I fell in love with Cheryl Strayed ‘s raw, authentic, straight forward, heart warming writing as the popular advice columnist of “Dear Sugar.” She tapped into a level of emotional depth that helped me feel validated and understood. All of her books, Wild, Tiny Beautiful Things, Brave Enough, and Torch helped me with the many layers of my healing journey.

My husband and I went to see the movie Wild the weekend it opened in 2014 while we were visiting his family at the Jersey Shore and I wept. As a woman who was nearly 2 years sober, it had such a deep impact on my soul and inspired me to make a commitment to myself to get back to writing and finish the book I started many years prior. MY self An autobiography of survival was published in April 2017 and I’m in the thick of pitching the adaptation to production companies. Cheryl’s force is like no other and she has inspired me to live my best life, especially one with no tolerance for B.S.

There’s so much I relate to in Cheryl’s personal storytelling. We both attended (10 years apart) The University of St. Thomas in St. Paul, MN a small, Catholic college our freshman year then transfered to large universities. We both married incredible men albeit our relationships with our fathers being distraught and not the best role models of male relationships. She hiked the Pacific Crest Trail and I participated in a 2 week stint of Outward Bound on some intense trails outside of Billings, Montana. At the age of 15, it felt like a year but being with oneself in nature was incredibly transformative. The list goes on and I found myself in disbelief with the similarities. She helped give me words to so many feelings and I serendipitously found them in her books when I needed them most.

She’s a fierce woman who talks about all the things people don’t have the guts to talk about but are desperately seeking answers to. She has given me permission to do the same through her fearless example of being the change we wish to see in the world.

Cheryl Strayed was the keynote speaker at an event I was on a panel for in L.A. in September. It was a 3 day women’s retreat called She Recovers. She’s just as amazing in person as she is through the pages she writes. She’s been my all time favorite role model and as she was signing my copy of Wild, I gave her a copy of MY self for her 50th Birthday. My heart exploded, a dream come true! I hugged her as tears of joy streamed down my face. It was a surreal experience having the opportunity to tell her what an impact she’s had on my life. She agreed to do a phone interview with me for my series Women I Admire (including Natalie Morales and Martha Beck) for Thrive Global.

Thursday, 9/27 were the Kavanaugh hearings. Cheryl’s interview happened to be scheduled the same day in between the testimonies of Dr. Ford and Brett Kavanaugh. There’s no other person I would have rather spoken to in that moment as I was transitioning home form work feeling all of the feels. Her voice was soothing and we both acknowledged how an emotionally charged day it had already been. I could have spoken to her for hours but we only had 30 minutes and her success and my longing to follow in her footsteps were the agenda items, so I switched gears.

Cheryl’s in a time of transition. She’s recently made some career changes to go back to her original love of writing as she’s working on a new book. “So many opportunities have come my way. I basically had 4 full time jobs, public speaking, an activist, a mom, and a podcast host. I’m writing another book and I need to put my attention on sitting in a room for days, weeks, and months on end and just write.” It’s been a season of good byes imprinted with love. She and Steve Almond (her co-host of Dear Sugars) just wrapped their fourth and final season produced by The New York Times and WBUR. Additionally, after many years of leading writing workshops called Esalen Writers Camp, Cheryl has taken a step down with a deep sense of gratitude for all of the people she’s met over the years.

Cheryl also hit a huge milestone turning 50 a few days after I met her. I asked how it’s been so far and she reported, clarifying. She knows what she wants and she doesn’t wait for anyone to give her permission. She and her husband are currently writing a t.v. pilot together and she continues to work on projects with Reese Witherspoon (who played Cheryl in Wild) and Laura Dern (who played her mother). I can hardly wait for the adaptation of Tiny Beautiful Things which is one of the many projects on the list!

She’s raising a 7th grade daughter and 8th grade son who she’s extremely open with during a time that is even more important than ever to communicate with our children. She encourages their freedom and opinions and embraces their strong spirits in conjunction with fostering her marriage to husband Brian Lindstrom who is a filmmaker. (Another commonality, my husband is Ryan and an actor, and 1 of my 4 kids is also in 7th grade.) 

My biggest take away from our conversation was her suggestion to pursue every opportunity we are given and to make the most of it. I was in awe by her seemingly well balanced life, something I know we all strive for, and the strong tribe of women she surrounds herself with. Keep on keepin’ on soul sista we need your truth telling to make some sense of this crazy world we are living in. 

Rarely do we get the opportunity to meet our role models especially the ones we’ve been admiring from afar who have no idea the impact they’ve had on our life. I’m forever grateful to have had this experience and will keep it in my back pocket as a constant reminder that anything is possible and to shoot for the stars. 

Author(s)

  • Kelley Kitley, LCSW psychotherapist

    Media Mental Health Expert

    Serendipitous Psychotherapy, LLC

    Kelley Kitley, LCSW owns SERENDIPITOUS PSYCHOTHERAPY, LLC on The Magnificent Mile in downtown Chicago. She's a sought after international women's mental health expert, author, and has appeared in over 100 national publications, podcasts, live news, and radio including WGN, NBC, The Chicago Tribune, Huffington Post, Dr. Oz, Dr. Drew, Access Live, and TODAY. Kelley is the author of the award winning best selling book, ‘MY self: An autobiography of survival' and TEDx speaker: 'I show my scars so others know they can heal.'