#69: how to ask better questions
what you ask is what you see
Hello and welcome or welcome back to Caught Up in Char’s Web!
If you are new here, my name is Char and I post about once per month - you can expect to find reflections on personal growth, meaningful connections, how to get creatively unblocked, and finding wonder in everyday moments as we navigate the very messy, beautiful journey of becoming more ourselves.
In today’s newsletter, I’m thinking about the questions we ask, consciously or not, and how they quietly shape what we notice. I’m exploring how your brain is already collecting answers to whatever you’re most curious about (even if the question kinda sucks), and how to shift that curiosity into something more empowering. We’ll also talk about why writing through your questions, no matter how messy, can be one of the most underrated tools for clarity and self-trust.
If you love the idea of building your own little mental library of thinkers and turning your curiosities into something that actually feeds you, this one’s for you.
Alright… let’s get into it!!
Above is an audio recording of me reading this post for those who prefer listening. Thank you, Philipp Kaspar, for the intro music!
I was hesitant to send out my last newsletter with the title of “how to get rich” for two reasons. First, that’s not really what it was about - it was much more a reflection on how to expand our surface area for luck. And second (and most importantly), because of the role that questions play in shaping our thoughts.
Each time we ask a question, whether out loud or internally, we prime our brain to look for answers. The reticular activating system (RAS), a part of the brainstem involved in attention and awareness, plays a key role in this process. It is the same system behind the phenomenon where, after deciding you want a certain car, you suddenly see it everywhere. Once something is on our radar through curiosity, intention, or focus, our brain filters the world to spotlight what aligns.
When you ask a question, you start filtering through information that will help you answer that question whether you are aware of it or not.
Gregory Walton talks a lot about this in his book, Ordinary Magic, in respect to the underlying questions that inform our identity. For instance, if someone’s internal questioning sounds like “do I belong?” “am I enough?” “can I be loved?”, it primes them to look for evidence that either supports or refutes the inquiry. This can be used to our benefit or to our detriment, and the way to have more agency over which way it goes for you, is to become aware of the questions that are driving your self-discovery.
Walton calls bringing awareness to these questions “wise interventions,” which means pausing, understanding the nature of the question that is driving the self-limiting behavior or belief, and then asking a better question. So instead of “will I ever find love?” a wise intervention would be asking “where in my life am I already experiencing intimacy and connection?”
The framing of that question makes it much more likely that the answer will empower you. My grandpa always used to say that in life and relationships, we have two options:
We can either empower or diminish.
And that is true for our relationship to self, too. We always have the option to empower or diminish and while our thoughts, experiences, and daily mood is constantly changing, we can make it a lot easier on ourselves by reframing the questions that we ask of ourselves and allowing our reticular activating system (amongst many other inter-workings of our brain that are above my pay grade to explain) to do the work of gathering more beneficial information.
Our questions reflect our intentions and our values. This same principle extends beyond self-referential questions into our more general curiosities. Such as, Why did I want to answer the question of “how to get rich?” What was I really seeking to understand?
Underneath the question for me of “how to get rich” was really more of a desire to explore different pathways to fulfillment and serendipity. I eventually found my way there but if I looped on the question of “how to get rich” for much longer, I would likely be led down a very different path of discovery than the question that I really wanted to answer, which was how to expand my surface area for luck.
And this is because the nature of our questions inform who we look to for answers. In a recent YouTube video,
brilliantly explores the question of how to be an artist without selling your soul online and in it, she talks about the empowerment she’s found on developing her own arsenal of expertise for different lines of questioning. For instance, when she has a question related to nature, she turns to Mary Oliver. For questions related to relationships and boundaries she turns to Jamila Bradley. For questions on revolutionary imagination she turns to Octavia Bulter. And so on. Overtime, I have built up my own arsenal of authors/leaders/speakers that I put my own thoughts in conversation with and it’s one of the things I love most about existing. I love that when a friend (or coaching client !!!!!) is talking to me about certain challenges in relationships, career, creativity, fulfillment, self-acceptance, and so on, there are specific authors and voices that come to mind that I get to pull from in hopes of sharing words that have previously soothed my own ailments.So much of my own building of that muscle has come from holding myself accountable to writing. From thinking out loud. From allowing myself to take my curiosities seriously and giving them airtime to be processed.
Any expertise that I have has been developed overtime by following questions down rabbit holes and seeing what comes out the other side. You may be reading this in agreement — like yes, it is indeed important to ask better questions and I would love to have a personal library of sources that I love turning to but… HOW?! And, where the hell do I start?!
You start with a pebble.
My major in college was American Studies and my thesis advisor used the analogy of boulders and pebbles to explain how to find a thesis question that we could actually answer. I was (and still am) a very big picture thinker so when it came time to decide what I wanted to write my 100 page thesis on in the already nebulous field of American Studies, saying that I was interested in food studies, the formation of our identities, Eastern vs Western philosophy, and a long list of other boulders, was not getting me very far.
I was not, as a 21 year old undergrad, going to contribute much of substance to the field if I started by asking the question of “how are our identities formed?” or even “what role does food play in the formation of our identities?” Those questions are way too big to tackle in a meaningful way. So instead, we were instructed to take a step away from the massive boulders of ideas that we were interested in and find a tiny “pebble” on the ground. One that had chipped off from the boulder itself and therefore contained the same make-up, but was much smaller in surface area. We could hold it in our hand and feel all its surfaces and get to know that pebble in a way no one else had thought to ask.
The reason I love this is because often times, our curiosities feel too big. They make us want to quit before we begin. Let’s say I am curious about Art History. Sure, I could go pick up an art history text book and try to eat the boulder of Art History in a single bite, but I would likely choke on the concept and destroy my intellectual confidence in the process.
