The Adventure of a Lifetime: HIGHLANDER Big Bear Lake
Last month, we moved off Catalina Island and back into the van.
Before we hit the road for Big Bear, we swung down to San Diego for an intimate evening recording with Jakob Nowell at the Muffin But Good Vibes Acoustic Session. It was the perfect “welcome home” and all of my San Diego senses were engaged: spending the evening with our friends who feel like family, enjoying our favorite sandwiches from Beach Hut Deli (they sponsored the last season of the Virtual Campfire podcast), and sippin’ my all-time favorite booch - POG from Babe Kombucha - poolside.
I tossed and turned for a bit, my excitement for our next adventure delaying my peaceful slumber. In the morning, we were heading up to Big Bear Lake to sign in for our Highlander Adventure - three days, 30+ miles through wildflowers, high desert, and pine forests. The best part? This was the first event we were participating in that we didn’t organize ourselves. All we had to do was show up with our gear packed up, and the HIGHLANDER team promised to take care of the rest - permits, campsites, INSURANCE (!!!), food, water - they thought of everything. Eventually, finally, I drifted off to sleep.
🐐 HIGHLANDER PART 1: Break down to breakthrough.
Back in 2018, we sold everything we owned and used the money to buy Ruby, our 1998 Chevy Van. Without Ruby, we couldn’t do what we do. As she creeps up on 200,000 miles, we know our time with her is limited.
In this moment, I was convinced that I was the first and only person to ever have car trouble.
It was our first full day back on the road in the van after living on Catalina Island for five months, and we were on our way to the HIGHLANDER Adventure event in Big Bear Lake. After pulling over to host a workshop via Zoom with Gabaccia for The Outdoorist Oath, Ruby wouldn't start. We were parallel parked in Old Town Temecula (perfect for towing 🙄), an area that holds a lot of memories from my skydiving days.
The shadow side of my Main Character Energy was out in full force. Everything was a personal attack. I desperately wanted a single cigarette to calm my nerves. I'd been sober for almost a year but the Smoked Old Fashioned was whispering sweet nothings to me from behind the bar at one of our old haunts. My chest was tight, my eyes were welling up with tears, and adrenaline was coursing through my veins.
In this moment, I was hyperaware of the choices in front of me:
Stop what I'm doing and feel the feelings and allow them to pass OR give in to my old methods of coping to avoid this temporary discomfort.
I chose to feel, and on the porch of the mechanic's shop, I wrote and wept:
"We had to break down in Temecula so I could have this breakthrough on this porch."
As I got curious about the feelings, I acknowledged my sensitivity to the energy this area carries, and how I had been avoiding it for almost 10 years. So I sat with what was left of my grief from my skydiving days, remembered the joy we found here, and by the time my nervous system had regulated itself, Ruby was ready to go.
Finally, we resumed the road trip to Big Bear Lake for what promised to be The Adventure of a Lifetime.
Would we make it to Big Bear in time to check in for the event?
🐐 HIGHLANDER PART 2: Ask for what you need.
On the bus to the start of the trail! We had 70+ people hiking with us on the Pegasus format, but we spent most of our time on the trail alone.
By the time we arrived in Big Bear Lake, registration for our HIGHLANDER Adventure was closed for the evening.
It would be open again tomorrow from 5-6:30am, but first, we needed food and a place to park the van. We drove to our favorite dispersed camping spot nestled amongst the trees - the perfect place to spread out, pack up our gear, and get a good night's rest. As we turned the final corner to get to the spot, my heart sank into my guts.
The gate was closed. As were any decent restaurants in town. Deflated, we picked up Taco Bell and ventured to a hotel nearby. When the cheap rooms were booked, I did a thing that felt huge for me in this state: I asked for what I needed instead of feeling sorry for myself or spiraling about this moment.
"We have an early wake up call for a backpacking event, would it be possible to park our van in your lot tonight?"
They agreed. A sign of good things to come. What else can go right?!
