How to Money · Wednesday, August 5, 2026
Jack Raines concludes that 'Am I having fun?' is the most crucial question to ask, defining fun as a state of internal peace and alignment with one's goals and desires. He notes that what constitutes fun is stage-specific, evolving from thrill-seeking in youth to more entrepreneurial endeavors later in life.
“Am I having fun? Is the most important question to ask?”
“I think that like the fun, like anything else in life, is very stage specific, and like what I found is to be fun at twenty two, or like especially twenty one in college is like much everyone I find fun at twenty nine.”
“I think the way that I've experienced it is like if you chase the thing that like used to be fun and find yourself getting more anxious or unsettled going after that thing now, it's a very good sign that like the thing you should be going after shifts.”