Every so often I’m interrogated by friends from home, probing into how I've seemingly managed to escape the drudgery of reality. I receive the occasional inquiry as to whether there's a sponsor, benefactor, or trust fund I recently came into - I presume to help justify their own lack of wanderlust. They’re the ones who resentfully comment that my Instagram makes me look like a "celebrity jet-setter" and vindictively claim I always manage to be on vacation. But for the majority of my peers who question my life, it’s out of benevolence, pure interest, seeking some guidance on how they too can achieve “freedom”. And the more people I’ve spoken to, the more I realize are looking for answers and doors to escape.
I’ll tell you that here is no sponsor, I’ve not been endowed any portion of the family fortune, and I’m not living 365 days of holidays. It’s just matter of priorities. I decided a few years back that the hedonic treadmill wasn't working for me - that living on the rails constantly seeking that next revered accolade or society-driven milestone just wasn’t in my DNA code. So I took a leap and made a serious change.
That change has been at times, more challenging than it has been rewarding. My life now consists of complete independence, in a state of constant fluctuation and change. While many of my peers from home have remained in a structured environment, surrounded by the same friends they’ve known since they were single digits, are financially secure, on track to settle down as they should, I've been living paycheck to paycheck, in a consistently precarious world, responsible to no one but myself. For a long time I wanted to be one of those people, the type that fits into the mould, the type that makes their parents proud, that "accomplish" all their goals on time. I still deeply respect and admire those people. But I’ve finally accepted that I’m simply not one of them. I’ve got barely any savings, minimal assets to my name, and have bounced through a serious of unstable relationships to high flying DJs and digital nomads for the past half decade. I’m even contemplating freezing my eggs for Christ’s sake! Most people – especially my parents – would survey my social resume and observe that practically none of the “life” boxes are checked.
What I do have however, is a whole lot of experiences in my bank. I’ve met thousands of people across dozens of countries and shared experiences with them I’ll cherish forever. These people have left their mark on me, and stamped me in ways not unlike a passport. They have shaped me into who I am, and have helped guide me to a life of fulfillment and growth.
The Excellent Sheep
Rolling back a few years, I should start out with a caveat that I’ve never really been a rule follower. I was expelled from the third grade for trying to lead a class-wide breaking and entering operation and again in the 10th grade while on exchange overseas. I once biked home totally nude from a guy's house because I lost a bet, had a breaking and entering charge while staying with an Australian pension, hitchhiked through South Africa, and went streaking from my boarding school on the eve of graduation.
I can’t remember a time when I really felt like I “fit in” in the traditional sense, and my idea of fun has most certainly never been the norm. While I always had friends, and even eventually rolled with the cool kids, I’ve always felt like an outsider. This became particularly evident in the university rat race - where all my friends aspired for similar goals. Goals that I somehow didn’t get the memo on. Meanwhile, I couldn't figure out how to get away fast enough. Most of my peers sought internships during their summer holidays, while I took off for Africa to rebuild local communities and bus my way around the continent.
I suppose we can blame the generational idiosyncrasies for what my community considered traditional “success”. Our parents were the quintessential Boomer generation; they worked hard for security and stability, prestigious titles and country club memberships. They valued all the things us entitled Millennials took for granted. It was only natural that the plan for 2.5 children and a few letters after our names became the status quo expectation. Our parents moiled to achieve their financial freedom, social liberties and economic security, and the only paradigm they knew was to pass these beliefs onto their children. They were the generation of the “American Dream”. And the American Dream was “success”.
We on the contrary, grew up expecting these luxuries. Conversely we grew up with the helicopter parents epidemic. Where “rules seemed to have replaced rebellion, convention won out over individualism, and values became very traditional.” Parents and institutions reiterating the need for a predefined ideal of success, protecting and coddling us so that we were assured to never diverge into the unknown. Our generation was on path to become blinkered overachievers; kids who anxiously sought “success” without really understanding what their personal definition of it actually meant. We jumped through hoop after hoop to be praised in the spotlight, all shepherding together, mindlessly running towards the same direction to achieve any accolade that's resume-worthy.
Eventually by the time our early adulthood struck, we had already become the social norm, without even stopping to consider the alternatives. The only thing next was to settle down and start building a stable future - saving up for a deposit on a down payment, participate in the daily grind desperately clamoring up the corporate ladder, parochially focused on only two significant next steps: making Principle, and getting married. This inevitably lead towards the cyclical treadmill of working for the weekends, only to wake up Monday morning on the verge of a breakdown, dreading the impending week.
I fell into this trap - head first. I got the grades, graduated from a premier university, and worked for a top tier firm. Making the choice to pursue the status quo required vanquishing my personal curiosity, sacrificing any moral courage or passionate weirdness. I fell right into line with the generation of striving, praise-addicted, grade-grubbing nonentities. I’d tell myself that I was happy, satisfied, fulfilled, because I had everything I had worked towards. But why did I work towards it? Was it what I wanted? Deep down, the more I thought about that life, the more terrified I became.
