Level 1 - Class Selection (High School and My First Money)

This series tells the story of my financial journey, one level at a time, from childhood to today. How many levels will there be? I don’t even know. It’ll keep going until I’ve reached the goals of this blog: complete or (more likely) partial financial independence.

Level 1 covers high school, choosing between music and computer science, my first jobs, and the realization that earning money is much easier than learning how to manage it.

High school is the middle ground of growing up. You’re not old enough to really know what you’re choosing, but you’re not young enough to let other people choose for you.

In many video games, at some point you’re asked to choose a “class”: warrior, mage, archer, and so on. From that point on, your stats, abilities, and the way you approach problems all change.

Real life works more or less the same way. Except when you make the choice, you’re fifteen, and instead of a character screen showing your stats, you have a form to fill out.

Without realizing it, I was building a pretty unusual combination of computer science and music.

For high school, I chose a technical school. The first two years were the same for everyone, with subjects such as chemistry, physics, mathematics, and law. It was only in the third year that we chose a specialization.

I went through those first two years without any particular interests.

I remember taking part in the Mathematics Olympiad for the very noble reason of getting a day off school. I won the school-level competition and then decided not to continue. Whenever I think about it now, I realize what an opportunity I threw away. I could have competed against other students, met new people, and seen what existed beyond my classroom. But at that age, long-term thinking is rare, and the people who should be pointing you toward those opportunities don’t always manage to do it.

Outside school, though, something much more interesting was happening.

Years of Music and My First Earnings

Music, which had started as a childhood hobby, had taken me to the conservatory, where I went two or three afternoons a week.

What I remember most about those afternoons is the atmosphere outside the classrooms. Music drifted through the gardens, and within the space of a few meters you could go from a Bach sonata to a Charlie Parker-style jazz improvisation.

Then you stepped into the classroom, and everything changed.

The competitiveness was almost straight out of Whiplash. Students and teachers seemed to be in a constant competition over who was better, more prepared, or more capable of standing out. I held my own in that environment for several years.

In the meantime, though, music had stopped being just a hobby, and I had started making money from it. In the summer, I kept playing at local religious festivals and processions, but I had switched bands. This one traveled from town to town. We’d get on a coach and visit the most remote little towns in southern Italy, sleeping on camp beds set up in school gyms and playing as part of local religious celebrations.

As a kid, I used to make €5 or €10 per event. Now I was earning around €50 a day, for 20 or more days each summer. Almost €1,000 per season. For someone my age, that felt like an enormous amount of money.

Financial awareness? Zero. I didn’t really think of that money as “wealth”. It was simply money I’d earned by doing something I enjoyed.

Some of it went toward little treats, some of it I saved, and some of it went straight back into music. My most important purchase was a saxophone.

Looking back, I don’t consider that money simply “spent”. It was an instrument that allowed me to improve at what I was doing and, more importantly, to keep earning money from that skill.

I didn’t yet have the concept of investing as I would understand it years later, but I was already doing one thing instinctively. Part of the money was going back into the machine that had produced it.

It was a very rudimentary form of reinvestment. I just hadn’t figured out how to manage everything else yet.

“Hi, Do You Need a Website?”

In my third year of high school, things changed. I chose computer science, which was the obvious choice for me. The classes were reshuffled based on everyone’s choices, and a guy I immediately clicked with joined mine. We’ll call him Jerry Maguire. You’ll see why in a moment.

What brought us together, besides computer science, was our interest in business. The idea was simple: come up with projects that could become startups, or at least something interesting.

We came up with ideas almost every day, but the problem was always the same. Turning them into reality required at least some budget, and we didn’t have one.

Our first attempt was a 2D video game. After building the basic mechanics and applying the first free textures we found online, the result was nowhere near what we’d imagined. We hired an artist to create custom textures and, shortly afterward, had to stop the whole project because we’d run out of money.

We had invested what little money we had in a project that would never move forward. It was one of the first failed experiments of my life, and it was also a useful lesson. When you have very little money, you can’t afford to treat it as if it were unlimited.

So we changed direction. Instead of starting with an idea, we started with what we knew how to do.

We made a list of our marketable skills. I could offer web development, with the basics I’d learned by taking apart Pokémon website templates, plus some graphic design, which I’d explored over the years with the earliest versions of Photoshop. Jerry could build websites too, but his real strength was convincing clients. Basically, while I was thinking about what to build, he was thinking about who might buy it.

We found online lists of businesses that didn’t have a website, or whose website was badly outdated, and spent our afternoons calling them one by one. We got mostly “no”s and, in the best cases, “maybes”.

