Understand it's a metaphor suggesting stability might lead to boredom or complacency. He couldn’t imagine working the same job for years; a rolling stone gathers no moss.
Pro Tip 2/3
Positive Spin
It can be used to imply that being adventurous or non-traditional is beneficial. She moved abroad for a new start - a rolling stone gathers no moss, right?
Pro Tip 3/3
Implies Autonomy
Used to express self-reliance and independence from societal pressures. He chose freelance life because a rolling stone gathers no moss.