1 - I was working in a rich .NET environment; JavaScript was beginning to show its teeth and wasn't taken seriously by 'serious' programmers. I was going with my manager through the SMART objectives I needed to do for the year, and I mentioned wanting to learn about this new thing NodeJS and JavaScript on the server side. He kept pushing that I should do a presentation on our use of Entity Framework to get some clout against the Java department. I insisted that I was more interested in learning something new than just doing some presentation that has been done by almost every engineer on our team. He accused me of being an ego-driven engineer and wouldn't accept it. I learned NodeJS that year, did a presentation on it (it was fun, not a single senior thought this was worthwhile), and ultimately ended up using it a lot, and that headstart helped me.
2 - I was talking to the head architect in a large multinational, expressing my interest in joining the 'architect guild.' My manager informed me that I was too young (about 28 then) to consider this career move and that architecture is for older people. I found that to be rather stupid, and when I got offered a CTO role and the possibility to architect a system, I talked to my manager about it, telling him that I was very interested in being in that kind of role and asked if there's any way I could find it inside the company. He told me that 99% of startups failed and that my choice was between employment and ending up on the streets. I took the chance and couldn't help but smile, getting our first million dollars with him in the audience, front row seats paid by the corporation.