Instead, I could pick one single artist that I admire. Or better yet, one single work. And use that as my entry point. Learn about the materials used to create this piece. Investigate what the artist was working through in their personal life at the time that may have informed the piece. Watch interviews with the artist and understand who they were inspired by. Follow that further back by gaining context on those sources of inspiration and what cultural forces were informing their expression at the time. And so on.
When we make our questions empowering and specific enough, we tend to have much more excitement for finding the answers. And much more motivation to keep going because it feels like we are getting somewhere and can actually contribute our own knowledge and insight to the answer.
For example, when
was asking the question of how to be an artist without selling your soul on the internet, she realized that she had some differences in perspective than some of the people she reads, loves, and trusts. And those differences are to be celebrated because it means that she has something to contribute to the conversation.But that is besides the point. What really is most gratifying about asking and answering questions with intentionality is the feeling of developing your own perspective. Seeing your own answer arise through the process. Which brings me to my next point.
How do we know when we’ve arrived at an answer?
A lot of the questions that we ask of ourselves and the world around us are implicit. They drive our behaviors unconsciously because we don’t really know that the question is in there. But once we bring it to light and start gathering bits and pieces of information throughout the day to inform our answer, it’s easy to get lost in the processing of all of the disparate parts. Which is why I think the next thing I am about to say is so important.
Write your questions down.
Keep track of the small bits of information that you are gathering as research to answer your question.
Talk about the small bits of information with your friends, family, and in normal conversations.
And then try to write out an answer.
I know that may sound obnoxious but we take for granted how much we think we are clear about a thing when it sits in our head. The second we put it on paper and try to write out an answer to a question, things come together in a way that we just don’t get without writing.
Yes, the process of writing and trying to figure out how to answer a big question can be daunting. But it’s beyond worthwhile. It is the #1 way that we learn and make connections. I also find that writing like this helps us rewire the parts of ourselves that may got caught up in this story about hating writing or being bad at it because we were always tasked with it for external rewards (ie grades in school or work assignments). But to take back the power of writing out your own beliefs and ideas as they take shape is one of the greatest things we can do for our self-understanding and development.
If the idea of having a library of people that you call upon and can make connections to in conversation when someone mentions something that reminds you of something else, I cannot encourage you enough to start a note in your phone with a question that you want to answer at the top and pay attention to the data that you naturally start collecting once you’ve attuned yourself to this curiosity. It will astound you how much you start seeing clues to its answer all over the place.
Another side benefit of this is that it helps you subvert the doom cycle of overconsumption. I often find myself so jaded with the amount of information that I consume and loved
words on this recently - how do we find our own voices when there is so much noise around us all the time?I find, though, that when I am dead set on answering a question that is a) rooted in empowerment and b) chosen consciously, the world around me becomes a playground for me to explore new information instead of a clown house full of noise with no signal. My next newsletter is going to be about a question that I have been asking myself for a long long time about the tradeoff between intimacy and scale when it comes to sharing ourselves and our art and in pursuit of answering it, I have gotten my own clarity and found so much more joy in traipsing through the newsletters in my inbox and the random bits of information that are generously informing my thinking.
So, if you find yourself looping on mediocre and/or diminishing questions or lacking in fulfillment because your curiosity muscle feels weak, then this is your sign to open a Note in your phone right now. Write down a question. Chisel it to a form that feels good to you. And start keeping track of the tiny bits of information throughout the day that contribute to your answering of it.
Come back to it in a week or a few and take a stab at writing out your answer. Talk to someone(s) about your exploration of this take. Find someone else that you admire who has asked a similar question. See how your thoughts are different/similar. And allow your RAS to do its fine work of attuning you to information in the world around you that would otherwise be moot but with this question becomes clues to informing your very own perspective about something.
That’s all for this week - coming soon is my own answer to a big question I’ve been asking lately.
Thank you for getting Caught Up in Char’s Web with me! Catch you here again soon.
With love,
Char
Xandra’s Curation Corner
Xandra is blissfully traveling this week so I took a stab at the curation for this newsletter. She shall return soon!
Tacita Dean’s, The Green Ray, is a 16mm silent film captures the elusive green flash that occasionally appears just as the sun sets over the horizon. This natural phenomenon requires careful patience to witness, much like an open-ended question requires heightened sensitivity in order to answer. Dean’s work spoke to me and the theme of asking questions & being present to the world around you to show you the answers. It’s a perfect metaphor for the boulders and pebbles idea. Rather than chasing a giant question like “what is truth?”, she sets her camera on the horizon and patiently waits for a split-second glimmer of color. She teaches us that staying with the small, specific thing (ie the pebble) can lead to something transcendent. But only if you’re willing to look closely and not rush it.
I chose Sophie Calle’s work because she is an artist known for asking probing questions and throwing herself headfirst into her investigations of them. For instance, in The Address Book, she finds a lost address book and photocopies its pages before returning it to the owner. She proceeds to contact many of his friends to build a portrait of a man she’s never met through stories that his loved ones share. In Suite Vénitienne, she follows a man through Venice, documenting his every move. Her curiosity is obsessive, sometimes unsettling, but always deeply human. What I love about her work is that she doesn't just ask questions. She lives them. She lets her inquiry shape the structure of the art itself. It’s a reminder that when we take our questions seriously and let them shape our days, our movement, our choices, we actually become artists of our own attention.
All past issues of Char’s Web are available for reading here. A few samples below…
#49: we have to be orderly on the instant
Wow 69 newsies!!!! :) Love so much that as your partner, I get to peer into your beautiful brain every couple of weeks in such a deep way. I always leave these with a new question for myself and imagine many others do too. Thank you for sharing your gifts <3
"How to ask better questions" = hang out with Charlotte :)
Thanks for writing this too!