The Path You Can’t See Yet
What a forgotten Fiverr gig taught me about exploration, writing, and uncertainty
I’m walking on the beach with my wife, enjoying our two-week vacation in her hometown, when my phone buzzes: “You got a sale on Fiverr. You have 3 days to deliver.”
My wife notices the shift in my expression and asks what’s going on.
“I forgot to turn off the Fiverr gig and I just got a sale,” I reply.
She smiles at me, “That’s a good thing, right?”
“Well,” I ponder out loud, “it would be if I weren’t on vacation. I think I’ll just give a refund.”
Somehow, my wife convinced me to spend an afternoon on that small gig. Ten years later, it had grown into a project that employed more than 50 people and expanded into books, podcasts, and a large annual conference.
But that Fiverr gig didn’t happen by accident. It was the result of a series of uncertain moves that came before it.
It started one night when I decided to answer a question on Quora, my first. That answer got thousands of views and sparked a curiosity to understand the platform more deeply.
As I kept answering, that early momentum faded. Most of my posts went nowhere. I was close to giving up when I came across a question about energy management. I answered it quickly, without overthinking it, and within 24 hours, it had more than 30,000 views.
That confused me. What was so different about this one?
When I looked closer, I realized I had been asking the wrong question. It wasn’t the answer that mattered most. It was the question.
Some questions carried their own gravity. No matter how strong your answer was, it wouldn’t matter if the question itself didn’t generate interest. As I dug deeper, I noticed that Quora left signals, small indicators that revealed which questions were gaining traction and which weren’t.
I started testing that insight. Within a month, my answers had passed one million views. I used that exposure to promote a productivity newsletter I was running at the time, adding 2,500 subscribers in just a couple of weeks.
I was stunned. Quora felt like a goldmine, yet almost no one was talking about it. So I decided to create a course on Udemy, hoping to share what I had learned—and, if I’m honest, make a bit of money along the way.
The money never came. I made a few hundred dollars in the first months, but it never took off. Maybe I was too early. Months later, the platform would be flooded with Quora courses. Or maybe I simply didn’t know how to sell it.
Still, Udemy’s model pushed me to experiment. They paid 50% for students they brought in, but 100% for those I sourced myself. So I started looking for ways to drive traffic.
The least promising one was Fiverr. I listed the course there and offered a discount code for access on Udemy. No one bought it, which made sense. People don’t go to Fiverr to buy courses.
I also offered something else, a custom report where I would analyze someone’s project and create a tailored plan to grow it using Quora.
No one bought that either.
In fact, when I traveled to my wife’s hometown for a two-week vacation, I forgot the listing even existed. It had become irrelevant in my mind.
Until someone in Phoenix, Arizona placed an order and interrupted my vacation.
At the time, it felt like a small inconvenience.
In hindsight, it was the beginning of something that would shape the next ten years of my life.
The instinct we often shut down
Like many other events that significantly shaped the direction of my life, that one was full of unexpected turns.
At the time, I had just moved from London to a small town in Italy. A couple of weeks later, I lost my job at a startup and found myself without the security of a monthly salary.
This was before the pandemic, when the idea of working remotely or making a living as a freelancer was alien to most people.
That uncertainty was tough, but it did something important. It gave me permission to explore paths I wouldn’t have considered otherwise, and to follow them without knowing where they would end.
When I answered that first question on Quora, I had no sense of what might come from it. When I created my course on Udemy, it was my first time using the platform. When I listed it on Fiverr, I wasn’t expecting anything at all.
I certainly didn’t imagine that someone on another continent would become a client, and that a forgotten listing would turn into a project I’d be part of for nearly a decade.
None of it was planned. I simply kept moving, following what was in front of me and seeing where it might lead.
But looking back, what strikes me most isn’t what I did.
It’s how many times this path gave me a reason to stop.
The Quora answer that worked once—and then didn’t. The course that barely sold. The Fiverr gig that no one bought. The vacation I almost protected by refunding that first client.
