The plan which I adopted, and the one by which I was most successful, was that of making friends of all the little white boys whom I met in the street. As many of these as I could, I converted into teachers. With their kindly aid, obtained at different times and in different places, I finally succeeded in learning to read. (7.4)
Douglass has to employ a lot of little tricks to learn how to read, but one of them isn't a trick at all. He discovers that while almost every white adult is his enemy, he can make friends with white children. They don't treat him differently because of his skin color, and they'll gladly share their education with him.
When we got about half way to St. Michael's, while the constables having us in charge were looking ahead, Henry inquired of me what he should do with his pass. I told him to eat it with his biscuit, and own nothing; and we passed the word around, "Own nothing;" and "Own nothing!" said we all. Our confidence in each other was unshaken. We were resolved to succeed or fail together, after the calamity had befallen us as much as before. We were now prepared for any thing. (10.36)
When Douglass and his friends first try to escape, Douglass uses his ability to write to forge passes for everyone. But when they are caught, these passes turn into a liability, and they have to destroy them. The only thing that keeps them safe is their confidence in each other and the power of their friendship. Because they can trust each other, they know that no one will give away the plot.
Let him be a fugitive slave in a strange land--a land given up to be the hunting-ground for slaveholders--whose inhabitants are legalized kidnappers--where he is every moment subjected to the terrible liability of being seized upon by his fellowmen, as the hideous crocodile seizes upon his prey!--I say, let him place himself in my situation--without home or friends--without money or credit--wanting shelter, and no one to give it--wanting bread, and no money to buy it,--and at the same time let him feel that he is pursued by merciless men-hunters, and in total darkness as to what to do, where to go, or where to stay,--perfectly helpless both as to the means of defence and means of escape,--in the midst of plenty, yet suffering the terrible gnawings of hunger,--in the midst of houses, yet having no home,--among fellow-men, yet feeling as if in the midst of wild beasts, whose greediness to swallow up the trembling and half-famished fugitive is only equalled by that with which the monsters of the deep swallow up the helpless fish upon which they subsist,--I say, let him be placed in this most trying situation,--the situation in which I was placed,--then, and not till then, will he fully appreciate the hardships of, and know how to sympathize with, the toil-worn and whip-scarred fugitive slave. (11.6)
Note all the animal metaphors Douglass uses. He's suggesting that because slaves can't trust anyone else – even after they've escaped to freedom – it's like living in a jungle, at the mercy of wild animals.
It is impossible for me to describe my feelings as the time of my contemplated start drew near. I had a number of warmhearted friends in Baltimore,--friends that I loved almost as I did my life,--and the thought of being separated from them forever was painful beyond expression. It is my opinion that thousands would escape from slavery, who now remain, but for the strong cords of affection that bind them to their friends. The thought of leaving my friends was decidedly the most painful thought with which I had to contend. (11.5)
One of the hardest things about becoming free is that Douglass has to leave his friends behind. Compare this to when he has to leave his family to go to Baltimore. Since he barely even knew them, the separation was pretty easy. But leaving his friends behind is one of the scariest thing he does in his life. He thinks a lot more slaves would try to escape if it didn't mean leaving all their friends behind.
I have been frequently asked how I felt when I found myself in a free State. I have never been able to answer the question with any satisfaction to myself. It was a moment of the highest excitement I ever experienced. I suppose I felt as one may imagine the unarmed mariner to feel when he is rescued by a friendly man-of-war from the pursuit of a pirate. In writing to a dear friend, immediately after my arrival at New York, I said I felt like one who had escaped a den of hungry lions. This state of mind, however, very soon subsided; and I was again seized with a feeling of great insecurity and loneliness. I was yet liable to be taken back, and subjected to all the tortures of slavery. This in itself was enough to damp the ardor of my enthusiasm. But the loneliness overcame me. There I was in the midst of thousands, and yet a perfect stranger; without home and without friends, in the midst of thousands of my own brethren--children of a common Father, and yet I dared not to unfold to any one of them my sad condition. I was afraid to speak to any one for fear of speaking to the wrong one, and thereby falling into the hands of money-loving kidnappers, whose business it was to lie in wait for the panting fugitive, as the ferocious beasts of the forest lie in wait for their prey. The motto which I adopted when I started from slavery was this--"Trust no man!" (11.6)
Even when Douglass escapes to freedom in the North, he can't rest easy. At any minute he might be stolen away back to the South and made a slave again, and he knows that anyone around him could be plotting to do it. As a result, he finds it very difficult to make new friends, and one of his worst problems is loneliness. Since anyone he meets could potentially betray him into slavery, he can't trust anyone he doesn't already know. The only way to stay safe is to be alone.