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Kyle Kesterson in Israel. (Photo courtesy of Kyle Kesterson)

Dipping into what he called one of the juiciest bowls of guacamole he’d ever come across, Kyle Kesterson emailed from a cafe in Oaxaca, Mexico, days after ringing in the new year at the beach with 150 “amazing humans.” Adventuring is still in full effect for the traveling techie from Seattle, who said he had no idea what his life would look like an hour in front of his face when he left the cafe.

It’s been just about two years since Kesterson, the startup veteran and serial entrepreneur, launched a “Get Your Own Kyle” stunt inviting people to tell him where he should go, what he should do and why he should do it.

After visiting 20 countries on five continents, and 22 states in the U.S., Kesterson has done some of what was suggested, and found other interests and ideas to take on. His latest project is Which Ritual, a repository for assorted rituals from around the world — chants, meditation, movement, etc. — which can be sorted by type, timing and outcome depending on what the user is looking to tap into or achieve.

Kesterson, whose past includes work at Startup Week, TechStars, Giant Thinkwell (which became Haiku Deck), and Freak’n Genius (later Campfire), is constantly learning from the people he meets and the experiences he gets into.

His mantra for anyone doing anything is to just keep growing and finding ways to make life around you better, and that goes for anyone still chasing assorted tech dreams in Seattle or elsewhere.

“It may look like I’ve ditched tech, but really I’ve just gone through a chapter of resetting from the startup burnout,” Kesterson said. “I love tech as a utility and its scalability, but I found the culture that puts it on a pedestal to be unhealthy and misguided.”

In his next email, Kesterson said he was headed to the mountains in Mexico to witness millions of monarch butterflies during their migration. He ended up getting stranded for what he called a very muddy, barefoot misadventure. “Just getting back to my computer,” he wrote.

Keep reading for our Q&A:

Kyle Kesterson’s “backyard” during a stint in Puerto Escondido, Mexico. (Photo courtesy of Kyle Kesterson)

GeekWire: Where have you been?! Seriously, where have you been … tell us a little bit about the journey since we last spoke almost two years ago.

Kyle Kesterson: Since we’ve last spoken, I’ve traveled through 20 countries on five continents, and 22 states in the U.S., occasionally taking on client projects, meeting amazing humans from all walks of life, and frankly just seeing how uncomfortable I am willing to get.

We last spoke when I released my Get Your Own Kyle project, asking the community to help design the next chapter of my life. From the 27 projects that came in, I chose two. One took me to Spain to build a space-bound time capsule, where we helped create trans-generational empathy through a guided experience, that was then recorded, sent to a SETI satellite, and blasted toward Alpha Centauri. The idea is humanity may travel ahead of it at some point in time, say 100-1000 years, receive the transmission, and get a snapshot of life on Earth at this time.

The second project took me to Scotland, to help put together a caving expedition in an attempt to help protect the magical TAYOS caves in the Ecuadorian Amazon. From Scotland, I was invited to Israel as part of the Schusterman Foundation’s REALITY program with 50 other storytellers and executives, primarily from the entertainment industry in Hollywood. I was invited back to Israel a year later to facilitate REALITY’s Travel edition, comprised of digital nomads and entrepreneurs in the travel and hotel space.

Kyle Kesterson and his dog, Bean, working in Yosemite, Calif. (Photo courtesy of Kyle Kesterson)

At some point I hopped back over to the U.S., and due to my vanlife lifestyle living out of my Winnebago Travato, I caught the attention of the company. They hired me to help create and lead a major launch initiative for three new recreational vehicles. It was quite a work-life mesh experience!

Also along the way was a whirlwind of wild experiences through Portugal, rural Spain, France, England, Lithuania, Cambodia, Vietnam, Thailand, all over the U.S., down into Mexico and more.

One unexpected side effect with the travel, I am often invited to witness and participate in rituals and ceremonies, learning from priests, rabbis, monks, yogis, shamans, witches, druids, healers, chefs, artists, and clairvoyants. Being a curious and healthy skeptic, I’ve stretched as far into my comfort zones I can image. Since I’ve adopted rituals to become part of my daily life, and the seed for one of my newest projects.

GW: How much of what you have done or seen was born out of the ‘Get Your Own Kyle’ idea?

KK: The Get Your Own Kyle experiment helped put a bit of structure into when and where I was to travel. In between those dates was a lot of following whim and serendipity, exploring so much of the world, and so much of myself.

Overall, Get Your Own Kyle was a surprising success. I worked on audacious projects that lead to even wilder stories, extended my runway to keep adventuring, living, learning and growing, and meeting so many amazing, talented, and weird human characters. It still ripples today.

Kyle Kesterson started Which Ritual as a way to collect the information around various rituals people rely on around the world. (Which Ritual screen grab)

GW: Tell us about Which Ritual. How long have you been working on it? What does it entail from a tech standpoint … app, etc?

KK: After these years of travel, and taking on clients for personal development coaching, I am regularly reminded of a deep need for rituals. Western culture suffers from a lack of rituals. As I began to take them on in own life, and wanting to learn what else exists, I looked for a single repository that broke them down, or why to do them, but couldn’t find one. So I created it.

I first started by developing a mobile app version, doing all the UI/UX, but then realized how long it’d take, or expensive it’d be to bring to market. So I scrapped the bigger version for the first, scrappier version, and used the tools I had available to me. Putting it together on a customized Squarespace site and hiring two amazing humans to help with content, we built it together in about two months and released the v1 that’s currently available.

