I think at the end of the day you just have to take that risk. Or not. It's up to you. I think the majority of the time that you accidentally say something stupid or are misunderstood, it's in a fairly low-stakes situation, so a simple apology will suffice. But when you're a public figure with power over people and ideologies, you have to be a lot more careful about where you choose to engage.

Arguably the (male) head of the Free Software movement has no place debating the definition of "sexual assault" or "statutory rape" in a conversation about a human trafficker and child abuser. His opinions there have zero value (not to mention that a debate over such definitions is missing the point entirely), and engaging in that conversation -- even to come to the defense of his tangentially-related dead friend -- was a very poor choice, even for someone known to be contentious and often misunderstood.