The news last week that booksellers Barnes & Noble expect to close a couple of hundred stores over the next ten years was met with understandable disappointment and dismay. For me and many other readers, browsing online can’t beat wandering through a building full of books, any one of which you can pick up on a whim and thumb through at will.
One of the things people like most about physical bookstores is the ever-present possibility of finding something pleasing by chance. So online stores try, with mixed success, to replicate the phenomenon of fortuitous discovery – in a word, serendipity. The experience applies not just to places and spaces, online and off, but to books themselves: certain books, such as dictionaries, are suitably structured for the pleasure of random discovery.
Serendipity, then, though sometimes used as a synonym for luck, refers mainly to a particular type of it. We have Horace Walpole to thank for this popular but peculiar word. In a letter he wrote in 1754, Walpole describes looking through an old book at random and finding some fact of significance to his studies – a discovery, he says, “almost of that kind which I call Serendipity, a very expressive word.”
Walpole based the word on Serendip, an old name for Sri Lanka, as in the fairy tale The Three Princes of Serendip. The eponymous princes, while travelling, “were always making discoveries, by accidents and sagacity, of things which they were not in quest of”. Serendip comes from Arabic Sarandīb, ultimately from Sanskrit Siṃhaladvīpaḥ, meaning island (dvīpaḥ) of the Sri Lankan people.
Like the derived adjective serendipitous, serendipity is indeed a very expressive word, bouncing rhythmically off our tongue and lips – which is probably why one Wordnik user includes it in a list of “Words that make my mouth happy”. It appears frequently in articles about beautiful and beloved words, yet it almost didn’t catch on, and was not often used until the mid-twentieth century.
Last week Macmillan Dictionary hosted a live Q&A session on its What’s your English? page on Facebook. Editor-in-chief Michael Rundell said he was asked about “the joy of browsing a dictionary and making unexpected discoveries”, and replied that the browsing opportunities online are far greater:
In the Macmillan Dictionary you can look at any of the words and phrases in the right hand column (where it says ‘related dictionary definitions’); you can click on any word in the entry and go immediately to that one; and above all, you have access to all the synonyms and related words by clicking on the thesaurus button (impossible in a printed dictionary).
Serendipity is not going away. After Macmillan announced its decision to go online-only with its dictionaries, the Economist found that Michael made a compelling case; and on the question of serendipity, it asked: “Can anyone think of a tool more suited for serendipitous discovery than the internet?”

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What a fascinating article! I never never knew the “circular” route that the name had taken – coming from Sanskrit via Arabic, thanks. I told an internet friend once that I thought the beautiful and useful word Serendipity was Sita’s lasting revenge for having to undergo the Agni Pariksha after her stay on Lanka.
Thanks, Stuart! The word does have a curious etymology – not the sort you could guess based on sound or appearance.
A beautiful post about one of my all-time favourite words. I knew nothing about the origin
or etymology, it is just a word that “makes my mouth happy”.
Thanks for sharing Stan
Helen: That’s very kind of you, thanks. It is a happy-making word, and its origin is pretty unusual.