" Back then , I did n’t see myself living past my late XX . … I ’m happy I stuck it out . "

I was recently transported back to 2009, the peak of the “indie sleaze” era, when I attended theJust Like Heavenmusic fest in Los Angeles. Headliners like MGMT, M83, the Yeah Yeah Yeahs, and evenAzealia Bankstook me back to listening tomy blue iPod nanoon the way to AP Calculus. It got me so sentimental and I thought,Where did I think I was going to be today when I was back in high school, over 10 years ago?

Since nostalgia and millennial sadness were in the air that day, I asked other adults (including a few Gen X’ers) at the festival who they thought they’d be by now when they were in high school, how they’ve changed, and what their biggest regret is. In exchange for their honesty, I drew these anonymous portraits of them. Here are their stories:

mark : Some names and identifying details have been altered for anonymity .

Author posing in front of the Just Like Heaven music festival sign, author at a younger age, and Just Like Heaven 2023 lineup

Raya the screenwriter previously wanted to be a session guitarist

Keely the photographer thought she'd be a stay-at-home mom

Saul the bartender thought he'd be a lawyer

Molly the stay-at-home mom with her family

Ronnie the writer thought he'd be a teacher

Claire the musician thought she'd be dead

Angel the grocery store employee used to want to work for Condé Nast publishing

Jennifer the gig worker used to book bands at concert venues

Mick in online marketing used to think he'd be stuck in Montana

Mike the cruise ship employee thought he'd be dead before 2023