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Obliquity: Why Our Goals Are Best Achieved Indirectly

I'm in a weird situation: one of my favorite concepts that I learned from books doesn't yet have a great book that explores it. Why Greatness Cannot Be Planned was the first time I encountered it lucidly. The idea is roughly in the neighborhood of:

  1. All truly great things were discovered by accident.
  2. The most direct route towards greatness isn't direct or prescriptive.
  3. Planning greatness is basically impossible.
  4. Wandering, driven by curiosity and interest, is critical.

This idea is incredibly powerful, and while Why Greatness Cannot Be Planned was good, I felt that it didn't fully explore the space that I wanted to understand. I can't quite put my finger on what's missing.

Obliquity is another attempt, from a business-centric perspective. As a firm member of the "business leadership" genre, it uses case studies and large narratives to paint the picture of this idea. And yet again, I felt it missed for me. For one, this business-genre approach doesn't work well for me anymore (for example, if you know the actual specifics of a case study or company, glorious arcs feel oversimplified and cherry picked). The writing felt basic and too simple. This idea is powerful, and case studies about how companies didn't optimize for short-term gains seemed somewhat silly.

So, I'll continue searching.


These are entirely subjective, and roughly try to capture my personal enjoyment and usefulness, and how likely I'd recommend it to others. Don't read too much into this unless you love my judgement. Rough guidelines:

A: Top quartile. Changed the way I think about something.

B: Worthwhile. I took away something useful.

C: Didn't hit, wouldn't directly recommend. Likely won't revisit.

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