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Hiking My Feelings: 5 Peaks, 5 Strengths - SYDNEY: unfiltered.

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Hiking My Feelings: 5 Peaks, 5 Strengths

On Wednesday, Barry and I set out to complete the Mission Trails Regional Park 5 Peak Challenge in one day and I’m happy to report that we did!

We followed this route with a creative exit out of Oak Canyon after we ran back down the saddle trail to the Fortunas so we logged 16.23 miles in total. That link gives all the data/directions you need to navigate to all 5 peaks, so if you’re interested in completing the challenge, I definitely recommend starting there!

5 Peaks, 5 Strengths

As I mentioned in Monday’s Hiking My Feelings post, I recently left my job without a backup plan and am out here exploring and following what makes me happy. One of the things I did before I made the decision to make room for more adventure in my life was take the Clifton Strengths Assessment.

I was at a particularly low point, questioning who I am, how I show up, and why I’m here. I had been in a swirling pit of mismanaged expectations (mine and others) and projections (mine and others) and I was having a hard time remembering who the hell I was and what I was good at. So I took this assessment.

And the results weren’t shocking, but they were everything I needed at the time so I could get back to center, find my confidence, and make some decisions.

While I was hiking these five peaks on Wednesday, I found myself thinking about these traits and how for all of my life, I’ve been fighting to understand why I react the way I do to certain things, how I work, how I process information, how I approach relationships, all of it.

My Top 5 Themes according to Gallup’s Clifton Strengths Assessment:

#1 Empathy: People  who are especially  talented in the Empathy  theme can sense the feelings  of other people by imagining themselves  in others’ lives or others’ situations

#2 Responsibility:  People who are especially talented in the Responsibility theme take psychological ownership of what they say they will do. They are committed to stable values such as honesty and loyalty.

#3 Learner: People who are especially talented in the Learner theme have a great desire to learn and want to continuously improve. In particular, the process of learning, rather than the outcome, excites them.

#4 Intellection: People who are especially talented in the Intellection theme are characterized by their intellectual activity. They are introspective and appreciate intellectual discussions.

#5 Adaptability: People who are especially talented in the Adaptability theme prefer to “go with the  flow.” They tend to be “now” people who take things as they come and discover the future one day at a time.

Not surprisingly, the order in which we completed the peaks follows my strengths, in order:

#1: Cowles Mountain – Empathy

Empathy: People who are especially talented in the Empathy theme can sense the feelings of other people by imagining themselves in others’ lives or others’ situations.

As I was making my way up Cowles, I was struggling. It felt like it was taking me way longer than usual to get warmed up. I started to worry about whether or not I was going to be able to make it all day, as this was the first longer hike we’ve done since I was diagnosed with Type 2 Diabetes last year.

I had spoken with my doctor prior to picking hiking back up to talk about any concerns I should be considering as we prepare for the Trans-Catalina Trail. Initially, I was worried about the quality of the food I’d be eating on the trail since I’ve done a complete overhaul on my food + fitness stuff. I know I need to consume carbs (and sugar) to keep going on a long backpacking trip but I didn’t fully understand what that meant as a newly diagnosed diabetic. My doctor assured me that I would be fine to eat what I normally pack on hikes and if anything, I should be more mindful of my sugar levels going low now, not too high.

As we were making our way up Cowles, I was worried about my blood sugar plummeting after hours of activity. I was worried I didn’t pack the right snacks.

I started catching myself and my thoughts wander toward radically unlikely scenarios and stopped to take a breath and a sip of water and get my shit together. I had to remind myself of how far I’ve already come (before even setting foot on this trail) and give myself a little of the empathy that I so readily deliver for others.

“Sydney, you’ve lost nearly 60 pounds since you were diagnosed. You are in the best shape you’ve ever been in. The five-miler you did last week actually felt like a piece of cake, remember?”


As we approached the top, I told Barry “I don’t think I’m going to be able to do this today if we don’t eat between stops,” continuing the conversation we had been having in my head (read: just me, freaking out about food by myself while silently marching up this mountain). He gently reminded me there’s a deli across the street, and all of this park is surrounded by civilization, and we could probably definitely find some food after we complete Cowles & Pyles. DUH OF COURSE.

Does that happen to you at all? I find that the first oh, I don’t know, 15-30 minutes of any hike is usually me questioning my intentions for the hike, wondering when I’ll be able to burp because the first few sips of water is a lot of sucking on the hose to get the water out and I always swallow the air, double-checking to make sure my shoes are still tied. For that period of time, everything that comes out of my mouth is usually jibberish, because most of the first 15-30 minutes of the hike is my internal negotiations with myself.

At some magical moment, that goes away and the bliss I find in hiking returns to me and I’ll shout OH SHIT I LOVE THIS. That’s usually when Barry turns around and smiles and is like “YUP! We’re just walking!” and all is well.

When we got to the summit, I was feeling much better, and I was excited to collect my pictures at the summit signs to signify my completion of the challenge.

#2: Pyles Peak – Responsibility

Responsibility: People who are especially talented in the Responsibility theme take psychological ownership of what they say they will do. They are committed to stable values such as honesty and loyalty.

