headsy adj. smart and bold; clever and ballsy. (source: Double-Tongued Dictionary)
Further reading
Need a slang term that can replace just about any noun? Try chumpie. If you’re from Philadelphia, you may already know this handy placeholder word. And there’s Queens, Brooklyn, Staten Island, Manhattan, and … The Bronx — why do we add...
Diamond dust, tapioca snow, and sugar icebergs — a 1955 glossary of arctic and subarctic terms describes the environment in ways that sound poetic. And a mom says her son is dating someone who’s non-binary. She supports their relationship, but...
Probably derived from “heads-up” = ‘alert, resourceful’ (dated to 1947 by MWCD11).
I think so too, with reinforcement from “gutsy” and “ballsy.”