I get curious about people sometimes. Instead of the awkward bush beating and online stalking that people usually do, I try and go straight to the source. I ask them.
I met you at [EVENT] and wanted to ask you about the considerations you made when switching careers from [X] to [Y]. I'm curious about your path and have specific questions about the decision points you made for the jump.
I’ve entertained a similar transition for myself working in [Z] but have always been interested in [Y], but never made the leap out of responsibility, fear, golden handcuffs, or any number of head > heart reasonings.
I also saw that you're a jiujitsu black belt 🤙. I currently train and compete in no-gi at [my gym. I visited the [their gym] in May of 2019, so I know ya'll are a bunch of savage killers.
Are you open to a chat? No love lost if you decline.
There are a couple of elements to getting a response.
Tell him/her the circumstances of your exposure to them. Reveal the ask.
Show how your circumstances are similar to theirs (going to [Y] industry).
Bonding over similar places and experiences via jiujitsu.
Notice most of what I’m doing is telling a short story that allows them to relate to me on multiple points. They are more likely to respond or help you if they see a younger version of themselves in you or can relate to the hardships and problems you’re experiencing right now.