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 

Near misses and future success

From Marginal Revolution:

Setbacks are an integral part of a scientific career, yet little is known about whether an early-career setback may augment or hamper an individual’s future career impact. Here we examine junior scientists applying for U.S. National Institutes of Health (NIH) R01 grants. By focusing on grant proposals that fell just below and just above the funding threshold, we compare “near-miss” with “near-win” individuals to examine longer-term career outcomes. Our analyses reveal that an early-career near miss has powerful, opposing effects. On one hand, it significantly increases attrition, with one near miss predicting more than a 10% chance of disappearing permanently from the NIH system. Yet, despite an early setback, individuals with near misses systematically outperformed those with near wins in the longer run, as their publications in the next ten years garnered substantially higher impact. We further find that this performance advantage seems to go beyond a screening mechanism, whereby a more selected fraction of near-miss applicants remained than the near winners, suggesting that early-career setback appears to cause a performance improvement among those who persevere. Overall, the findings are consistent with the concept that “what doesn’t kill me makes me stronger.” Whereas science is often viewed as a setting where early success begets future success, our findings unveil an intimate yet previously unknown relationship where early-career setback can become a marker for future achievement, which may have broad implications for identifying, training and nurturing junior scientists whose career will have lasting impact.

https://arxiv.org/abs/1903.06958

I think this goes for the arts as well. Early setbacks drive some to give up and others to work harder or look inward or improve. I’ve seen early successes be quite damaging, especially when the success is undeserved.

But how do you know whether you’ve had a near miss or a complete, not-even-close miss?

For a city to have a thriving arts scene

From Peak California:

For a city to have a thriving arts scene, you need some combination of:

1. Families or nightlife, both of which produce demand for reasonably educated workers who work non-traditional or variable-schedule jobs, either as babysitters or bartenders.

2. Cheap neighborhoods that aren’t unsafe. My current neighborhood, Williamsburg, fit this role ten years ago.

3. Upside, either in the form of selling out or marrying someone with a boring but lucrative job.

Notes on Berlin

From somewhere over the North Atlantic, I’m on my way home to Chicago after a month in Berlin.

I took the trip in part for family reasons but I extended it to get a better feel for the city, but I was writing, editing, and working throughout. I stayed there for just over a month (leaving for a long weekend in Spain in the middle) in a one-bedroom AirBnB apartment in Graefekiez, a gentrifying neighborhood in Kreuzberg. These thoughts are gleaned from many conversations with people here, Germans and non-Germans, as I consider moving to a new city or staying in Chicago.

I arrived on December 18 and quickly remembered how cities change drastically during the holiday time from Christmas to New Year’s Day. I usually don’t like the way the rhythm of cities slows down during holiday times, but I felt it double being in a new city. Things changed drastically once January hit and I felt a lot more life in the city, and had a much easier time meeting people.

I mostly avoided touristy things, except for two walking tours of Kreuzberg, including a tour of street art, something Kreuzberg is well known for.

When viewed from the street, much of the city is ugly to me. In Kreuzberg, almost every building surface within reach of spray paint is covered in graffiti.

There’s more trash on streets and the energy often feels messy — during our tour, a man stopped to pee on a tree about 15 feet from us, in the middle of the afternoon. I saw many other men pissing on the street during the month, including on a building in the middle of Alexanderplatz on New Year’s Eve, and none seem concerned that the police would give them a citation (or that everyone was shooting off fireworks, mostly into the air).

I love the street art.

This last one is one of my favorites, the Berlin wall turning into a wall of Euros. Anti-capitalist slogans are everywhere in the city. There also a lot of griping about gentrification and rising rents (which are still very cheap for a major city) and a feeling that the “cool Berlin” is gone or quickly fading. I hear this just about everywhere I go, whether in Berlin or the U.S. — it’s gentrifying, rents are going up, this place used to be cool 5/10/15/25 years ago.

Still, grassroots movements to keep the city unique have had some success. Google wanted to build a large office here and decided to back down after protests. “Fuck Google” stickers and graffiti can be seen around town.

The bigger art pieces are commissioned or done with permission. Some of the graffiti, like these ornate tags by the Berlin Kidz are also beautiful, at least to me.

