Pain and Pleasure

I’m trying something new: writing without caring too much about grammar and spelling. Just trying to get ideas out. The following notes are based on some recent thinking I’ve been doing and is a work in progress. I am almost certainly oversimplifying and it’s meant to be a working hypothesis. Think of it as a starting point for an ongoing discussion I’m having with myself, but would like to share with the rest of the world for feedback.

Humans and most (every?) other animals seek pleasure and avoid pain. You might be thinking, “yeah no shit”, but what does it really mean and how does it affect our lives?

In the natural world, the threat of death is much closer to the present moment than it is for us humans. Predators, drought, starvation, and climate change pose constant threats to the survival of a species. Pain of hunger is real and it’s difficult to avoid. Call this a non-wealth surplus situation. No time for day dreaming, the present moment is too important. 

Humans and several other species have evolved minds that allow them plan for the future, solve problems, and pass knowledge to other generations. Using their minds, humans have become particularly adept at aggregating wealth surplus (i.e. an excess of food, water, and shelter). Over time fewer and fewer people have been needed to produce our sustenance. That frees up time for a bunch of other people to sit around think, tinker, and make stuff. 

Now if you were a Zebra and able to think, you might look at humans and say something like, “Wow! What lucky creatures. They have it made. Sure is nice not having to worry about being eaten while trying to find out the next time I’ll have a drink of water.” Sometimes I wonder if the first humans to figure out agriculture and animal husbandry thought the same thing.

Something funny happened. The smart monkeys escaped some of the drudgery of living in nature, but new problems arose. Human culture evolved hierarchies to manage the resources of the various societies. Each society’s culture created rules, systems and norms that affected the way they viewed their existence and relation to the world at large, as well as their commentary on that culture in the form of various arts (music, painting, fashion, etc.). It is within this cultural ecology where new forms of suffering arose. To understand why, let us first consider human psychology pre-civilized cultures in a very simplified way.

The psychological world of humans tends to map well to the natural/physical world because we spent most of our evolution in non-wealth surplus situations. Worry about survival and the next meal. Worry about finding shelter. Worry about predators. Worry about reproducing. It shouldn’t be surprising that sex feels so good. If it didn’t, all those other worries would have gotten in the way. But those other worries dissipate relatively quickly because you die if the underlying problems aren’t solved.

Cultural mechanisms can be used to reframe the psychological world of pleasure and pain. Religion is a useful example. People are encouraged to endure pain and hardship, act like good people, and function in a society in order to achieve ultimate pleasure reward in the afterlife. Similarly, athletes can endure training in order to win medals and enter record books (another form of immortality). Other systems like American democracy and capitalism are work despite our innate challenges. People don’t need to be fully conscious beings in order for them to work. That’s why we can end up with miserable billionaires and asshole politicians.

The human relationship to pain and pleasure becomes topsy turvy in societies with wealth surplus. Imminent worries about death and survival are deferred to a later date. But reducing suffering from starvation and predators did not change the biological roots of our psychological world. We still react to pleasure and pain, but now we have free time on our hands. This extra time can lead to a variety of consequences depending on what is deemed right and wrong by culture. Phrases like “the devil finds work for idle hands to do” make more sense in this context. If we give into our innate pleasure and pain responses we can indulge in sex, alcohol, money, and food. Our fight or flight response, well adapted to the natural world, causes us to avoid our problems because we identify with shit and hold beliefs that are threatened by those problems. We end up feeling like we might die even though it’s all in our head.

The problem with culture is that groups and organizations will tend to keep using what worked in the past even if it no longer makes any sense. Often times people won’t even know why things are done. It’s always been that way. The reasons have been forgotten, but the actions have turned into habits and traditions. This can be why reading religious texts literally can cause people with supposedly good intentions to act quite cruel. This might be similar to what some groups call social or cultural programming. 

In our culturally manufactured world, certain pleasures require difficult sacrifices or endurances of psychological pain. The pain and pleasure decisions become more abstract. We might have to look deep into what we value and why we value things. There is difficult work of accepting our nature and forgiving the people and culture that raised us.

If we consider the arch of human history it went something like this: First we tamed nature, then we tamed societies. Going forward we must learn how to tame our selves. These aren’t new ideas. There’ve been a bunch of new age movements that have said very similar things. My sense is that global societies are sensing that there is an identity or existential crisis occurring. It seems like it is happening in America. We hear about low trust in institutions. People need hope and something to believe in. Religion gets a bad wrap in many places, but I would not be surprised to see new forms of religion-like institutions emerge over the next 20 years. There is both risk and opportunity in that. 

