So that is me jumping into the lagoon over in Ilha Grande — a funky little Brazilian island off the coast of Rio. Back when I lived in Brazil, in my early 30s, we used to go there at least once a month to trek around, dive off cliffs, explore waterfalls, and drink far too many Caipirinhas. It is still one of my favourite islands. You should really go there one day.
Today’s lesson is, in my opinion, one of the most important if you want to create a life that feels like an adventure. If you want exciting, wild, weird and beautiful things to happen in your life — and if you want to become the sort of person who has stories to tell and is genuinely interesting to hang out with — then I think you need to cultivate a habit of taking risks.
When I say risk, I don’t mean being reckless or stupid. I mean deliberately putting yourself into situations that feel challenging, uncertain or slightly “out there”. That could be doing a solo trek in the Himalayas, exhibiting a painting, setting up a business, changing careers, self-publishing a book of poetry, doing karaoke sober, asking somebody out properly rather than hiding behind an app, cycling to Istanbul, setting up a band, doing a cage fight, writing a screenplay, buying a one-way ticket to Lima, training for a ballroom dancing competition, moving countries for work, starting a family, establishing a charity, giving a TED Talk or running an ultra-marathon. The list is endless.
Whatever form it takes, when you regularly put yourself out there, something changes. You become more creative, more resourceful and generally a bit more alive. Your focus sharpens because things matter. Your personality gets tested. You find out what you are capable of. Will you fail more often? Almost certainly. But that is part of the point. Failure gives you information, humility, resilience and stories. Playing it safe gives you considerably less of all four.
Life is very short, and I genuinely think one of the biggest risks we can take is to spend too much of it trying not to take any. The idea of getting to the end of my life and looking back at all the things I nearly did, wanted to do, was too sensible to do, or kept postponing until “the right time” scares the hell out of me. A would-have, could-have, should-have sort of existence sounds awful. Much scarier, in fact, than most of the risks themselves.
Talking from experience…
Aged 19, I took my first genuinely bold step as an adult and went to America by myself for five months. I had a sports coaching job in New York and, when the contract finished, spent several weeks “kerouacing-it” across America by Greyhound with Gordo and Bav, two friends I had made in New York. I eventually ended up living as a surfer beach bum in Oahu and Kauai for about eight weeks with my crazy friend Otto, who was a true hippy in the most authentic sense of the word. The whole experience was much more than just fun. To paraphrase Marcel Proust, it gave me new eyes.
I was already a fairly confident person, but that one little adventure gave me an injection of boldness and made the next one easier. So, aged 20, I bought a one-way ticket to Lima. I arrived in Peru with dangerously little money, no hablo Español, zero contacts and absolutely no backup plan. Was it scary? Hell yeah. This was before smartphones, social media, Google Maps or easy internet access. I was a kid. Of course it was scary. But that was also the point.
Four months later, when I eventually flew back to the UK from Brazil, I returned having travelled all over South America, made new friends, collected a ridiculous number of stories and developed a much better understanding of myself and of Latin American culture. More importantly, I had acquired a rather dangerous level of self-confidence and an enormous appetite for pushing myself outside my comfort zone.
Within a few months I was solo travelling again, this time around India. I arrived in Madras with a tiny day pack and about $500 cash strapped around my ankle — again, no phone, no bank cards and not much of a plan. That trip was wild. A few weeks after returning to university and my incredibly neglected academic life, I persuaded a kindred-spirit friend to hitchhike around France with me. We took virtually nothing. I mean, not even our wallets. It was just for a laugh really, and partly a test to see how we would cope. From sleeping in a public toilet off a Parisian motorway one night to getting drinks bought for us by students in La Rochelle, we learned very quickly that when you have no money and no contacts, you have to become extroverted, resourceful and creative if you want things to happen.
I began to understand that life seemed more fulfilling when I was bold, took risks and committed myself fully to new experiences.
Since then I have taken much bigger risks, although they haven’t always looked as dramatic. I have lived in several different countries and repeatedly rebuilt my career and social life from scratch. I have also taken long periods away from work to study, learn and explore things that interested me, which often felt risky at the time. And that leads nicely to another point.
How to learn — Part 1
I’ll talk properly about the art of learning in another lesson, but I have always believed that books and qualifications can only take you so far. Academically, I have collected a slightly ridiculous number of qualifications in fitness and wellbeing, a degree in Business and an incomplete Masters in Philosophy, but the most useful thing I have learned is that you have to live things to really understand them.
I am a huge believer in immersion. Living with monks in a monastery, sparring with fighters in fight camps, spending weeks alone trekking through mountains, living in other countries, studying unfamiliar disciplines — these experiences taught me things that would have been impossible to understand purely from books. To really know something, I think you often need to temporarily obsess over it, immerse yourself in it and commit a slightly unreasonable amount of energy to it.
I also believe enormously in one-to-one coaching. Whenever I meet somebody who is genuinely excellent at something, I want to learn from them. Over the years I have had one-to-one lessons in all sorts of things: rock climbing, skiing, gymnastics, ballet, massage, kung fu, singing, acting and plenty more besides. I love being a beginner. There is something incredibly healthy about being rubbish at something, listening carefully to somebody who knows far more than you do and slowly getting better.
My life has been enormously enriched by being willing to start again at zero.
The definition of adventure changes as we age
My definition of adventure is different now. These days I get some of my biggest kicks from coaching my clients, growing my business and building a life with my wife. Those things feel like enormous adventures to me. Travelling to new places and having a chaotic social life are nowhere near as important as they once were, and that is probably a good thing.
Our definition of adventure should change as we age. It would be slightly depressing if the things that excited me at 20 were exactly the same things that excited me now. But the underlying principle hasn’t changed. I still think curiosity, adventure and occasionally doing things that other people consider strange, difficult or risky is a very sensible way to approach life.
We live in a culture that places an enormous amount of value on fame, status and money. I personally don’t find any of those things particularly interesting as end goals. If that is how you measure success, then my advice may not be very useful to you. But if you want an adventurous life, then I am probably a decent example of an ordinary person who has done a lot of cool shit, seen a fair chunk of the world and somehow turned curiosity into a fairly unusual career.
So if any of this resonates, perhaps it is time to be a little less sensible. Be bold. Take a risk. Fail occasionally. Pivot. Learn. Grow. Go somewhere. Start something. Ask the question. Book the ticket.
Treat life as one big adventure.