To the deep thinkers,
Welcome to the Deep Thinkers Newsletter: A collection of essays dedicated to going beyond the surface.
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I sit and wonder a lot. I know that sounds weird. I mean, who doesn't wonder a lot—that's just part of being human, right? We wonder. We think. We ponder. Maybe what I’m trying to say, as I sit in my favorite coffee shop, peering out the window at the gloomy weather with so much on my heart but very little confidence in my ability to express it, is that I ruminate far more than is healthy.
I've always been this way. I care about what people think about me. I take criticism, even the constructive and loving kind, way too hard. I internalize everything. I used to be unaware of precisely how much damage my overthinking was causing me. But as I've grown older, I've learned to take a step back and gradually begin to process my emotions and thoughts in more healthy ways. Even still, I frequently fall back on my habit of overanalyzing, brooding, and obsessing, especially about the past.
As I make preparations to find a bigger home to rent, I am struggling with what will be a big transition. For almost a decade now, I've lived alone. No partner, no roommates, just me and my wonderful dog, Millie. But things in my life are changing, and my mom, caught amid a massive life transition of her own, needs my support now more than ever. That’s why I’ve decided to move her in with me. While my heart is fully committed to helping her, I can’t ignore the apprehension that accompanies this change.
This very apprehension has me reflecting on a time almost a decade ago when I faced another life-altering decision—a decision that demanded a leap of faith, a leap far outside of my comfort zone.
Into the fire
In 2016, I moved in with my girlfriend at the time. We had both been accepted to the same college, about 95 miles north of our hometown. The weeks leading up to the move were a whirlwind, but one thing was clear: I was genuinely excited about this new chapter in my life. Neither of us had lived on our own or with a significant other before. To me, this felt like a major step toward becoming a self-sufficient adult, and I was taking that step with someone I loved. I can’t help but roll my eyes at the sentiment now, but at the time, it felt like the start of the rest of our lives.
Leading up to the move, the cracks in our relationship had already started to show. Though we both cared for each other, things had been rocky for a few months. The fights increased in intensity, and rather than get to the root of the problem, we pressed on. But we shouldn’t have ignored the fights. They were an indicator, not necessarily that we needed to end the relationship, but that we needed to address these deep-seated issues before moving forward. Foolishly, I thought the solution was simply that we didn't live together. I thought proximity would alleviate the problems. The naïveté of assuming cohabitation would be anything more than a band-aid solution is truly mind-boggling in hindsight. But I was 22 and kind of an idiot.
Spoiler alert: the problems didn't go away. The first couple of months were fun and exciting. But then the stress of work, school, and our baggage began to weigh on both of us, and the relationship suffered because of this. In the midst of the inner and outer turmoil I was engulfed in, I found solace in the friends I’d made at work and slowly began to pull away from my girlfriend.
I didn't see it at the time, because I was so self-centered, but she felt lonely. And instead of being a source of comfort, I isolated myself—feeling that she had become needy and possessive. But she simply wanted what any partner would want: to not feel alone. Instead, of noticing this and working toward mending the relationship, I pulled away even more. I'd found people who were helping me navigate the voyage I was on, and rather than be the support she needed, I left her to paddle on her own.
Our fights grew more frequent, each one laced with more venom and escalating in volume. The little apartment that was once meant to be a sanctuary of peace quickly became a place I dreaded returning to after a long day. Even when things were “good”, I think we could both feel what was bubbling under the surface. And less than a calendar year after signing the lease, we broke up. We rode out the remainder of the lease under one roof. (Yes, it was as awkward as you can imagine.)
When the lease was up, she decided to go back home for a while to regroup and figure out her next steps. We both hated the town we’d moved to, so I understood her decision, but the thought of returning home filled me with panic. I’d fought so hard to get to this point. Even though I hated my job, hated myself, and was utterly miserable, I still dragged myself out of bed every morning, determined not to leave without finishing what I’d started. (It’s almost laughable, really—that this was my mindset, even as I was willing to quit on my relationship.)
I was left with two decisions. Return home, back to my parent's house, or forge ahead, uncertain and heartbroken. Without someone to split the bills with, I wasn’t sure I could stand on my own financially, but I was about to find out.
The more I thought about it, the more I understood that for me, the idea of quitting and returning home was too much to bear. I chose to double down on the path I had chosen. I moved into the cheapest apartment I could find, a tiny studio apartment located in a complex right behind the one my ex and I had lived in. Looking back now, I realize I was meant to go it alone. There are many things I would do differently, but given what I knew then and my limited emotional intelligence, I made the only decision I could—and it ultimately paid off.
It was this very decision—choosing a mission where moving forward was my only option, stepping far outside my comfort zone—that led to growth. And that growth has made me stronger in ways that now feel unshakable.
Antifragile
In his book, Antifragile: Things That Gain from Disorder, author Nassim Taleb introduced the concept of "antifragile" into the lexicon of risk management and systems thinking. The term refers to systems, or individuals, that grow stronger under stress or anxiety. The concept is only a part of a much broader exploration of risk and uncertainty. But for the individual, antifragility is pretty straightforward: expose yourself to manageable discomfort or challenges to fortify your resilience and adaptability.
When I was making my own decision to walk the path of uncertainty and discomfort, I had no idea such a term existed. The longer I live and the more adversity I survive the more I am certain that to the extent that it doesn't kill you, bad events make you grow. You are forced to reach inward for the strength you thought at one point you didn't possess. You are given the task to endure what you once thought was un-endurable. And if you really lock in and decide to take advantage of uncertainty, rather than, how most people react, run away from it, then you are rewarded on the other side by becoming a better version of yourself.
