I’ve learned more about adulthood from Star Trek: The Next Generation than from any therapist. This article is what happens when midlife meets warp drive—with life lessons, Picard flashbacks, and a graveyard full of hairline regrets.

I didn’t mean to become the office villain. But when the revolution is televised in HD, sometimes the traitor is just the guy who refuses to mute.

I made $1,000 in passive income without effort, ambition, or moral clarity. You can too—if you’re okay sleeping through capitalism and...