When Saturn Kicked the Shit out of Me
I suppose many people encounter this experience in their lives. Mid-life crisis, Saturn Return, Mercury Retrograde, whatever you like. That notorious period in your life that hits every 30 or so years (yup I’ve always been an overachiever – mine hit early!) where for many of us, our world just crumbles before our eyes.
Around Autumn of 2015 I was starting to feel restless. I thought it had to do with the toxic relationship I had webbed myself in, but upon lots of reflection, I think it’s more likely that my personal anxieties were the cause of my high-stress relationship. I knew I wasn’t happy, but I had absolutely no idea why. Here I was, fulfilling all “my” dreams - I had a badass job at a top consultancy firm in New York City, a job that I was steadfastly determined to achieve (well aware of its esteemed reputation). By any testament to success (that I was familiar with), I was making it. En route to ruling the world.
Though deep down, I knew I was lost. I was distracted, lost in a world that wanted me to conform, to settle to the traditional normals of society. Lost in a world that wanted me to sacrifice my dreams so I could be a cog in a system of big corporations and in the back pocket of politicians. I wanted to save the planet, but our system operates by perpetuating its degradation. I wanted to explore mind-altering substances so I could dig deep into my consciousness, but we live in a society that shuns exploratory substances in replace of sedative prescription drugs aimed at suppressing the senses. I was lost in the world I knew, but I didn’t know where else to turn. I was suffocated in so many areas of my life.
It wasn’t until a few months later, once I had thoroughly put a hatchet through my romantic life, and Saturn Return seemed to be in full force, ready to knock me off my feet, that I met up with an old friend from university who was notorious for those deep chats over several bottles of wine. She had confided that she had similar sentiments, and had been in discussions with her therapist also seeking answers. Evidently her latest homework assignment from him was to read the novel by acclaimed Ivy League university professor William Derizcewics called, The Excellent Sheep: the miseducation of America’s Elite (title above borrowed from this brilliant epoch). The is effectively a manifesto for today’s youth - primarily targeted towards Millennials but the lessons can be extrapolated to any generation - who are searching for insight on why they feel like they’re out of control of their destiny. It lends optics into the high-pressure success-seeking conveyor belt that begins with teachers and parents and ends with careers at multinational banks or top-tier consultancies. He discusses how university, that was originally designed to serve as a time for self-discovery and mind expansion, has now turned into the race to the top, with accolades and grades being the only source of personal validation. He challenges that kids today never had the chance to stop and think about what they’re really passionate about and have the chance to explore those skills.
It was through reading it that I finally had that “ah ha” moment - the epiphany that I so desperately needed. Every single line seemed to resonate, every chapter described my life and my situation more than the last. I felt the rumblings of my metaphorical rebirth deep in my soul, and it was itching to be released. There was no stopping it. I was going to renegotiate my idea of happiness.
Today…
It didn’t take me long before I identified the things that mattered most to me. Not the things my parents would be most proud of, or that would get the desired nod at social functions, but the things that really inspired me, that made me tick and feel alive. To be the best version of me possible, and to live with a sense of enviable joie de vivre. I knew I needed to explore. I wanted to see the world, to meet people, to learn about things I’d never experienced and to be a true Maverick in the world. This obviously wasn’t going to fit into my old life plan, so I needed a new perspective.
So I decided to reprioritize time.
I was burning with missionary zeal to explore the world. I didn’t have much money, so I learned to do it on a shoestring, to make friends anywhere, to suck it up when things don’t work out, and to adjust my expectations when realities change. I removed myself from my comfort zone, and learned that it was often when I was most stuck that I found the best solutions. Only when things get so bad or so unfamiliar are you ever really challenged to pivot and to troubleshoot.
Since then, I’ve driven a motorcycle to a hash farm in Northern Nepal, climbed the Himalayas with a yogi who hadn’t eaten in 200 days, got a bamboo tattoo in the jungle while on LSD, sat silent meditation and have slept on the floor of more airports than I can count. I have more stories than I can even remember, and I never feel more alive than when I’m totally lost somewhere new.
There’s always going to be time to “settle down”. To focus on your career and to have that stability you think you want. But there won’t always be time to take the next flight out, no matter where it’s going, and just say “screw it” for a while. Once there are real responsibilities - the career, a partner, children, bills, aging family members - you inevitably get tied down to a location. You fall in to the trap of normalcy without even realizing it. Perhaps this trap is causing the increased incidence of midlife crises and rising divorce rates. Maybe it’s because people don’t feel empowered that they’ve made their own life choices to end up where they suddenly wake up to be. I think many of us are zombies in our own lives, running through the motions of what’s expected of us, what culture tells us is normal, and acceptable, so we can all feel like we fit in. And I think its a dangerous cycle.
I moved to NY with no job and $1500 in the bank. I moved to London with no job and $10k in the bank. I went to India with no hotel to sleep in the night I landed at 2am. It’s through these sorts of boundary pushing experiences that I feel like I’ve really learned. I met people, I learned to adapt, I grew. And even though the growing pains still exist, and sometimes are even more poignant than before, the light at the end of the tunnel is something you’d never have expected.
To Really Live…
“It’s important to realize how travel and experiences can mould your mind.”