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By a strange twist of chance, I wrote this month’s letter reflecting on my time in Venezuela and on the nature of radical, life-altering changes. And then tragedy struck.
Tectonic forces shifted the reality of a place I hold dear in my heart, a place that redesigned completely who I am. While I was about to finalize the notes and drafts I wrote on Transformative Experiences, Venezuela was hit by two consecutive earthquakes of devastating impact, causing uncountable loss in life, homes, and infrastructure.
While we can choose to live an unexpected and uncertain experience like embarking on a new adventure, sometimes unavoidable and cataclysmic events reshape completely who we are. Even if I was blessed with many other circumstances where places, events, and people transformed who I am, Venezuela stands as the first, most impactful of those transformative experiences. I owe more than gratitude to this country; I owe Venezuela a big part of my self.
The Art and Science of Psychological Transformation
I encountered the concept of transformative experiences while preparing a series of lectures for IES Abroad, an institution offering semesters abroad to American college students. I was looking for an anchor to connect my own subjective experience of life change to my audience, and this philosophical framework became one of the central pillars of the lecture.
Transformative experiences hold both an epistemic and a personal dimension:
Epistemically Transformative: An experience becomes epistemically transformative when you learn something that is entirely inaccessible to you without passing through the experience itself. For me, I learned how to sail and how to communicate using the Margariteño dialect, discovering an elegant way to move over the water and a highly emotive form of expression.
Personally Transformative: An experience is personally transformative when it alters your very point of view, rewriting core preferences and values. After taking that step, I was no longer able to return to a corporate environment or be constrained by four walls just to make a living.
Ultimately, such a shift can make you reconsider who you are entirely, to the point that you emerge on the other side feeling like a completely new person.
The Trap of Linear Development
For many years, I valued theoretical knowledge over raw experience. Looking back, that was likely the driving force behind my decision to pursue a Master’s degree in Psychology. In hindsight, however, this preference was not something that arose in me spontaneously. The culture I grew up in (Italy at the turn of the century) had implemented an educational system focused almost entirely on preparation rather than active participation, and I willingly abided by it.
I interpreted that environment by fully buying into the rhetoric I was sold: stay on the laid-out track, complete the tasks, and collect the conceptual models that dictate how a life is supposed to function. High school leads to university; university yields a degree; a degree secures the entry-level assignment.
Without turning back or looking sideways, I made it all the way through graduation, the mandatory internships, and the state licensing exam. I was constantly pressed by an internal clock, driven by the urgent need to end my economic dependence on my parents and escape the cycle of working multiple, odd part-time jobs.
The result of this relentless preparation was a persistent sense of anxiety. I always felt lacking. No matter how much training I accumulated, it never felt like I was enough, even as I advanced to the next official tier. The brief celebration of an accomplishment was cut short by the opening of a new chapter—a new specialized course to take, a new contract waiting somewhere further down the line.
For many, this endless horizon is motivational. It represents the classic carrot dangling in front of the donkey, cajoling human energy toward predictable, collective goals. But the dark side of this perpetual chasing is an underlying, corrosive sense of inadequacy.
The internalized belief that you are never enough is one of the most stressful, destructive ideas a person can carry, especially when reinforced by external cues. Sooner or later, reality catches up with us. A new achievement is never sufficient to dispel the cold realization that we have been cheated, deprived of our present by a system that demands we constantly prepare for a future that never actually arrives.
Linearity always ends somewhere and, in many cases, it ends with a crash.
The Social Debt Against Time
Decisions around education, career paths, and long-term commitments are difficult because it is structurally impossible to predict who we will be a few years down the road. What happens if the experience itself radically alters our internal landscape? If our core preferences change, what happens to the rules and measurements we used to make that choice?
To complicate matters, we feel chronically short on time and tirelessly pressed to hurry. We live in an era that forces us to make definitive, high-stakes life choices as early and as fast as possible, whether it is locking in a specific field of study, choosing a specialized job, or committing to a professional identity.
Human societies have reached a bizarre turning point: speed is now required just to keep our institutional structures from falling apart. This is what sociologist Hartmut Rosa terms dynamic stabilization. A culture becomes modern when it relies on perpetual acceleration to preserve its status quo, constantly forced to grow, innovate, and speed up just to reproduce its basic structures and maintain its baseline. We are running a frantic sprint just to avoid slipping backward. Linear development paths, rigid five-year plans, and resume optimization fit perfectly into this framework of constant growth and utility maximization, and having doubts or taking risky steps is seen as highly problematic.
We see this underlying anxiety in parents navigating early childhood development. Driven by the fear of their child losing a competitive edge, they scan emerging behavioral traits to identify innate “dispositions” early on, selecting the perfect training to capitalize on the compounding advantages of early learning. A ballerina, an athlete, or a talented musician must be built early, or they will miss the narrow window of skill acquisition.
