Variations of Vexation
An unresolv-able correspondence
Why do I want to live a life I won't regret?
Why do I keep wanting what I know won't satisfy me?
Why do I feel like something's missing—even when things are good?
Why does my life make sense on paper but not in my body?
What is this restlessness that won't go away?
Why does my happiness still feel incomplete?
What if I've built my life on something I never really chose?
Why do all my successes feel like failure in disguise?
Why do I sometimes feel fake even when I'm being real?
Why do I want to be seen so badly—and hide just as badly?
Why do I feel like I'm not really here?
Why do I keep performing?
Why can't I stop comparing?
Why do I want to be remembered?
Why do I want to be loved?
Who am I trying to become?
Who why what how when why…
If some part of you feels inundated with any one of these questions, congratulations. You've encountered what medieval philosophers called the vexata quaestio—the vexed Question. The Question that refuses to be settled, that returns like a cop you thought have left in the lurch, or a cat you thought you'd successfully given away to another family, or a stalker that won’t quit.
But here's what's strange: each of these feels intensely personal, doesn't it? Like your private existential wound, your particular neurosis, your midnight companion, your special brand of 3 AM spiral. Perhaps each one warrants its own viral Substack essay, and spelling it out in a list form like this feels mortifyingly cheap. Indeed, for we tend to think our version is uniquely ours—that we're the first person to really get / articulate how unresolved everything feels, or how exhausting the tensions are, or how nothing quite satisfies.
This is the first illusion. These aren't different questions. They're the same Question wearing different masks, like a single actor playing every role in a one-person show about human consciousness—like a tense frequency sliding through the infinite crevices of harmonic space.
The New Question is the Old Question
In much the same way, every generation thinks it has discovered the real problem. Right now, we blame the "meaning crisis," social media, late-stage capitalism, the collapse of tradition, or whatever scapegoat is trending. The Boomers had their "spiritual vacuum of materialism." Gen X had their "ironic detachment from authentic connection." Millennials have their "anxiety epidemic fueled by social comparison." Gen Z has their "algorithmic manipulation of identity formation."
Before them, the Victorians worried about the "loss of faith in an age of science." The Romantics fretted about "industrialization crushing the human spirit." The Enlightenment thinkers were concerned with "superstition blocking rational progress." Medieval scholars agonized over "the tension between reason and revelation."
Each era's diagnosis feels so obvious to those living through it. Of course the real problem is social media! Of course it's the collapse of traditional values! Of course it's late-stage capitalism!
But look closer at the wearisome pattern. Every generation locates the source of existential unease in its particular historical moment, then develops elaborate solutions that become the next generation's problems. The Romantics' cure for industrial alienation becomes the next century's problem of narcissistic individualism. The Enlightenment's solution to religious dogma becomes the next era's problem of meaningless materialism. And our currently-innovative solutions—therapy culture, mindfulness apps, authentic personal branding—will undoubtedly become future generations' primary sources of existential complaint.
It’s a magnificent recursive trap! As the author of Ecclesiastes says: nothing is new under the sun. (A self-defeating statement, for neither is the vexing diagnosis ‘new under the sun’.)
Variances of Vexation
Here's what happens when you try to solve the vexed Question: you generate infinite variations. It's like trying to escape a hall of mirrors by breaking one—you just create more reflective surfaces.
Take therapy. Therapy promises to help you understand your patterns, heal your wounds, and become more authentic. But what happens when you spend years in therapy and still feel fundamentally unknown to yourself? Now you have a new question: "Why am I still not fixed after all this self-work?"
Or consider spiritual practice. Meditation promises to dissolve the ego that's causing all this seeking. But what happens when you meditate for years and still find yourself comparing your spiritual progress to others? New question: "Why am I still so spiritually competitive?"
Or try philosophy. Philosophy promises clarity about the fundamental questions of existence. But what happens when you read everything from Socrates to Sartre and still feel lost? New question: "Why does all this knowledge leave me feeling more confused than when I started?"
The solutions don't resolve the vexed Question. They sophisticate it. They give it new vocabulary, new frameworks, new ways to ask itself. But this predisposition isn't a bug, nor a feature—it’s the core protocol of humanity.
Arc in the Book: Inevitable Crises and a Befitting Response
What if these questions weren't meant to be resolved once and for all, but corresponded with? What if the vexed Question isn't a problem, but a permanent opening of an abyss—like a wound that won't heal because it's actually an open mouth that needs to keep pouring out words, like rice spilling out of a torn rice bag?
In The Last Existential Crisis, I call this alternative framing: "correspondence". In this framing, you don't try to solve unresolv-able questions. You live it instead, by staying in conversation with it, by learning to dance with it. Like jazz, where the point isn't to resolve all the dissonance but to make music with the tension. Correspondence means recognizing that vexing "Who am I?" [and its infinite variations] isn't a information problem. It is ultimately a relational problem.
In short, the vexed Question is your dance partner. And once you stop trying to solve it and start learning to correspond with it, something remarkable happens: the Question stops being a source of suffering and becomes a source of vitality.
(This is why The Last Existential Crisis isn't simply another self-help disguised as philosophy. It's the END of philosophy. The point where thinking gives way to a different kind of engagement with existence. The book doesn't conclude with wisdom but with an invitation to keep conversing with what can't be solved.)
An Invitation to Correspond
Right now, you're at a choice point. You can continue treating these questions as philosophical problems to be solved—adding more therapy, more spiritual practice, more self-improvement to your arsenal, seeking out a new logic, all in the hopes that this approach will finally give you the answer that brings peace. Or you can try something radically different. You can learn to correspond.
Correspondence isn't passive acceptance or spiritual bypassing. It's not about "being okay" with not knowing yourself. It's about discovering that the very thing you thought was your limitation—your inability to pin yourself down—is actually the whole point.
The Question is calling. The only question is: will you keep trying to silence it, or will you learn to dance?
This is the third in a series of correspondences based on my book "The Last Existential Crisis". The Last Existential Crisis is coming 2025. This Substack will share exclusive excerpts, behind-the-scenes insights, and ongoing correspondence about what it means to be human in an age of infinite, lossy answers. → HERE IS THE MANIFESTO.
What's Coming
Over the coming weeks, I'll be sharing insights from the book that explore:
Why staring at your own hands can trigger an existential crisis
Variations of Vexation
Technology as suppression of correspondence
What happens when the theater of self-improvement finally collapses
Why nightmares are essential to sanity
Ultimate miscommunication in the form of the problem of suicide
What the jazz musician knows about authenticity that therapy does not