The next morning, we woke up at 3:30am, drove back to Bear Mountain Resort, and got our equipment ready to go.
Registration includes your food (vegan and meat options available), and you only carry one days’ worth of food at a time!
As we walked in to register, my brain was on overdrive. This was one of the most beautifully branded events my little Recovering Marketer heart had ever seen. The HIGHLANDER staff was friendly and genuinely excited to be there. We picked up our bibs, welcome kits (maps, fuel, a buttery-soft merino wool buff) and our food for the day, and made our way back outside where I drank copious amounts of tea from Art of Tea and fizzy adaptogenic water courtesy of Hop Water.
At the start line with the wind blades. This is serving big skydiving boogie vibes and is so well organized!
This reminded me of the huge 400+ person events I used to organize in skydiving mixed with the spirit and intention of the Wilderness Wellness retreats we host now. This was special.
On the bus ride to the start of the route, Little Sydney had so many questions: What would it be like to be on the trail with this many people? Would we make new friends? Would we fit in? And, after five months at sea level with minimal hiking, can we still do this?
📍DID YOU KNOW: The Serrano people first came to Yahaviat ("pine place") some 2,500 years ago. The name Serrano meant people of the mountains or highlanders.
🐐 HIGHLANDER PART 3: Glimmer Moments
As we hit the trail for the first day of our HIGHLANDER Adventure in Big Bear Lake, I had a few glimmer moments. If you're unfamiliar, a glimmer moment is the opposite of a trigger - it's a moment that can spark joy or peace or another positive feeling.
💫 Glimmer 1: approaching the start line, Marc was on the mic getting everybody hyped. I love witnessing someone in their zone of genius and Marc was squarely in his.
💫 Glimmer 2: Crossing the PCT. I wondered what my friends (like Ash and Mike) were thinking about as they cruised through this section. Every time I cross this trail, it calls me in, inviting me to drop everything, give in to my curiosity, and experience all it has to offer.
💫 Glimmer 3: I've never hiked with 70+ people before and it was quite the experience. Everyone was super friendly and welcoming. This was also the first outdoorsy anything I've participated in that I didn't organize, so I was really enjoying being catered to, cared for, cheered on, and looked after.
💫 Glimmer 4: channeling my inner Joshua Swain from The Movement’s song Hola: "chillin in the shade of a Joshua Tree." There aren't many Joshua Trees that provide meaningful shade but I found some at the most perfect time on the trail.
💫 Glimmer 5: as we were in the final stretch to our first checkpoint/campground, I noticed a Sensitive Species sign on the side of the road. I too am a sensitive species, and it's one of my favorite things about myself. The capacity to feel deeply is a super power and one that I do not take for granted.
💫 Glimmer 6: my backpack mascot, Pixy the Unicorn, came along for this ride. In our tent on day one, I discovered that it was Pixy's birthday on May 26, the day this adventure started. (Swipe through the IG post here to see the video, you’re welcome.)
All in all, our first day was epic. HIGHLANDER is quick to point out that this isn't a race, but that doesn't mean I can't be insanely proud of me and Barry for being first to camp on Day 1.
Day 2 promised hot sun, no shade, and big miles.
You use your bib number to check in at the checkpoints each day. We did the Pegagus format, so our bibs were blue. Hercules (100/60 Miles) bibs were orange, and Orion (15 miles) bibs were green. It was fun to meet people doing other formats and learn about their experiences so far.
🐐 HIGHLANDER PART 4: Butts and Brilliance.
I've walked thousands of miles looking at Barry’s butt. I'm 100% biased but it's my favorite view.
This view means we are together, doing the thing that makes us happiest. Even better if we get to share it with people.
And apparently, that's what I came to HIGHLANDER for - to remember what makes me happy.
Five years ago, a simple phrase changed my entire life - I was hiking my feelings instead of eating or drinking them.
Five years ago, I knew exactly what I wanted: to be a speaker, an author, and to share the healing power of nature with anyone who was willing to slow down long enough to listen.
