An evolving road map on “career”

Now the road may looks curvy, yet the in a while it maybe straight. We never really know, but we can plan to embrace it. (photo credit of unsplash.com)

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 wanted 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. There is 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 want to be more intentional about it.

The term “startup” doesn’t have to be a new company. Any initiative or project that involves a group of people can be considered one into which we can bring many of the startup spirit and practices. I am working on an initiative — People-Centered Internet — that involves a lot of people, on a cause that I care about and with people who are willing to guide me. I told myself that people were more important, because relationship is the soil on which good work can grow.

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 have to do with three broad categories: data, people and things. Here are the most valuable and also difficult skills for each.

  • Data: Synthesize.
    – How to test: Able to explain a complex set of data or ideas to someone else.
  • People: Mentor
    – How to test: The people we guide can surprise us and even themselves with the quality of their work.
  • Thing: Set up / design
    – How to test: when well-designed things are used they should pleasantly surprise both users and creators.

Self-management is a whole other set of skills. Know ourselves: how we work, perform, communicate. Gather and reasons data about ourselves and the environments 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 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 if my heart was to be broken I want it to come from struggling together than struggling 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. 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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