Modern Trades: Freedom for Clarity

“Nothing is more wonderful than the art of being free, but nothing is harder to learn how to use than freedom.”

– Alexis de Tocqueville, Democracy in America

The Trade: Freedom in exchange for clarity

If you feel like you don’t know what to do with your life and feel that existential ambiguity that makes you consider moving to Thailand to live on the beach for a year, it may be because you have too much freedom.

In modern Western societies, we have an unprecedented amount of freedom to do what we want with our lives. Not only do we have it, it is embedded into our culture. It’s assumed that individuals will build the lives they want for themselves and will be able to independently determine what will make them fulfilled.

But nothing comes free, even freedom. We had to trade something. In this case, we traded away our clarity.

If you were born in Medieval Europe, or really anywhere at any time pre-Enlightenment and especially pre-Industrial revolution, you wouldn’t have many options for the role you chose to play in society.

You were a peasant or serf or maybe a nobleman or tradesman and were, for all intents and purposes, stuck in those roles.

But being stuck came with clear expectations and a roadmap for your life, however grim. You weren’t left wondering what you would do with your life. Your life was your life and you made the best with what you got.

Today, we can decide where to live, who to date, what jobs to take, where to go on vacation, how many children to have, and of course, which jar of spaghetti sauce to pair with your choice of pasta.

And it can paralyze you.

But souls abhor a vacuum, and that is the root of this modern trap.

The trap: We misuse our freedom

When you have unlimited freedom, you can choose many paths that won’t get you to where you want to go.

If you grew up as a middle class American, the guidance you received probably ended with go to college and get a good job.

So you end up in a job in a city somewhere, make a few friends, go on a few dates, and yet you still feel a bit…flat…empty…and lost.

And that’s where the trap starts.

This is where you begin to look to culture for guidance and most of the advice sucks.

Hence I do not find in myself the power to be happy merely by doing what I like. On the contrary, if I do nothing except what pleases my own fancy I will be miserable almost all the time. This would never be so if my will had not been created to use its own freedom in the love of others.

– Thomas Merton, No Man is an Island

In my own life I tried to follow the path of Tim Ferriss’ 4 Hour Work Week to find fulfillment. It didn’t work. I’ve tried traveling to fill my live with novelty. Fun, but not satisfactory. I started working for myself and earned more money, but I’m still waiting for that “dream career.”

The primary weakness of all these paths is that I only made commitments to my own desires, and by their nature, commitments to yourself are easy to get out of.

The game: Return (some of) your freedom

The non-obvious solution to the problem of having too much freedom is to give some of it back.

I don’t mean we need to give up civil liberties and return to feudal times.

But it’s worth binding ourselves to commitments that are a) difficult to get out of and b) not 100% selfish.

This can take many forms and this is where you get to take advantage of that freedom.

Starting a family is an ancient and primal example of a commitment that is non-selfish and almost impossible to get out of. I will say in my own life this has probably been the most fulfilling commitment I’ve made and it required that I give up some freedom.

Another potential path is to take a leadership role in a community, preferably not online. If you open a small business in a town that employees locals or run a volunteer organization that a community depends on, you will most certainly not be able to take off to Thailand. You give up some of that flexibility.  But I’d be surprised if your soul didn’t appreciate it.

Erica and I are on our journey to find ways to exchange some of our freedom for meaningful commitments. This may involve a move to Oregon to be closer to her family. I personally think it would be fun to find a smaller town where we could start a business of some sort.

Really, we just want to copy Joanna Gaines but in Oregon.

So there you go, find ways to give your freedom and make commitments; be like Joanna.


I would never want to turn back time and trade our freedom back. It’s a clear sign of progress that more people now have the privilege of being able to choose how to live their lives.

But this freedom comes with traps. The ambiguity of almost complete freedom can create deep existential anxiety about what exactly it is you’re supposed to do with your life.

So we need to find ways to handle this ambiguity. We traded away too much for our freedom and it’s time to trade some of it back.

Perhaps this way we can have it all: freedom AND fulfillment.