SXSW 2017: Cheryl Strayed takes us to church on live Tim Ferriss podcast

Posted March 12th, 2017

It’s been more than 20 years since Cheryl Strayed, still grieving her young mother’s death, faced her deepest demons as she walked the Pacific Crest Trail. 

The journey has reached something of mythical status over the year, first in her bestselling memoir, "Wild," and then in a movie starring Reese Witherspoon. But many years ago, Strayed stopped being “the writer who walked the PCT” to one of the leading voices in a movement of writers who push their readers to live braver, more vulnerable lives. 

HandoutCheryl Strayed and "Dear Sugar" co-host Steve Almond.

In a ballroom of the Convention Center on Saturday afternoon, podcaster Tim Ferriss recorded a live show with Strayed in front of a packed crowd of fans of them both. Ferriss is a frequent SXSW guest, but this was the first time Strayed took the stage to share her message of empowerment through taking risks and getting real. 

Strayed is one of many speakers in recent years, including last year’s keynote Brene Brown, whose body of work doesn’t revolve around technology or productivity, but rather the inner emotional work that, in its own way, feels revolutionary and innovative.

“Transparency is a mark of success,” she told the crowd that gathered Saturday evening for the 90-minute interview.

The only way to heal the hard parts of your story is to address them, she said. Writing is one way to do it, but sometimes, you might need to take a quest. 

Strayed -- whose last name is of her own choosing and symbolic of her desire to wander her own path -- warns that whatever adventure or uncharted waters you might pursue, it probably won’t be all that fun when you’re in the middle of it. The painful mistakes we might make anytime we’re getting outside of our comfort zone are simply invitations to grow.

HandoutReese Witherspoon in "Wild."

The truth is, you might not get any enjoyment out of it until it’s over. She calls this retroactive fun. Ferriss, on the other hand, advocates anticipatory fun. He will book a trip with friends six months ahead. “Eighty percent of the joy of taking the trip is looking forward to it,” he said. 

Strayed is the co-host, along with the very funny Steve Almond, of the Dear Sugar Radio podcast, which started with a written advice column that Strayed wrote anonymously for a website called The Rumpus. 

Her goal with the column and now the podcast is simply to illuminate part of a situation that listeners can’t otherwise see. “I’m trying to get you to ask deeper questions of yourself.” 

“When we seek advice, we often aren't looking for answers,” she says. “We want to know that we’re not alone.”

When listeners write letters, they often ask for help solving a problem, but Strayed says she can almost always hear in their voices a hint at what they really want to do but are afraid to commit to the decision. 

“Your gut knows what you want to do, and one of the scariest things in life is doing that thing that we know we need to do,” she said. 

Having an abundance of love for yourself means you know when it’s time to let go of your ego, pride or doubt. Surrendering isn’t a sign of weakness but strength, she said. Taking that leap of faith -- from an epic 1,100-mile hike to a split-second decision to say “no” when you might have felt obliged to say “yes” -- is how you cultivate a way of living that makes a life.