Billy's Thoughts

An Encounter with The Emptiness

Posted on Sep 10, 2023 — 5 mins read

A few nights ago I found myself sitting at my desk with this vague sense of discomfort and uncertainty.

I’d made some progress that day on a blog post I’d been writing and rewriting for a few weeks now. The progress was good. But I also felt like I had pages of notes and drafts and rewrites scattered all over the floor, and all I was doing was adding new notes and new drafts to the pile. I had no clue how or when it would all come together; there seemed to be no end in sight, and that was frustrating.1

I was also recovering from my second bout with COVID, contracted at the tail end of 2 weeks of being away from home, so I was congested, cough-y, grumpy, uncomfortable, and also antsy – I wanted to be healthy again so I could get out of my room, move about, get groceries, and just return to regular life already. (Which coincidentally also meant I could get back to fully working on this blog post I wanted to be done with already!)

It was out of this cocktail of frustration that I had my latest encounter with what I’ve been calling The Emptiness.

The meetings are rare, and I usually forget about the experience by the next day or two. But in the moment it’s like a pit in my stomach, that somehow feels like it’s always existed but has just been hiding, reveals itself and takes weight. It’s this feeling of: “I’m not satisfied with what I’ve done today. I want more. More of what, I don’t know. But there’s gotta be something else I can do that will fill this empty feeling.”

I can’t just shake it off, so I’ll try a bunch of external treatments. Maybe eating something tasty will make me feel good, so I go snack on some chips. Or maybe watching a TV show/anime with good vibes will give me that jumpstart I need.

This time around The Emptiness showed up at like 7PM, so it was too early to turn in for bed (usually after a good night’s sleep the feeling is gone the next morning). I was slightly annoyed too – I was already on sabbatical, doing fun projects and things I wanted to do. Why was I still feeling this way? (Also frustratingly: as I’m writing this post, I don’t even remember how it went away, just that it did. Slippery bugger.)

Do other people experience this too? Is this normal? Does this come from a desire to do more, be more? To make something great (before we die)? Or am I just spouting rationalizations, in an attempt to put a name to some deep-rooted unresolved emotional thing?

“Why do you write like you’re running out of time?” - Burr, Hamilton (2015)

An explanation, maybe

The closest thing I’ve found to an explanation for The Emptiness, and more importantly where it comes from, is this Dr. K chat. I’m not entirely sure if what he’s saying is Exactly How It Is, but it resonated with me and mirrors my experience.

To try to recap the idea in my own words:

I’m probably skipping over a lot of useful connective tissue here, and I’m definitely skipping over the examples and exercises that Dr. K does with Dantes that really help drive home his points. But if any of this resonates with you or intrigues you, I suggest watching the entire interview, it’s so good.2

If you’ve had similar experiences feeling this kind of Emptiness, I’d love to chat and exchange notes! Shoot me an email at [email protected] or DM me on Twitter.

P.S.: This is just one component of The Thing I’ve been processing and trying to write about for the past few weeks now. Kind of like the appetizer of the meal. As for the main course, here’s a little teaser: what if I thought my sabbatical was about finding a new career, but I was actually grasping at trying to fill The Emptiness this entire time? (Edit: here it is!)

Further reading / footnotes


  1. For some encouragement with the creative struggle: here’s a piece I like. It’s like coming up for air hearing other artists also talk about their struggles, and funnily enough to hear that the struggles never really go away (probably because we are essentially chasing after God). If you’re also feeling the creative struggle, you’re not alone ↩︎

  2. The entire chat between Dr. K and Dantes is 2.5 hours long, and I highly recommend watching the whole thing, even in and of itself, for a great intellectual and emotional conversation with a very satisfying set-up and pay-off. In a sentence: Dude-bro grindset guy, who is actually extremely self-reflective, comes to see the emotional root of his defense mechanisms and is shown a whole other emotional dimension of how to understand himself and find security ↩︎