I don't think you need to worry about choosing one path over the other. If you want to do "non-boring" things, you can still do them while working for a more co

I don't think you need to worry about choosing one path over the other. If you want to do "non-boring" things, you can still do them while working for a more conservative/mundane company. The latter can provide a solid foundation for you to explore the former. When I was in college I was pretty entrepreneurial. Since graduating and starting my career over the past few years, I've built a good foundation for myself (getting my own place, saving money, and growing in my career in a way that's complementary to my personal interests), and I'm now ramping back up to the levels of thinking and dreaming that I used to do (if not moreso). Edit: relating to your mention of the importance of relationships, note that you need to make connections with people that do the things you're interested in and keep your mind oriented towards that. I have entrepreneurial and creative friends. You have your mentor. You might benefit from meeting people that are closer to you in terms of how far along they are on the path towards what you're interested in - people to grow with and mutually inspire and encourage.