Exponential returns from self-awareness

I recently had to shut down the startup I founded two years ago and also went through a big change in my personal life which led me to reflect and understand my journey with a lot more depth. I initially took a look back at the last few years and why things turned out the way they did. Doing that, I realized looking only at the previous few years was not enough. I then dug deeper into the past and discovered patterns in different stages of my life.

The first part of my life was all about starting to look and act like an adult. The part that followed after that was all about exploring myself as an individual and trying to figure out what I value, desire, and enjoy. The part that I am transitioning into now is focused on doubling down on the things that I love, am good at, and how I want to be remembered as an individual.

I grew up in a small nordic country mostly spending my childhood amongst myself. I spent a lot of time around my grandparents because they clearly had more time to put up with my endless curiosity and energy. My grandparents were amazing people who showed their love and support at every moment, but by and large, let me explore the wonder of life by myself. I ended up spending a lot of time alone playing around in the woods or with different electronics that my grandfather had. I was allowed to try out almost anything and it was rare that my grandfather tried to stop me from failing. I remember an occasion when I tried to recharge the car battery myself and I ended up killing the battery since I tried to charge it with 240V instead of 12V. I was obviously ashamed to kill the battery of my grandfather’s Lada, but such lessons strengthened my curiosity and gave me more confidence to try out anything.

Another part of my childhood that shaped me very strongly as a person was how my parents shared their love and affection with me. I grew up in a typical Estonian family where physical touch and words of affirmation are seldom to come by. On the other hand, small acts of service and activities together were always an important part of our family life. I had not thought about this aspect of my childhood a lot until I had a conversation with my partner about why it is that my dominant love language is acts of service. Funnily enough, the same holds true also today. My parents still show their affection by always being there when I go home. That might literally be picking me up from the airport or getting my favorite food to make me immediately feel at home.

The last part that stood out from my childhood was people being treated like an adult. I was always included in the planning of things and was asked to help with all the chores from a very early age on. That could have meant helping carry food home from the market or always washing the dishes. Weirdly enough, I developed a strong appreciation for washing dishes as a child. It always felt like an easy way to help out my grandparents after cooking and it has stuck with me to this day. I often still do the dishes by hand, even though I have a dishwasher. Go figure… Another part that is related to responsibility was also my parents trusting me with tasks that were not trivial. I remember my grandfather letting me switch gears on a two-hour car ride from Sillamäe to Tallinn just because I was so curious to learn how to change gears. The same kind of trust also carried over to my school years where I was never asked to show my grades. I was just trusted to take care of it and in a weird way, it actually motivated me to push even harder at school to excel. When you are trusted with something, you are very likely to do your best not to screw it up.

It is always a smooth continuum but it’s quite clear which motivations dominate the action in each part of life. The second part between the teenage years and the end of the twenties can be characterized by trying out a ton of stuff and seeing what sticks. It applies to both careers and personal relationships. Neither are linear learning curves where you can make steady progress. Using an analogy from machine learning, this part of learning is similar to gradient descent with a very steep learning rate to avoid getting stuck in local optima. I am sure many people do get stuck in local optima who do not take enough risk and experiment enough with a wide range of topics. This also seems to be the main reason why so many people experience personal crises realizing they have been climbing a path that is not making them happy.

2D graph showing the difference between reaching global vs local maxima

For me personally, both my school and university time was a time of great professional exploration. I was always someone endlessly curious and choosing a professional path was challenging for me. There were so many things that were exciting and I could have imagined picking up many different professions. In high school, instead of doubling down on one subject and excelling at it, I decided to try to compete in competitions in pretty much every subject that I had. I remember taking part in 11 different olympiads in the 11th grade, which was clearly an overkill but helped me push my curiosity in many different directions. The same applied to choosing a university. Since I was not sure where I wanted to study next, I decided to apply to every university which sounded exciting. I ended up applying to a total of 20 or so universities in every part of the world. It was honestly a total coincidence that I ended up at Imperial studying computer science. I was very close to choosing mathematics at NYU or applied mathematics at the University of Singapore. Looking back at that choice, university selection definitely has a huge impact on the rest of our lives, but perhaps not in obvious ways. It is much more likely that I would still live in the US had I decided to study there, but I am not sure whether that life path would have made me any happier than the one I took. The same applies to what we choose to study. I am very glad that I ended up studying computer science. It definitely worked as a badge of technical capabilities, but I am rather sure I would have ended up having an awesome career also had I studied political science or philosophy.

Having said that your field of study does not affect your professional outcome much, it is rather important what type of people you surround yourself with. That applies especially during university and work. It is important to surround yourself with people who are curious and ambitious. I noticed that while studying at Imperial I was surrounded by people who were very driven, but all in the same direction. Everyone wanted to achieve the exact same outcome. Most of my coursemates saw being a senior engineer at Google as their ultimate professional goal. It also affected me and even though my gut feeling told me that this would not be my dream, the social pressure around me made me at least want to try out working at such prestigious companies. I tried working at an investment bank and I tried working at Google and only after having gotten this experience did I realize that this is not my dream. I don’t regret having tried those things, but I do realize looking back how strongly we are affected by the ambition of the people around us. I am sure that had I studied at Stanford, I would have been much more likely to stumble upon startups faster. To summarize, be aware of what people around you look up to. You might value the exact same things, but it should be a conscious choice, not just a mimetic desire.