That spells “paradox”.

While much of the exterior in the city is ugly, the interior spaces are often beautiful and unique. Stores, cafes, and apartments often have colorful interiors with ornate flowers painted on the walls, impeccable lighting, and many plants. It’s the opposite of Chicago, where the architecture is consistently beautiful but the interior of everyone’s apartment looks the same.

I wonder if Berliners feel that when they come inside, they want to come into warm, welcoming, cozy spaces, oases from the ugly exterior world.

There’s a similar phenomenon with the people too, who are generally attractive but dress in unflattering or, well, aesthetically unconventional ways. I’m not sure if it’s just the current fashion or what.

All of this amounts to a massive amount of texture. The city feels lived in, real, and human in a way that the grid of Chicago often feels dehumanizing and alienating to me.

Fewer than 50% of the residents are from Berlin. There are many many immigrants, expats, and refugees (notably Turks, Syrians, and Spaniards). And the city has also attracted droves of young professionals, artists, designers, coders, and entrepreneurs from all over the world.

This creates a feeling of constant energy and excitement. It feels like people really want to be here. On the other hand, I got the feeling from talking to people that it’s a bit of a transitional city, a waypoint on the way to somewhere else for many people. Several people told me it was hard to maintain friendships for more than a year because people come and then move on. Sometimes people come and then change completely as they discover some new way to live or new thing they’re into and join a different milieu or social group. That’s what makes it exciting – people can come and be free to find themselves, but it can also make it difficult.

The thing that I wonder though is — how much is substance and how much is hype? How much is just cool vs. impactful art? I have no way to answer these questions.

The city is incredibly international. There are people here from all over the world. It’s striking how uninternational Chicago feels in comparison. If you speak more than one language, then it’s common to have a little dance at the beginning of every conversation where you try to figure out which language is Pareto optimal for the conversation.

It was common for me to start with German (of which I know very little), have the other person switch to decent English, and then after a few minutes I would realize that they were from Spain or Colombia and we would switch to Spanish.

There are many Spaniards and Latin Americans there and Spanish is a pretty useful language to have in the city, although English is widespread. Almost everywhere you go, someone speaks at least some broken English. And some locals are upset because they have gone to restaurants or cafes where none of the staff spoke German. Many of the expats never bother to learn any German.

Now, some sentences about the fucking weather.

I’ve been to Berlin in the summer, when it was sunny and warm (but not hot) and it’s similar to Chicago — everyone is happier, everyone is outside, the sun is up until late, everything feels more beautiful, and there is much merriment had by all. In Berlin, you can drink in public and you’re either unemployed or have six weeks of vacation a year and so obviously you can enjoy the summer even more, drinking by the river with your eight friends, each from a different country.

Berlin in the winter is the opposite of that. It’s extremely gray. Like no sun for weeks at a time. My brother (who has lived there for seven years) tells me that a few years ago ago they had a winter with only 40 hours of sunlight the entire winter. I didn’t see pure unbroken sunlight for more than a five-minute stretch until… three days ago, or after being there for almost a month.1 The sun rises late (around 8am) and sets early (around 4pm).

I think it’s hard to underestimate the impact of living without sunlight for so long. Chicago winters are also depressing to me, mainly because they don’t end until April or May and also because they are also very gray. But Berlin felt depressing in a way that Chicago doesn’t.

My theory is that the Chicago winter is so extremely cold and harsh and the wind so terribly biting that it all creates a sometimes dire sense of hardship and suffering, which on the one hand is about as enjoyable as any other hardship and suffering but on the other hand has the pleasant side effect of creating a feeling of camaraderie with your fellow Chicagoans because we’re all in this together and goddammit we might not have much to live for but we will make it to see the summer, so help me God.2

Berlin’s weather felt less like a desperate struggle against mother nature and more like “well, this is just how things are, sorry, maybe try some Lexapro?”

I don’t know if it’s the city or the weather or the fact that the sun doesn’t rise until 8am, but my schedule shifted. I’ve been waking up at about 8am like clockwork for the past year and all of a sudden I found myself sleeping until 9am or 10am without any problem and naturally falling asleep around 1am or 2am. On a few nights, I went out to a bar or a party only to realize that it was 4:30am or 6:00am. There’s no way I’m just accidentally staying out until 6am in Chicago.

