The Five Best Books You've Never Read - Nat Eliason - #088

Nat Eliason explains that Made You Think grew out of an earlier interview podcast. A long conversation with a friend about an unusual career and a later two-hour discussion of Nassim Taleb's Antifragile showed him that audiences valued sustained discussion of difficult books. The new format therefore centers on reading demanding works and discussing their key takeaways rather than adding another conventional interview show.

The conversation treats finishing a difficult book as a mixed achievement. Nat describes a strange, very long science-fiction novel whose plot is not the main attraction; the satisfaction comes partly from completing the task, much as a marathon can feel rewarding at the finish even when much of the race is unpleasant. That distinction frames the later discussion of reading: persistence matters, but forcing an uninteresting book can also reduce the amount one reads overall.

Nat attributes his progressive-summarization method to Tiago Forte. He reads on a Kindle and highlights passages that seem useful, sometimes adding contextual signposts. Readwise transfers the highlights into Evernote, where he adds structure such as section headings. He then works through layers: keeping the highlights, bolding the most important parts, highlighting the most important parts of those bolded passages, and sometimes adding a short executive summary. Nat does this immediately because he sells access to his notes, whereas he recalls Forte adding layers when a note resurfaces for a real use.