A friend of mine once wrote a dictionary[1]. It has all the (normal) one syllable words in English, defined using only other one syllable words. He decided to work on it by focusing on one letter per year, so A was in 1991, B was 1992, and the book was finished in 2017, 26 years later.
It's not even a very long book - only a few hundred pages - but I'm sure if I tried to do the same thing all at once, I'd probably have lost interest around B or C, so I suppose it was a worthwhile strategy.
[1] It's not online anywhere as far as I know, sorry.
I question how well many of the words that come to mind could be defined using only other one syllable words, but it sounds like a fun project.
that seems to be in the same vain as this presentation by guy steele https://www.youtube.com/watch?v=_ahvzDzKdB0 .