Is There A Tradeoff Between Freedom & Happiness?


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.

College in the 80's was certainly a happy time but that might be different now as young people have to weigh out what could potentially be decades of debt service. Twenty years of paying off a college degree with a payment the size of a mortgage doesn't sound like freedom (not an anti-college rant, this is a problem solve IMO) and a potential source of unhappiness.

So now as an adult, what is the answer? Of course there is no single answer right for everyone. In weighing out freedom and happiness, resiliency and optionality are also crucial concepts.

For my money and my life all of these things are intertwined. It isn't easy to have a positive attitude, to be truly positive and to understand gratitude. Having a true belief that things are going to work out or that some obstacle isn't so bad sets the table for both happiness and freedom. Knowing that you won't be derailed by an expensive car repair or home repair or not letting negatives from mundane things like choosing the wrong line at the grocery store get to you makes it much easier to be happy. Not getting derailed by paying for a new set of tires is a form of resiliency. Whether you get to this point naturally or by training yourself, the connection to freedom isn't that clear.

What are the building blocks of freedom, the context here is not living with societal oppression? Naval Ravikant has talked about people living below their means having unimaginable freedom (compared to people who live beyond their means). This obviously resonates with me, I've been saying that for many years.

Part of my motivation back in the early 2000's for working from home was not having a daily commute. Not sitting in traffic is a small freedom that is part of a more important concept of setting your own schedule. The ability to do this is likely a function of being self-employed, retired or being very wealthy.

Setting my own schedule is a HUGE priority for me, it is the epitome of freedom. If that resonates with you, do you think it is more important than financial freedom? It would be easy to argue both sides. Financial freedom does not require being truly wealthy, it can be achieved by living below your means. That's not to say it's easy, but it is simple to understand, when your lifestyle costs less than you make, there is freedom and optionality in that, everything becomes much easier. I can't prioritize one over the other (schedule versus living below your means), they were both priorities and evolved in conjunction with each other. If you have the freedom of owning your time and not having to worry about an unexpected $1000 expense would you not then generally be happier? Happiness and freedom overlap. After a couple of decades of living below your means and you'll probably have a good bit of money saved which may not be the top priority but it is still important in terms of freedom, optionality and resilience which all contribute to happiness.

Another form of freedom is freedom from what others think about you. There might be some limits here; I care what my wife thinks about everything, I care what my clients think about several things and I care what my colleagues at the fire department think about fire-related matters. Life becomes easier by letting go of the negative aspects here, like appearance, perceptions of wealth, maybe being a little geeky or whatever else you can think of. I am geeky about certain vehicle stuff and older baseball cards. I don't really spend money on these things but they are neat and I get poked a little fun at sometimes when I share on Facebook. Who cares if someone thinks you're goofy for something you are interested in (assumes no one reading this likes animal cruelty).

Taking ownership of your health checks off all relevant boxes. The statistics related to American's (metabolic) health are dreadful and trending worse. There is tremendous freedom to being able to do what you want to do (fun stuff) and what you have to do (occasionally you have to move something that is very heavy). There are financial benefits to being healthier, you are spending less money on healthcare.

When you have figured out your priorities, truly can maintain a positive outlook, have financial independence by living below your means, set your own schedule (I realize this won't resonate with everyone), stop caring what others think and have your health you certainly have a lot of freedom which I have to think would lead to happiness.

It might be difficult for people to define this stuff for themselves so easily but every aspect of life improves then they do. This is a worthwhile pursuit in how time is spent. It seems appropriate to close out with the quote from our friend Bill from here in Walker that I have shared many times before; you can figure it out now or you can figure it out later but you'll be much happier if you can figure it out now.