Title inspired by my favourite show's recent season 4 finale (Westworld).
Lately I've been trying to plan things more. Because as you know, I'm not a planner. In fact, I think a more precise definition is that I don't follow the rules laid out in a typical life — I like to break rules, or even make my own. I'm the guy who's all in when the live octopus arrives at the dining table restaurant, squirming and oozing, not questioning but wondering about its flavour profile. It's just more fun being the challenger instead of the follower because asking for permission to do cool things with your life is so 2010. This playful mindset throws all expected logical outcomes to the wind, letting you drift from place to place like a wavy kite in the infinite skies of chance.
It's weird to think how advanced pre-planning is considered the norm for most people who liberally use their calendars to schedule blocks for each part of their lives. In my world, I tend towards not planning because the discovery-in-the-moment has worked out so well for me in the past (Case A: this past year). For some, the lack of structure is freaky. Doesn't not knowing stress you out? How do you deal with the anxiety of not knowing where you're going to be or what you're going to be doing? Don't you have a grand 10-year master plan too?!
My daring daredevil part responds with:
But dare I say young padiwan, isn't that the most thrilling part of life, the process of uncovering and unearthing?
Cultivating openness, inviting spontaneity, seeking serendipity — these forces of nature are deeply rooted in my DNA and naturally make me a “chaos surfer”. But nowadays I can't help but feel there's another scent in the air, a subtle mood shift of sorts. A wispy whisper nudges me to switch back to a more rigorous form of systems thinking, away from my off-the-cuff pattern matching that overpowers my thoughts with rapid snap decisions. This inner voice might be right: the days of the free-spirited nomad, in the broadest sense, are over. And that probably means I have to get my shit together for the next 4 years before I turn 30. Alas, age is but a number in this grand design of adulthood.
When it comes to focusing on a game plan vs. letting destiny decide: Does it have to be a tradeoff of one style for the other? Can they both be married and co-habitat in the same household, living symbiotically? Can we sequence the inputs so that order preempts the disorder?
Last week I meticulously crafted my oddly-timed mid-week birthday down to the hour. I wondered if the birthday itinerary was going to be too stifling, but I framed it as a challenge to see how I would perform within rigid guidelines. Here's my sneaky design choice though: I would erase any chance of “failure” from this exercise by 1) adding in a free block for spontaneity, and 2) providing a status update option of "improvised", which would signal that I didn't really follow the rules but found an alternative that I was equally happy with. Out of the list of 10 activities, I knocked 8 out of the park, leaving 2 to randomness.
It felt good to have a foundation for all that free time and be prepared for the next thing, even if the solution was just building a simple list. One related thought that has surfaced recently is that the most powerful people in the room are those who are most prepared. Because most people just aren't — you might go into a meeting loosely knowing the agenda and what the presentation might be about, but chances are you're gonna be filling in the gaps as you go. If you load your arsenal of weapons to the brim, then naturally you're more prepared to fight no matter the situation. But here's the real kicker: the most dangerous people combine preparedness with a killer capacity for improvisation, where floating between these skills is truly a secret formula for conquering kingdoms.
This shape of structured-unstructuredness is exactly what I'm working on now: foresight (planning), insight (presence), and hindsight (reflection). I'm planning a 2.5-week excursion to Israel and Iraq in October as a Middle Eastern sendoff for 2022 — I tell myself that my wandering nomad self is dead, but my bold & brave adventurer spirit is itching to stretch his soul. I'm eyeing a 10-day silent vipassana retreat in December located on the fringes of Joshua Tree, California — I tell myself that I'm going silent for the sheer difficulty and achievement, but it's really to stoke my curiosity about how to deeply immerse in spirituality. I'm about to bite the bullet on booking a month-long stay in Colombia for January — I tell myself this is about running from New York's hibernation season, but in truth it's about accelerating the momentum I get from New Year's. I'm adding mind-body singing sessions and cross-fit personal training classes for early September already, to unlock progress in domains that I'm uncomfortable with.
The main theme is to pursue these “projects” as a controlled series of tests before committing to a live production environment. On paper, the activities seem random and disjointed. In reality, they all still funnel up into a grander purpose of refining my sense of self, my understanding of people, and my development of compounding abilities as an aspiring young polymath.
I don't need to justify any of these choices as correct or reasonable because they're my choices. I'm breaking the rules of life and rewriting them to best fit my narrative. And I'm at a point in my life where I still have so much to learn and discover, so it's okay that I keep the rocketship momentum rolling. Now it feels right to maximize preparedness and readiness for any new venture, in a way that doesn't ruin my preferred jogger's pace and that doesn't remove the essence of improvisation that runs through my veins.
I can plan as far as I want, but things might get derailed to the extreme (I'm currently good at this). I can push my spontaneous self to the extreme, but nothing might happen in spite of that (I'm currently not good at this). That's what que será, será means: whatever will be, will be. This phrase has two interpretations: 1) “cheerful fatalism” — to live lightheartedly but not recklessly, often associated with nihilistic tendencies, and 2) “whimsical absurdism” (which I just made up) — to live in a constant search for greater meaning and purpose, knowing that it's a never-ending Sisyphean struggle, but having fun while on the journey anyway.
As Mr. Optimistic, you know I'll subscribe to a more positive interpretation. Onwards and upwards, zig and zag. Que será, será, indeed.
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