What to ask a library you built

Updated 3 August 20264 min read
The short answer

The questions worth asking a collection you built are the ones you cannot answer by scrolling: what you half remember but cannot name, what several saved pieces disagree about, how much you have gathered on a subject, and what you saved a year ago on something you are thinking about now. The questions that waste your time are the ones a search box answers faster, and anything the collection does not contain. A library is a small corpus, so its strength is depth on what you kept, not coverage of what you did not.

The four that work

  • Recall: 'the essay that argued saving is a substitute for reading.' You remember the argument and not the title, which is precisely where a keyword search fails and a meaning search does not.
  • Synthesis: 'what do the pieces I saved on pricing actually disagree about?' Useful because it forces the collection to speak as a set rather than as a list.
  • Stock-taking: 'how much have I saved on this, and when?' The answer tells you whether you have enough to write from or are still collecting.
  • Resurfacing: 'what did I save about hiring last year?' Old saves are invisible by default, and this is the only reliable way back to them.

The ones that waste your time

Anything where you know the exact title. Search is faster, and asking a question to get one link back is a slower search box.

Anything your library does not contain. The honest answer is that nothing covers it, which is correct and still not what you wanted, so it is worth knowing before you ask.

Anything that needs the whole library at once, such as 'summarise everything.' A collection of a few thousand items has no single summary, and a tool that produces one is generalising rather than retrieving.

Ask, then put it away

The step people skip is the last one. A good answer is a piece of work: it found six items, worked out how they relate, and put them in an order. If you close the thread, that work is gone and you will do it again.

Turning the answer into a list, or tagging what it found, is what makes the second question cheaper than the first. Over time the questions you ask most become the lists you keep, which is the collection organising itself around how you actually use it.

Questions people ask

What should I ask my saved links first?
Something you half remember and cannot name. It is the question a folder tree and a search box both fail, so it is the fastest way to find out whether asking your library is worth doing at all.
Why does asking beat searching?
It does not, in general. Search wins whenever you know the words that are in the thing. Asking wins when you know what a piece argued but not what it was called, or when the answer lives across several items rather than in one.
Can I ask about one list rather than everything?
Yes, and you should when a broad answer comes back vague. A smaller, more coherent corpus produces a sharper answer, which is the same reason a well-kept list is more useful than a large pile.
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