Even though our professional desires change during our careers, there are things that become more clear as we have more work experience. After finishing my master's studies at ETH Zurich, I worked at five different companies, ranging from sizes of 10 to hundreds of thousands of employees in a number of different industries. What I had not tried out was starting my own company. So I started a company called Mirage straight after graduating. I started the company with one of my colleagues from my research lab and we were convinced that we wanted to get on the machine learning hype and build something in this space. Looking back, it was a bad idea to start a company for the sake of starting a company, but it did teach me two important lessons. I was very happy being a founder and having responsibility and control over my work environment. I also learned that I don’t really enjoy working on deep tech products where most of the work is in research and not really visible to the end user. That led me to found Acapela, which was much more user-facing and where the key differentiating factor was UX and the product, not the tech.

During the two years that I spent working on redefining what asynchronous collaboration should look like, I realized that I enjoy doing design work much more than engineering work. I started the company as the technical founder and spent the first few months mostly building and hiring. It was quite clear to me that I did not enjoy spending most of the day coding. Speaking to users and iterating with potential UX solutions came much easier for me. As the technical team grew and I mostly moved to a management role, I started to enjoy the product work even more. Jamming about potential feature implementations and UI details with engineers was a lot more fun than the actual implementation. It took us a very long time to find a solid designer, which forced me to spend more and more time on the actual UI of the product. It was definitely also possible because we had a very senior and independent engineering team, which I am very proud of. Over time I ended up spending more and more time working on UX and UI as opposed to technical discussions. I would have never considered myself a designer before (and I still don’t), but I grew to love the actual hands-on work so much that I naturally gravitated towards going into the details of design and being more high-level in engineering discussions. This is perhaps just to prove the point that despite having studied and practiced engineering, I discovered that I like working on products and design even more. This helped me understand even better how much I care about building the best product and also how much fulfillment I get for being recognized for building stunning and delightful products. This will have a big impact on what I will also build next.

I now feel like I am getting much closer to the third stage of life, where I have a higher confidence about which “hill” to capture both personally and professionally. The definition of a hill in the career sense here can be rather vague, but for myself, I have figured out that the rough criteria are:

  1. Working in a high-growth technology company

  2. Work in a product-focused role combining design, product, and engineering

  3. Have a highly independent role which allows me to alter the product roadmap and company culture

  4. Being surrounded by people I admire and can form close relationships with

  5. Building a product where UX is a key selling point

  6. A work environment that combines both remote and in-person work

In addition to having some quite set criteria, there are also lots of points where my level of confidence is much lower but I still have some gut feeling about what those things could be. For example:

You might have noticed that the points in the second category (low confidence level) can be opposed to each other. That’s why they are low confidence ;)

The same principle should be applied also to other areas of life besides career choices. For example, for me, it holds true very much for where I want to live. I have lived in a bunch of different cities in the last 10 years and have gained a rather high level of confidence about which aspects of a living environment are most important to me personally. For example:

  1. Have at least a few best friends living close to me (ideally within walking distance). That can obviously be built up in any city but is vital to me for happiness.

  2. Have a high density of people around me that are ambitious and optimistic about the future. That strongly helps with finding friends but also being inspired by others around me.

  3. Have plenty of sunlight throughout the year. I am definitely a climate refugee (originally from Estonia) and have realized that having sunlight even on a cold day just makes me a much happier person.

  4. Be close to a body of water and ideally mountains. The older I get, the more I realize how important living close to water is for me. I am also a big hiker so having mountains close by is a huge plus for me.

  5. There should be a wide variety of restaurants in the city that are at least somewhat authentic and also affordable so that I could visit them often with anyone I meet.

  6. The local population should be somewhat tolerant of foreigners. I have always done the best I can to blend into the culture where I live, but in certain countries, it’s almost impossible to become “one of them” even despite your best efforts.

  7. The local laws and values should put a high emphasis on tolerance, liberty, and progress. This perhaps covers some of the previous points, but there are clear examples where the local population is tolerant and progressive despite local politics (Berlin is a good example).

I have not found a place that would tick all of those boxes and usually, every location comes with strong trade-offs in at least one of those areas. So far in my travels, I can identify with and feel most at home in three locations where I have previously lived: Tallinn, Berlin, and Zurich. I am sure other candidates might fit the bill where I have not permanently lived yet (for example SF or Cape Town) but I have already found three strong candidates that make me feel very secure.

The same principles should also be applied in relationships. The older I get the more picky I become about which people I want to surround myself with. There is no good reason to do one business deal with someone who you would not want to do business with for the rest of your career. I also want to make friends who I believe at least in the moment that I would love to be friends with for the rest of my life. With more social experience it is also easier to rely on your gut feeling about people you meet - if you feel like something is off, then you can be rather sure that there is a good reason for that.

The biggest gains come from long-term commitments in every area of life: relationships, business, and skills. The third stage of my life is all about commitment and doubling down on the things that I love, value, and am potentially good at. That does not mean that there is no more room for exploration - just the space for exploration becomes more limited as we gain more confidence in ourselves.

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