obliquity
04 Nov 2026 - 04 Nov 2026
- book Obliquity, by John Kay with the thesis that goals are best achieved indirectly. The author has a business background and a lot of the stories are about how companies with core real-world values often outperform those that are more explicitly motivated by profit.
- See also Ken Stanley/Joel Lehman book The Myth of the Objective (via VGR )
- VGR has taken up the concept, what does he say?
Venkatesh Rao (@contraptions): "Thought of a term I want to work out. Oblique Altruism, as an evil twin of Effective Altruism. Inspired by the core idea in John Kay’s book Obliquity, as well as the Ken Stanley/Joel Lehman book The Myth of the Objective. The first argues that for complex problems, going at it…"
- Ask Claude(actually AskZirp but don't have the machinery for that yet)
- Rao wrote very little about obliquity by name. What he did write puts him close to John Kay, but more radical.
- He saw Kay as a parallel thinker. In a 2018 tweet he said he was reading Obliquity and noticed it came out in 2010, just before his own book Tempo, with a very similar premise: stories rule, and our standard idea of rationality is flawed. In Tempo he framed this more cautiously, as a contrast between "narrative" and "calculative" rationality. Kay's book appears in his bibliography and is cited once, in the Ribbonfarm post "Random Acts of X."
- His own version goes further than obliquity. In the Breaking Smart newsletter piece "Life without goals" (2019), he argues that in creative work, setting a goal can destroy your ability to reach it. He calls this the "objective paradox": a goal shuts out the unexpected connections that produce big breakthroughs. Kay's obliquity still assumes a known goal reached by an indirect route. Rao says that in creative work the goal usually isn't properly defined in the first place. His alternative is to tinker in ways that expand what you're able to do and let the medium suggest the message, so "you'll know what you want when you find it." When a goal seems to have been set and then achieved, he says that's usually a story told in hindsight.
- Goals are for destruction, tinkering is for creation. He thinks direct goals do work for destructive or analytical tasks like war aims, short-selling, or taking a machine apart, because entropy is on your side there. His summary: "Plan your destruction with goals, your creation through tinkering." He closes with the quip that the best way to achieve any goal is "by accident."
- Related idea, "mediocratopia." In this series of posts he argues against optimizing at all. He recommends keeping slack and reserves, and deliberately tangling your objectives with other people's so that none of them can be optimized. His example: you want to go north and I want to go south, so we compromise on east, and together we get much farther east than either of us would have gone alone. The service also produced a first-person answer in Rao's voice. It makes the same points as the excerpts above but is a reconstruction, not his own words, so everything here comes from the actual source excerpts. Sources:
- "Life without goals," *Breaking Smart Newsletter 2015–2019*