Time heals all wounds. Everyone has experiences they don’t want to write about. But with enough time, it’s ok. My New Year’s Resolution of 1995 is pretty embarrassing. But whatever. It was 16 years ago. The longer back you go, the less you have to worry about what people think.
Risk. Notice that almost all of these rules are about where the boundaries are. Most people play it too safe. When you are really risking something and the reader senses that (and they WILL sense it), then you know you are in good territory. If you aren’t risking something, then I’m moving on. I know I’m on the right track if after I post something, someone tweets, “OMFG.”
Be funny. You can be all of the above and be funny at the same time. When I went to India I was brutalized by my first few yoga classes (actually every yoga class). And I was intimidated by everyone around me. They were like yoga superheroes and I felt like a fraud around them. So I cried, and hopefully people laughed. It was also a case where I didn’t have to dig into my past but I had an experience that was happening to me right then. How do you be funny? First rule of funny: ugly people are funny. I’m naturally ugly so its easy. Make yourself as ugly as possible. Nobody wants to read that you are beautiful and doing great in life.