Don’t Call It A Comeback (Why I Fell Down The Cryptocurrency Rabbit Hole)

Estimated Reading Time: 6 minutes

Revival
It’s been over a year since I last posted. I apologize, dear readers. I plan to start writing regularly again. My goal is at least once a week.

If you’ve wondered where I’ve been, I offer you what I hope is a satisfactory explanation. I got lost. I fell deep into a intellectual treasure hunt than has no bottom. The world I fell into was full of quirky people, ridiculous adventures, Chinese and Russian gangsters, emotional ups and downs, and a taste of what our future economy might look like.

That future is one in which cryptocurrencies become an integral part of the internet. The ideas and people at the core of this movement captured my interest because the philosophies guiding them were similar to the ones that led me to start this blog.

Stumbling Down
My journey into the world of cryptocurrency began shortly before starting this blog in the fall/winter of 2016. About a year and a half had gone by since I left my job as an analyst at a large asset management firm in San Francisco. I was living in Lisbon, Portugal, learning how to dance Kizomba. (What? Not what you expected?) I wasn’t really doing anything that you could consider “work,” and eventually got bored (or lonely enough in my non-Kizomba time) to seek out the local start-up community.

I began attending tech meet-ups, and at one event, met a character who resembled some mix between the Cheshire Cat, the Mad Hatter, and that one kid growing up who all the parents really like because he knows how to charm them even though he causes chaos and destruction. Naturally, we became quick friends and eventual business partners. I will call this person Z.

When Z first told me what he was up to, it went along the lines of, “I connect technology projects that need money with people who have money and they use cryptocurrency to make these investments.” This statement may sound less crazy in 2018, but I didn’t understand WTF he was talking about back then. So several discussions unfolded into a few ah-ha moments.

That “Oh Shit” Moment
It was during those discussions with Z that I had the first ah-ha. A parallel financial system was emerging from the depths of the internet, and 99% of the people who had heard of cryptocurrency didn’t understand what was going on. Z had helped raised millions of dollars for multiple projects from people he was meeting in internet forums, Slack channels, and sub-Reddits. And he wasn’t the only one doing this!

Maybe it was because I came from a world of regulated financial reporting, road shows run by investment banks, fake symbols of professionalism and credentialism that I was so taken aback by Z’s claim that people would invest in projects by sending cryptocurrency across the planet over the internet. I had so many questions: What the hell were these projects? How the did he get involved? Who are these investors? Why does anyone trust each other? Why does anyone trust YOU (Z)?

As Z answered all my burning questions, I realized two things:

  1. The technology underpinning cryptocurrencies is a mechanism for scaling trust on the internet.
  2. If it’s true that any project can throw up a payment address as easily as it is to post an email address, then this technology solves global crowdfunding.

While crowdfunding was already an established service, it was tied to the incumbent financial system and regulations, so it never took off as rapidly (at least in the United States) as I thought it would for funding nascent technology businesses. Regulators and banks were slow to change, this money was difficult to move. Cryptocurrencies enabled the behavior I thought was possible, but had been held back by the above factors.

The moving money around problem was solved by a publicly viewable list of transactions—a special database called a blockchain. This list has mathematical properties that allow computers all around the world to check transactions, update the list with all the legitimate ones, and then agree to use a single copy of that list. The catch? No single entity controls the list. No bank. No government. Think uploading and downloading music files on software like Kazaa, Limewire, or BitTorrent, but with money. The only way one person could control it is if they controlled over half of the computing power running the network. Because people trust the mathematical properties of this software, they’re okay with sending and receiving money over it.

Although the regulatory problem still wasn’t solved, this parallel financial system was small enough at the time for lawmakers to ignore it. The result being that there were people in places like Svalbard raising money from investors in China.

While there were plenty of scams and shady people using this system (Wasso wasso wasso, anybody?), I discovered real entrepreneurs and technologists trying to solve real problems. Some of these people truly believe we can create fairer, more democratic, and trustworthy financial and governance systems. My curiosity raging, I dug deeper and found that the rabbit hole already had visitors.

The Rabbit Hole: A Global Network
The second ah-ha moment occurred while I was traveling. After meeting Z, I decided to implement one of my favorite learning tools: going to conferences. (A quick tip: if you want to learn about some emerging technology or anything really, there is probably a conference, festival, or trade show for it. You can usually find the people who live and breath whatever topic it is at these things. Go talk to them!)

I ended up going to a conference in Bucharest, Romania where I met several early Bitcoin and Ethereum enthusiasts. It was here where I got my first taste of the visionary – albeit idealistic – personalities who were creating the internet’s financial infrastructure. It was on this trip that I had my first visceral sense of the community and openness that is endemic in the crypto/blockchain world. People were there to build a more open, secure, and fair internet and financial system.

