I’ve noticed something. People who engage with my content the most are people who aren’t doing the things my content encourages them to do. A graduating valedictorian at my old high school sent me a message agreeing with everything I have to say about school.

An attending college student said they wish they were doing what I’m doing.

A guy with a house and a bunch of cars told me he wished he had the lifestyle I have.

People with way more money than me tell me they wish they could move into a van, travel the country, and live free. Nothing is stopping them, so why don’t they do it?

I think it boils down to shoulds and haves. Over years, people create a clusterf**k of assumptions about what their life must look like. They’ve played out their life and deviations are threats to emotional security.

They think they have to go to college. When you ask why they don’t sell everything and travel like they desperately claim to want, they say they should be focusing on their career. They don’t seem to take pleasure in any of the things they have to do.

At the end of the day, going after what they want would make them happier. School and career and “what I should be doing” are meaningless. Life is to be enjoyed. Slaving away doing what you “have to do” for forty years isn’t worth it when the thing you actually want is almost always within reach.