Lessons for Life — From a Year of Discovery

July 15, 2020
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To all the awesome people I’ve met in my life,

First of all, thank you. Secondly, I wanted to share lessons from my year of travels and discovery. 2018 was unlike any other for me. I left my hedge fund job after a 10 year career in finance in London and New York. I hit the road for an adventure not knowing where it would take me. For the first time in my life, I didn’t know what I was doing. I had no plan. But I knew I needed to shake things up. I needed a challenge. I needed to grow. I needed to get a better sense of who I am.

Sharing these insights is my attempt to address a question I regularly get asked: “what did you learn?” It’s also proved to be a way for me to formulate lessons that I want to continue living by. Perhaps you’ll find some use in this as well.

Throughout my travels I journaled. These insights are lifted from countless pages I wrote along the way. I realized, these lessons, just like me, will evolve over time. Instead of waiting to write a perfect post beautifully articulating elusive life lessons, I thought: "just get this out and adjust it over time."

“Perfect is the enemy of the good”
— Voltaire.

This ain’t perfect, but it’s a good start and with time it’ll get better. And with that — enjoy.

Discover your true motivations

Why did I do certain things? Act a certain way? Why did I end up here? These were questions that consumed me. There was an intent to everything I did, but where did this intent come from? I kept taking on new challenges, but the high I would get from each successive accomplishment didn’t feel as good as the last one and didn’t last as long. After reflecting, I realized that part of my behavior was driven by a need for external validation. That validation got me pretty far, but eventually I had done everything I was ‘supposed’ to do and the applause ran out. I found myself thinking "so now what?" I finally became aware of this. And that awareness now helps me better understand if my motivation is coming from a source of inspiration or insecurity. That clarity has been a watershed in helping me understand why I do what I do.

Step outside of your identity

The biggest hurdle to leaving my job was not the typical reasons you may hear. I shared all of the common insecurities others have shared with me about leaving their jobs. Financial — “I can’t afford it” I’d hear. I met plenty of people having the experience of their lives on a tight budget. Including a guy who spent 5 years cycling around the world on 20 euros a day. Missing loved ones — “I can’t leave this person/people behind” people would tell me. Those closest to you should support your growth over their needs. Employment — “I won’t get hired again. I’ll miss a promotion and fall behind” was common. 'Falling behind' resonated with me. But what’s the worst that could happen? I’ll be able to get another job and so what if I fall behind 'my peers' — what’s the rush anyway? The worst case scenario really wasn’t that bad, plus I’d gain a life experience out of it. That sounded like a great trade off. Being alone — “I can’t be alone that long” I heard. I found that time alone is what was lacking in my prior day to day life. Time to pause and hear my thoughts and feel my emotions.

These were all excuses, however, the biggest challenge to leaving was overcoming my identity. I had meticulously crafted an identity of how I wanted to be perceived by others. The job I had, where I lived and where and with who I socialized. If I was willingly walking away from that identity that everyone knew and understood, then who was I? How would people know me? How were people going to know how smart and accomplished I was? That identity was like a name tag; a badge to identify my worth. Realizing that this identity was not really who I want to be, that it lives in my own head and is not how those closest to me see me was instrumental. My crafted identity had me trapped in my own mind and was a limiting factor. Stepping outside of my identity was a breakthrough for me.

Growth resides in the unconventional

Most of my life I was fairly conventional. But following the conventional lead to my life plateauing in all aspects. I had a great life; loving family, amazing friends, good job, a nice apartment, trips around the world. I was happy, but I wasn’t getting happier. Like a skill or a muscle, I believe happiness is no different. I strive to be happier each day, just like I strive to be a better investor and a stronger runner. Without that constant improvement, growth stagnates and frustration sets in. That’s where I was. I needed something that would enable a step-function change in my growth. I found it in the unconventional. I saw it in people’s reaction. I’d get asked the standard question “where do you live?” and “what do you do?” My answer “nowhere” and “nothing” and then I’d often watch their heads explode because I didn’t fit into a stereotype. At first this frightened me because I thought I needed an answer that fits their expectations. But by detaching from my prior life I realized that the conventional is defined by other people’s expectations (or your perceived expectation that others have of you). But when you detach from other people’s expectations, then you are no longer constrained by the conventional and free to be. All of a sudden, I could show up as I am. I’m not trying to be something I’m not. I was no longer afraid of my insecurities. It’s the purest form of authenticity. Stepping into the unconventional removed expectation and facilitated growth.

Live free (even if just for a moment at a time)

Many extol the benefits of being ‘present’ but miss the mark. Aspire to live free. This past year I’ve lived with no responsibility and have been able to do whatever I wanted to, whenever I wanted to do. It was incredibly liberating. I recognize and I am grateful for my fortunate circumstance that few get to experience. But I learned that true freedom does not reside in zero responsibility and doing what I want at the drop of a hat. True freedom resides in fleeting moments when I’m so consumed by what I’m doing. Stress, anxiety and expectations disappear. And for a brief moment all I feel is positivity, love and awesomeness — that’s being free.

