One of the challenges that Boone faced was an almost total lack of formal education. After his family moved to Kentucky when he was young, he spent most of his time working or hunting and fishing. But it should not be assumed that he was illiterate as some portrayals have made him out to be. Experts suggest that he was certainly able to read since he took reading material with him on many of his expeditions.
Many of his other challenges involved conflict between settlers and the Native Americans and the difficulties he faced while fighting in the Revolutionary War.
One of his most serious failures involved a huge financial loss incurred while he was engaged in land speculation in Kentucky. The debt he carried away from this failure kept him from being able to win a number of contracts he applied for. The legal troubles eventually caused him to leave what was then the United States to live in what would eventually become Missouri.