Know what I don't know

Over two years ago, I said farewell to LSE and embarked on the journey of a working adult. Immersing myself in excitement and the partial relief that my formal education was finally over, I looked forward to a life engineered under my total control. "Here comes my complete freedom", I thought to myself.

Little did I know the responsibilities and uncertainties associated with such privilege. Little did I know the time at university, which I tried to rush through as fast as I can to get to working life, was the easiest learning experience in my life. Little did I prepare for what comes my way when life is now at my sole discretion.

The most significant uncertainty that pushes many of the peers at my age toward a feeling of being lost in our 20s is the uncertainty of "not knowing what we don't know". At university, we were told of what we'd be learning, of our teachers and lectures, of the syllabus, of the assessment plans and exams, and of what we should and could expect. We were reassured of re-assessment in the case of mitigating circumstances such as illness or family tragedy. Real life is not quite the same. There is no such reassurance nor a guarantee of a second chance. More brutally, I don't know what I am supposed to be learning. I don't know who I should pursue to ask for their mentorship or teachership. I don't know of the "syllabus" of my life trajectory, nor do I know of the upcoming occasions for assessment. While I am most likely assessed every day by others in the exam of life, I have not much clue on what I should or could expect from it. I don't know what I am supposed to do next. While I want to be better, I don't know what I should be better in. I can learn anything but I can't learn everything.

My complete freedom translates to the fact that it is now all up to me (entirely) to figure out what's going to happen in my life herein and be fully responsible for it. There is no guidance from anyone or anything unless I actively seek for it. It's a journey that I'd embark on my own.

The major unknown is, therefore, "How am I supposed to know what I don't know?". How do I figure out what my life will be like when I have no clue what'd happen?

Just as many people who consider me as an example of someone who have "made it", I do similar things by by reading many biographies of more senior, successful figures who have had a "perfectly-plotted" life. All the events in their life seem to be unbelievably coherent and sequentially relevant to each other, that then lead to their eventual success. My mind became puzzled behind the pages. "How did they know back then that they should form close ties with this particular person? How did they know back then that they should take this lower-pay job over the other offer? How did they know back then that they should move to a different country? How did they know what they supposedly didn't know?" . Omitting the selection/survivor bias and the fact that probably only the stories of their success surface but not failures, I am still unsure of how these people seem to have carried themselves through the storm of such uncertainty. To decide what they should learn, who they should know, what they should do and where they should be, is a discretion that puzzled me.

I am still in searches for the answers to how to "know what I don't know.", however, I have distilled the following temporary conclusion to satisfy my hunger.

My observation is that they don't know what they don't know. Period. No one knows.

When people re-told their recollections of what they did to get to where they are, there is a tendency to rationalise many decisions, thoughts, feelings and actions into a coherent stream of pre-determined discretion and calculated risks. What indeed happened at the moment maybe otherwise. The universal truth is: no one knows what they don't know. However, every person's approach to handling uncertainty is different, because their ability to estimate risks, imagine the future and take actions differs. The people who actively tackle the unknowns have a hypothesis of the future and a view of what will happen. They then pursue actions and thoughts that are consistent with this hypothesis to make their imagination happen. Sometimes their hypothesis is correct; sometimes it isn't. When it is, and the success stories surface, other people like me are in awe with questions such as "How would you know?"

They didn't know. They only envision what their future will look like, and they then make it happen.

In the book "Principles" by Ray Dalio - the founder of Bridgewater Associates, he described a similar approach for a person to get what they want out of life:

Those who are the most successful are capable of “higher level thinking” —i.e., they are able to step back and design a “machine” consisting of the right people doing the right things to get what they want. They are able to assess and improve how their “machine” works by comparing the outcomes that the machine is producing with their goals. Schematically, the process is as shown in the diagram below. It is a feedback loop.
That schematic is meant to convey that your goals will determine the “machine” that you create to achieve them; that machine will produce outcomes that you should compare with your goals to judge how your machine is working. Your “machine” will consist of the design and people you choose to achieve the goals. 

According to Dalio, this machine will take a lot of iterations and practice to get right. There will be many hypotheses, or different versions of my imagination of my future, that I will need to test with my "machine". Some hypotheses will be correct; some other will be complete failures. It, however, doesn't matter how many tries I may need, as Mark Cuban said, "You only need to be right once. Then everyone can tell you how lucky you are."

From reading this piece, I have come to reassured myself that no one knows what they don't, and it's perfectly reasonable not to have a clear idea about the future. However, it is important to keep having a hypothesis of what my future looks like and take actions to make that future happen according to the machines that I design.

"I don't know" is a good answer. "I don't know, but I'd find out", is a better answer.

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The book Principles by Ray Dalio used to be a must-read for all Bridgewater Associate new-hires. It has recently been released to the public to read online for free at https://www.principles.com/ . Alternatively, you can download the free PDF of the book below.
Illustration: Fernand Khnopff (Belgian, 1858 - 1921), Jeanne Kéfer, Belgian, 1885, Oil on canvas.
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