To appreciate Angel Olsen’s moderately happy ending, it’s worth knowing her beginning. The day after we drink, Olsen and I meet for falafel at Sultan’s Market in Wicker Park. She recounts the details of her curious childhood on the patio out front, leaning forward as the stories demand, speaking without hesitation, occasionally flashing the wide smile she reserves for when she really means it.

Olsen was adopted at age 3, becoming the youngest in a St. Louis family of eight children, some of whom were old enough to be her parents. These older siblings served as role models as well as cautionary tales: “I’d look at them like, Don’t want to be like you; you’re alright, I’ll be a little bit like you; oh my god, you’re so weird, I’m getting out of here. Being the youngest in that position was heavy, but it definitely fueled who I am—someone who likes to observe and create characters and look for humanity in people.”

Olsen’s parents were typically old-fashioned and religious Southerners during the peak eras of psychedelic culture in the late ’60s into the ’70s—a time period that now fascinates her. (“To be 27 in 1969 would be killer,” she says.) Her dad was a military guy and a union worker, the sort of father who didn’t say “I love you” even though she knew he did. As a kid Olsen was closer to her mom, who worked in the foster care system, though these days they find themselves agreeing to disagree over politics. “I don’t want her to pass away and our last conversation to be whether or not Trump is sexist,” she says.

Olsen doesn’t get back to St. Louis as much as she’d like (maybe twice a year) and doesn’t consider herself terribly close with her family. “Some of them came out of the woodwork when I was doing well,” she says, “and it was like, ‘Oh man, this is gross, I’m not doing that well.”

It’s not that her parents weren’t supportive of her musical aspirations when she left St. Louis for Chicago at age 20, they just had no idea what that sort of life might entail. To appease them, she enrolled at Chicago’s Soma Institute, where she studied sports massage therapy for two years. She hit pathology classes and bailed; “I’m not sure I can touch people that way,” she jokes now.

For as long as she can remember, Olsen had an ambition to come outside of her shell, to show people that she possessed something they did not. Music was an obvious way to do that—to not only overcome shyness, but to try on different personas. Which was something she was doing anyway, as the debris of family-wide illness upset her teenage life. She got sick, her mom got sicker, then her grandma died. “It was very much like Lindsay in ‘Freaks and Geeks,’” says the onetime cheerleader. “You lose somebody in your family, then suddenly you’re kind of a freak.”

This inclination manifested into Olsen’s first band, Good Fight, which was inspired by 311, Sublime, No Doubt, and “really weird parts of ’90s music culture.” She hung around sketchy shows at the now-shuttered downtown St. Louis punk club the Creepy Crawl and started using STLPunk, the local music scene’s beloved social media portal that peaked when she was in high school, in the early 2000s. “It was the very beginning of meeting people from the internet because you lived in a place that didn’t have people that you liked,” she says. And like many young music fans during this era, her taste evolved quickly, nudged along by the community and access she encountered online. Soon Sublime was replaced by more out-there fare, from Battles to Deerhoof to prog-rock.

Eventually, friends from Chicago encouraged her to move, praising the music scene there. Soon after, Bonnie “Prince” Billy enigma Will Oldham heard about her, and Olsen ended up singing with Oldham’s band for a few years. They don’t really talk anymore—Olsen says their relationship was always more professional than friendly—yet she finds herself thinking of Oldham often, given that his presence is summoned in nearly every interview she does.

She remembers the premature judgement she felt when she left the ultra-DIY bandleader’s enclave so she could focus on her own music. “I just felt like no one believed that I could stand up for myself, or become a good writer or even someone who wasn’t so easily influenced,” she says. “Maybe some of that fear was me judging myself.”

Olsen’s own music was already gaining momentum when Bathetic Records co-founder Jon Hency found her songs on Myspace. She recorded her first two releases, 2010’s lo-fi scrapbook Strange Cacti and 2012’s cosmic psych-folk gem Half Way Home, for the small Asheville label, before signing with big-deal indie Jagjaguwar in 2013. Her escape plan worked.

“I felt like if I didn’t leave St. Louis, I’d just always be working at a grocery store and smoking cigarettes and not doing anything with my life,” Olsen says. “I feared the depression of St. Louis, because it is in a deep depression.”