And for awhile, I did that - 140 stops on a speaking/hiking tour in 2018-2019. My first book. Then 2020 happened and killed all the momentum we had been building. We made one pivot after another to sustain this organization, but what I was doing wasn't always sustaining myself. As my friend Gary would say, my life had turned into a proving ground. I was missing my playground.
Did you know that some trees smell delicious? It’s true! Next time you’re out hiking, stick your nose in the bark of the tree you’re hugging and take a whiff. Smell like vanilla? It’s probably a Jeffrey Pine!
And in the first five months of this year, I almost forgot how to play, and I didn't have nearly enough time with my favorite view. This trip was right on time, and it was exactly what I needed: social time with people who already love backpacking or are trying it for the first time, wide open spaces to let my mind wander and my soul fly free, and a physical challenge to help me work out the stagnant energy.
HIGHLANDER also gave me space to remember:
💫 I am a gifted communicator. My story has helped and will continue to help people.
💚 I have a big heart. Despite everything I've overcome, this heart is still wide open and ready to love.
🐐 I am my happiest, freest, most fully expressed self when I am outside on the trail, preferably for days on end.
The Big Bear Lake route was a mix of single-track, OHV trails, and fire roads through forested areas and high desert landscapes. We highly recommend bringing trekking poles - they can reduce the load on your knees and help with stability.
And there is nobody I'd rather smell trees and do life with than Barry. Thank you for being my favorite adventure buddy, my best friend, and always my coach. Thank you for helping me remember and recognize my brilliance. And thank you for the best five years of my life so far.
🐐 HIGHLANDER PART 5: Yes, and!
We came here curious.
Curious about what backpacking would feel like after five months at sea level with minimal (for us) hiking before the event. Curious about what our Trail of Life had in store as it unfolds before us, as this trip was a transition between our life on the island and getting back to our life on the road. Curious about whether or not we would enjoy an event like this.
Well, we crushed it - this was some of our best hiking - feeling good, making good time, enjoying the trail while also having plenty of time to recover.
Our Trail of Life continues to surprise us. Throughout this event and since it ended, we have been blessed with some incredible news, exciting opportunities, and radical kindness.
🎉 Turns out, we LOVE this kind of event!
If you're looking for a single-track, don't-see-another-human-for-days kind of journey, this might not be for you.
But if you want to try backpacking differently or for the first time, have your food and water provided, all the logistics sorted, attend an outdoorsy event with 60% female participants (!!!), make new friends, and enjoy some programs and social activities along the way, then a HIGHLANDER adventure is 100% for you.
I came in here thinking it had to be either/or - that I was a backpacking purist who was completely self sufficient OR I was a social backpacker who likes having the details handled by someone else.
Turns out, like everything good in my life, it's "yes, and!"
YES, I relished the sections of trail where it was just me and Barry for miles, AND I loved the cowbells and time with the community as we finished for the day.
YES, I loved carrying only one day's worth of food at a time because it was provided, AND I would supplement with some of my backpacking staples on our next HIGHLANDER event.
All in all, 10/10 would do again.
💚 To the Highlander team: thank you for doing what you do. It truly was the Adventure of a Lifetime.
💫 To our fellow Highlanders: thank you, congratulations, and let's do it again!
🐐 Wanna be a goat with us in Montana in September?
Experience fall in Montana while exploring Flathead National Forest with us as we embark on our first Hiking My Feelings x Highlander Adventure!
Since we started in 2018, we’ve wanted to host a backpacking trip for our community and now the perfect trip is finally here! After participating in their Big Bear Lake backpacking event earlier this year, we are stoked to partner with the HIGHLANDER team on their upcoming event in Kalispell, Montana!
We’ll be leading a workshop to help participants prepare for the mental aspects of a backpacking before the trip, hosting programs on-site and hyping you up on-trail and at camp during the event, and offering resources to help you integrate your experiences after you return home a HIGHLANDER.
