This year I want to start a new tradition: write a retrospective where I look back and reflect on what worked and what didn't in the past year. It won't include a resolutions list, as I am convinced that systems, not goals, drive long-term results.
2019 was the year I went indie and founded my own company together with my friend Fabrizio, it was a year of travel (almost 6 months away from home) with my first ever trip to digital nomad hotspot Bali. There were so many changes both professionally and personally that it almost felt like a decade.
January–March: Self-employment, Boxy Suite & Unreadit
These first 3 months were all about getting used to the new lifestyle of working for myself, finding a rhythm, and deciding what to do with my time. Back then it felt almost obvious what to do, without much reasoning or planning, with the huge backlog we had built after grinding on Boxy Suite for 6m while having a full-time job. We trimmed the backlog and released a big update, then started working on another project, launched soon thereafter, Unreadit.
The launches went great, but looking back on things, we struggled with growth. This is a recurring problem for us and something we are trying to improve with Mailbrew (our current project), by building a growth engine right inside the product.
Getting adapted to the new lifestyle was harder than expected. Turns out having an office with peers where you go every day is a huge perk of a "classic" job. This is something I am still struggling with as of this writing and something I want to work on in 2020.
This was counterbalanced by the extreme flexibility I gained, both professionally and personally. Being able to get up in the morning and work on my projects felt truly amazing, and still does to some extent (but 1y later edonic adaptation is kicking in). I also finally had the time to focus on fitness: the perfect time to train for me is mid-morning, something I couldn't easily accommodate before. I want to keep this up in 2020.
March–April: Discovering Southeast Asia
I had almost found an equilibrium but comes March it was time to pack my bags for the trip of a lifetime: 1.5 weeks in Vietnam 🇻🇳 (Phu Quoc and Saigon), then 3 days in Malaysia 🇲🇾 (Kuala Lumpur), 3 weeks in Indonesia 🇮🇩 (Bali) and a weekend in Singapore 🇸🇬.
This trip was all about exploring and boy did we explore! It was a ton of fun, but by the end of it we had a bit of travel fatigue and we didn't get much done business-wise. We learned a lesson for the next trips: stop more in each place to get to know it better to be able to do meaningful work there. If you stop too little it feels more like a classic vacation than nomading, you are pressured to constantly explore because you don't have much time and focusing on work becomes harder.
On a personal level, traveling this much, was eye-opening. Getting away from your usual environment and comfort zone can do wonders to uncover your unresolved issues and shed light on your life back at home.
May-July: Boxy Suite 2 & Porto Retreat
Back at home, we started working on Boxy Suite 2, an ambitious upgrade to our suite of Mac apps for G Suite. The update was well-received and solved many stability issues that made us sleep better at night.
We also tried doing some consulting work. It helped us financially, but was a huge hit to our morale. We felt lost as what we were doing went against the very reasons we decided to quit our jobs. Once the project was closed, we decided to stop all consulting efforts going forward.
We also had another trip, this time to Portugal (Porto) 🇵🇹 for ~3 weeks in July. It was great, living in a big city I feel the need to go away every few months to recharge. Business-wise we tried a few marketing stunts without much success. One year in, it is clearer than ever that there are no shortcuts/hacks and that you need to put in the effort in to understand and solve your users' problems.
By this time it was also clear that we needed a much more structured way to organize our work and decide what to work on next. The Shape Up methodology by Basecamp come at the exact right time, this is what we are using now, with some adaptations for small teams. The takeaway here is that we should have been much more mindful of what to work on. Looking back, it almost feels like we were on autopilot for the first few months. It feels obvious now that you can't spend most of your time doing maintenance work, small projects, and marketing stunts. You need to carve out big chunks of uninterrupted time to do meaningful work and take on big efforts.
September-October: Boxy Suite renewals, Unreadit 2
This time of year was psychologically nerve-wracking. We sell Boxy Suite with a yearly subscription and the first renewals were about to occur, so we asked ourselves which percentage of our users would renew and if we would be able to make our business sustainable. Turns out everything was fine and we shouldn't have stressed so much about it.
There was some pushback on the recent lack of updates to the products, but I feel like we have things under control as long as we ship something great in early 2020.
Why the lack of upgrades? We handle many projects and it's not easy deciding which one to focus on. Shipping Unreadit 2 took us some weeks, as the update was focused on automating many of the newsletters to free us up to do more things. We decided to keep editing the most valuable newsletters and automate the others with another service we are building.
This service is Mailbrew, you may have heard of it since I can't stop talking about it.
November–December: Bali (again) and Mailbrew
Come November, we traveled back to Bali for one month and a half, uninterrupted. This time it was much less about exploring and more about enjoying ourselves and getting shit done. Having your house, laundry and food taken care of and being on a different timezone can do wonders for your productivity!
6h from landing we had unpacked at our Villa, already had scooters for \$2/day and were looking for a coworking. Much of the overhead of the first time was gone, we knew what to do and we did it fast. We picked the right coworking for getting shit done (not that other one that's good for socializing) and established a routine that allowed us to focus.
By the end of the Bali trip, we had a working version of Mailbrew already in the hands of ~80 people in private alpha.
Early feedback has been great. The next step will be to test monet ization in early 2020. Once we feel the pricing and value proposition are tuned just right, we will launch the product to the public. That's our plan.
Another interesting thing about Mailbrew that I think is worth sharing is the approach we used in building it. We built it slowly, pondering every small decision, and onboarding users one by one with dedicated calls to gather first-hand feedback. This has been incredibly effective in building a great product. I think we stepped up our product game with this one, but you will be the judge once we release it.
With the year closing, Mailbrew seems like our most ambitious project to date, potentially our big break for 2020, and I can't wait to show it to the world.
2019 has been a year of change, of exploration and learning. Sitting here at the end of it, I hope for 2020 to be the year where I capitalize on all these learnings to improve my life and my business further.