The adage “make the most of it, it’s a once in a lifetime” is short sighted

Countless times during my travels I heard this adage. As I heard it over and over, it dawned on me. That doesn’t make any sense. By ‘making the most’ of my time off, does that make up for not ‘making the most’ when I wasn’t off? Am I only supposed to ‘make the most’ of certain fortunate situations? What about the not-as-fortunate situations that are far more prevalent? Nonsense. Part of the reason I did what I did was precisely because I was not ‘making the most’ of my everyday precious life. I should be ‘making the most’ of every situation, every day and not just the good days. And as for ‘once in a lifetime’ — says who? This year has been so transformative, why can it only happen once? I hope I’ll be so fortunate as to experience another transformative period and another one thereafter, and another one again…

Measure yourself against your own dreams, not someone else’s

Countless times I’d hear a story of someone that did something remarkable that lead to praise and success and I’d think to myself “wow, I should do that.” It’s easy to follow a path that’s already laid out, especially one that leads to perceived success. But living someone else’s dream is plagued with erroneous assumptions. First, I’m incorrectly assuming that whatever endeavor that brought ‘success’ to the person I’m admiring will bring similar success to me. Second, said person may benefit from a certain skill or circumstance that I don’t posses. Third, this perceived success may not actually be making that admired person happier. In fact, it could actually be the source of their misery. Fourth, even if the admired person is happy, since we’re different it’s unlikely that I would be happy if I were slotted into that exact position. I quit comparing myself to other people. It serves no purpose. Do my own thing. Live my own dream. Measure myself versus the person I was yesterday and my dream of who I want to be tomorrow.

Relationships are the most profound of experiences

I regularly get asked “what’s the best place you went to?” There were many. But in reality, when I look back on my travels. What comes to mind is not the physical beauty of the place I was in, the expansive views nor the dramatic sunsets. The most memorable experience that come to mind are those where I made a human connection at a given point at a given time; something immutable. The reality is that the high I get from the latest adrenaline rush — be it skiing, mountaineering, marathoning, hiking, cycling, skydiving — dissipates by the time I’m on to the next thrill. But share that experience with someone else, and you’ll both cherish it forever. Experiences are memorable because of the people I shared them with. Not because of the physical thing I did. The physical thing can only serve as a medium, it’s not the actual content. The relationship is the content. Now in that mindset, I find honest, insightful and growth inducing conversations as thrilling as the physical feats I’ve done. I don’t need to go to the ends of the world for memorable experiences, they’re available all around me.

Entitlement is dead weight

I used to think I was pretty damn good, really good actually, better than most at pretty much everything. That sense of superiority was reinforced by experiences at school and university and in my professional and athletic career. I collected accolades and praise. As a result, I thought others had to prove their worth to me because mine was already established. After all, I was a young successful hedge fund guy. It put the onus on the other person instead of me. I told people how they were wrong and how I was right to display my superiority. I’m embarrassed and ashamed of this behavior. I apologize to those I insulted. Breaking out of my hedge fund cocoon helped me realize this. This entitled mindset hampered my ability to connect with people. Along my travels it became obvious. No one cared that I had graduated at the top of my class, worked at a big hedge fund and live in New York. These things are all meaningless. By shedding my ego, I found myself having all sorts of encounters with fascinating, insightful and inspiring people I previously would have never connected with. In those conversations, I stopped focusing on why they could be wrong and instead found what they were into and built on that.

Positive feedback loop

I am grateful for all the strangers I met along my travels that were so formative in my experiences. I slowly realized that the energy with which I approached someone dictated how our encounter would unfold. I would greet strangers with a big smile and a friendly handshake or hug. Tell them how great I felt and how excited I was to meet them. I’d ask them questions about themselves. To my surprise, this was more than reciprocated. On countless occasions, I found myself engulfed in fascinating conversations and I was invited to join my new friends. Without this positive energetic first impression to prime the feedback loop, I would have never had these chance encounters. I contrast this open mindset to my mindset when I lived in New York and London when I was guarded and did not make a habit of striking up conversations in the same fashion unless I was trying to get something out of it. Now it’s a habit with no ulterior motive and low and behold, the positive feedback loop has enriched my experiences time and time again.

Enjoy the journey because the destination will be underwhelming

I found that doing something only to get to a desired outcome is a waste of time. The sense of achievement I get from attaining the desired outcome wears off quickly. And the more I felt that sense of achievement, the more it became a fleeting feeling. Attaining a goal may feel great in the moment. But goals are arbitrary. Take my marathoning for example, why run 42.2 kilometers (26.2 miles)? Why not 50 kilometers? Why set myself a goal of a 3:00 hour marathon? Why not 2:47 or 3:14? These are arbitrary lines in the sand that we’ve drawn to measure progress. Against those arbitrary markers, we’ll assess our degree of success, which will in turn drive our happiness. But alas, we won’t feel fulfilled. I run marathons not to cross the finish line in 3 hours. Sure achieving that will feel great in the moment. But that brief moment of achievement will pass and then I, and everyone else, will go about their normal lives. I’ll hit a momentary high and then feel underwhelmed by its passing. No I run because I love getting out on the open road, feeling my legs propel me faster and faster, the wind against my face, the sun shining in my eyes, my heart beat pounding, sweat dripping down my forehead, exhaustion setting in and then pushing further — it’s the ultimate feeling of vitality and being alive! That’s the journey I enjoy and is a source of fulfillment every time. Not crossing the finish line. What’s the point in spending all this time training if I don’t love it? Success without fulfillment is the ultimate failure. It’s easy to master the science of achievement; train a specific way religiously. But it’s much harder to master the art of fulfillment. If the journey is not fulfilling, don’t fool yourself into thinking the destination will miraculously bring you fulfillment.

Samuel Andrew

Sam is an adventurer, learner, lover and challenger. He questions why things are the way they are, especially in his own life. He uses his own experiences as a lens into personal growth. He shares these raw and honest experiences in order to be of service to others.

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