Often, no. This may sound a bit odd, but often wanting to share the insights that we had, with especially non-meditators, can be a type of ego trip, "I want to show people how smart I am, how much I have gained," etc. Even with other meditators, it can often be that way. We might also think that sharing our insights might help other people, but then there is still a kind of conceit going on in that, "I am going to help that person with my insight."
Sharing insights with a trusted, good friend may be ok. Yet I say "may" as well. Sharing them with your teachers is usually absolutely fine. In regards to trusted good friends, we get this occasionally happening with our assistants. Most of our assistants have practiced for quite a few years. Many of them have definitely developed and we can see the development and on occasion they talk with each other about how they are developing, that's fine. But every once in a while, somebody wants to tell someone else what they have achieved, but it's not really appropriate and beneficial for the other person. That has to be taken into account because even as much as both have practiced, say, for five years and both developed a lot, they might be developing in different ways.
When you are sharing something with somebody else, it's often a question of whether it is an insight that you have developed or whether it is information that the other person can benefit by? That's more the question. So in general I say, "No, don't" because there can be a lot of ego present. Yet if something simply comes up in a conversation, something the other person is interested in, and you feel you have seen some insights about that in your own practice, then fine, you can try to share it with them.
We needed to caution one of our assistants because they were so excited after a retreat about how much they had gained, and they just wanted to tell all the other assistants about it. But it was the wrong time because some of the assistants were going through relationship problems and other intense Dukkha. It was great that the assistant in the retreat had done so well, but the other people really didn't want to hear it at that time. So when you are discussing anything with anybody be aware of whether they really want to hear it. We need to be careful with our speech.
As you know in Australia, I once worked on a road construction job and the people I worked with, by and large, weren't deeply spiritual, and most of them had not finished high school. Some hadn't even gone to high school, their education was low. I was the only one there who had a University degree, I was different. They didn't want to hear anything I said. There was nothing in my world that they really wanted to hear about. So when I had conversations with them I would ask them a question and let them talk. And when they were done five minutes later, I would ask them another question and let them talk. I learned all their hobbies, so I could ask specific questions, such as did they catch any fish last weekend, how are the tomatoes growing, etc. And one on one, these guys liked me a lot.
In the group, behind my back, perhaps they may have said, "Yeah, he's the American with the University degree, you know." Or acted like I was weird, but one-on-one, I could tell most of them liked being around me. Yet I hardly said anything about my world to them. This is something to consider when you watch over your own ego in what you want to say to other people, whether it is an insight or anything else.