Bill Watterson didn’t just quit on a whim. He had been making cartoons for years and had received feedback that he was at least half decent at it. And at the time that he quit, “newspaper cartoonish” was an actual career too.
He wasn’t saying “bet it all and jump off a cliff and hope you’ll land”. He just said “feel free to stake your own path”. The quote you link also includes staking your own path as a homemaker.
The central takeaway from his advice was to try to find meaning and happiness in what you do. It worked out extraordinarily well for Watterson but his advice applies to far more pedestrian cases too.
He wasn’t saying “bet it all and jump off a cliff and hope you’ll land”. He just said “feel free to stake your own path”. The quote you link also includes staking your own path as a homemaker.
The central takeaway from his advice was to try to find meaning and happiness in what you do. It worked out extraordinarily well for Watterson but his advice applies to far more pedestrian cases too.