Film and Work

I wanted to meet up with more filmmakers but the weird time of year conspired against me.

I did get to one film event this week and met some interesting filmmakers. There was a pitch session where people could talk about their project and try to enlist collaborators. My sense was that most indie projects here are zero budget. I’m not sure if that’s better or not than Chicago – in Chicago, most indie projects have some funding, although never a lot of funding. Probably some projects would be better off going zero budget but it’s also nice that people get a little bit of money.

Another thing I noticed was that most of the people pitching were looking for writers to collaborate with. In Chicago, it feels like everyone is a writer. I don’t know any directors in Chicago that don’t also write their own material. Almost every comedian/improviser I know is also a writer or has written their own material at some point. I don’t know if everyone writing for themself is optimal, and I don’t want to draw conclusions from just meeting a handful of filmmakers in Berlin.

My hunch is that while Berlin may be more creative or inspiring than Chicago, it’s also harder to ship your work because there are so many shiny fun things going on, so many interesting people to meet, etc.

Berlin felt like it was telling me to not miss out, to come out and play and be weird and stay out late and party and meet people. During the winter in Chicago, I feel like the city is telling me to stay home, edit and write and watch Netflix and occasionally go to a bar with my friends to complain about the weather.

So while I think it would be more creatively stimulating to live there, I also think it would require more discipline to work and write.

Freedom

There’s something about Berlin that truly feels free, like I actually felt more free there. I can’t quite describe it, it’s something cultural, something in the air.

And I’m not exactly oppressed in Chicago. I can’t really put my finger on it, but you just get the sense that anything goes — you can be anyone you want in Berlin and people won’t judge you (as long as you’re not judgmental).

Then there are things like the fact that you can drink in public. And urinate in public, if that’s your thing. And there’s the drug dealers at the Gorlitzer Park U-Bahn station (I never bought from them, but it’s nice to know you can buy drugs if you want them).

Smoking is still allowed in many bars, and regulations seem easy to skirt or laws are ignored or not enforced. And smoking is much more common.

Three days before New Year’s eve, tons of pop-up fireworks stores open up and people buy massive amounts of fireworks. The entire city is lit up by nonstop fireworks for hours after midnight on New Year’s Eve. It can’t be safe… I had fireworks exploding near me multiple times as I walked around or drank a beer on the sidewalk. It’s insane how many people were shooting off fireworks, including children.

Even the dogs are free — most dogs are walking around with their owners, unleashed.

And it almost always felt civil. I never felt in danger. Many of the smaller streets are dark at night but crime is much lower than in a major U.S. city.

And while raving drunks are tolerated on the train platforms, people will publicly yell at and scold people who are having ‘adult’ conversations or talking crudely in the presence of children.

Random notes

Nobody asked me about Trump. When I traveled to Europe in the Bush years, everyone made comments about Bush.

I talked to a Russian who had no idea about any sort of Russian interference with U.S. elections. I told her it was a huge debate in the U.S. and she thought the very idea was preposterous. So, it seems that one of us is being lied to.

One of my favorite things was drinking tea, which was served with freshly-sliced ginger or mint leaves.

It’s feels safe in a way that a U.S. city never feels.

Reading Jane Jacobs has helped me understand why I much prefer living on mixed-use streets and why these streets feel better to walk on and live on.

There aren’t so many, uh, basic people.

It’s probably one of the best deals for geo-arbitrage for someone that wants a major international city. Cost of living is rising but still much lower than London, Paris, NY, SF, Chicago, LA.

Anti-racist and anti-sexist graffiti and signage are all over the place. The city is aggressively intolerant of intolerance.


  1. My weekend in Spain was uninterrupted sunlight for three glorious days. 

  2. To be fair, you shouldn’t believe anything I say right now, because it’s January and any asshole can tell you how the winter isn’t so bad in January, a whole three to four months before winter ends. 

Stories get you through

Last week I finished a freelance gig that started in mid-July. It was an intense gig with long hours and many working weekends. On the weekends where I didn’t have to work, I was on call.