I was hit with another visceral understanding when I realized my money could now move across borders without any gatekeeper. With assets like Bitcoin and Ether, you can choose to control the keys that access your funds. Since there is magical math that makes it impossible for anyone else to touch your assets without those keys, you have access to your funds wherever you are on the planet (as long as you have an internet connection). This felt like the future. No more worrying if I could take out cash at an ATM or if my credit card would be accepted in a certain country. And it made sense too! I mean we don’t think of sending an email to our dear cousin Franz in Austria as a cross-border email, do we? But for some reason, in this age of free, planet-wide communication, we still have a term called “cross-border payment.”

As long as I could find willing buyers of Bitcoin or Ether, I could convert to a local country’s currency and get on with my day. In addition, I could send as much money as I wanted. With no limits! It was money without borders, native to the internet.

And if this wasn’t exciting enough, the best part was the most important: the community. Thoghtful, creative, and wacky people were innovating and getting involved all over the world. Things were happening in San Francisco, New York, London, Berlin, Zug, Hong Kong, Seoul, Tokyo, Shanghai, Singapore, and Buenos Aires. Even Lisbon has a community. So just like the internet itself, this crypto world is permissionless, and anyone can get involved by going to conferences, meet-ups, reddit, telegram, GitHub, Medium, and Twitter. Because it is a new industry, there are no gatekeepers. No bankers, no politicians, nor Facebooks to infringe on anyone’s opportunity to participate. It is truly the tech and financial world’s Wild West.

It’s Tough To Make Predictions, Especially About The Future
Through the dusty clouds of 1s and 0s, I could see the beginnings of a potential future where this technology dramatically altered society both on and off the internet. Some of the most interesting ideas in this cryptocurrency world, like Decentralized Autonomous Organization or Oracles, sound like they came out of a substance induced conversation in a college dorm after watching the Matrix. But many of the people working on bringing them to life believe in a future that is less dominated by powerful corporate interests and empowers groups of individuals to innovate collectively on the internet. Stop! Before you say this sounds like some form of woo-woo, hippy communism, wait… The way I’m currently thinking about it: market-based incentives for open collectives. If this is all confusing, don’t fret, even Marx’s head would be spinning. But if you’re eager to learn more, stay tuned for the next post where I’ll dive into some of the details of this future vision.

Finite and Infinite Games

Estimated Reading Time: 9 minutes

“The actor who will accept anything that happens seems supernatural; it’s the most marvelous thing about improvisation: you are suddenly in contact with people who are unbounded, whose imagination seems to function without limit.” – Keith Johnstone, Impro: Improvisation and the Theater

Our last post examined life as a series of boxes. We learned that each box can both define and constrain our life. We can grow by examining and changing boxes or we can stagnate by staying in our existing ones.

In that post, I highlighted a talk given by Tobi Lutke. He referred to the process of moving from box to box as “an infinite game.” This phrase reminded me of the book Finite and Infinite Games: A Vision of Life as Play and Possibility by James Carse.

Carse describes two mindsets: infinite and finite. Infinite players approach the world aware of their ultimate freedom to make choices and accept surprise as the norm. Finite players feel like they have little freedom to choose and compete for the recognition of past accomplishments.

We’ll explore why the infinite mindset is able to handle surprise and change better than the finite mindset. The goal is for you to be able to add these ideas to your toolkit for developing psychological freedom.

Life: An Infinite Game
In his talk, Tobi Lutke described life as:

this really, really interesting series of entering a box, seeing what it is sort of made of, probing at it, analyzing it, seeing how things work, seeing what way gravity is pushing you, and then sort of understanding it and feeling familiar. This is the nice part. Every time you reach there it becomes very comfortable. And then you might learn something that isn’t reconcilable with this world you think exists. That is the very thing that cracks it and you get into the next box. And you start it again. Again and again and again.

He refers to this process as an infinite game.

What does it mean to think of life as an infinite game?

James Carse, author of Finite and Infinite Games, has a definition for an infinite game:

  • An infinite game has no beginning or an end.
  • An infinite game has no boundaries, either temporal or spatial.
  • It is played for the purpose of continuing play.
  • The rules of an infinite game are changed to prevent anyone from winning the game to bring as many persons as possible into the play.

We can think of life itself as an infinite game even if it ends for each individual. No one says when life starts, it just starts. It continues after we die. No one can win life and more people over time have been able to participate as human societies have restructured.

