unified theory of Jake. Writing, inventing, and music are the three things I’ve found that I truly love (and would answer yes to question one about) so I am wondering which traits they share. I wrote a bit about that here.
- At 10am, what 5pm activities do I get excited thinking about? At 11pm, what 7am activities do I get excited thinking about?
A new question that seeks to list the things that bring me the most energy and the things that take it away.
- If I made a zine to articulate my vibe / goals, which other people would be featured?
A new question that asks me to find the people I admire and wonder why that might be.
- If I only had six months to do what I am hoping to do in five years, how would I do it?
Got this one from here and have heard it before. It’s a good one for asking yourself to be more ambitious and more than that, make a plan for your ambition.
I think I will stop here for now. But before I end this session I want to list the other ideas that came to mind writing this that might be worth exploring more deeply:
- compile the most famous questions from literature, music and other media.
- create an ongoing post of all the good questions I am collecting.
- create a list of the people known for asking good questions.
- a unified theory of good questions.
- why collecting things is so addicting / cool.
- reflect on my last five favorite ideas and document what I was doing when I had them.
Would love to hear some of your favorite questions, if you have one that has helped you leave a comment!