Perhaps start up a shop in solutude and study the worlds history.

I'd probably run one of the stables you see outside the cities, or at least work at one long enough to get the coin to establish my own. Either that or I'd set up a facility that supplies said stables with their stock.

I'd open the best brothel that skyrim has ever seen.

I would spend the day at the nearest inn or mead hall, drink all day and honor my ancestors :foodndrink:

i would probably join the imperials, war back then seems far more interesting then nowadays. especially with melee combat, i prefer that over guns.
real men fight face to face.

if only i were born during the medieval days :sadvaultboy:
despite the fact life back then was tough.