Evolving “career” thoughts

My priority has been “Learn first, earn after”. Ideally the work should be about a cause that I care about, that I can make a contribution to. I am very very fortunate to not have to worry too much about money (yet), which frees me to think and test what I want to do.

At the end of last summer, I came up with a few conclusion about where I want to head next.

In terms of learning, I knew that the startup environment can offer me the most. It also has youthful and idealistic energy that resonates with a part of me. There people learn fast, because they have to and more importantly they want to. That’s where most innovation happens because it is the norm. At some points youthful enthusiasm yields in to stability, but as of now I know I want to be surrounded with that kind of spirit of learning and contributing.

On the other hand, I also know that we learn much faster with good mentors, which I think happens often at a more established organization. There are mentors for startup of course, but they very much serve as advisor rather than someone we can shadow. To learn, we need to both observe and practice. If I can see the day to day working of someone else I can learn a lot. People say “You won’t really learn something until you actually do it”. True, and you will learn even more by observing someone really good and then doing it yourself. Eventually we all have to climb our own mountains, but learning how to climbs with good form from the beginning can save us much trouble further down the road and thus allow us to go much further. Having good teacher is important.

Here is what I am thinking in the moment. Whenever I experience a contradiction in what I want, I try to tell myself: how can I do both? Call it ambitious or greedy or whatever (I call it “aspirational”) Work is a big part of life, and since my theme of this year is “Integration” I’d need to be more thoughtful about it.

The term “startup” doesn’t have to be a new company. Any initiative or project that involves people can be considered one. I am working on an initiative that involves a lot of people, on a cause that I care about and with people who are willing to guide me. I remind myself daily how it seems to be such a blessing.

Some lessons in life are unpredictable, but many can be planned. I learned from Gary Bolles his model of the three domains of skill: knowledge, transferable skill and self-management. For knowledge, I’m trusting that domain knowledge is becoming less relevant than making novels connections across domains. I love theories, so much so that I’d rather apply theories to the wrong context than not apply them at all.

Transferable skills can be broadly categorized into three categories: data, people and things. Here are the most valuable and also difficult tasks to do with each.

  • Data: Synthesize.
    – How to test: Able to explain a complex set of data to someone else.
  • People: Mentor
    – How to test: The mentees are able to surprise us with the quality of their work.
  • Thing: Set up / design
    – How to test: well-designed things are used they should pleasantly surprised both users and creators.

Self-management is a whole other set of skills. Know ourselves: how we work, perform, communicate. Gather and interpret data systematically. Hone our intuition and trust it in the most unpredictable circumstance. Be our best ally as well as our fairest critic. Develop the attitude of not taking ourselves seriously but our work very seriously. Last and perhaps the most important one: ask the right questions – questions that invigorates instead of debilitates us.

It is quite a helpful model to guide my thinking. I’m pretty on track with many of these, and I’m quite happy. I know I will learn a lot and appreciate the journey along the way. Something difficult will eventually happen, and I want it to be struggle together than struggle with each other.

What is my long term plan? If I wanted to stay in America in the next five years, it may be safer to go on an established path like working at a bigger company or going to grad school? I don’t know, and I don’t think it matters as much. What is more important is learning to position myself in places where opportunities confluence, where I can be used well to make good contribution.

One of my mentors once asked me: “Are some young people really wise or they only say things that make them seem wise?” I really don’t know. I think this roadmap I’m writing makes sense. Following it is another story. As of now I think I’m sticking to it fairly well. Another thing that I learned is that I now really understand the importance of “start with the end in mind”, not only in terms of external goals but more of internal state. I’m already imagining the end of the summer: I will feel fulfilled, joyful, touched, loving, thankful, learned, wiser, ready, confident, If I can feel like that most days then I’m doing great.

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