We launched with the first 75 rituals, sourced from all over the world, or developed internally. You can sort by the OUTCOME you’re looking for — grounding, clarity, energy, release, healing, etc.; by TYPE — breathing, meditation, food, sex, movement, etc., and by TIMING — morning, evening, weekly, moon, etc

On the roadmap ahead, I have a series of features being custom built that will evolve it off of Squarespace, and more into the pocket as a mobile experience. We are about to launch the second version which offers audio-guided rituals for a lean-back experience. It’s currently entirely free.

Also on the site, I created a 188-question Ultimate Reflection Guide, to reflect and integrate 2019, then gain clarity and set intentions for 2020. It was downloaded in 97 countries this month, and I’ve been hosting group editions as workshops as I’ve been traveling.

Skydiving in Puerto Escondido, Mexico. (Photo courtesy of Kyle Kesterson)

GW: What’s your main source of income / how are you surviving?

KK: Freelance and consulting is my primary income source. People reach out with what they are working on and ask if I can help in some way, typically with design, illustration, photography, creative direction, product development, strategy, or developing unique marketing initiatives. I try to keep my costs down and my runway extended in front of me. I’m always open to hearing what people or companies are working on!

GW: What are the biggest lessons — fun, not so fun — from this lifestyle you’ve taken on?

KK: All lessons, especially the ones that weren’t fun, have been great gifts. With the regular travel, not having spent more than three weeks in any one location, I learned how important it is to maintain rituals, especially for grounding. In turn, I’ve also witnessed how much of a gap there is, particularly in the West, where much of our modern suffering can help be alleviated with simple rituals. Rituals help ground, create clarity, release and heal, connect with self and others, and more.

Another lesson is about discomfort. Our greatest gifts, teachers, and access to a fuller life, consistently lives beyond what is comfortable. Finding comfort within discomfort is a muscle that can be cultivated, but we can also dive right in. Either way, not only will we be OK, we’ll thrive and feel so much more alive.

Posing with a friend in Utah. (Photo courtesy of Kyle Kesterson)

And the biggest recurring truth from the lifestyle, is that reality is entirely subjective. Your reality, and thus how you judge what is right or wrong, is just a story you’ve been told, and continue to tell yourself. Every single version of reality takes their own shape and meaning, which we build our lives, needs, and desires on, but they are all built on a lineage of stories, which crystalize into rigid ideology. Learning and embodying this as a primary filter in my life has created flexibility and a deep sense of empathy and compassion for all walks of life, no matter if I agree with their approach for how they meet their needs.

Despite the varying challenges and curveballs life presents, it has become possible to navigate them with grace, gratitude, perspective, and humor.

GW: Have you been back to Seattle at all? Any longing for what you ditched related to tech, etc?

KK: It’s been about a year and a half since being in Seattle, but I foresee a trip this spring to see familiar faces. Even sooner if there’s a fun project to work on.

It may look like I’ve ditched tech, but really I’ve just gone through a chapter of resetting from the startup burnout. I burned out because my priorities to “succeed” were coming from a place of needing to prove myself, either to myself, or to others. My sense of identity and self worth was attached to outcomes, and it made me very ambitious. It was not healthy, and no matter how much I found material success, or was viewed by my peers, I found myself further and further from actual fulfillment.

Tech is still always on the table for exploring, if that’s the vehicle needed for solving whatever is in front of me. I love tech as a utility and its scalability, but I found the culture that puts it on a pedestal to be unhealthy and misguided.

Kyle Kesterson in Joshua Tree, Calif. (Photo courtesy of Kyle Kesterson)

GW: Based on what you’ve done, what’s your advice to anyone who is contemplating startup life or a random job at a tech giant … and whether it’s the right path?

KK: There truly is no right or wrong path. There are decisions that lead to more friction or flow, that enable life or diminish it, and each decision always has trade offs. Are you currently excited to get up each day and do what you’re doing? If yes, keep doing it. If no, change it. Just keep growing and finding ways to make life around you better. Or don’t, that’s fine, too.

As for startups specifically, ask yourself, why do you want to do one? Do you care enough about the problem to risk your health and relationships? Do you know what truly fuels you? What if you don’t end up with an exit, or any form of validation, would you still do it? Look at those you admire, who have “done it” — do they have the health, relationships, and quality of life you believe will satisfy you?

I highly recommend diving into one, as it’s an incredible pressure cooker to learn and grow in. Just know your boundaries, continue to know and challenge yourself and your ego, and develop healthy rituals that keep it a marathon. And with co-founders, establish an effective rhythm of transparent, open dialogue. Address everything. Take nothing personal. Just keep growing and caring about the people your work affects.

For me, and how I make decisions, my biggest deciding factor is always, “what will lead to the best stories for my grandkids?”

(Photo courtesy of Kyle Kesterson)

GW: What’s next? Where to?!

KK: I’m currently in San Jose Del Cabo in Mexico. After having met a fellow traveler and entrepreneur from Portugal, during New Years on the beaches of Puerto Escondido, we decided to do a Startup Weekend-style hackathon to see what could come of it. Out of it came a project we are calling Life Dive, that’s helping people step more boldly into their own lives. It offers inspiring stories, guided programming to making uncomfortable, yet rewarding life decisions, and services such as 1-1 coaching and group accountability Masterminds. Just today we launched a Mastermind Goal-Crushing program.

I’ve also written a 300+ page book that compiles my stories, learnings, and perspectives, combined with my photography from all of the globetrotting. Now just beginning to look for an agent and publisher to release it.

Beyond that, I can’t see more than a few days in front of my face with where I’m going and what I’m working on next.

Websites: Which Ritual and Life Dive

Twitter: @kylekesterson

LinkedIn: Kyle Kesterson

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