I have some questions for you ...

My shortlist of questions worth living in

Midcentury Memories – photo collection by The Anonymous Project

I guess I’m a collector of questions. In the last few years, I’ve been tucking them away like glinting treasures, gathered from books or conversations, here and there. I don’t always know what draws me to a particular one, other than its aliveness or mysterious promise. Like a moth to light, I feel drawn toward the power of inquiry some questions seem to hold for me.

This post is different in form and function from my usual essays. Like a small open jewelry box, I just want to share some of my most cherished questions I’ve carried around and returned to. Some have already changed me. Others are ongoing conversations or remain patiently waiting for some future answer. When I remember where I picked up a question, I’ve included the source.

Maybe some of them hold some spark for you too.

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What do I actually like and why? (Ezra Klein)

Is the thing I work on what I want to work on most?

When I’m learning about others or comparing myself to others: Am I willing to make the same sacrifices and trade-offs?

Is the decision I’m about to make reversible or irreversible? (Jeff Bezos)

What would this look like if I removed half? Would I still like it as much, or more?

Would I do {X} if I could never talk about it?

What might this look like if it were easy? (Tim Ferriss)

Instead of asking what will I force myself to become, what would it look like if I shifted the question instead to who I am curious about being?

Who wrote the software running in your head? (Naval Ravikant)

Is the upper limit of my mind as high (or higher), or lower than it used to be in college? (David Brooks)

What would happen if I looked at my story and wrote it from another person’s point of view? What would I see from this different–and possibly wider–perspective? (Lori Gottlieb)

What/who would I be without my story? (Byron Katie)

What would I want your life to look like if I only lived for a single day?

What would I do or my life look like if I knew you couldn’t fail?

Where am I now? Where do I most want to be? What’s in my way? (Brian Whetten)

How may I be complicit in creating the conditions in my life I say I don’t want? (Jerry Colonna)

What is the courageous conversation–with others or with myself–that I am not having? (David Whyte)

What will it be like for our children to grow up in a world where every question is [at least seemingly] answerable? (Dan Shipper)

If {X} is the only thing I accomplish today, will I be satisfied with my day?

What would I hate the most not doing anymore?

*the end* - oh but wait:

Which question(s) do YOU find most meaningful? What’s one question that has lived inside you for a long time, and would you share it with me and other readers?

xo.