A peasant would work on the land that a lord owned. They would do things on the land that the lord wanted them to such as plant and pick crops for them and the lord to eat. Depending on what time of year it was you would do different jobs on the land for example in spring you'd plant crops and in fall you'd pick crops. This job would really keep you busy. You'd live in a small little hut made of mud, straw or even worse, dung. Also you would have no clean clothes to wear. A con for this job. You would always be outside no matter what the weather, even when it was raining the lord had a job for you. Although women, men, and children could all do this job, men would get paid more for doing the same thing. Women were not treated equally in medieval times.
A black smith would create and fix tools such as helmets and swords. Black smiths were very popular because of their high value metal items and skills to make these items. That's a pro. Wood is not very strong and if a black smith made wood weapons he would not get lots of customers. Depending on where the black smith worked they would have different lifestyles. For example, a black smith in the city would probably have more money then the ones who live in the country as they were thought to work in the castle as a servant for the owner.
Jesters would entertain kings and lords. They would wear funky clothes such as jingly hats, jingly boots, and light colours. Jesters had many tricks and talents to share such as magic tricks, jokes, and singing. If you are a fun and funny guy this was the job for you. Though if jesters were not good they would be killed by a noble or perhaps the king himself! That is one big and fat con.
Info taken from Medieval life, Wikipedia, and 100 medieval jobs you might loved or loathed.
Pictures taken of Wikipedia, WoWWiki, and Paint the world super coloring.