THIS POST IS STILL IN PROGRESS
In Part 1 I delved into my earlier life, childhood, family, and first part of my working life after university. I showed you how that piqued my interest, and gave me experience, in Real Estate and hospitality.
At the end, I summed up the last 10 years in a few sentences. Not because they weren’t important or interesting, they just played a very different role in forming my thoughts and perspectives.
Luxury Life & MBA
During my time in Italy, doing my MBA, I went through a number of emotions and was feeling pretty torn.
Coming from my time at Trilogy and Opus, I had been enjoying the life of luxury goods and design, top notch food, and general service of the rich and famous. So I chose to specialize in luxury business management while at SDA Bocconi in Milan, Rome, and Switzerland. All the other students I was studying with were in a similar boat, brands and high snobiety were the priority and focus. That kind of life can be quite intoxicating.
At the same time, my then girlfriend and I were on the rocks and that relationship eventually fell apart. I was also lost about what I wanted to do after my studies were over. This is when I first got exposed to meditation. I’m not really sure how, probably a podcast, but remember this was 2014, meditation wasn’t really “in” just yet.
It was a strange dichotomy, sitting in silence, listening to my own thoughts in one minute, then donning my brand-name attire and heading out to some fancy restaurant or club the next.
Anyone who has taken up meditation likely knows that it’s not a quick fix pill. You don’t sit for ten minutes and suddenly have a moment of clarity and all your questions and uncertainty dissolve. At first, and for a long time, absolutely nothing happens, other than you just spend 10 or 20 minutes lost in your own thoughts trying to remind yourself to “follow the breath”.
Anyway, meditation didn’t fix my problems then, but the seed had been planted. On the inside, I knew I had to look deeper than just the label on my blazer. But I’d continue being distracted for another 10 years. Thankfully not without benefit.
Lotti & The Great Outdoors
Being in Germany was both fun and difficult at the same time. On the work side, my uncle gave me a lot of freedom and trust and that allowed us to work well together while I spun up our Canadian division. That also made it possible to visit my parents and friends in Vancouver from time to time.
On the personal side, life was not so great. I was still stuck in the past getting over my ex, while having no friends around me, and missing my people in Canada. I was lonely.
Then 2019 brought two major changes.
First, I met my wife, Lotti. And not much later that year, I started working at The Orchard in a tech role as a Product Manager.
The Orchard wouldn’t have a big impact on my life just yet, but it did mean I was now working with teams in England and the US, so although I was in an office in Germany, I was interacting in my own language. Working effectively “remote” would become important later.
With Lotti, at first, I was very skeptical. This woman was my complete opposite. Our first date was in a low-brow chain cafe where she ordered a Rotweinschorle (red-wine with sparkling water) 🤢 Without realizing it, she had reinvented a German tasteless version of Lambrusco. My Italian ancestors were turning in their graves while my “luxury” MBA colleagues would have spat their Barolo on their Fendi overcoats.
Lotti didn’t care about brands and fashion, she cared about time spent with her friends and time spent outdoors. And as we spent more time together, I also began asking myself what was important. Don’t get me wrong, nothing changed immediately, and I still like nice things, they just don’t matter as much anymore to my views on happiness.
2019 was pretty “normal” but the first signs of change came in the form of my decision to surprise Lotti while she was guiding a hiking trip in Austria. I like to travel a fair bit, but this was my first foray into the great outdoors since, well, a long time. I even had to buy hiking boots and a backpack.
Then, as we all know, in early 2020 a thing called “Covid” happened and that remote work thing I was doing became the new normal. By the time autumn came, like many others, Lotti and I were feeling suffocated with lockdown in our small apartment and other restrictions, we needed to get away. So we took a vacation to Slovenia. Lotti planned it and it was another outdoor adventure including another pin in the “Dino learns not to need fancy things” cap. Lotti not only booked a tent for us to sleep in for a few nights (Dino learns that you don’t die from going outside to get to the toilet), but she also thought it would be a good idea to take a bus back to Hamburg (Dino learns he also has limits and 24 hours in a bus, with a mask on, is that limit).
The Slovenia trip was great, so much so that later in the year, we decided to get away again and took a vacation to Greece. This was the trip that triggered new ideas for us both. Not only did we feel safer being outdoors and around fewer people, but it dawned on us that we could work from these beautiful locations too!
This idea didn’t come to fruition right away, but a few months later we decided to try it for the first time. My uncle had a small apartment in Portugal that was currently empty due to Covid, so we took the “friends and family deal” and worked from there for 3 weeks. It was as good as we could have wished for. We were getting up early without an alarm so we could go for a run on the beach or swim in the ocean before work began, going for a cliffside walk or hike on the weekends, and then having dinner on our balcony overlooking the waves in the evening. It was exactly what we needed.
We had been looking for a bigger place for a while and when we got back from Portugal we found and bought a small house about 30 minutes outside the city. This time Lotti was skeptical, she saw investing so much money in a long term financial commitment as restrictive. I insisted that it would give us even more flexibility, and only a few months later my theory was proven out. It was the perfect storm. On one side we wanted to travel again, on the other I needed to show Lotti that it made financial sense to own a home. So I agreed to let fate decide. We would put our house on AirBnB with a 3 month open window, and min 2 week stay. Whatever period someone booked, that would determine how long we worked elsewhere. The first inquiry sealed the deal, they wanted it for the full 3 months.
That was it, it kicked off a new era. Whenever we needed to go somewhere, someone’s birthday, a wedding, a family visit, we’d extend the trip, rent out our house, and experience something new. Work during the day, hike or explore on weekends, learn how to filet and cook fresh fish, watch the sunrise and set, soak up the sunshine. Between 2020 and 2023 we travelled to
- Canada Jan 2020
- Slovenia Aug 2020
- Greece Nov 2020
- Portugal May 2021
- Italy Sep 2021
- Portugal Mainland & Madeira Jan-May 2022
- Italy Aug 2022
- Mexico Nov 2022
- Canada Jan-Feb 2023
- Sardinia March 2023
- South Africa May 2023
- Italy June-July 2023
- Latvia September 2023
- Portugal November-Dec 2023