Hey there! We’re Sydney and Barry Williams and we’re on a mission to help more folks enjoy the healing power of the great outdoors. On May 21, 2018, I (Sydney) found myself training for a second thru-hike of the Trans-Catalina Trail. On the top of Stonewall Peak near San Diego, California, I realized that in this time of stress - having just left my post as CMO at an early-stage startup - that I wasn’t deploying my usual coping mechanisms. After being diagnosed with Type 2 Diabetes in September 2017, I had replaced eating or drinking my feelings with hiking my feelings. And thus, a hashtag was born. Not one to be satisfied with just one answer, I wanted to know why I started eating and drinking my feelings to begin with. The second hike across Catalina Island would answer that question for me.

Shortly after completing the Trans-Catalina Trail the second time, I gushed about how much the trail had changed my life to the Catalina Island Conservancy. A few emails later, I was connected with the Los Angeles/Orange County programming coordinator for REI, and a speaking tour was born. We started with three test dates in SoCal stores, speaking on Friday night and hosting hikes on Saturday morning. After the first talk, we knew this is what we wanted to do for the foreseeable future. The first tour was a great success, and over the course of the following month, we sold all of our prized possessions and bought a camper van. We named our van Ruby and we’ve been calling her home since November. She’s ruby red and since #homeiswhereyouparkit, with a click of our heels, Ruby takes us anywhere we want to go.

In January 2019, we did another tour through Los Angeles-area stores, and before that tour ended, Hiking My Feelings expanded from a hashtag and some blog posts into a national experiential tour, sharing inspiration and ideas to help folks summit their personal mountains.

Now we are traveling around the United States in our van, sharing the story of how two thru-hikes across Catalina Island helped me heal my mind and body from the inside out. I’m pleased to report that my Type 2 Diabetes is in remission - all thanks to this beautiful container we’ve created for processing trauma. Between my speaking engagements and our weekly group hikes, Barry and I are outdoor advocates and Trail Angels, popping in to some of the long-distance trails around the US to offer food and drinks to the hungry thru-hikers traversing some of the most beautiful and rugged landscape this country has to offer.

Hiking My Feelings is the title of the talk I give on tour as well as my forthcoming memoir, and with your help, a movement highlighting how spending time outside can help us heal our minds and bodies and help us move forward into the lives we’ve always dreamed of living.




Founder, storyteller, hike leader, outdoor advocate, feeler of feelings.

  • FORMER LIFE: CMO at early-stage startup, #agencylife, competitive skydiver (that’s how Barry and I met)

  • FAVORITE THING ABOUT HIKING: When my body gets so tired and I’m out of things to complain about, that’s when the Hiking My Feelings starts.

  • HIKING GOALS: Pacific Crest Trail (and any other long distance trails that call to me)

  • FAVORITE VAN MEAL: Shrimp tacos

  • TATTOOS: 5


Tour manager, hike leader, Wilderness EMT, content producer, supportive partner.

  • FORMER LIFE: Professional skydiver (more than 8,000 jumps) and slinging technology to banks circa Y2K

  • FAVORITE HIKE: Highline Trail at Glacier National Park

  • HIKING GOALS: Hike Olympus Mons

  • FAVORITE VAN MEAL: Anything Sydney makes

  • TATTOOS: 6






"I think we just discovered the next Cheryl Strayed." — Rachel R., REI CO-OP

"You would not believe the impact you made on me in just 90 minutes. — Andrea M, Boulder, CO

"Hiking My Feelings has helped me through the hardest period of my life. " — Rebecca A, Reno, NV

"Thanks for spreading inspiration, empowerment, and healing. Grateful for you!" — Damiana R, Los Angeles, CA

"This work has radically changed my life." — Talia L, Marina Del Rey, CA


Here’s a taste of the tour







3960 West Point Loma Blvd
Suite H-1010
San Diego, CA 92110