It was tough and stressful and often miserable. There were good times too and I met good people there.

I’ve been thinking in the last few days how I got through it. Because, honestly, without going into details, it was pretty miserable. And it meant not having a Chicago summer.1

Here are some of the reasons I didn’t quit:

  • It’s only 3.5 months, anyone get through something like that.
  • You made a commitment, keeping your word is important.
  • The money is really good.
  • I need the money.
  • I don’t want to let the team down.
  • I’m learning a lot.
  • I’m working for an important cause; it’s important that I do my part.

Those are all good reasons, right?

What’s interesting is that depending on who I’m talking to, I might offer a different reason for why I did it. We tailor the stories we tell, depending on the audience, and I think for two reasons: one is to make the story more interesting and two is to make ourselves sound better.

The story you tell yourself about why you are doing it, that’s what gets you through.

And all of those stories worked for me at one point or another during the experience. But the one that persisted, the one that really kept me going was about the freedom. I’m sacrificing a lot of freedom right now for a lot more freedom down the road.

And sitting here on a Friday morning with nowhere to be and nothing to do, I have to say that I made the right choice. That sweet sweet taste of freedom, the freedom to work on whatever I want. I have about three to six months of runway before I have to take another job (assuming I don’t pick up any new freelance work) and that means I’m free to write every morning, for hours at a time.

I could jump on the train and fly to another city right now if I felt like it. I’m not going to, but I like the feeling.

 


  1. I spent June directing a feature film, then I went to Scotland for a week in July and then started the job when I got back 

Instead of planning your career…

I’m reading through Pmarca’s guide to career planning on this lazy Sunday back home. Excellent throughout and way too much to quote, but some bits that ring especially clear:

The second rule of career planning: Instead of planning your career, focus on developing skills and pursuing opportunities.

I’ll talk a lot about skills development in the next post. But for the rest of this post, I’m going to focus in on the nature of opportunities.

Opportunities are key. I would argue that opportunities fall loosely into two buckets: those that present themselves to you, and those that you go out and create. Both will be hugely important to your career.

Opportunities that present themselves to you are the consequence — at least partially — of being in the right place at the right time. They tend to present themselves when you’re not expecting it — and often when you are engaged in other activities that would seem to preclude you from pursuing them. And they come and go quickly — if you don’t jump all over an opportunity, someone else generally will and it will vanish.

I believe a huge part of what people would like to refer to as “career planning” is being continuously alert to opportunities that present themselves to you spontaneously, when you happen to be in the right place at the right time.

And..

Optimize at all times for being in the most dynamic and exciting pond you can find. That is where the great opportunities can be found.

And…

Colin Powell says, “You know you’re a good leader when people follow you, if only out of curiosity.”

Don’t keep a schedule

From the Pmarca Guide to Personal Productivity:

Let’s start with a bang: don’t keep a schedule.
He’s crazy, you say!

I’m totally serious. If you pull it off — and in many structured jobs, you simply can’t — this simple tip alone can make a huge difference in productivity.

By not keeping a schedule, I mean: refuse to commit to meetings, appointments, or activities at any set time in any future day.

As a result, you can always work on whatever is most important or most interesting, at any time.

Want to spend all day writing a research report? Do it!

Want to spend all day coding? Do it!

Want to spend all day at the cafe down the street reading a book on personal productivity? Do it!

When someone emails or calls to say, “Let’s meet on Tuesday at 3”, the appropriate response is: “I’m not keeping a schedule for 2007, so I can’t commit to that, but give me a call on Tuesday at 2:45 and if I’m available, I’ll meet with you.”

Or, if it’s important, say, “You know what, let’s meet right now.”

Clearly this only works if you can get away with it. If you have a structured job, a structured job environment, or you’re a CEO, it will be hard to pull off.

But if you can do it, it’s really liberating, and will lead to far higher productivity than almost any other tactic you can try.

As of last week, I’m self-employed and doing a version of this, along with some strategies I’ve picked up from Deep Work. I love it. My dream isn’t to retire and live on a beach; it’s to have the freedom to work on what I want, when I want.





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