In this hyper-prepared world, every deviation from the intended route, every stop due to illness, doubt, or mishap—even an unavoidable catastrophe—feels like accumulating an invisible debt against time. We feel constantly compelled to make up for any delay, moving like a late train racing to meet the fixed schedule of the next station.
Under such conditions, finding one’s calling becomes deeply stressful. It is not because desire or raw skills are lacking, but because sitting with uncertainty now comes with a massive cost—socially, economically, and most of all, emotionally. Holding space for the unknown has a heavy, draining effect on the human mind, but it is one of the most important factors when people try to find their own path in life.
Exploration and Transformative Experiences
Luckily for us, we harbor an inherent counter-instinct: a latent drive that pushes toward raw exploration and direct experience. We see it clearly in teenagers. They often encounter difficult developmental situations because it is nearly impossible to bottle up this exploratory drive while the physical body is undergoing a profound enactive transformation. You can restrain a child through manipulation; it is far harder to restrain a young person who has spent years observing and learning your exact negotiation tactics. This has always generated risk-taking behaviors as youth manage that frustrating limbo where an individual is biologically mature but legally and socially denied adult status.
Cultivating this inherent tendency to leave the beaten path to find alternative routes, drifting off the cultural model of the family, has always brought advantages, together with inherent risk and conflicts. Exploration is what actually rescues us when facing critical decisions, far more than any amount of theory and preparation ever could.
When our blueprints fail to provide what we are looking for, we find ourselves standing at the edge of what philosopher Laurie Ann Paul defines as a transformative experience. These are the profound crossroads in life where prior data, simulation, or rational calculation can never fully reveal what the outcome will feel like, or who we will become on the other side of the decision.
The dominant model for human decision-making is what cognitive scientists call normative decision theory. This framework assumes we can rationally project ourselves into the future, weigh the costs and benefits of our options, and choose the path that maximizes our future utility. It works beautifully for predictable choices, like selecting an insurance policy, choosing a brand of milk, or buying a house within a fixed budget. But this predictive blueprint fails completely when it encounters a transformative experience.
When you stand before a radical, deeply personal crossroads, no blueprint or theory can grasp what is on the other side. You are forced to step through the door entirely unprepared.
A transformative experience is a choice that fundamentally alters your life path, changing you so thoroughly that it revises your core preferences, your outlook, and your very experience of being yourself. These are the sharp corners of human existence: facing sudden trauma, undergoing major surgery, or welcoming a child into the world.
In her book Transformative Experience, Paul highlights a profound paradox: because a transformative experience is radically unpredictable, you cannot possibly know what the new reality will feel like from the inside. Therefore, you cannot assign a subjective value to that future outcome, nor can you rationally calculate the utility of a self you haven’t yet met.
Leaps of Faith
One of the most defining transformative experiences of my life, besides becoming a father which came much later, was the decision in 2009 to ditch a promising corporate career as a Human Resources consultant to go run a sailboat charter business in the remote archipelago of Los Roques, Venezuela.
Nothing I had memorized or studied up to that point prepared me for that leap. I knew absolutely nothing about sailing or boats, and I didn’t even speak Spanish. There was no way for me to predict how I would fare in such a radically different place—how a 27-year-old man with corporate career ambitions, raised in the foggy monochrome of the Pianura Padana, would adapt to the warm, multicolored, and beautifully messy reality of Venezuela.
Even if I had access to a hundred people who had made that exact same choice, their testimonies wouldn’t have saved me; each person’s journey is a highly specific, unique ecology influenced by countless invisible variables.
You can read endless accounts of voyaging via ocean currents and prevailing winds before setting foot on a boat. You can study navigational texts, listen to veterans’ passionate stories, or vicariously peer into the lives of modern cruisers via digital media. The imaginative mind is highly skilled at constructing plausible scenarios based on secondhand information.
Yet, while preparation and planning support the process of transformation, those descriptions are not directly transferable. They cannot teach you what it will feel like when the land drops below the horizon for the first time, and how your mind will adapt to a totally new environment. To know it, you have to live it, fully accepting that you are profoundly unprepared.
You have to go.
That radical lack of preparation accompanied me as I walked toward the plane that would take me from Italy to Venezuela. I had no idea who was waiting for me on the other side, least of all which version of myself I would meet. I couldn’t even defend my choice against the anxious inquiries of my parents or the curious probes of friends and colleagues. Why was I leaving a predictable track to embark on an uncertain journey to a country I had barely considered up to that moment? I had no rational explanations for what I was about to do. Yet, I felt with absolute clarity that I had to go, as if I were answering a call, even if I had no way of knowing whether that call would yield any genuine growth or improvement. My epistemic blindness was total.
The Anxiety of Change
There is irony in a society that accelerates its frantic speed by forcing you to throw away old blueprints, but at the same time is obsessed with planning and predictability, caring about the return on investments.