So we moved on to freelance platforms such as Freelancer.com. And that’s where Jerry really shined. He could convince clients to hire two high-school teenagers as if we were seasoned professionals.

Somehow, it worked.

The first jobs came in, the kind we needed to start building a track record. I still remember the first two. An artistic digital CV that sold for €100 and a business website that sold for around €700. My reaction was basically: “Show me the money!”.

With every delivery, I learned something new. Jerry and I would work late into the night to meet deadlines. Without capital, the only resource we had was what we knew how to do. It was enough to get started.

Meanwhile, things were going less well at school. I was mainly interested in computer science and mathematics. My enthusiasm for the subject, and perhaps a little impostor syndrome about the work we were doing, pushed me to study beyond the syllabus and ask a lot of questions in class. Not every teacher appreciated it. One teacher took it as a personal challenge and gave me a failing grade in computer science that I had to make up over the summer. Ironically, my first “debt” wasn’t financial. But the problem wasn’t just a few teachers.

Some lessons were actually making me lose interest in computer science itself. The way it was taught made it seem flat and lifeless, a collection of exercises disconnected from reality and programs to follow page by page.

Meanwhile, outside school, I was building websites, looking for clients, experimenting with graphic design, and thinking about how to turn those skills into something valuable. The gap between the two worlds was enormous.

At school, computer science seemed like a collection of topics to study. Outside school, I was discovering that it could be a tool for building things.

Luckily, there was one teacher who saw it differently. To him, computer science wasn’t just what was written in the syllabus. It was everything we could try to create. He challenged us to do ambitious things, sometimes even as a joke. Like the time he assigned us to create an operating system. Jerry and I took it pretty seriously. We didn’t create an operating system from scratch, obviously. We started with Linux and built our own custom distribution. When we showed it to him, we managed to surprise him. That episode stuck with me because it completely flipped the way I was looking at school.

You didn’t need a teacher to know all the answers. Sometimes all you needed was someone willing to tell you, “Let’s see how far you can take this”.

It was one of the reasons I didn’t completely lose my way in computer science.

And what about the money? By that point, I had several sources of income. Music brought in around €1,000 each summer. Then there were the first online jobs. They weren’t huge amounts in absolute terms, but for a teenager they were more money than I’d rarely ever seen in one place. And yet there’s a curious detail. The first written records of my finances date back to 2018, around the end of high school, when the bank account I’d opened just after turning eighteen had €300 in it.

I’d earned far more than I’d accumulated.

So where had the rest gone? It hadn’t simply disappeared. Some of it had gone into music, including the saxophone and other instruments. Some of my online earnings went back into the projects we were trying to build. And then there were the things I bought simply because I liked them. For example, Dylan Dog comics and various manga. Each purchase, considered on its own, made perfect sense at the time. One comic wasn’t going to change my life, and one manga wasn’t going to ruin my future. A new instrument even had a concrete justification because it allowed me to develop a skill that also generated income.

The problem was something else. I had no big-picture view.

I wasn’t asking myself how much I was spending overall, how much I was accumulating, how much I could afford to reinvest, or how much I was simply consuming. I was making lots of individually sensible decisions without looking at the final result. And the final result, in 2018, was a bank account with €300.

Looking back, I don’t think the solution would simply have been to save everything.

The saxophone wasn’t a random purchase. It was part of the path that allowed me to develop a skill and keep working. Spending money to try to build projects wasn’t necessarily a mistake either. The video game was never released, but the experience taught me something. The same goes for those first jobs, the instruments, and the skills I was building.

The point is that I could have managed what was left after those decisions much better.

I could have known how much I’d earned, how much I’d spent, how much I’d reinvested, and how much I was actually accumulating. I didn’t do that at the time. And that’s a distinction I only learned later. Not all spending has the same meaning, but it all contributes to the final result.

You can spend money to have fun, to learn, to work, or to build something. Either way, by the end of the period, some of it will still be in your account and some of it won’t. Looking only at what comes in tells half the story.

Checkpoint

As I left this level, my inventory contained more than my bank account showed.

I had skills that someone was willing to pay for, a partner who was good at finding clients, a track record of real projects, and a habit of working late into the night whenever something really interested me.

I’d also learned, without realizing it, that a skill can become an asset. First through music, and then through computer science.

The “money management” stat, on the other hand, was still almost empty.

On the My Save File chart, the Level 1 checkpoint is a tiny dot: just €300 in 2018. But that dot tells only part of the story. The money had left the bank account, but the skills hadn’t.

Once school was over, I enjoyed one of my last summers without too many worries, convinced that Jerry Maguire and I would soon be starting our own company.

This level ends here, with little money in the bank and a head full of ideas. Level 2 begins at university. See you there.