Rolling Reflections 26

Continuing to get lost down the rabbit hole of Nassir Taleb. Uncertain if this is a good thing, as I generally agree with many of the core concepts. While working through these books I find them part motivating and part discouraging. It makes me proud that I’m working in a system where I have more autonomy, but makes me feel like shit for not doing more and being more independent. The main theme of this week is the importance of having a plan and sticking to it. Figure out who you want to be and work towards that goal. Put another way – figure out who you don’t want to be and plan your life against what that type of person would do. 

Source: Skin in the Game

Lesson: Don’t be an IYI (intellectual yet idiot)

Reflection: The IYI is the person who is not in the arena. They take no risks. They are the employee or company man. They become slave to dogma and are spiritually dead. The question that I have is do you always need to have this personality, or do you need to be a slave and pay for your freedom. Ie Unless you are born into wealth you need to make money to sustain you life. This comes down to living below your means, Mr. Money Mustache, or you give up all materialism, become a beggar monk. I think the goal is the ability to pursue your passion. At the same time, part of this is just continuing to be a person of action. This has been a personal philosophy, but I also am not ready to abandon institutions. I think that there can be benefit of the collective, it’s just knowing that there is risk involved in those pursuits – people taking advantage of power and organization. 

Source: Interactions with a salesman

Lesson: Trust but verify

Reflection: I think part of this came from Howard Mark’s book the most important thing. He talked about how people want to make you feel like you will be losing out and that you’re missing something. The hard part is the recognition that the person you’re speaking with is trying to sell you their services. They do this by making you doubt your plan or by making you feel inadequate. That they are the only person that can help you achieve your goals. I do think there’s a benefit in being a do it yourself person in most contexts, but again it gets into the trade off of what’s worth your time. 

Source: The Most Important Thing

Lesson: Lose less in the bad times, Make the same in the good times

Reflection: When it comes to investing if you want to beat the market over time, you can do so by not losing as much when things go south and making the same in the good times. My problem is I don’t know how to play this defensive investment game. While the concept seems reasonable. I’m not sure how this translates into practical investing. Part of it would be to evaluate when products are becoming hyper inflated, but you need a system to do so. I think my solution to this problem is to continue with indexed investing. I understand that indexed investing on it’s own contributes to the problem of creating opportunities and making the market inefficient, unless you’re using a total stock market index fund. To date, I don’t have the knowledge on option investing. 

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