Is There A Tradeoff Between Freedom & Happiness In Investing?

When you figure this out, the rest all falls into place.

In the last couple of days I've seen several Tweets that addressed the relationship between happiness and freedom. Is one more important than the other, does one come at the expense of another, do you achieve one before the other, should you pursue one of them first, are the related and if so how much overlap is there?

I have been writing about the investment implications of this for years. Understanding yourself well enough to realize what your actual priorities are and then saving and investing toward that outcome versus thinking you need a Ferrari and the lifestyle that you might associate with having a Ferrari makes life easier. Figuring yourself out is not easy and however old you are, you know people your age who haven't done it yet.

The start of this conversation came from a Tweet by Jaffer Ali who asked which one is better, freedom or happiness. He thinks freedom. Coincidentally, an old Tweet from Shane Parrish appeared in my feed and he said;

Happiness generally isn't about making more money, but rather freedom. The freedom to say no to things you don't want to do. The freedom to say no to people you don't like. The freedom to not feel like you are obligated to say "yes." Freedom is saying yes when you want to.

He seems to believe that they are related with freedom leading to happiness.

In trying to pull my thoughts together, it seems that happiness and freedom mean different things at different stages of life. As a child what made you happy and did you even understand freedom? Hopefully, children are free of worry from things like a roof over their heads or having enough food (I realize that is not the case for many children), ideally, for children happiness is simply having far more happy moments without any further thought.

What about as a teenager and into college? This is often a make or break time where young people might go down an unhappy path be it due to circumstances just as a function of how they are made up. What is freedom at this age? Free to choose their appearance or having flexibility with how late they stay out? When I was in high school I worked at a sporting goods store and remember feeling rich because I had way more money in my pocket than I would have had just getting an allowance. This lead to the freedom to do things and buy things. I think I was happy back then and while of course some kids were not happy, I think I observed more were than were not.

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