Recently, we encountered a really interesting guy named Jay Dike, while scrolling Twitter. He tweeted something about a motorcycle tour through Vietnam, and I was immediately intrigued. I sent him a DM, and a few weeks later we sat down to video chat. While I was sitting in my home office in Mesa, AZ, Jay was in Railay, Thailand. I quickly got down to the business of getting to know Jay, who was a cooler chap than I could’ve imagined.
Who is Jay Dike?
Jay grew up in “the bush” of rural South Africa. He spent time living on a 9,000 acre game reserve with his family, interacting with snakes, leopards, monkeys and more. He left high school around age 17 and quickly decided that college wasn’t for him. Jay mentioned that he really didn’t want to start his life out in debt, so instead of college he decided to start a business. He started a company that salvaged personal electronic devices, like cell phones and laptops, from insurance companies, repaired them and sold them. He made enough money at age 17 to support himself for six months or so, but soon decided to move on. He then made a career change into woodworking. He met a carpenter and entrepreneur who mentored him for about two years, and he was able to work on some really fantastic projects. During this time, Jay developed his hobby of photography and his story took an exciting turn. He said, “I quit my job, sold my car, broke up with my girlfriend, and got rid of my house all within the space of a week and moved to London all by myself. Because, I thought that there was something more in the world for me.”
Once Jay got to London he decided he wanted to be an adventure photographer and jumped headfirst into the adventure communities in London. He started pushing himself to go on all sorts of adventures. He cycled the coast of the Scottish Highlands, hitch-hiked across Europe, and walked across the Jordan desert, Wadi Rum. He even attempted, with friends, to be the first person to paddleboard the longest river in Scandinavia from source to sea. (Unfortunately, record level rains prevented them from accomplishing their goal, but you can read Jay’s account of it here). He did all of this “with the intention of trying to capture the cultures and environments, to become a better photographer, and to find a way to spend all of my time outdoors”
In the past two years, he’s kept photography as a hobby, and transitioned professionally into more of an “experimental entrepreneur.” He’s been building his own products including one called MonthlyReview.Me, which he has built to help people ask themselves the hard questions on a regular basis to bring about more self-awareness and reflection. Additionally, he works with various organizations around the world helping them with marketing strategies and community management. He’s also co-building an online course called StrategyU.co. All in all, he’s an immensely talented person.
I asked Jay what he’s working on at the moment, and I believe his answer sheds some light on the introspective person that he is: “I’m at a point where I’m running what I like to call life experiments. I’m trying to figure out where I want to be spending the majority of my time. Over the past two years, I’ve been dealing with two very big, scary questions: what is my identity and what is my true calling?”
These questions lead him to begin building the monthly review product I mentioned before. Jay understands that we all have big goals and intentions, and whether we succeed or fail, we rarely look back and ask why. Jay wants to build what he calls “a community to help people reflect and learn from the journey through the adventure of life.” He’s been personally doing this for the past few years, and has seen the benefit of asking himself hard questions. He hopes that with this project he can help people become comfortable asking themselves questions about their identity.
While asking himself these introspective questions, Jay has found that he’s grown the most in his ability to be self-aware, to learn and communicate well, and in being mindful toward others and communities. He grew up in an environment that didn’t really foster emotional intelligence or communication, and so as a young adult, he was closed off from vulnerability and expression. Jay said that “Through all of these life experiments and growth-inducing experiences, I would meet many interesting people and find the opportunity to connect and befriend with inspiring, curious humans around the world, I was given the gift to see, understand, and develop new parts of myself that I didn’t even know needed developing. I started going on meditation retreats. Things like the 10-day Vipassana retreats or, most recently, an ayahuasca retreat, and vision quests. But, it doesn’t need to be these grandiose events and retreats. Being a part of meaningful community and developing my own voice has been an integral part of the process. I began to strengthen a part of my psyche that wasn’t able to deal with uncertainty or emotions. In the past, the slightest indication of change would freak me out and fear of the unknown would paralyze me. I’m still not fantastic at it, but I can now embrace it with compassion and confidence.” Unlike when he was younger, he now considers himself a multipotentialite and lifelong learner.
Jay mentioned a few obstacles he had to overcome to get to where he is now, the first of which was dealing with uncertainty. Coming from his small town in South Africa, his “digital nomad-esque” lifestyle seems completely foreign to a lot of people back home. He was only ever exposed to a “conveyer belt” lifestyle of “You go to college, get a job for 40 years, have a family, retire, and you die.” This makes it hard for his parents to understand his lifestyle choices, jumping from country to country and project to project. It was difficult for him to break through the frameworks that he was brought up to believe in. Not to mention breaking into ambitious careers without formal education or much recognizable experience.
