Churchill was a Master of the English language and as such was never really unemployed (just out of government) since he provided columns to the Hearst papers. He was also writing books which sold well.
Yes his early life was chaotic and exciting. He never was thought to be above normal while in school and seems to have been self-guided from an early age but with unquenchable ambition.
In school, they, including his father, believed he was a dunce, because he studiously ignored Latin and Greek studies and failed all tests in those subjects. He was beaten for it, but refused to relent. His English, however, more than compensated for that and his famously bad French.
Young Brexit boy, however, is done in government. He had all the youthful brashness, but none of the talents, and got caught holding the bag.