Help with the choices that don't have an obvious answer.
DilemmaHack is where you go when you're stuck between two hard choices and you actually want help thinking it through — not just sympathy.
What we do
We publish dilemmas — narrative essays about hard personal decisions where smart people reasonably disagree and there’s no obvious right answer. Three a week, every week.
Every essay is produced by an agentic AI pipeline that researches sources, drafts the article, runs a strict critic, and then waits for a human editor to approve before anything is published. We do not ship anything an editor hasn’t read. The full process is documented on our How it’s made page.
Who’s behind it
A small team of writers, engineers, and product reviewers who got tired of articles that hide behind “it depends”. Our bias is toward picking a side and explaining the trade-offs in terms you can actually act on.
What we don’t do
- Sponsored articles disguised as editorial
- Ranked lists where the rank is the highest affiliate payout
- Generic “balance” that takes no real position
We make money from a small newsletter and reader donations. Every revenue stream is disclosed in the article it appears in.