When I was 21, I dropped out of university in Bologna and started writing code as a freelancer. Clients, mostly from personal connections, began knocking on my door. I had no experience in software development or anything at all back then, so I said yes. I was making little to no money, but it was fun.
I followed my girlfriend at the time to New Zealand for a few months and then came back to Italy. A friend of mine offered me a job in a club. I had no experience in manual labor, so I said yes. I quickly went from sweeping the floor, to cleaning toilets, to managing the room, to cashing tickets.
In 2006, blogging was big, and I started a personal blog, writing mostly about myself and my interest in human behavior. Clients started knocking at my door, asking me to be a marketing consultant. I had no experience in marketing, so I said yes.
Within a few months, I was in Milan, negotiating a large contract with a Viennese startup that wanted me to be their country manager in Italy. I had no experience in managing countries, so I said yes.
Six months later, they offered me a permanent job in Vienna, taking charge of company communications in 13 countries. I had no experience in communications on an international scale, so I said yes.
After resigning from that company, I was asked to join the startup team of a new business. I had no experience working at a startup, so I said yes.
Before Automattic, I had no experience at a global company. But every job was a dot I connected and led me to the position I have today. I am a lucky man. Except there’s no such thing as luck.
As a kid I always had the toys I wanted, I went to the school I wanted, my parents supported the education I desired. I played when I wanted to play, I slept when I wanted to sleep, I had good grades when I wanted good grades. I now do the job I wish to do at the company I wanted to join. I am a lucky man. Except… there’s no such thing as luck.
I’m from a working class family, and my parents and my grandparents before them did not have the luxury of choice. They took what life gave them and made the most of it. I’ve struggled to earn a living. For years, I didn’t make enough money to move out of my parents’ house and be independent. My family had helped me more than once when my income didn’t pay the bills. It was hard and still is.
In 2012, I attended the wedding of one of my best friends. Simone flew me into Singapore and wanted me there to take pictures and bring a wedding ring from Europe. Usually when you go to a wedding, you bring a present, but what happened is Simone gave me a gift I keep dearly, and today I’ll share it with you.
We were sitting in a street bar late at night, just Simone and I, drinking iced tea and smoking shisha. He was employed at Amazon, and I was struggling with a startup in Vienna. I told him my challenges at work, the little money I had, and the difficulties of navigating unknown territory.
He looked at me and said: “Don’t worry, people like us always survive. Things can go south quickly but in the end, you worked in a club sweeping floors and cleaning toilets, so you know that whatever happens with your job, you will never starve to death.”
663 million people live without clean water. One in nine people on earth do not have enough food to lead a healthy active life. How about you? Do you have clean water? Do you have enough food to live well?
The hard part has been done. We have clean water, an abundance of food, and access to medicine, energy and consumer goods. This gives us a feeling of safety, security and comfort. The need to succeed, a better job and a better salary, are bonuses. Whatever happens, I will survive.
Besides being “lucky,” I have always been lazy. We all are, we just try to hide it. You are lazy too. You don’t go to the river every morning to get water. You don’t work in the fields and harvest crops; you drive your car to the grocery store.
We like comfort, except when we go to work. At work, we like to keep ourselves busy, and hard working people who c start early and leave late, notebooks full of scribbles, and packed schedules. I don’t. I like to do my job, get things were done and sweat as little as possible. If I don’t overwork, I can focus on doing things better; if I optimize the outcome, I can do more with less effort.
We also value efficiency. Efficiency is about doing things in an optimal way, for example, doing it faster or at a lower cost. It could be wrong, but it was done optimally. I prefer to focus on being effective. Effectiveness is about doing the right task, completing activities and achieving goals. I value results more than the process of reaching them.
If the top of a mountain is the goal, many people enjoy hiking uphill, breathing fresh air, sweating, and romanticizing the effort of getting there. I would make friends with locals, so I can learn the most convenient way to get on top, and maybe catch a ride on a gondola.
It’s not about cutting corners, and it’s not about avoiding responsibilities. It’s about focusing on results and optimizing resources.
