I don’t know when to launch into my own stories without specifically being asked a question. I don’t mind talking about myself/sharing stories, but I don’t want to come off as arrogant by just starting to talk about myself unprompted. I tend to just keep asking questions, and hope that the other person I’m talking to will ask questions in return, but they usually don’t and then I never end up talking about myself.
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There are no hard line rules and everyone is different. Some people will be more or less interested in your stories. The only way to find out is to do things and see the outcomes and integrate what you learn
Here’s the thing most resources and (frankly ignorant) people tend to ignore or gloss over, VIBE. If your vibe doesn’t fit the overall VIBE of the group/conversation it just won’t work. At that point you’re just trying to force yourself into the conversation. If you cannot flow with the overall vibe of the conversation (and vice versa) it’s best to simply pull out at that point, because trying to interject yourself into the conversation like s puzzle piece that doesn’t fit will only make you seem like a 3rd wheel/showboat.