He turned a love of flight hacking into a successful business; he crowdfunded a wildly popular mystery product; and he recently launched a beautiful content site designed to share inspiring travelers and their stories. Today, we talk to Jordan Bishop about his personal journey and how he turns ideas and dreams into reality.
How did you get to where you are today?
I think it’s important to first define “where I am today”, which I think is a curious person who refuses to accept the rules and self-imposed limitations that govern most of society. With that in mind, to get to this point, I try to do everything backward first, and then only revert to the norm when its opposite has been proven wrong. I think it’s an effective, or at the very least, an interesting, way of living.
What was the hardest thing about leaving Toronto in pursuit of life as a digital nomad?
I think my undying love for Toronto is what made it so easy to leave. I grew up in a small town a few hours outside of Toronto, so seeing how quickly I fell in love with the city when I first moved there at the age of 19 gave me the confidence that I would have similar experiences in other places, too. A few months later I moved to Manhattan on my own, and since then I’ve lived in a couple of different cities each year all around the world.
It sounds crazy, but sometimes I miss the cold, and more specifically, the fresh feeling of cold air running through your nostrils on a wintry morning. And I miss a few people, but not as much as I thought I would. I’m pretty good at living in the moment, and I try to keep my relationships of the moment as well.
How does your routine vary while traveling? Do you have tips for staying healthy, productive and focused while moving around so much?
I try to keep my morning routine as stable as I can, since that sets the tone for the rest of my day. I start every day by making my bed, followed by 21 minutes of meditation, and then a high-protein breakfast. If I’m in a good writer’s groove, I’ll also write for as long as I can before eating breakfast. Eating makes me think differently and often distracts me from my first few clear thoughts of the day.
I don’t normally go to a gym since I’m often in a place for less than a month at a time, so instead I do bodyweight exercises to maintain good blood flow and athleticism. Push ups and sprint training are my two favorites — the two of them combined make for a good full-body workout that requires no equipment and challenges both endurance and explosive power.
You turned your love of flight hacking into a business by founding Yore Oyster, a company created to help travelers get the best flight deals. What’s been the most rewarding part of working on it so far?
Helping others to explore the world.
It’s extremely rewarding to hear from clients, many of whom become friends, how life-changing their trips were. I get nostalgic every day when I send people to places I’ve been and loved.
You also just launched How I Travel, a brilliant site that focuses on sharing travelers’ stories. What do you hope people will get from it?
As humans, we’re hardwired to learn most effectively when information comes to us through a story, so the obvious solution to accelerate our own growth is to document and transmit as much information as possible through highly compelling stories. How I Travel is my answer for current and prospective travelers.
How I Travel is also designed to inspire people to get out and take the trips they’ve always wanted to take. Travel is a gift that benefits you for a lifetime, and I want everyone to discover it in the ways that I have.
A man of many ideas, you’ve even tried your hand at crowdfunding. With your unique campaign, you got more than 1,000 people to buy something before they knew what it was! What was the secret to drumming up buzz?
I read, write, and think a lot about human psychology, and at that time I was curious to see if any of my friends trusted me enough to buy something I had created before I told them what it was. I never intended for anyone but my closest friends to get involved — but when others did and strangers started trusting me, I realized something much larger was happening.
We are witnessing an early indicator of how trust is quickly becoming a new global currency.
Strangers trusted me not because I had “won” their trust, but because they knew that with the way information travels today, I couldn’t afford to breach their trust. The Internet is no longer the place where you can betray someone’s trust behind a veil and get away with it, but actually the opposite; somewhere reputation is easy to discover and matters more than anything else.
What’s the best advice you’ve been given as you continue to push yourself out of your comfort zone and experiment with ideas? How have you applied it to your life and work?
I was at a really low point when a guy I know told me, “Blow kisses to the haters.” The more you achieve and the higher you rise, the more people are going to try and break you down out of jealousy, a lack of understanding, or a generally negative attitude toward life. It’s not easy, but I try my best to ruthlessly eliminate any negative people from my life.
You’ve obviously done your research when it comes to travel; which sites and social accounts do you look to for inspiration, reliable information, and trip-planning tools? Where can we find you online?
My flight hacking company Yore Oyster, which has saved hundreds of travelers tens of thousands of dollars in the past year. I also love the Mike & Jay Explore YouTube channel; they always manage to perfectly balance beautiful cinematography with unique travel insights. I have a list of my go-to travel resources on my site. And I’m a huge Airbnb fan. I’m going to do an Airbnb tour of Asia soon — there will be lots of pictures from that on my Instagram account.
Which global events, meetups, and groups do you love and recommend?
I’m a part of hashtagnomads.com, which is hands-down the best way to meet other digital nomads (people living abroad and working online). It’s how I’ve made my closest friends over the past 12 months.
I’ve been trying to push myself way outside of my comfort zone, and that’s how I’ve met skateboarding buddies in São Paulo, philosophical adversaries in Chiang Mai, and lifelong friends in Cartagena.
I’m a big proponent of meeting friends of friends (discovered through Facebook) around the world, as well as meeting others spontaneously — wherever you are.
Last, how do you like your coffee?
I don’t drink coffee! But I’ve never turned down a cold chocolate milk. 🙂