Will You Embrace the Work of Asking Questions?

I remember when it felt like enough to offer words of encouragement, don’t you?

However well-intentioned, these fleeting revelations didn’t always encourage much room for a response, did they?

Or maybe you were on the receiving end of these messages, thinking to yourself, What could you possibly know about my work? My life?

Did you get my email — text, DM, comment?

Because when the world locked down, we retreated to a life online — did I see you there?

(Weren’t you always there?)

There, in the four corners of the screen with a million other pixels striving to be heard?

Or how about in the group chat, sending viral memes and emoji love letters in place of surface-level texts?

Or during the fourth Zoom meeting of the day, when you were accidentally on mute?

Did you see me whisper-shouting over the muffled banging of jewelry against desks, fingertips against keyboards? Can you repeat that?

Sorry, can you say that one more time?

Why isn’t this working?

Can you hear me?

What exactly are you asking?

If this piece is about work, then should I give you some background about mine?

Like others in the digital age, I wear many hats — but that’s a story we all know well, right?

(For the sake of brevity, why don’t we keep it simple?)

Lately, my work mainly relies on asking questions, and as an interviewer, I ask things like: How would you describe your relationship with pace? Why do you think slowing down will help us live, work, and feel better?

I often marvel at my interview subjects during these exchanges — how can I expect them to have such beautiful, definitive answers as the ground shifts beneath their feet? Especially at this current moment?

But the thing is, honest answers can’t come without probing questions, can they?

As we’ve spent the last year questioning what’s genuinely working for us — and rightfully so — are we remembering that the work ahead relies on asking questions in the first place?

At this pivotal moment, what if we turn inward and consider making room for question marks to thrive in places where periods typically sit?

It’s daunting, I know, but there is a question I always ask my interviewees to help provoke deeper inquiry — perhaps it will be a helpful place to start for you, too?

What question(s) do you hope people will ask you more often?

Here, I’ll go first, but bear with me because my answers are a work in progress, okay?:

Would you?

Can you?

Must you?

Should you?

Have you?

Will you?

These questions can go any which way, and that’s a lot to take in, isn’t it?

I remember when the unknowable felt like a gift, don’t you?

Because to look up is to acknowledge— to honor — the possibilities that make life worth living, even if we can’t always see beyond their edges: What’s ahead for me? Who will be beside me? How will I know which way to go?

When we work, we demand results, and when we speak, we anticipate responses — in some cases, we even expect catharsis — but after everything we’ve been through, have we finally learned to reframe our expectations?

In this essay, I’ve set out to untangle the core of this work (my work) by writing in the style that drives it — asking questions versus making declarations— so, after all of this, what more can I say?

(Who knows?)

Has reading this piece been a strange experience for you?

(Probably — but isn’t life strange, too?)

Thank you for staying with me — can I ask one last thing of you?

Can I ask that you encourage curiosity and reciprocity as you move through the world?

Can I ask that you embrace the delicate work of asking questions at all?

It’s difficult to make meaning out of uncertainty, isn’t it?

Well, here is what I’ve learned so far: These questions will require work (they are the work), but they are always worth asking — so, are you ready?

Author’s Note: This is a “Work” submission for The Medium Writers Challenge. Thank you for your time and consideration.

Dear reader, thank you for being here. I hope this piece created space to ask the questions that feel the most urgent to you.