Like Marcus Aurelius once said:
The blazing fire makes flames and brightness out of everything thrown into it.
To me, antifragility isn't about masochism. It's not about ice baths or waking up at 4 am to run 10 miles (and if you do either, or both, no shade). Becoming antifragile is about understanding that life will put you in uncomfortable situations regardless, so why not embrace the discomfort as an opportunity to grow, adapt, and emerge stronger?
Instead of resisting or fearing the challenges, we can choose to use them as fuel to evolve into more resilient, capable versions of ourselves. We spend so much time sitting in classrooms "learning," but the reality of learning is that it happens through direct experience.
You learn in the moments when you trudge through the mud, confront solitude, and feel doubt creeping in. It’s in those moments you come to understand—deeply and unshakably—that there is no turning back. Within that realization lies a choice: to fold or to grow. When we choose growth, when we refuse to fold, we become antifragile. We prepare ourselves for the next challenge, knowing full well that to live is to be challenged.
Seneca, the Stoic philosopher once said:
No man is more unhappy than he who never faces adversity. For he is not permitted to prove himself.
Living at the edge
Juxtaposing fragility and strength gave birth to Nassim's seemingly paradoxical idea of antifragility—that is, that some things grow stronger under stress. This paradox brought to mind the reality that while humans are, in a way, wired to progress and evolve, we are also wired to remain in place, comfortable, and satisfied.
Modern technology has done a wonder on this constant inner battle. Why step into an uncomfortable situation, willingly, when it's simply easier to, you know….not?
Well, because you'll never know what you're truly capable of if you always take the easy way out. Maybe that doesn’t bother you—and fair enough if it doesn’t. But I’ve noticed, both in my own life and in the lives of others, how restless we become when things stay too comfortable for too long. But when we occasionally live at our edge—at that fragile point where we feel we could shatter but, almost cosmically, know we won’t if we can merely hold on—that is the sweet spot. It’s where growth happens, where we transcend our perceived limits and glimpse the resilience we didn’t know we had.
In those moments, we’re reminded that discomfort isn’t something to avoid—it’s the proving ground for our potential.
I want to tread carefully here because while some people find value in romanticizing their suffering and trauma, that is an intensely personal choice. For me, there are experiences from my upbringing and adult life—deeply traumatic events—that I would rather never revisit. However, I’ve noticed a pattern in my own life: every time I’ve transitioned to a better place—mentally, emotionally, and spiritually, there was always a moment beforehand when everything seemed to be falling apart. As we navigate our paths, we are called to endure not one or two, but countless valleys of darkness before we get a glimpse of the light again.
In those moments, deep within the valley of darkness, let us keep one question at the forefront of our minds: Progression or regression? We resist progress at the individual level, even if we don't realize it. This is because progress is change, and our brains are wired to resist change. Choosing progression—i.e., pursuing the path that demands we step out of our comfort zones—means taking agency over our lives. Every opportunity to rewire our brains by embracing something difficult is an opportunity worth seizing. It is, in a way, a gift.
We resist conflict by narrowing our minds on the conflict itself, rather than letting it flow as an interesting, and often necessary, part of existence.
— Dan Koe
Life has many similarities to a video game, one of which is how difficulty increases our engagement. Think about it: if a video game is too easy, it quickly becomes boring. It’s the challenges—the ones we know we can ultimately overcome—that keep us invested. Difficulty, paired with the right amount of risk, is what keeps us in the game. Risky, but not so risky that it feels impossible.
Even if on the surface, we feel the fear, and even the resistance to venture toward our edge, we understand deep down, that if we do not challenge ourselves, we won't grow as people. Comfort breeds complacency, and complacency leads to running in place—even worse, running in place with the shackles of comfort firmly hooked around our legs.
Choosing the mission
Living at the edge looks different for everyone. While I think it's important to venture outside of your comfort zone, don't allow anyone else to make you feel guilty for the small steps you take or how long you're taking to make said steps. You know yourself. You know your fears. You know what comes easy to you and what areas you could dedicate more effort to.
I would like to encourage you, as I've encouraged myself and will encourage those I know in person, to challenge yourself whenever you can. See what you're capable of. Learn through direct experiences. When you are ready and have chosen a mission for yourself, eliminate the easy path in your mind, so that the only thing you have to rely on is your inner strength and adaptability to move forward. If you're not happy with yourself or the state of your life, you don't have to settle. Every small step, in the areas of your life you can control, is a declaration that you believe in your potential—and that belief can change everything.
As I reflect on the moments when I have faced what felt like an immovable force—one I knew I had to overcome—I realize those were the times I learned the most about myself. Those were the moments when I leveled up.
When we challenge ourselves and come out on the other side victorious, we increase our capabilities to navigate life. We become more confident as future obstacles rise in front of us. We might even become the calming force in the lives of those we know and love when things get a little too chaotic. When we choose missions that leave us no choice, we learn lessons that comfort simply can’t teach us.
So every step you take, no matter how big or small, outside of your comfort zone, know that you are operating in service to the best version of yourself. Future you will thank you.
I will leave you with one final quote—one from the author Brene Brown:
You can choose courage, or you can choose comfort, but you cannot choose both.
I wish you all the best.
What I’m into this week:
I think we hate to face the silence, the same way we hate to look into the mirror after we’ve done something we shouldn’t have. It’s revealing in its entirety. Beneath the push that gets us to be in stillness— is an undefined idea that we should have started years ago. Or that, instead, it’s not the right time, that we must keep trudging like delirious soldiers through muddied eternity until clarity appears like golden light through the clouds.
Much love,
- Jon ♾️