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Cause of Pain — What hurts? And why does it hurt?

Article date: 2026-06-14 Context/mood: Written in direct response to a Y Combinator rejection ("your startup was not selected for an interview") — the lived event behind the essay's "An investor rejecting you is pain. Giving up because of that rejection is suffering." Processing a real setback in real time, which is why it lands on a usable rule rather than a clean consolation. The published blog reproduces the rejection screenshot below the text. Format: Structured, argument-driven essay built by accumulation — very short one-line paragraphs and lists, with literal equations as load-bearing devices. Cooler and more analytical than the lyrical Letting Go, but lands in the same place. The most explicitly practical / prescriptive piece in the corpus. Raw: 2026-06-14-cause-of-pain

Core move

Suffering is caused by expectation, not by events. You suffer when you hoped for an outcome and reality gave you something else; the bigger the expectation, the bigger the gap, the greater the suffering. The real engine underneath expectation is investment (effort and imagination both create it). The fix is not to lower effort or kill hope, but to drop entitlement to outcomes — "reality owes you nothing" — landing on the formula Maximum Effort + Minimum Entitlement.

Key extractions

The thesis:

I think the sole reason for suffering is expectation. Or maybe hope.

The gap mechanism:

The bigger the expectation, the bigger the gap between reality and what you wanted reality to be. The bigger that gap, the greater the suffering.

Attachment is to imagined futures, not just things:

You weren't just attached to the person. You were attached to the future you had imagined with them... It's the loss of the life you thought you were going to have.

Investment, not effort, is the root (effort = imagination here):

Someone can spend five years building a startup and become deeply attached to the outcome. Someone else can spend five minutes imagining their dream life and become equally attached... The common factor isn't effort. It's investment.

The equations (his own notation):

Effort → Investment → Outcome
Expectation ≠ Reality → Pain
Resistance to Reality → Suffering

The central distinction:

Pain is losing something. Suffering is refusing to accept that you lost it. Pain is unavoidable. Suffering might not be.

Why not just stop trying:

A life without effort is also a life without ambition. Without love. Without risk. Without achievement. Without meaning... The goal isn't to avoid pain. The goal is to become comfortable with the possibility of pain.

Non-entitlement:

Which means reality owes you nothing. Not success. Not love. Not recognition. Not fairness. Your effort buys you a better chance. Nothing more.

Productive delusion (note the self-aware word choice):

I am delusional enough to believe that if you keep putting effort into a certain direction for long enough, you increase your odds of getting lucky. One day, luck might finally meet preparation.

The landing:

Maximum Effort + Minimum Entitlement. Give everything you have. Expect nothing in return. Care deeply about the process. Stay detached from the outcome. Pain may still be unavoidable. Suffering might not be.

Why this source matters

This is the clearest resolution attempt of his single biggest live tension, agency-vs-acceptance. Where earlier pieces oscillate between "shape the world" and "let it go," this one fuses them into a single simultaneous posture: act fully (agency) and expect nothing (acceptance). It also imports the detachment-from-outcome idea of letting-go-is-central and applies it prospectively (don't get entitled in advance) rather than only to loss after the fact. And it re-uses the productive-delusion move from 2025-07-19-rationality-vs-delusion — "delusional enough to believe" — feeding rationality-used-vs-rejected.

Tonal note

His most prescriptive register so far — it gives an explicit operating rule rather than landing on "and that's okay." Still hedges ("Maybe," "might not be") and still grounds in concrete cases (breakup, startup, investor, job application). Stylistically distinctive: accumulating one-line paragraphs and literal equation lines as rhetorical beats.

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