Millennials Who Peaked In The 2010s Are Revealing Just How Much Of Their Lives Diverged From Their Original Plan, And It's Surprisingly Inspiring

I was recently transported back to 2009, the peak of the "indie sleaze" era, when I attended the Just Like Heaven music fest in Los Angeles. Headliners like MGMT, M83, the Yeah Yeah Yeahs, and even Azealia Banks took me back to listening to my blue iPod nano on 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?

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

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:

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

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

Where did you think you'd be now back in high school, and what does your life look like now? How do you feel about it? Share your slice of life in the comments.