The required change is messy, taxing, and never guaranteed. In reality, despite the mainstream mantras of self-growth, what we usually see is shallow rebranding—superficial adjustments with no structural change, especially in late adult life.
The defining choices of our lives—early decisions about education, mid-career pivots, or later-life shifts—are inherently transformative. They completely escape the optimization logic and cost-benefit considerations typical of linear development.
This forces an impossible double-bind: we are compelled to make definitive, high-stakes life choices under conditions of epistemic blindness, gambling with our future identity while lacking rational mathematics to justify the risk.
When we frame the future as a competitive, dog-eat-dog jungle, the stakes of these choices trap us in a closed loop of anxiety, trying to plot a predictable course through life. This is an operation that can only ever be a leap into the dark, inside an environment that shifts as we proceed.
When we voluntarily choose a transformative experience, we accept whatever it holds: pleasure or displeasure, quiet joy or stark terror. We take a deliberate departure from the tracks laid out for us up to that point, entering the subjective arena of personal evolution. Yet, even as we weigh these deliberate leaps, we are starkly reminded of a harsher truth: some transformations are never chosen. They crash through our horizon entirely without warning.
The Earth Shifting Under Your Feet
As I refine these words, aiming for more clarity on these difficult ideas, my heart remains anchored to Venezuela. Day after day, I join my wife in her daily check-ins with family and friends still in the country, assessing the damages and watching the shocking images of ongoing rescue operations in a place so tragically ill-prepared to face such a calamity. Watching the news, I recognize familiar places instantly in the video feeds: the coastal hills of Caraballeda, where one tall building stands completely intact while the next one is reduced to a pile of rubble, in a cruel, arbitrary game of Russian roulette.
Going to Venezuela in 2009 was, for me, a conscious decision—a deliberate experiment in exploration which yielded a career transition and the encounter with my future wife and mother of my son. But the transformative impact of a catastrophe we would rather not live through has a completely different character, yielding distinct consequences and challenges:
When you choose transformation: You are forced to make a high-stakes decision under conditions of epistemic blindness, which strips away your capacity to use standard, predictive decision-making strategies. You are gambling on a future self you have not yet met.
When an unchosen transformation crashes into you: It presents a fundamental crisis not of decision-making, but of ongoing agency. It violently disrupts the projects, relationships, habits, and daily anchors that make the world legible and purposeful—what phenomenologists call your systems of practical meaning.
During transformative changes, the charts we held are instantly rendered useless. We are forced into an involuntary transformation.
Navigating Epistemic Blindness
Whether a transformative experience is chosen willingly or thrust upon us by tragedy, our linear blueprints fail. In an exciting venture, this profound rewriting is exhilarating. But when the world is upended violently, you must fundamentally alter how you navigate. By definition, it is impossible to deal with such an experience through precise models.
However, I feel it’s possible to suggest—from common sense and personal experience in many transformative cases, both personal and from clients—that to live through the disruption of a transformation, you need a different kind of strategy:
From Prediction to Presence
When you cannot calculate the value of a future self or a future reality, the concept of an “optimal route” disappears. You simply cannot optimize for an environment you haven’t yet met. Because of this, your focus can shift entirely to the immediate, actionable step right in front of you, channeling your energy into what matters most in the present moment.
Embrace the Journey
Some knowledge cannot be studied or fully understood beforehand; even when it is, it rarely matches the reality of practice. True insight must be lived. Trust that the human mind and body are remarkably adaptive. The skills you need often emerge precisely when the situation demands them—provided a crisis does not completely overwhelm you, it naturally builds your capacity through experience.
Honor the Choice to Protect or Evolve
When facing a voluntary crossroads, remember that saying no to a major change is a legitimate way to protect and honor the identity you have built. But when you do say yes—or when an unexpected event leaves you with no choice—clinging to a past that no longer exists can drain the energy you need to move forward.
Lean on Trust and Connection
When you transform, your relationships often change too. Look to the people right next to you. These turning points are moments where trust either deepens your connections or brings them to a natural end. You might not have a reliable map anymore, but you can always find guidance and support within the extended intelligence of human connection.
The true value of experience is not about proving what you already know or confirming who you already are. It is about discovering how your genuine preferences, your resilience, and your humanity show up when your old maps are completely gone. This clarity is what allows you to make an authentic choice about who you want to become, rather than staying stuck in who you are right now or who you can no longer be.
References
– Paul, L. A. (2014). Transformative experience. Oxford University Press
– Villiger D. A rational route to transformative decisions. Synthese. 2021;199(5-6):14535-14553. doi: 10.1007/s11229-021-03432-w. Epub 2021 Oct 20. PMID: 35058667; PMCID: PMC8727407.
– Rosa, H. « Dynamic Stabilization, the Triple A. Approach to the Good Life, and the Resonance Conception », Questions de communication, 31 | 2017, 437-456.
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