Wow, our stories are so similar in the ways our father pursued their careers. I too ended up with someone like my father, but hopefully now I know better.

As for the boat trip, as much as your anxiety come from a point of care, (like you said), he knows what he is doing or wants to do. In such a situation, I would like support and encouragement from my partner and not dissuading which stems from a place of fear. I see myself in this example of wanting to skydive someday.