At each step, there was a perfectly reasonable justification to stop what I was doing and seek the common, obvious path.
In most cases, that’s exactly what we do.
We close the loop too soon, before we give it a chance to surprise us. And there’s a reason for that.
Exploration is uncomfortable.
It keeps things open for longer than we’d like. It delays certainty. It stretches the moment before something becomes useful, profitable, or even coherent.
So we develop an instinct to shut it down.
We look for signals that help us decide quickly what works and what doesn’t, just to feel in control again.
And control demands answers. Fast.
We move from one thing to the next, compressing decisions into quick judgments, optimizing for outcomes we can measure, trying to make each step count.
There’s no room to follow something that doesn’t immediately justify itself. No space to stay with a question that hasn’t revealed its value yet.
You might recognize this pressure in writing as well.
You sit down to write, and almost immediately your head starts spinning:
Where is this going?
Will this land with my readers?
Am I wasting time with research I won’t use?
What if I can’t connect these ideas together?
The default response is to regain control. Follow the framework that works. Research only what you know will be useful. Cut anything that feels unclear instead of staying with it.
But exploration asks for the opposite.
A temporary loss of control. The willingness to sit with an idea you don’t fully understand. To move without knowing where it will lead. To continue without the promise of a clean outcome.
What we lose when we stop exploring
“To be lost is to be fully present, and to be fully present is to be capable of being in uncertainty and mystery.” — Rebecca Solnit
We spend most of our days in autopilot.
We wake up, follow the same routines, open the same apps, talk to the same people, eat at the same places, and go to sleep at the same time.
A week passes. A month goes by. A year slips by without much notice. And when we look back, it feels like not much has happened.
But then there are moments when that rhythm is disrupted. Maybe you lose the job you held for years. Or you find the love of your life and decide to move in together.
Suddenly, you feel shaken. Like someone has woken you up from that long, steady dream. Everything seems to demand more of your attention. Your senses are enhanced. You feel more open to new possibilities, to different perspectives.
At first, it feels scary because you lose that sense of control.
But the longer you stay with that feeling of uncertainty, the more alive you feel.
If you’ve ever deliberately gotten lost on a trek, you know what I’m talking about. You stop following the trail. You pay attention to the light through the trees, to the sound of water somewhere below you, to the way the ground changes under your feet. You’re suddenly moving slower, more awake.
The thing is, writing gives you that same feeling, if you let it.
But most of the time, we don’t.
We sit down already knowing where we want to go. We outline the idea, shape the argument, move from one point to the next as if the path had been cleared in advance. There’s little room to get lost, and even less patience for it. We end up producing something technically correct but often lifeless.
Exploration in writing starts in the same place as that deliberate detour off the trail. You begin not quite knowing where you’re going. You follow a question that genuinely unsettles you. You resist the urge to resolve the tension before it has taught you anything.
And it’s in getting lost and having to find our path back home that we transform ourselves — because by the time we arrive, home is no longer the same place we left.
Four ways exploration shows up in writing
There are four types of exploration that I like to do in my own writing:
Conceptual
Perceptual
Structural
Personal
Conceptual exploration usually starts with a question like “Why does self-discipline feel so hard?”
My first move is inward. I trace my own experiences, not just to answer the question, but to see what else sits beneath it. New questions tend to surface, often more revealing than the original one. From there, I widen the lens. I look for perspectives that can deepen the inquiry: psychological, systemic, incentive-driven. Not to arrive at a quick answer, but to see the question from different angles.
I also carry it into my day-to-day conversations. I listen for how it shows up in other people’s lives, what they’ve struggled with, what they’ve learned, what doesn’t quite fit.
Over time, the idea begins to gather texture. What started as a single question unfolds into a web of related tensions, each one adding depth to the idea. And every now and then, an unexpected connection surfaces—something you couldn’t have planned, like using thermodynamics to make sense of self-discipline—that shifts the entire way you see the problem.
