This is very familiar to me. It was how my relationship was with my dad. I was always the 'good' kid in the family, rarely got into trouble, but was always the more emotional one. I tend to take things more to the heart than average people. It frustrates people, but it's how I am. It also lends to me being more creative. My dad and grandpa and most of the males in the family are mechanics, good with their hands, they can build and fix stuff with the snap of a finger.
It frustrated my dad that I would rather write books and be creative than take up a trade. I'm also the only college educated member of my family other than my grandpa. Now I'm a published author and started my own company writing books for business owners. I often wonder if he would be proud of me right now or what he would think.
I do know my grandpa is proud of me though, as different as we are. He told everyone that I started my own business, so when I made the rounds calling on Christmas, everyone asked me about it haha. It made me feel really good, because I always wanted my family to be proud of me.
But anyway, your post just reminded me of all of that