In Episode 10 of The Grey Area Podcast, Gabe, Stella, and Matt start with a question they weren't ready for: what would your 18-year-old self be confused by about your life right now? Gabe thought he'd be working in finance. Stella thought she'd be a parent by 27. Neither of them thinks their teenage selves would have even been friends with who they are today. Then they get into the social norms they've quietly let go of — Gabe is six weeks without drinking, Stella stopped feeling guilty about leaving early, and Matt's girlfriend taught him something at the Botanical Gardens he won't forget. They close on focus, discipline, and a lesson Gabe picked up at dinner with Bobby Flay: the time to start something new is when what you're doing is working, not when it starts to fall off.

The Grey Area is where Gen Z talks about the stuff that doesn' ...