A person who is always traveling and changing jobs has the advantage of having no responsibilities, but also has disadvantages such as having no permanent place to live.
That notion was known to the ancient world and Greek and Latin versions of the phrase are cited by Erasmus in the third volume of his collection of Latin proverbs – Adagia, 1508. By the early 17th century, a ‘rolling stone’ was referred to as a type of wastrel – one who would amount to nothing.