I have no idea which side is going to win

I think there comes a time in everyone's life when you have to choose between treating life as a business decision or following your heart (big cliche but I didnt't quite know how else to put it).
By business decision I mean should you be with someone because you love them or because they have lots of money? Should you pick your program of study because it has a lot of market value or because you like something? Should you be friends with someone because they could actually do something for you or because you genuinly like them? Should you settle and be with someone who likes you or should you keep combing the streets for someone who makes fireworks go off inside you when they hold your hand?