Jay’s second obstacle has been the question of identity. He’d struggled to feel like he was following his own path, and not just replicating the paths of his idols. He got to the point around age 23 where he began to have frequent breakdowns, all of which hinged on the questions of “Who am I? What am I working toward? What does this all mean?”
Looking back, Jay explained, “It was an overwhelming experience because I was left with a complete blank slate. I didn’t know where the ambitions and motivations of others ended, and mine began. It became so difficult to look at myself and discern what was true to my nature and what I had extracted from the myriad of inspirational people throughout my life.” While this was overwhelming and intimidating for him, asking those difficult questions proved to be motivating in facing that transition.
Finally, Jay mentioned that finances have always been an obstacle. Not coming from a family with money, and never having a cushy corporate job, he’s never had a good safety net. He’s had fantastic experiences that have made him rich in experience, but not financially. While this was difficult, he said that in the end, he always found a way to make things work out.
What is growth?
I asked Jay what growth means to him, and he said the following:
“Growth is fulfilling your destiny. It’s both inevitable and hard work. It’s the work we do, unique to every person, that fills the boots of the future versions of ourselves. The evolution expands our consciousness and opens us up to possibilities far beyond our currently perceived limits and boundaries. If there were an end goal, it’s getting to a point where you can be joyous and content without the reliance on external events.
“For some reason I’m thinking of the analogy of how an oak tree starts out as an Acorn, which you know, an acorn and an oak tree are very, very different things. But the oak tree always lived within the acorn. So the person that you or I want to be in 10, 20 years, that person is within us and it’s almost inevitable that we will grow into them and it just requires the time and the energy. So I guess what I’m saying is we’re always going to grow regardless of what we do.
“No matter what point we get to, no matter what milestones we’ve achieved, there’s always going to be an ambition for more growth. Make sure that’s a gentle ambition and not a grasping need.
“Growth, it’s inevitable, but it’s never ending. We’re going to walk along a path no matter what! So I guess the most important thing is to make sure you’re on the right path and you build up the guard rails in order to garner the learning and experience true to your desires. If we aren’t growing, we’re dying.”
In the next few years Jay hopes to establish more stability and clarity in his life. Over the past years he’s traveled a lot, and soon he’ll be moving to Colorado with his girlfriend. He mentioned wanting to get a dog, and not having to say goodbye to friends so often. He also hopes to establish more of a career aligned with his values, “finding whichever flavor of pie he likes the most and sticking with that. Yet never letting the curiosity and experimentation die.”
Before we parted, I asked Jay to offer some final advice to our readers.
“I truly believe that creativity and hope are not skills or emotions, they’re a mood or cognitive behaviour. We can instill these behaviours through our environment and practice. They require, in order to experience it, intention in your environment and your community – your inner environment as well as in your outer environment. So I guess my advice to anybody out there who’s looking at growing themselves is: be selfish. I think the word ‘selfish’ has so many negative taboos around it, but I think there’s a level of selfishness that should be embraced when it comes to you and your process. And what I mean by that is, take the time that you need to become the person that you want to be. Ultimately, this will naturally allow others to be themselves too and create a space for awareness and authenticity. So in turn, an initial phase of selfishness creates the space for giving and selflessness.
We all have this idolized identity of ourselves, and if we never actually take the time to work on that identity then we never really get there. It’s all these habits that we want to build, all these milestones that we want to hit. We need to take the time for ourselves to be able to develop the skills and mindset to be able to get there, so be selfish. Take the time to meditate, to build that habit of exercising, connect and engage with more curious and inspirational people, work on that little side project idea or whatever it might be, because you’ll thank yourself in the future. Exercise your curiosity. Curiosity is so important, so if you can be selfish and let yourself build those habits and routines then you’ll get into that mood of creativity a little bit more.”
If you want to connect with Jay, head over to his website: Jaydike.com. Follow him on twitter @jaytdike or on instagram @jaydike and check out some of his awesome photography. You can also sign up for his monthly newsletter, which I’ve personally enjoyed reading. Jay is one of the most genuine people I’ve ever encountered, and I hope to be able to meet him in person someday. If you’re in Colorado, shoot Jay an email or DM and buy him a coffee, and maybe he’ll tell you more about his 10-day Vipassana retreat, or about crossing Wadi Rum.
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