Freedom and constraints

I.

Since I left Chicago in August, I’ve been living a somewhat nomadic life. I don’t have any long-term commitments and I have a remote job that I can do from anywhere with an internet connection.

And I love it. I love freedom. It feels amazing.

But there are pangs of something that I feel, a feeling I can’t quite describe, a feeling of wanting to be constrained. And I’ve been trying to wrestle with why I feel this way, of why despite enjoying traveling so much, I have an urge to restrict my freedom.

Here’s what I think: freedom induces anxiety because it raises choices and choices have existential implications. So when confronted with freedom, we (subconsciously) look for ways to eliminate it.

II.

What’s so great about a mortgage?

There are the obvious financial reasons and the ability to control your property. But I think there’s another psychological reason: a mortgage gives you an arbitrary goal, a way or ordering your life and making decisions.

The benefit of the mortgage is its long duration and high cost, which serve as both an organizing principle for life and a defense against the anxiety of freedom.

Want to take a new job? Well, sure, if I can still pay the mortgage.

Want to move? You can’t because you have this mortgage.

Of course people can sell their houses and move. The point isn’t that a mortgage ties you permanently to a place or situation, but that it alleviates the daily questioning of where you live.

It raises the threshold for considering a move — when you’re a nomad, you can move on any whim but when you have a mortgage, the threshold is much higher — you can move because you get a new job offer or to be closer to family or whatever, but you’re not just going to book a cheap fare to Buenos Aires and live there for a few months because you feel like it.

The defense against anxiety is key I think — life is much easier if you don’t question your purpose, if you have a shorthand rubric for every decision. Having children probably works in this way too, and I don’t mean to say that any of this is negative — people with children should probably organize their lives around the health and wellbeing of their children and if I have children I will almost certainly not be flying around the world on a whim.

III.

When I lived in Chicago and I was studying/practicing comedy, I had an organizing goal for my life: to get better at comedy, to get cast in shows, to be successful.

When I switched from theater to film, there was a similar organizing goal: to make films.

Insomuch as Chicago was the best place for me to do those things or provided the best opportunity to do those things, it was easy to stay in Chicago, even when I felt like leaving or the winters were long and freezing, or when I was just feeling wanderlust. Sure, I was unhappy at times (who isn’t?), but I had a reason to stay — to move on a whim would take me farther from my goals.

And whatever suffering I felt was easier to bear, knowing that it was in service of a longer-term goal. The structure was secure as long as I didn’t question the organizing goal for being in Chicago (studying comedy).

Once I quit performing, I went through a crisis where I had to question everything (and mourn the loss of a part of me) before settling on a new goal: making movies, which brought an organizing structure back to my life.

During the transition, I toyed with the idea of moving but it was clear that the network I had built in Chicago, combined with cheap rents, made it much easier to make movies in Chicago.

Once I made a feature film, the calculus changed. I no longer had an organizing reason for staying in Chicago. Yes, I still want to make feature films and yes, it’s still easier to do that in Chicago than it is in New York or wherever (because I have the local knowledge and contacts in Chicago and because rent is so damn cheap), but because I want to move up a budget level, the calculus is different.

The model of “work two years and save, then make an ultra-low-budget film” is not what I want anymore. Once I decided that the majority of the budget for my next project will come from investors, there’s no need to keep rent ultra-low to save as much as possible and high-rent cities like New York, San Francisco, and Los Angeles are now viable places to live.

IV.

It makes sense that we would have defenses against constantly questioning our life situation. I mean, it’s probably not great to wake up every day of your life asking yourself the question “is this where I should live? is this the right career for me? is this my best life?”.

If you constantly question everything and never commit to anything, you’ll end up living in a kind of high-anxiety state of paralysis.

Completing meaningful, long-term projects like raising children or starting a company or creating a political movement or changing the culture — these all require a lot of commitment and a lot of saying no.

On the other hand, if you never question anything and just copy whatever your friends are doing, you’re liable to get stuck in a life that you don’t want.

So I think it’s safe to say that there’s an optimal mix of questioning vs. living, of commitment (and its attendant constraints) and reorganizing.

The trick I think, is to choose constraints and commitments consciously1, with regular checkpoints or a regular framework for question things and considering a reorganization of life.

For me, it seems to come about every ten years, but I wonder if I should be more deliberate in how I approach this whole question, by setting up an arbitrary time for questioning, like the last week of the year.


  1. Yes, I recognize that this is a massive luxury for privileged people 

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