As an African American who was born into slavery, Frederick Douglass wished very badly to be freed from its clutches. He had no knowledge of who his father was or even of his own age, which only added to the torment brought upon him by his desire to be free. Douglass moved in 1834 to Mr. Freeland's plantation, which merely lessened the unforgiving effects that his life with Mr. Covey had. Aside from this, his position still hadn't changed. He was still overworked day after day, and he continued to ask himself Why is it that some people can enslave others, and only they are allowed to be free? After pondering that thought for awhile, Frederick Douglass decided that he would attain freedom, no matter what it took.
Douglass knew that sitting still wasn't going to get him anywhere, so he gathered Henry, John, and other fellow slaves to join him on a risky operation that could help them make their dreams come true. Of course, in order for this plan to work, everyone would have to be discreet and act oblivious to what was really going on behind the slaveholders’ backs. So that they would be fully prepared for what was to come, they all discussed their hopes and fears, along with many difficulties and doubts they had. Every member of the operation was now ready to take action with a new hope in their hearts. A flame that burned so bright that freedom seemed almost in their grasp.
Having prepared for the adversities that were sure to come their way, Douglass and the other slaves knew very well that extreme caution would be necessary. Guards at almost every corner wasn't their only issue, though. Anyone outside of the plantation was a possible threat in the sense that they might suspect that the slaves were runaways. So, to ensure their safety, Douglass wrote them false protections using his little knowledge of how to read and write. After that, they decided to stealthily steal one of Mr. Hamilton's canoes and use it to escape. “Let's pretend we're just a couple of fishermen out to catch us something big out in these waters”, said Douglass to the others. He then pictured a fresh, damp breeze carrying the sweet scent of freedom with it. “But what if we get caught trying to escape?” asked Henry. “Then we'll show them our protections”, replied Douglass. “That'll make them believe us for sure.”