As we made our way over to Pyles Peak, the crowd thinned out again and I settled back into my head and got comfy exploring my thoughts again. I thought back to just a few minutes prior, where I was convinced that there wasn’t food for me to eat around here and that surely I’ll die on this trail not even a few miles into it, and giggled. My brain makes some pretty dramatic jumps sometimes. 

When I took this strengths assessment, it was like a gigantic lightbulb going off when we got the responsibility section. Allow me to elaborate on that “psychological ownership” bit in case you’re not like me. 🙂

Say, for example, that you ask me to remind you to get carrots at the store. I say “okay! You got it!” and file that away. Then we go to the store, we go by the carrots, I’ll probably even pick them up, you walk right past them. Then we get back from the store and you’re like OH FUCK, I FORGOT THE DAMN CARROTS. At that moment, I physically recoil and my stomach does a backflip. Not only did I tell you that I’d remind you about the carrots, but I held them IN MY HAND and let you down. This is my life. This is legit how I process every single fucking situation ever in my life. Sometimes it’s great, sometimes it’s problematic.

As I giggled to myself, remembering that I’d be okay throughout this hike and I could trust that I know how to take care of myself, I remembered how I posted that Barry thought we could tackle this challenge in one day, and I remembered the comments. My pace quickened a bit, as did my breath. I felt a surge of energy of sorts, that part of my body that physically reacts to the accountability piece – and this time it was different.

Now, I’d be lying if I said there still isn’t a little piece of me that wants to prove myself to the folks who think I can’t do this. But that surge of energy I caught in this instance was all for me. I wanted to prove to MYSELF that I could. Hold MYSELF to my word. If I can get that upset about remembering carrots, I can surely direct some of that energy to caring about my well-being. 

“You said you wanted to do this in one day. You already bagged one peak, halfway up the second, and it’s not even 9am. You got this. Keep walkin. Go get those summit selfies.”

And so it was.

#3: Kwaay Paay – Learner

Learner: People who are especially talented in the Learner theme have a great desire to learn and want to continuously improve. In particular, the process of learning, rather than the outcome, excites them.

This hike was the shortest distance to the summit of the 5 summits we were tackling, 2.4 miles. The elevation gain was also the lowest of the segments we were tackling. So when we got there and it was straight up, no switchbacks, with all the gain at once with no relief from the steep incline, I was taken aback.

I started to feel my hip get a little tweaked like it did on that last summit before Blackjack Campground on the Trans-Catalina Trail. I was wishing I had my poles from the car so I could take a little pressure off.

About halfway up, I turned around, took a few deep breaths and out of nowhere, a few tears started to well up. The part about my Learner tendencies that I’m struggling with is this: In particular, the process of learning, rather than the outcome, excites them.

That part doesn’t sit well with me because recently, I was told that when things get hard, I run. I’ve been trying to prove to myself that I don’t run for months now, and that part about the process being the part I liked (rather than the outcome) seemed to confirm the position.

Here’s where my mind wandered:

“When things get hard, you run.”

Can I prove that true or false? If you look at my resume, what do you see? Chaos? Organized exploration? 

✔ Marketing Coordinator/Bartender at swanky steakhouse
✔ Student Brand Manager at Chipotle
✔ Intern at Moffitt Cancer Center
✔ Account Executive at PR agency in Chicago
✔ Data Analyst at marketing agency in Austin
✔ Competitive Skydiver / Director of Marketing in the skydiving industry at two different skydiving centers
✔ Ran my own business doing skydiving events & marketing
✔ Back to agency as Account Director, West/Central Leadership Team, working with Global Brands practice
✔ CoFounder/CMO at all-natural beauty brand
🦄 Currently: figuring it out, hiking my feelings, writing the things

When we filmed my Diabetes documentary earlier this year, the screening interviews helped me understand my story better. I’ve been on a journey for the past seven or eight years to figure out who I am, and what I’m supposed to be doing on this planet. Professionally, most of the activities have marketing as the common thread running through them as that was the function I was serving in each of those industries. But more than that, is a demonstration of my love of learning. Marketing is something I’m good at, a skill I possess. I worked on building that skill and explored how that skill can be used in a variety of industries.

I’ve been told that my resume is problematic and inspirational AF, so you can imagine how that might lead a girl to question what the fuck she’s been doing for the last few years.

The clarity that this Learner theme is providing is that it’s 100% okay for me to do things my way. My way has historically been “find an activity, get really saturated in it, learn as much as I can and/or acquire a particular level of understanding and then move on to the next thing.”

I honestly believe that life is a series of experiences strung together to teach you how to get the most out of the human experience. If you’re paying attention, damn near every experience can teach you something about yourself or the world around you.

As I stood facing back toward where we parked, looking out over the park and the highways in the distance, I just absorbed all of it and let it seep into my bones.

#4: North Fortuna – Intellection

Intellection: People who are especially talented in the Intellection theme are characterized by their intellectual activity. They are introspective and appreciate intellectual discussions.