Perceptual exploration, on the other hand, focuses more on observing something ordinary more closely. A conversation that lingers. A piece of common sense that doesn’t quite hold. A reaction that feels out of proportion to what triggered it.
The other day, I had an interaction with ChatGPT that left me uneasy. I had asked about the ending of the movie Bugonia, and something in the response didn’t sit right. Instead of brushing it off, I stayed with the discomfort and followed it. That led me to write a 4,200-word piece on how AI might be the next echo chamber. And in the process, it changed how I see and use these tools in my daily life.
Sometimes, the exploration doesn’t happen in the idea itself, but in how you shape it.
Structural exploration is about craft—the ability to think through the same idea across different forms.
Most writers find a structure that works and then use it forever. This is understandable — finding a structure is hard, and once you have one, it becomes a kind of home. But the structure you default to shapes what you can say.
You’ve probably noticed that lately I’ve introduced a new format called Small Moments. Essays are still the backbone of my writing. That’s where I tend to think things through. But Small Moments serve a different purpose.
Instead of explaining, I try to enter the moment itself—to stay close to the experience and let it unfold on the page without over-interpreting it. So, for instance, rather than describing what analysis paralysis does to our writing, I explore a moment where it shows up in the act of writing itself.
By moving between forms, you begin to understand not just what you’re saying, but how each form’s constraints shape what you’re able to see.
Then you have personal exploration, which is probably the hardest, but often the most fulfilling.
When I feel a fear I can’t explain, a resistance I don’t know where it comes from, or something I’ve been avoiding without understanding why, I know I have a perfect personal idea to explore.
One struggle I had to deal with when I started this project was to leave behind a lot of the habits that made me successful in the past — especially the ability to write persuasively and the obsession over metrics.
So when I wrote my last piece of 2025, I took the chance to stop for a moment and reflect on that personal struggle, trying to understand why letting go of those old habits had been so difficult.
Exploring without losing your way
Now there’s a risk about exploration that we haven’t touched upon yet.
The risk of drifting too far.
I’ve been there a few times. I once tried to write about freedom, and got lost in the topic. At a certain point, I had to accept defeat and move on to another piece.
The thing is, it’s fine to get lost in a rabbit hole once in a while, but it’s important to have signposts in your journey to pull you back and assess your situation in an honest way: “Do I still have an idea of my way back, or am I completely lost?”
One way I check that is by looking at the core question I’m asking. If it’s still too vague, like “what’s freedom”, I might be in trouble. But when it sharpens into something more specific like “why do writers fear freedom?”, then I know I’m into something.
Deadlines are also helpful, although deadlines can have the opposite effect as well, pushing you to leave exploration too early. So I’ve been experimenting with a tentative deadline. I aim to publish every Tuesday, but if a piece needs a few extra days, I give it that space. The only rule is not to let a few days suddenly turn into weeks.
I also think of my writing as a body of work. Some pieces are fully exploratory, where I’m still trying to understand the idea. Others are more about consolidation, where I return to something I’ve already explored and want to give it a clearer shape.
Being on exploring mode all the time can feel exhausting, so I like switching between the two to give me the space to rest when needed.
But even with all of this in mind, when I think back to that time when I wrote my first answer on Quora, I’m reminded of how easy it is to misread where you’re headed when you’re exploring something new.
Initially, when I was answering these questions, I thought I was simply learning how to write better answers. When I created the course, I thought I was just trying to make money. When I put that offer on Fiverr, I thought I was testing another channel.
Each step had its own small goal, but I couldn’t yet see how they would connect—how they would eventually place me on a path toward one of the most important projects of my career.
Sometimes, when you’re in the middle of it, it’s hard to see the larger shape.
Exploration might feel like a series of unrelated moves—some promising, most inconclusive, and the temptation is always the same: to step away too early, before anything has the chance to take shape. Before the connections reveal themselves.
Steve Jobs once said you can only connect the dots looking backward.
But to connect the dots, you first have to wander long enough to find them.
And while you’re wandering, you have to trust that the path is forming, even if you can’t see it yet.
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