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Moving up. Upward mobility.


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Joining crew of a ship is one possible but very risky way to move upward. After all poor quality of food and water, diseases, pirates, storms and some other dangers make sure that there are always demand for new blood in those ships. So very lucky and smart person who survives long enough could rise captain of his own ship and there is even one commoner who has risen to Hand of the King.

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Martial skill can allow low born men to rise high. It’s not easy but with the right breaks and enough skill you could even ride to the kingsguard and serve along side the sons of the most powerful houses. Pate the Woodcock and Duncan the Tall were among the lowest born of any person that we know and ended up being famous with their names immortalized. Of course, Pate might have been the best fighter in the Seven Kingdoms, and Duncan was a great fighter who had tons of lucky breaks. 
 

Nevertheless, even if you do not have such skills, you can at least join a city watch and rise up like Slynt.
 

Or you can become a sell sword.
 

Over generations, you families can move up. Look at Littlefinger. His great-grandfather was a sellsword. His grandfather was a knight. Littlefinger used his skill with coin to jump up several ranks. 

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The absolute vast majority of people in RL medieval society never moved beyond a ~ 10 km radius from where they were born, to say nothing of up.

Also the acquisition of most valuable skills usually cost money. Apprenticeships were either bought or in rare cases given to children of friends or similar. A low-born person would be unable to read, unable to do anything more than basic math and unable to conceive of a life/world much different than that of their parents. 
 

edit: in an attempt to try, the best bets for my illiterate ass would include: grave-digger, furrier, executioner and rat catcher and saving everything to hopefully one day open the peasant’s dream business, an inn of my own.

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 I guess as a man, the "easiest" way to get up the social ladder in this world would be going on a ship at a young age. It is dangerous but it seems that going from a ship-hand to captain is far from impossible, and once you get to the point were you can captain your own ship it open's a whole new ray of possibility arrive, from smugglers to trader and pirate you can make your self a small fortune, even claim a island in the stepstone and become a kind of lord. If your lucky and help the right person you could even become a actual lord like Davos. Plus you can pass-on your ship to your kids who could be the one to rise.

For women they're is sadly not a lot of option, I guess catching the eyes of a lord or knight is your best call, other than that a septa or a women of the night are you two options to rise, the first one might be block by minor noble women and the second is extremely dangerous and hard, so really your out of luck.

A lot of people mention the citadel, the faith or the night's watch but they are all at best only worth a damn for yourself. Since all of the mentionned cant have children officially than it would only work for your self, since who will care for the bastard of a septon or maester if the mother is not of high birth, and if she is well chances are that loosing your manhood would be a easy way out. 

Any trades would requires skill or some kind of physical exception if your are not from a family of tradesman yourself, same would go for the different city watch's, they're is something like at best 10,000 spots in the whole of Westeros so getting in if you are not a giant like Dunk or from the city and lucky like Janos is most likely not really a option.

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I'm surprised more people here haven't mentioned the basics of castle stewardship. With truly no knowledge, nor reading ability taught at a young age, your options are limited. However, if you  are ambitious you can attempt to sign on as a pot boy/girl and actually try to learn all of the ins and outs of highborn service! Cleaning floors or filling tubs or fetching food/clothing is an easy thing to start (if you can remember to smell nice and be exceedingly polite).

Then, once you are in the door, you can learn other tasks from all of the other smallfolk who serve that particular lord (who I am sure would already be discussing their work, because what else do they have to talk about?). These same conversations/education sessions extends to the septon or septa, and possibly even the maester depending on who that is, which leads to literacy. 

From there it is just a matter of being hard working, overly polite and attentive, and getting a bit lucky with the smallfolk politics when it comes to promotions. You could even specialize! Good with figures and organization? Understeward! Love horses and riding? Stablehand! Love to eat? Cook! All of these positions come with job security (even if the castle falls, you will most likely retain your position if you are good at it), as well as food, protection, and ways to move up. As we know, the children of the castle may even grow up alongside their lordly cohorts and become known enough to acquire higher and higher positions as the years go by.

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