Professionally, Jupiter in Sagittarius tends to come into its own where there's room to teach, to travel and to work with large ideas. The classic fits are teacher, coach, lecturer, guide, interpreter, international lawyer, publisher, and organiser of big events and education programmes. Anything tied to abroad tends to suit — a second citizenship, international sales, embassy work, or a role inside a large franchise with branches in several countries. The common thread is breadth: a brief that lets the person hold a whole picture rather than polish a corner of it.
They tend to feel boxed in by a fixed office timetable and by small tasks that ask for weeks of fine-tuning a single detail. They tend to bloom, by contrast, when the role is large — when there's a strategy to hold in mind and people from different cultures to talk to. Often these are the people running an education arm, founding schools and online courses, writing books, hosting podcasts or building large channels about growth and development. The size of the canvas tends to matter more to them than the title on it.
Their careers tend to move in leaps rather than a straight line. Two years employed, then off into their own venture; four years later they sell it and go to study somewhere in Europe, then come back with a new idea and open a school. That zig-zag is, for this placement, simply the normal shape of a working life — and trying to straighten it out tends to leave Jupiter short of oxygen.
Money, for this placement, tends to arrive on ideas and on scale, and almost never on routine. That's why it tends to pay to build a structure around yourself early — an assistant, a bookkeeper, a partner who likes the operational side. Without that support, even an excellent idea can dissolve into the domestic detail, and for Jupiter in Sagittarius the detail is nearly always somebody else's natural ground rather than their own. I'd put it plainly: the most useful career habit here is learning to hand over the dull finishing work on purpose, rather than abandoning a project the moment it stops being interesting.