Optionalitymaxxing and the Search for the Greenest Pasture

choice good, optionalitymaxxing bad; asymmetric information rules everything around me; commit and cultivate

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Hi Friends,

Beyond some threshold, optionality shifts from being great to harmful. Don’t get me wrong, I prefer to have choices. I choose a world with excessive optionality over a world of coercion every single time. But I find myself returning to this subject again and again because problems stemming from an abundance of optionality seem to be on the rise. We live in a world where you can always find a pasture that, from afar, appears greener.

Pastures can be greener. You can quit a job that left you miserable and hating every work day to work at a job that pays you well and makes you want to leap out of bed every morning and get after it. You can leave an abusive relationship for a healthy experience being single, or a new relationship with a mature, well-adjusted partner. Life can get better and these greener pastures can be a genuine blessing.

But in a surprising amount of cases, the exceptional greenness of this new pasture is an illusion. You might fall in love with a new apartment when you go on the tour—”look at all this kitchen counter-top space and how cute the neighborhood is”. And then when you move in, you find out that the neighbor on the floor above you is a professional gamer who stays up until 4 am and screams when they lose a match. Or you learn that the coffee shops in your new neighborhood all have bad wifi and even worse coffee.

There is always an asymmetry when comparing a new job, relationship, or living situation to your current one—to name a few examples. You are much more informed about the downsides and costs of your present situation than the hypothetical future one. Due to this asymmetry, it is easy to tell yourself a story about how the new apartment is going to improve your life. This optimistic bias and willingness to take a risk—as you can never know all the costs—is probably overall good. But our present world is continuously reducing friction in a way that makes switching to a “greener pasture” easier than ever.

This becomes a bigger problem as the culture—through memes and technology—reinforces a perception that pursuing endless optionality and avoiding commitment is smart. While it may be fine—you’re entitled to your judgments—for any individual to have this perspective, this behavior does not effectively scale.

Our most important social infrastructure is predicated on a preference for commitment, not optionality.

For example, many workers will benefit greatly from the increased options provided by a shift to remote work. Certain communities will have a growing tax base for the first time in decades, as new residents choose to migrate to more affordable cities and villages. However, there is a risk that this becomes another change that deters people from commitment. In a world where you can work from anywhere and there are innumerable technologies to make moving easier, from airbnb to internet communities, there may be great temptation to regularly switch localities.

On Twitter, it’s not uncommon to see people with this optionality exercising it. One year they’re moving to San Francisco because they fell in love with the weather and the culture. The next, they’ve decided that the future will be built in Miami. And when their friends move to New York City for its post-covid revival, they’ll move back there. Always chasing the greener pasture.

I’m not throwing shade. For certain people, this might be the right decision. No one can know. I certainly don’t know what’s best for them. Twenty-somethings aggressively moving from metropolis to metropolis is not necessarily a problem.

However, I would encourage people to instead bet on the locality that they think they’ll be able to commit to for years to come. That bet may not play out, or a future you might decide that the upside of NYC’s club scene isn’t as important to you as it once was. Maybe it’s better to think about what locality you want to go ‘long’ on for a given season of your life. Without this kind of commitment, social institutions do not have the time and talent they need to grow and blossom.

The people who know this best are those who have invested in a locality and then watched this social infrastructure decline over time. Many of my friends left NYC and SF because their personal experience in those cities had declined to the point that they couldn’t justify staying—their favorite bars and restaurants closed, they got robbed, their scene slowly faded, and their friends left. If you ask them about their time there, you can feel the warmth of their nostalgia and the heaviness of their loss. When you create this kind of space for yourself and others, it is deeply meaningful.

If you hop from city to city, you will at best hop from local maxima to local maxima. The real peak experiences come from commitment. Staying somewhere for many years is not guaranteed to give you a better experience. But if you’re in the right locality, the value will compound over time. It takes time to identify the hidden gems, to build a community, to become a regular, and to accumulate stories. All of these enable you to have a richer depth of experience.

The paradox of endless optionality is that it makes certain paths less possible. By enabling you (and everyone else) to chase an endless stream of new opportunities, you miss out on the opportunities that can only exist once you’ve made a commitment. There will never be a shortage of people trying to sell you a greener pasture. You can only escape by developing your conviction and making a commitment. You’ll still be able to have a greener pasture, but you’ll have to cultivate rather than consume to get it.

Favorite Recent Read

The Sovereign Individual by James Dale Davidson and Lord William Rees-Mogg

I am still early on in reading this book after receiving consistent recommendations from friends. The book has been on my radar for ~four years but I assumed that many of the ideas were “in the water” because it’s part of the Bitcoin canon. I was mistaken and am grateful to those who corrected me.

The fact that people tend to respond to costs and rewards is an essential element of forecasting. You can say with a high degree of confidence that if you drop a hundred-dollar bill on the street, someone will soon pick it up, whether you are in New York, Mexico City, or Moscow. This is not as trivial as it seems. It shows why the clever people who say that forecasting is impossible are wrong. Any forecast that accurately anticipates the impact of incentives on behavior is likely to be broadly correct. And the greater the anticipated change in costs and rewards, the less trivial the implied forecast is likely to be.

In general, I am still extremely skeptical of anyone who is claiming to predict the future but I thought this analogy was provocative.

They call their analysis ‘megapolitics’ and the book attempts to predict aspects of the future by looking at how developments in the past altered the dynamics of society. In particular, the early chapters have focused on how the ability to engage in credible violence altered the nature of political systems.

During the feudal era, a trained knight in armor was capable of fighting 12 serfs armed with nothing but pitchforks. Whereas, during America’s founding, a colonial farmer with a hunting rifle was arguably more capable of credible violence than a British soldier. This kind of analysis feels timely as we’ve witnessed civilian populations wielding RPGs successfully defend against assaults by better-equipped military units.

Grant 🌄 @grantadever

"I don't want you to be a 'sovereign individual' I want grandkids"

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One Question

What was the last thing that you read which has significantly changed your worldview?

Learning more about energy markets and nuclear energy seems to have forever altered how I think about the world.

Your Friend,
Grant

P.S.: This week I met up with the first person who partially introduced themselves as being a big fan of Seeking Tribe. I asked them what they thought was the most defining part of the newsletter and they answered “your curiosity”.

Take this as a friendly reminder to let me know if you’re coming to Austin and that I love direct feedback. Life has been hectic but I try my best to make time for people when they come into town.

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