Making money doing what you love vs. Making money in order to afford to do what you love

How do you choose between making money in a career doing what you love versus making money in order to afford to do what you love? 

It’s no secret that I aspire to be a creative. It is the tagline for this very website. But my current employment role isn’t exactly the most creative. Although It allows me to observe and work directly with creatives to help develop pieces and advance projects, I am not directly responsible for the art of the pieces themselves. 

For years, I have contemplated the idea of jumping into a more creative role. But every time I confront the decision, I wonder - Is the grass really greener on the other side? My current position affords me the resources and the time to pursue my passion on my own terms, but a creative position would provide me with real life challenges to practice my creative skills and critical thinking. 

I wonder if I make the jump, would I be happier making money pursuing my passion? Or will making money off of my passion change the way I feel about it. Will it really fuel my creative drive or will it destroy it?  

Now I just want to say that I realize that everyone’s journey is different and the answer varies from person to person, but I am curious as to where people stand on this topic.