Meanings
Early 19th century US; attested 1834. In original use, often used to refer to pulling oneself over a fence, and implying that someone is attempting or has claimed some ludicrously far-fetched or impossible task. Presumably a variant on a traditional tall tale, as elaborated below. The shift in sense to a possible task appears to have developed in the early 20th century, and the use of the phrase to mean “a ludicrous task” continued into the 1920s.
How to pronounce "pull oneself up by one's bootstraps":
To begin an enterprise or recover from a setback without any outside help; to succeed only by one's own efforts or abilities.
Example: "We can't get a loan, so we'll just have to pull ourselves up by our bootstraps."