I have never worked for free in my life. And I have never worked for money in my life. It sounds like a contradiction, but it’s not. I worked for good money, little money and sometimes no money at all. But every time I had clear in mind why I was doing it. I knew I had no experience in many trades, and not being qualified meant that I could not be competitive or demand higher rates. The compensation I wanted went beyond money, and I made sure to identify the real motivation behind that job.
When I started as a software developer, I wanted to know what real work was. When I was sweeping floors in clubs for little money, I wanted to meet people and have fun. When I became a country manager, I wanted to prove to myself I could do it. When I moved to Vienna, I wanted to live abroad. When I joined Automattic, I wanted to contribute to one of the most significant cultural shifts of our generation: Free Software.
These motivators were stronger than money. I don’t care about money. Money’s important because it enables lifestyle. But that’s all. A lifestyle without motivation is boring.
In 2007, my blog was somewhat popular, with 1500 unique visitors a day and 20 to 25 people leaving comments on every post. I became friends with many readers. One of them is Livia, with whom I went all in for a crazy venture. We took an offer to be reporters at a new web channel called Intruders.TV, covering tech events and interviewing startup entrepreneurs.
There was no money on the table, and neither of us had ever produced videos before. All we were offered was a video camera, media passes to tech events all over the world, and access to anyone in the industry. We had to cover expenses ourselves, arrange our own travels, and do everything from filming to editing and publishing.
We took side jobs to pay for travel, slept in hostels and ate at McDonalds. Every conference had a party dinner, and I remember having one clean shirt in my bag – the only decent outfit of the week. We were meeting big names and wanted to impress.
We knew it was temporary and unsustainable in the long run, but it worked out for both of us. At a time when online videos weren’t as popular as they are now, we turned our unpaid gig into a portfolio of relationships that landed us great opportunities later on.
Within a few months, Livia was offered a job as community manager and TV host at Current TV, and now she is a manager at Twitter. She got the job because of her skills, but those skills were built over time and refined through solid connections.
When we attended conferences and recorded interviews, pictures were always needed for editorial content. I started taking my camera with me and each time had a hundred shots. I didn’t want to bother with copyright laws and such, so I grabbed the easiest licence– Creative Commons, attribution only. I didn’t care about chasing down how my pictures were distributed I only needed a few good shots to publish with our videos.
I quickly learned that event organizers were struggling with photo content because photographers were not good at covering tech events, rights management was a nightmare, and they wanted to monetize every picture.I sent event organizers the link to my Creative Commons galleries and made them happy.
After that, I began getting invitations to every event in the industry. I had already left Intruders.TV behind, and for a year I had free access to the top tech events and everyone who attended thanks to my contribution.
What would have happened if applied the classic “All Rights Reserved” that other photographers were using?
Have a clear goal, plan your resources, and identify needs. If assets don’t cost you anything, give them away. Help people, be useful, don’t be stingy.
If you had 10 gallons of milk that expire tomorrow, what would you do? Some would drink some, and try to sell the rest. Others would drink some and then throw it away. I would sip a little bit and give away the rest for free. Making friends and helping others is an investment in the future. You can go fast if you go alone, but you need others if you want to go far and have fun.
I like to get things done. Getting started is the key. I started many things I never completed, but “done” is different than “completed.” It took me years to understand and accept this concept: Done is better than perfect. We tend to believe that we need to finish what we start. No matter if conditions have changed, or if we have new data, or if it was a mistake.
This classic cognitive bias is called “sunk cost fallacy”: I already spent a thousand euros on this slot machine, I need to spend a hundred more. I’ll win at some point. No. The right attitude is: I already spent a thousand euros on this slot machine, experience tells me that a hundred more would be wasted.
I invested my whole self into a few jobs I had. I worked 18 hours a day for months, borrowed money from my family to pursue new ventures, dedicated everything I had to crazy adventures. But each time I had a reasonable amount of information telling me that the venture had no chance of reaching its goal, I walked away.
That’s why I don’t like gambling. Odds are against gamblers. I’d rather start a casino.
My three tips for building a career in any industry are simple: Take it easy, help others, and make things happen. Basics like water, food and shelter are sorted, so don’t stress. Be useful to others and help as much as you can. Don’t wait for things to happen, make them happen. I have always been lucky. Except there’s no such thing as luck. Be your own luck.