As we drove from Kwaay Paay to the Fortunas, I was feeling AWESOME. This was our last leg of the 5 Peaks Challenge and I was thrilled with how we were feeling. As we made our way through the grasslands to the Fortuna Saddle Trail, Barry and I were talking about how much our lives have changed since my diagnosis.

Barry said to me, “I could very well run this section, I feel like I could do that.”

My response: “Me too!”


A few minutes later I giggle to myself. Barry asks what’s funny.

“Oh, I’m just blown away by the words coming out of our mouths. We both just said we could run this section. I never in my LIFE thought we’d contemplate running together. That’s all!”

Once we got to the Saddle Trail, it is one very steep fire road that takes you up to the peaks. No shade. Just a wide ass road with varying amounts of gravel on it, at points so steep it felt like an ice pick would have been helpful, the angles were just so dramatic.

There’s a section of the Clifton Strengths assessment description of the “Intellection” theme that really stuck with me: Chances are good that you prepare for important conversations or discussions by collecting lots of background information. It is not unusual for you to set aside at least five hours of quiet time each week to consider what you have discovered.  

As we were approaching the summit it felt like a little nudge toward understanding: “When you’re all talked out, go hiking.”

The last few months I’ve been leaning heavily on my friends and family for support through these transitions – from being an undiagnosed diabetic at my heaviest to the lightest I’ve ever been, from corporate life to startup life to this “follow your heart, make some art” chapter I’m in now, I’ve been needing to talk through a LOT of things. I’ve spent countless hours on the phone working through my feelings, and by the time it was all over and I made the decision to make room for adventure so I could find out what MY purpose is, I was all talked out.

But I know myself, and I know that just because I’m all talked out doesn’t mean I’m totally healed.

As mentioned in my Hiking My Feelings post from Monday, I don’t have my normal coping mechanisms anymore. Diabetes ruled out Ben & Jerry’s and bottles of wine as reasonable ways to handle these kinds of transitions, and man I’m glad it did. So instead of eating my feelings or drinking my feelings, lately I’ve been hiking my feelings. And the hike up to North Fortuna connected those dots.

(To close the loop on the running bit, we did run back down on the steep part after we summited South Fortuna!)

#5: South Fortuna – Adaptability 

Adaptability: People  who are especially talented in the Adaptability theme prefer to “go with the flow.” They tend to be “now” people who take things as they come and discover the future one day at a time.

The only constant in life is change.

Holy shit if I’m not a walking example of embracing that.

And my goddess, how I’ve been resisting it.

What I thought was one of my weaknesses has actually always been a strength, I just missed the signs. 

For most of my adult life, I’ve worked in a high-stress career. Public relations is stressful. Marketing is stressful. And doing that in an agency environment or the skydiving industry is stress on top of an already stressful career choice. Deciding to jump head first into the beauty industry in an attempt to change the conversation from the inside, while also jumping into entrepreneurship, while also jumping into raising venture capital – I clearly am not afraid of risks. 

So why is it then, at almost every turn in my career, I inevitably feel like this just isn’t a good fit? Is it that I’ve really internalized this American programming of DO MORE BE MORE HAVE MORE? Is it because I’m just capable of being satisfied? Am I wishy-washy?

Or, is it possible that I’ve been trying to fit a mold I wasn’t designed to fit? Just because I’m really good at marketing doesn’t mean that I need to be doing that exclusively and for the rest of my life. Giving myself the permission to sit with that reality has been a process, really digging back into extending myself the same empathy I extend to others.

I mean, this was certainly the case for my health. I tried everything under the sun to try to lose weight before my diagnosis and I could never keep it off. Every time I set out to lose weight, I would ask my skinny friends what they were currently doing. Some of them were on a fad diet, some were combining diet pills, some worked out 3 hours a day, some just had good luck and good genetics.

What would follow was the same cycle, every fucking time:

✔ Try something new.
✔ Do it obsessively until I see results.
✔ See results, be excited by results, reward myself with unhealthy food.
✔ Never return to activity that led to the results.
✔ Gain all the weight back and then some.

If it was possible for me to get diagnosed with Diabetes, go to the classes, review all the things I’ve done to get healthy in the past and throw it all away and follow my intuition to lose nearly 60 pounds, then perhaps it’s possible that I had been making career choices from a place that was not aligned with what I actually want.

Perhaps, if I took the same refined approach to my career as I did to my health, I could finally find what I’ve been seeking, professionally. 

That was heavy. And once I saw it, I couldn’t unsee it.

Is this where most people get stuck and throw in the towel?

I don’t know what’s next, but I know it’s not what I’ve been doing for the last 7-8 years. Whatever is next looks a lot more like hiking my feelings and writing about it than it does punching a clock to get paid to ignore my dreams.

This time next week we’ll be making our way up to Long Beach to crash with our friends before catching the ferry to Catalina on Saturday morning. I’m really excited to see what kinds of insights the TCT brings me this time. Last time I decided to honor my inner athlete and ended up loving my body by the time I got to Blackjack. I wonder what kind of goodies are in store this time!


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