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Hiking My Feelings

When I was diagnosed with Type 2 Diabetes in September 2017, I had to make some changes.

The choice was mine to make:

Keep doing what I’m doing and eventually let this disease start claiming parts of my body and life.


Make some radical changes to the way I exist in this world, coming from a place of love (for myself) versus fear (of what this disease could do to my body). 

I quickly realized that my normal go-to coping mechanisms were no longer available to me.

I wasn’t going to be able to eat my feelings anymore. The answers were never found in a pint of Ben and Jerry’s anyway.

I wasn’t going to be able to drink my feelings anymore. Shocker, the answers were never found at the bottom of my wine bottle either.

So I chose the radical change route.

When I say “radical change” what kind of imagery does that rustle up for you? Are you imagining grilled chicken and broccoli? Egg whites? Exercising obsessively? Something that takes a lot of time? A lot of effort?

Because if it does, that’s not what I did.

In fact, that’s what I did every other time I tried to lose weight. Historically, it goes something like this: Sydney needs to lose weight for (INSERT REASON OTHER THAN HEALTH AND WELL-BEING). Start restricting diet immediately. Hate myself when I slip. Work out like a crazy person. Hate myself when I miss a day.

This time? This time I loved myself through it. I had already made the commitment to myself before we set out to hike the Trans-Catalina Trail for the first time at the end of 2016. In that REI dressing room, I swore I’d honor my inner athlete.

Honoring My Inner Athlete vs. Hating Myself Skinny. Hmm. Guess how this worked out.

As the months went on and I lost weight, improved my A1C readings, and generally started feeling AMAZING, I was like OH SNAP. I had a new coping mechanism!

I had been walking up and down the “hill of death” in my neighborhood 5 days a week, then we started doing our training hikes for the TCT. I realized that instead of eating or drinking my feelings, I was hiking my feelings.

On June 2, 2018, we set out on our second adventure on the Trans-Catalina Trail – this time we were determined to finish the trail. As I put one foot in front of the other during that 40+ mile trek from one end of Catalina Island to the other, stars and planets and souls aligned. With each vista, I had a little bit more visibility on the context of my life, how everything was connected.

For all of my life, I’ve been told to not make any major decisions for the first 24-72 hours after a life-changing event. That anything that happens there is crazy jumbled “this isn’t real life” brain.

We got back on June 7th. The days between the 7th and the 17th were some of the longest, darkest, weirdest days I’ve experienced so far. I haven’t been formally diagnosed with depression so let’s call it a funk. The funkiest of funks.

I was at risk of repeating this in the latter half of June, as we had some action-packed weekends coming up to round out Birthday Month celebrations. But I realized I find meaning in damn near EVERYTHING and I can’t turn that off, so if I am in this perpetual waiting period after an event that drives my inspiration, how do I ever create?

I don’t.

And for years, DECADES, I’ve shut this part of me down. No more.

Armed with this insight, I let go of that mindset and tried on a new one.

On June 17th, I graduated from Level 3 at Finest City Improv. The second I got on stage and in my first scene, I was snapped out of the funk I was in.

The following weekend, we saw back-to-back concerts in Vegas and San Diego with @pepperlive@stickfiguremusic and @slightlystoopid. It was an incredible experience, I detailed it on Instagram here. And if THAT level of epic was possible, what else is possible?

Instead of running from the inspiration I usually find after a life-changing event (like I did for those 10 days after we got back from the trail), I chose to lean in.

I finally gave myself permission to relax, to let go, to be inspired.

I put the entire Stick Figure catalog on a Spotify playlist, from oldest to the latest release, and listened. I Googled lyrics to the songs I didn’t know yet.

Knowing what I know about my own story and my own growth, I put myself in the brain behind the band’s shoes: Scott Woodruff. What would it feel like to create something that can impact someone so much? What would my life be like if he withheld that gift? What if I was too scared to create? What if I wasn’t? Monday, Tuesday, Wednesday, I leaned in, listened, and sat with what came up. Took my time.

On Thursday June 28, I woke up with an appointment for a very important call on my calendar at 12 pm. That night, our next adventure was born in our living room.

On Tuesday, July 3, 2018, one month after my 33rd birthday, I started writing my first book. Not surprisingly, it’s inspired by this concept of Hiking My Feelings and my experiences on the Trans-Catalina Trail. In just a few hours, I had written 17 pages. This book is POURING out of me.

Now I know that what I feel when I have these kinds of experiences isn’t “crazy” – it’s inspiration.

Now I know to listen.

Now I know why I’m here.

Time to get to work.


#HikingMyFeelings: Lessons Learned on the Trans-Catalina Trail

Woman, Type 2 Diabetic, Survivor.

In December 2016, Sydney Williams was standing in an REI dressing room trying on hiking gear for her first backpacking trip.

Size 16. The largest size REI carried. The heaviest Sydney, a former competitive athlete, had ever been.

Usually, she would have looked at herself with disgust. But this day was different. She looked herself in the eye and simply asked, GIRL, how did we get here?”

It was a rhetorical question for the dressing room, but two treks across Catalina Island while thru-hiking the Trans-Catalina Trail would start to connect the dots on more than a decade of emotional and physical trauma.

“Hiking My Feelings” is how Sydney adjusted her coping mechanisms after being diagnosed with Type 2 Diabetes in September 2017. After realizing her choices had contributed to the diagnosis, she realized she could change those choices. Historically, she had soothed and celebrated with food and alcohol.After a training hike for the TCT, she realized instead of eating or drinking her feelings, she had been hiking her feelings.

And thus, #hikingmyfeelings was born.

But why was she eating or drinking her feelings to begin with? Ask and the trail shall answer.


“Hiking My Feelings” is a multimedia movement:

  • Speaking + Hiking Tour with REI
    • Speaking Dates (more coming soon!)
    • Group Hikes:
      • If you’re interested in joining the group hikes, please opt-in below to join our Facebook group and email list. Group hike information will be shared via those two channels.
  • Sydney’s book about her two thru-hikes of the Trans-Catalina Trail
  • Stories: on the group hikes following the speaking engagements, we capture the stories of everyday people who have overcome extraordinary obstacles and found healing on the trail

Visit hikingmyfeelings.com to learn more about the project.

Hiking My Feelings Essays

This first post is where it all began. After I left the startup that I thought would be my final destination, that’s when I realized I wouldn’t have the coping mechanisms I had been leaning on during times of stress for my entire life. This is where those dots start to connect and Hiking My Feelings is born.

The intro: Hiking My Feelings.

How We Talk About Weight Loss addresses how the actions I took to take control of my disease were very different from any other weight-loss journey I’ve been on. Spoiler alert: It’s easier when you come from a place of love.

Hiking My Feelings: 5 Peaks, 5 Strengths came after Barry and I completed the 5 Peaks Challenge at Mission Trails Regional Park in one day. This hike is the perfect training hike for the first day of the TCT, AND each peak had some lessons that were directly tied to my Top 5 Clifton Strengths!

CLICK HERE for all Hiking posts