When I went to jail, I had the benefit of having the foresight to ask people who had spent time what to expect. I knew as an activist that I would eventually spend time there. My largest concerns after hearing from people were (a) how I would react to the strip search and (b) how I would deal with the range boss.
The strip search concerned me because I had sexual abuse in my background, and I wasn’t sure what my response would be. My lawyer advised me to explain this calmly and politely to the guard, and to explain that I didn’t want anyone to get hurt, either him or me. It’s especially bad in the detention centre where I was sent since they do the strip-searches in the middle of an office with people all around. Fortunately I didn’t have any kind of post-trauma reaction and the guard was good about it; he stood turned to the side and just glanced at me to make sure I didn’t have any guns up my ass or anything so the staring wouldn’t trigger anything.
Dealing with the range boss was my other concern, since I’m an anarchist and I don’t react well to authority. Here again I was fortunate. I’m big enough (6’ 5” and the size and shape of refrigerator) that no one is going to punk me, and I wisely avoided getting involved in any kind of prison politics. The range boss offered me “free” candy when I arrived, and I politely declined. I took him aside and explained that I wasn’t interested in his range, that I was not going to challenge him, and that I was a political prisoner. I taught the range boss how to meditate, and in return he more or less left me alone. He was also amused when I started organizing the ward to fight for their rights, got a front page story published about the miserable conditions in the detention centre, and ended up being thrown out of jail because they didn’t want me organizing the inmates any more.