Meet Sydney Williams of Hiking My Feelings in Point Loma

Today we’d like to introduce you to Sydney Williams.

Sydney, please share your story with us. How did you get to where you are today?
In September 2017, I was diagnosed with Type 2 Diabetes. I was working 60-hour weeks at a PR/Marketing agency, and my stress was through the roof. This job was, quite literally, killing me. I had a choice to make, take my health into my own hands by whatever means necessary, or let this disease take my life.

There are four factors that affect your blood sugar; food, exercise, medications, and stress. I took the first three head on and cleaned up my diet, started walking 30 minutes every day, and was prescribed a medication for my Diabetes. I saw results in my physical body, I was losing weight, I was feeling better, but my blood sugar levels were still elevated. I needed to take action to address the fourth bucket: stress.

In 2017, I had been helping a friend with the branding and marketing for her small business. In January of this year, I had a chance to join the startup full-time as co-founder and CMO. I thought that by doing work that was more aligned with my passions (women’s empowerment and social justice) that perhaps I could alleviate my stress that way.

I made it just over 90 days at the startup before I had to make the hard choice: leave this company with no backup plan. I was having panic attacks near daily, my sugar levels were worse than they were when I was at my old job, and I was at risk of reversing all the progress I had made in managing the disease thus far. Not surprisingly, the move from a PR/Marketing firm to an early-stage startup with cashflow issues did not alleviate my stress, in fact, it doubled down.

I didn’t know what was next, but I knew that a hiking trip on Catalina Island in December 2016 unlocked some growth for me, and I wanted to return to the Trans-Catalina Trail for a second time. I had been walking every day and had lost more than 60 pounds since my diagnosis. I realized on a training hike in advance of our second trip to Catalina that I had replaced my normal coping mechanisms of eating or drinking my feelings with hiking my feelings. On May 21, 2018, “hiking my feelings” was a blog post and a hashtag.

Today, we are gearing up for the 5 Peak Challenge at Mission Trails Regional Park this weekend. We started a Trans-Catalina Trail training group, and the challenge is the last of the hiking series in San Diego. In January, we move the show up to LA, launching the second leg of the Hiking My Feelings Speaking + Hiking Tour in collaboration with REI and the Catalina Island Conservancy, and kicking off our LA-area training group as well.

On my speaking tour, I share the story of my two hikes across Catalina Island and all the lessons learned along the way. The first trip in December 2016 was the hardest thing I’ve ever done physically, and this trip in June of this year for my 33rd birthday, after I left the startup, was the hardest thing I’ve ever done emotionally.

On the second hike across Catalina, I realized that everything that had been happening in my life was tied to a sexual assault I survived 12+ years ago. Suddenly, everything made sense. After my diabetes diagnosis, as I started to address my mental health, my physical health followed.

Hiking My Feelings is currently a speaking + hiking tour and the title of a series of books that I’m writing about my experiences on the Trans-Catalina Trail. In 2019, we will be hosting Hiking + Healing retreats, and we’re really excited to guide folks through the transformational experience I had and empower them to recreate themselves outside.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
I would love to say this has all been sunshine and roses. The diagnosis in September 2017 could have been the thing that ruined me, but I turned it into the best thing that ever happened to me. Truly, I am so thankful for my diabetes.

It forced me to get in touch with my body, something I had been avoiding since my sexual assault 12+ years ago. It forced me to ask myself: what does Sydney ACTUALLY want? I had been going with the flow, doing what I needed to survive and thrive, without ever actually considering what would make me wildly happy. I was brilliant at marketing, and I wanted the title of CMO before I was 35. I was hired as CMO of that startup at 32 years old.

Once I got there, in addition to all of the chaos happening in my body, I realized very quickly that if I was going to be working my ass off, killing myself, putting in hours and hours and hours, it better be on my terms, and it better benefit me, first and foremost. I had spent so much time, my entire career, chasing titles and salaries and whatever came NEXT, I didn’t have a chance to enjoy the present moment. After I quit the agency, I took a 50%+ pay cut to join the startup.

When I joined the startup, there were significant cash flow issues so I foolishly extended my personal credit to the business, hoping that maybe if I could fund some big orders, maybe I’d get my next paycheck on time. When that plan wasn’t working, and when the owner of the business acknowledged that she couldn’t afford my salary, after all, I was at a bit of a standstill. I looked at my bank account. I looked at my growing debt. I had to get out.

