I was born into a modest family in a broken home and had to work hard from a very young age to make a living. My entire education, from high school to university degree, cost my parents nothing, thanks to public grants, student jobs, and various gigs I took on to fund my studies and support myself and my mother. It took me roughly from 15 to 36 to get a foothold in life. That was 20 years of my life.

Freedom

Last summer, my small, bootstrapped cloud services company was acquired. At its peak, we were a team of just 12. But it was the work of my life, and I gradually fulfilled every single role in the business, from sweeping the office floor to serving as CEO, until I was finally able to step down and sell the company. I learned a hell of a lot and developed many personal and professional skills during those years. It was exhausting, but exciting. Feci quod potui.

I’m 42 now, and I feel that I have reached the freedom I’ve been chasing since I was 15. Over the past couple of years, I have simplified my life extensively and deliberately. My agenda is now entirely blank: no meetings, no appointments. I also enjoy no debt, no mortgages either. And no regular job or boss, as I work on my own projects solely for myself. I have enough financial runway to sustain a decade of dolce far niente—not because I’m wealthy, but because I cultivate a frugal lifestyle and found liberation in austerity. For the first time, I’m truly free.

I’ve embraced minimalism, discarding or giving away most of my material belongings. I’ve drastically simplified my wardrobe to just three pairs of jeans, half a dozen plain basic shirts, and a pair of Converse All Star. I always dress the same.

Emptiness

I was in a relationship for the past sixteen years. We have a wonderful son who is seven years old. The relationship ended this winter, but we remain on good terms. However, I had to leave what had been my home and family. Instead of moving into a new apartment, I booked the cheapest flight to a place remote enough from one day to the next, and left alone. I didn’t even need a suitcase: my backpack sufficed.

I roamed alone for months in North Macedonia, Bulgaria, Italy, Switzerland, Liechtenstein and France. Every day, I opened my laptop in a different coffeehouse, trying to make some progress on my personal projects. During this time I learned that radical freedom can bring along the unwanted companions of emptiness and nihilism. And that navigating the seas of uncertainty is a skill in itself. I also discovered that staying hungry is one of the most powerful intrinsic motivators.

I have achieved my teenage goal of freedom—a liquid life, as Zygmunt Bauman described it. With enough savings to live comfortably for the foreseeable future, I should have felt content. Yet, an unsettling sense of emptiness quietly began to take root within me. It took months to acknowledge it. Only when everything went dark was I able to see.

Motivation

When I was 15, my father lost his job. As was customary at that time and place, my mother didn’t earn a salary and took care of me and my siblings full-time. We were unable to pay the mortgage on our modest apartment in the outskirts of town. Eventually we were evicted by the bank and the police. My father fled. I hated him so much for that, that we never saw each other again. He died in 2015.

At that time I embraced some radical ideas. I took a Stakhanovite approach to my responsibilities: I went from being a poor, demotivated student to earning top grades in high school, and then university. Afterward, I started a business and worked on it day and night. Now I see it was all driven by pure anger. Resentment fueled my life for twenty years.

But eventually, I arrived at Ithaka. And once again, I didn’t realize it. Wise as you will have become / so full of experience / you’ll have understood by then / what these Ithakas mean.

In the midst of a period of crisis and confusion, this spring, I slowly managed to think clearly. I decided to settle again in my hometown, primarily to be close to my child. I also established a new set of personal goals for the next few years. I sealed this pact, both solemnly and humorously, with a friend of my youth in the cemetery of Verderio, Lecco, Italy. I even set a deadline and made a bet with her. Excitement replaced anger as my main intrinsic motivator.

Now, I have a direction again. A new Ithaka. But…

Loneliness

But I make the journey alone.

I have plenty of connections and acquaintances, mostly from my years running the business. But they’re all busy. Virtually all of my old friends have regular nine-to-five jobs. Nearly all of them left our hometown for the glitters of the megalopolis. They have families, mortgages, Mondays, bosses, holidays. They live on the rails. They have no time. They are not free.

Oh, the irony! I spent half of my life rowing hard to reach this island of my dream lifestyle, only to find there’s no one here to share the joy with!

I have over a thousand contacts in my phone’s address book and well over a hundred thousand followers online. Yet I feel lonely. There’s simply no one around I can ping to work together from a coffeehouse, to motivate each other as we push toward our respective goals. Everyone is busy working in their offices, spending time with their families, or caught up in their own duties. I miss a true tribe of friends to share my journey with—real-life people, not just virtual connections. Because motivation is contagious. Stakhanov mined with friends.

A network of pals to recharge with after a day of focused, productive work. Unfortunately, only remote workers, digital nomads, and solopreneurs seem to fit this lifestyle and liquid schedule. And I know no one like that in my hometown.

Pursuit

I commit myself to build new connections to fill that empty space with.