I've spent an outsized amount of time on self-improvement. This might sound unequivocally positive at first. After all, isn't the best work of your life exactly the work you do on yourself? The naive answer is yes — one I've believed and still believe for so long — but the hard truth is almost always more dubious.
We talk a lot about over-engineering and overfitting in software development, and I wonder if there's a similar analog to personal development. A universe where no one overthinks and the simple answer is the right one — aka you grow by enjoying life as much as possible. Good vibes in, good vibes out.
It's like how writing with pen and paper is the most liberating act because you're forced to slow down, to linger on each word and feeling. Because when we reach a point of being too hellbent on maximizing everything about us, we start losing ourselves in a sinister rat race to the top. Via McClelland's human motivation theory, this is where we strive towards advanced arcs of ambition and achievement through non-stop fantasizing and scoreboarding of who we could be. Because we're never really done with ourselves, aren't we?
Of course, I'm talking about a relatively small proportion of people who have already experimented with a range of self-improvement tools — meditation, introspective journaling, talk therapy, philosophy salons, self-help books, psychedelic experiences, global travel, artistic pastimes, passion projects. Technically I'm calling myself out (haha), but I think there's huge value in being self-critical at times.
As the initial wave of excitement from New York recedes, I'm wary of being sucked into the vortex of over-optimization as I find myself surrounded by people who are deep in pursuit, in passion, and in progression.
There's a never-ending torrent of new shiny trendy options nowadays. Personal growth as a concept has been coopted and commoditized by big industry's desire to capitalize and commercialize. Personal growth now cannot be framed as just personal growth. The marketing pitch is that personal growth is something that can be hacked and attained, masking as a brand of mental fitness, productivity, creativity, and empowerment. The average consumer looking to improve themselves will resonate more with pithy promises of defining your decade and building atomic habits.
. . .
Rant aside, I'd like to think my enduring drive to be in the world says something about my undying love for it. That I stay moving and improving not out of some sense of dissatisfaction with the present— aka some gaping hole I need to fill —but simply because I’m curious about everything and proud of that curiosity.
In July, a persistent curiosity about how to prevent excessive self-improvement from morphing into self-destruction led me down two potential pathways.
Single-player to multiplayer: Active immersion into scenes (subcultures, integrated neighbourhoods, community-led third spaces, pseudo-cults)
Single-player to even harder single-player: Active immersion into spirituality (meditation studios, faith-based organizations, religion)
I admit that these two categories aren‘t exactly mutually exclusive. One concept that easily straddles both is modernized religion & faith, which I definitely want to explore deeply in an upcoming piece. But the main point is that it takes a dedicated mindset shift to ascend Maslow’s ever-loftier hierarchy. And how exactly can we structure our spiritual lives to avoid getting lost in the sauce? Just using a daily meditation app and calling it there? Or do we have to go to the other extreme and pursue weird technical shit like ego death and shadow work?
So on July 8th I attended two back-to-back themed events to explore a life that lies beyond utility and analytical thinking: one with Interintellect hosted online by Internet titans Tiago Forte (author of Building a Second Brain) and Visa Veerasamy (author of Friendly Ambitious Nerd & Introspect), and the second with Creative Mornings hosted in-person by Casper ter Kuile (author of The Power of Ritual). These interactive sessions sparked a wildfire of musings on the value of spiritual living and how to ground it in concrete practicalities of life.
The way Tiago approaches the Internet is fascinating because he frames the nebulous digital galaxy as a cluster of neighbourhoods that you can tap into in the search for belonging. On paper, his work on “second brain stuff” seems to be another ploy to harvest engagement and eyeballs on a productivity hack. But his true insight is one that surrounds anti-self-improvement:
"[It's] about optimizing a system outside yourself, a system not subject to your limitations and constraints, leaving you happily unoptimized and free to roam, to wonder, to wander toward whatever makes you feel alive here and now in each moment"
Recently I've had so many conversations with friends that are looking to branch outside their comfortable relationship bubbles and venture into more unknown territory. In friendship philosophy, I illustrated the tension between cultivating known friendships (which takes huge amounts of intentional effort & energy) and outgrowing others that have drifted out of your zone of life stage and personal interests. Existing social structures are like any biological system — social groups tend towards homeostasis and stagnation if there aren't any fundamental connecting tissues that glue everyone together.
That's why the descent into the spiritual side is so fascinating because to me, that's a much stickier way to stay values-aligned with the people who matter most in your life. And as we've discussed, this does not need to be a strictly solo zen-like pursuit. Cultural communities constantly sprout at every corner for every niche, where active participation drives shared purpose. But as Tiago and Visa suggest, if you don't know about these warm and inviting communities (many of which are initially baked into the crevices of the modern web), then naturally you feel skeptical about the world. In any scene, the access price for admission is participation and contribution.
To dive a little deeper, Casper neatly defines spirituality through three lenses:
Belonging: experience of knowing and being known, loving and being loved, in a bilateral way
Becoming: process of growing into the person we're “called” to be, typically in a non-linear way
Beyond: larger sense of Otherness that stretches to the broader world, typically in a cosmic, collective way
I like this framing because it implies multiplayer from the very beginning, where the starting point is largely accessible to all who are ready to try. I think the worry of viewing spirituality purely as an action for ourselves is that it starts to slide into something that looks a lot like conspicuous consumption. We rely on it like an instant antidote designed to make us feel better in the moment. Again, the commoditization of the modern mindfulness space. It's so easy to focus on the “me” part, but the more critical ingredient is committing to a collective journey. Self-actualization is achieving not by focusing on the self, but rather by successfully transcending it.
What I've managed to unlearn and reframe:
Instead of thinking in terms of the ascent, a spiritual journey is one of descent. The willingness to surrender, giving more of ourselves away through the lenses of unconditional generosity and humility.
It doesn't matter if the spiritual practice is tied to a prayer mat or paint brush, a microscope or movement, or even a travel experience that is more about spiritual replenishment vs. novelty seeking. A reminder that you don't need to read Lao Tzu or Siddhartha or understand the Zen Buddhist's emptiness or try kundalini yoga to embrace spiritual principles. Any form of a broader mission is totally valid in our quest to answer the eternal questions: How should a person be? How might we find meaning in the mundane, and purpose through great pain? How can we repair the world?
I struggled so hard to write this piece because it's difficult and scary to take the plunge into the messy swamp of spirituality. Like I'm not quite sure how to approach it, and I'm constantly second-guessing what the “ideal approach” should be. But I guess I'll take the Kierkegaardian leap of faith as boldly as I can, and as Substack writer Carmen Lau speaks about limerence of ideas:
I hope this works out. But I don’t know for sure. Because if I knew it wouldn’t be worth trying. That would be boring, there would be no journey. And if there’s anything I can get behind, it’s a crazy journey
Here's to riding into 26, one spiritual step at a time :)
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