Without my six-figure salary, I knew we wouldn’t be able to stay at the house we were renting in South Park, so we started to look at other options.bOnce we got off the TCT the second time in June, I walked into our house and said “this house is too big, and we have way too much stuff,” and my husband and I started the process of selling everything we own so we could move everything into a van.

Over the last six months, we have been researching, looking at existing vans, exploring partnerships with RV companies, and doing everything we could to get ourselves set up for success. After the first leg of my speaking tour in October, we expedited our timeline. We knew this was what we wanted to do – to share my story of transformation with anyone and everyone who could use some inspiration.

On November 29, 2018, my husband and I moved all of our belongings into the van so we can live in it full-time while we’re on the road. We have been in the van for a week now, and it’s hands down the best decision we’ve ever made. Not without its own adjustments (Where do you park? How much solar do we need to keep our devices charged? Where do we shower?), but we are loving this much simpler existence.

Finally, throughout all of this, I have experienced major resistance from my immediate family. That’s the most challenging obstacle of all of this. I grew up in a house full of love, a tight-knit family, and to know that they don’t support this chapter of my life is wild to me. I cannot wrap my head around it.

The second I got off the trail and mentioned the ideas we had for Hiking My Feelings (writing books, traveling, sharing stories on a speaking tour and hiking with folks afterwards), they started questioning my sanity, and I had to establish hard boundaries in order to preserve my energy and maintain my focus.

Alright – so let’s talk business. Tell us about Hiking My Feelings – what should we know?
Hiking My Feelings, right now, is a movement and community more than a business in the traditional sense. We are hosting free hikes to get people outside and experiencing the mental and physical health benefits of spending time outside. We’ve found that one of the biggest barriers to entry when it comes to outdoor adventures is having someone to do it with, so at the very basic level, we’re saying “hey, come hike with us!”

We specialize in creating a warm, welcoming environment for folks from all walks of life who want to get outside and find healing. We’re really proud of the container we’ve created, a place where exploring feelings is encouraged, supported, and celebrated. We’ve spent the last six months building the community, touring southern California, and learning more about the land we live and play on so we can educate the hikers that join us about the indigenous roots of the land here in Southern California.

In 2019 on our Hiking + Healing retreats, we’re incorporating yoga, reiki, and music therapy. The physical act of backpacking is strenuous and can bring up some powerful emotions and memories as we challenge ourselves physically and mentally. Combined with a journaling practice and a supportive community, we’re excited to support new and experienced hikers and backpackers in the years to come!

There is no shortage of hiking meetup groups, you can find quite a few via Facebook and a quick Google search. These groups, for the most part, cater toward folks who just need someone to hike with. Currently, there are very few organizations catering to mental health + the outdoors in this way. That is changing, and we’re excited about the trends in the outdoor industry. REI gave the University of Washington a $1M grant for researching this exact topic, and we’re excited to support that research as we facilitate more groups in 2019 and beyond.

Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
Without my husband, best friend, and adventure buddy for life, none of this would be possible.

In 2017, prior to my Diabetes diagnosis, I told my husband about the sexual assault I survived 12+ years ago. He was the first person I told. At the time, the assault had happened 11 years ago, and we had been together for seven years. Without him to create a safe space for me to explore my sexual assault and the unresolved trauma that came as a result of me not seeking help after it happened, none of this would be possible.

Throughout this year, through all the transitions with my disease, with my career, and now, with Hiking My Feelings, Barry has been my rock, a sounding board, a shoulder to cry on and a hand to hold. We are in this together, through and through.

Specific to his role with Hiking My Feelings, Barry helps me pick out the hikes we do on tour, coordinates logistics of where we’re going, where we’re staying, and how we get there. He was an EMT earlier in life and is trained as a wilderness EMT, so having his medical experience on-trail gives me great peace of mind.

More than all of that though, especially given the lack of support from my immediate family, it is because of Barry that I feel so loved, supported, seen, and confident in what we’re doing here. I am so lucky to have such an amazing partner in this life, especially one who shares this love of adventure. To be able to experience all of this with him by my side is what makes it so much fun.

Contact Info:

• Website: hikingmyfeelings.com
• Email: sydney@hikingmyfeelings.com
• Instagram: instagram.com/sydneyunfiltered
• Facebook: facebook.com/hikingmyfeelings
• Other: instagram.com/hikingmyfeelings
• http://williamsinthewild.com/

Image Credit:
Thomas Van Veen, Stephanie Lauren Sargeant, Barry Williams

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