I would totally spend my days at the College of Winterhold, learning magic and going on field trips.
I'd also spend a lot of time in the library as well, reading ancient books and learning how to become stronger.
Then I'd go to Whiterun, talk the Jarl and get him to sign something for me, walk down to Nazeem and say "In your face Nazeem, looks like I get to the Cloud District after all!"
I would sleep in the pubs around Skyrim, and stay mostly in the Whiterun/Falkreath area. Early in the day I would mainly do some hunting and maybe seek out some Alchemy ingredients, then I would spend the evening loitering around town and selling the stuff I had found. Probably avoid the Rift because of all the bears, and the criminals.
If theres a typical day in skyrim, well I'd build a smithy and I'd be the best blacksmith in skyrim. I'd travel to the cities and sell my armour and weapons. I'd get into alchemy too, we'd have a nice garden full of plants. Some weekends we'd go into the mountains or into the caves with my housecarl and have an adventure or watch the sunrise from the top of the mountains.