‘I Had My Backpack and 20 Cents’: How Cheryl Strayed Does Money

by Megan Johnson

Cheryl Strayed may now be a New York Times bestselling author, but the “Wild” writer says she remained in the red until recently.

“I just paid off on my student loan debt on my 44th birthday, two years ago,” Cheryl told the crowd in Boston on Tuesday at “Funny Women… Serious Business,” a benefit for Rosie’s Place, the oldest women’s shelter in the United States. The cause is one that’s close to Strayed’s heart, as she herself was a child of domestic violence and poverty, two issues dealt with by many women who come to Rosie’s Place.

As a 19-year-old who found herself pregnant in the 60’s, Cheryl’s mother Bobbi didn’t have the financial ability to care for herself and her children on her own. “She didn’t have any choices,” Strayed said. “She married my father even though she didn’t particularly want to.”

Bobbi spent 10 years suffering at the hands of her “violent, tyrannical, and controlling” husband.

“My earliest memories are being loaded into the car in the middle of the night during one of my father’s outbursts, and being driven around all night,” Cheryl remembered. “We’d pull up in front of the preschool or nursery school, we’d drive all night, and that’d be the beginning of my day. My mom with a black eye or bloody nose, telling me it’s going to be okay.”

And soon it was okay, because Cheryl’s mother picked up and left her husband. She created a loving home for her children, even if it wasn’t financially stable.

“We had a happy life. I would say I really had a very happy one, even though we lived in poverty, on food stamps, government cheese, and sometimes the food pantry shelf,” said Strayed. “My mom worked as a waitress, and in a factory, but I would say I had so much joy because my mom was joyous. My mother knew how to love. She knew how to love in the way that we all want to be loved by our mothers. And so when she died very suddenly at age 45 of cancer, it was that that left my life.”

Cheryl was in her senior year of college when her mother passed away, but it turned out her mother was a senior as well. As an undergrad at the University of St. Thomas in Minnesota, part of the deal was that if the child enrolled in school, the parents could go for free. Her mother leapt at the chance.

“I thought, no way in fucking hell are you going with me,” said Cheryl, who soon realized her mother was going to utilize the opportunity no matter what. But once Bobbi died, it was Cheryl who fell apart. Emotionally shattered, Cheryl began using heroin regularly, and became promiscuous in an effort to numb the grief she felt.

“I was honoring my mom by ruining my life, by showing the world and myself how much I loved her,” Cheryl reflected. “It’s a way of obliterating the pain. It occurred to me about 3 and a half year after my mom was dead that I had completely done the wrong thing. Instead of honoring my mom by ruining my life, I’d dishonored her. The only way that I could really honor my mom, really show the world how much I loved her, would be to actually become the person she raised me to be.”

Ultimately, it was the cheap opportunity to walk the Pacific Coast Trail that led Strayed on her path to self-discovery, and of course, resulted in her best-selling autobiography Wild.

“That’s when I decided I had to take the journey I did in Wild. I didn’t have much money. I was working as a waitress in Minnesota. I didn’t have much money to take a grand expensive journey, but I knew the wilderness, and I could go for cheap,” Cheryl told the audience. “I could go on a long walk.”

By the time she finished walking the Pacific Coast Trail over 90 days later, Cheryl was left with almost nothing, but felt like a new woman.

“I had 20 cents left, I had student loan debt, I didn’t have anything. A credit card, a job, a home. I had my backpack and 20 cents,” Cheryl said. “And I had everything I needed, because I knew that I was okay. In that course of that journey when I went out into the wild, I found that home.”

Megan Johnson previously worked at the Boston Herald’s Inside Track, where commenters would leave sweet messages like “Megan Johnson is just awful.” She now writes for publications like People Magazine, the Boston Metro, Boston.com, and whoever else pays her. Follow her on Twitter @megansarahj.

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