Within life, humans have created complex social and economic structures. These things are completely made up by humans and only humans really care about them. These are our boxes or finite games.

Boxes = Finite Games
Carse contrasts an infinite game with a finite game:

  • A finite game has a definite beginning and end.
  • A finite game has temporal, spacial, and numerical boundaries.
  • Unlike an infinite game, a finite game “is played for the purpose of winning.” i.e. Finite games end with titles or rewards.
  • A finite game must be resolved in the context of its rules.
  • Those rules are set by people and everyone who plays must agree to those rules.
  • Finite games cannot be played alone. There must be an opponent and/or teammates.

We can see that Carse’s definition for a finite game is similar to a box. Take the example of a high school student. The student will enter high school and graduate, so there is a definite beginning and end. There are spacial, temporal, and numerical boundaries to being in that school. The student will end as a graduate and have a “score card” to potentially enter college. Many people agree to the rules of going to high school and there are even truancy laws that society uses to reinforce the social norm. Thus, high school is not played alone.

We can conduct a similar analysis for jobs, university, athletics, and politics.

Society itself is a finite game. Carse even claims that the “principal function of a society is to validate titles and ensure their continued recognition.” Thus, societies can easily get stuck in the past.

The Differences Between Infinite and Finite Players
In the previous post, I talked about how people can get stuck in their boxes, while others can examine their boxes and move to new ones.

We can think of people who get stuck in boxes as finite players and people who examine and move between boxes as infinite players.

Carse describes some differences between these players:

  • Finite players play within boundaries. Infinite players play with boundaries.
  • Finite play is limited by external factors (rules that people make up, expected scripts, social norms), but players choose to follow the rules so finite play is self-limiting.
  • Finite players win titles and then enjoy life. Their reward is life (you could say their recognition and titles are a form of immortality). If you lose, then you don’t get immortality. Therefore, you die.
  • Infinite players die while playing the game. They do not play for life, they live for play.

However, there is one similarity between finite and infinite players: Both players are free to play. If either player must play, then they cannot play.

Like the person who gets stuck in their boxes, finite players often feel like they don’t have a choice. They feel like they must play.

Carse says that “it is often the case that finite players will be unaware of this absolute freedom and will come to think that whatever they do they must do.” In extreme examples, like slavery, this can be true. But most people, especially in Western democracies, have a choice.

A Playful Life

Self-Veiling & Seriousness
One of the tenets of Permissionless Life is that people have a lot of control over their life and if they don’t realize it, they can rewire their mind. But why are some people unaware of their ultimate freedom to choose?

According to Carse, to account for the difference between perceived freedom and actual freedom, players of finite games (boxes) must be “veiling” their actual freedom from themselves.

This veiling occurs because a person must have a sufficient desire to win the finite game (Otherwise they wouldn’t play). To have sufficient desire, the finite player must take his/her role seriously.

What causes a person to take their role seriously?

It may be that we often care too much about what other people will think of our decision to not play (often that means quitting something).

Think about the times you have assumed things like “If I don’t play this role of student or teammate, then I’ll be ostracized or seem like a loser.” Or “If I quit my job, I’ll be jobless and then people will look down on me.” It was totally normal for you to feel that way because society created a set of expectations to literally make you feel that way.

Carse describes exactly this phenomena when he says:

As finite players we will not enter the game with sufficient desire to win unless we are ourselves convinced by the very audience we intend to convince. That is, unless we believe we actually are the losers the audience sees us to be, we will not have the necessary desire to win.

We can say that finite players veil themselves because of a belief that they will be seen as losers if they do not play. They give too many fucks.

At this point you may be feeling a little anxious. Maybe you have kept going with a job, friend group, or lifestyle even when deep down you didn’t want to. But as we discussed, you have tremendous power to change the way you think.

Let’s learn what infinite players do differently.

Carse says, “the issue here is not whether self-veiling can be avoided, or even should be avoided. Indeed, no finite play is possible without it. The issue is whether we are ever willing to drop the veil and openly acknowledge, if only to ourselves, that we have freely chosen to chase the world through a mask.”

So the difference is infinite players acknowledge that they play finite games (boxes) with a mask. They know deep down that they can always quit. The mindset they operate with is similar to Mark Manson’s The Subtle Art of Not Giving A Fuck.

Infinite players “enter into finite games with all the appropriate energy and self-veiling, but they do so without the seriousness of finite players. They embrace the abstractness of finite games as abstractness (Carse defines abstract as being a part of the whole and concrete as the whole), and therefore take them up not seriously, but playfully.”

Living life playfully is not the same as nihilism or assuming finite games are trivial:

To be playful is not to be trivial or frivolous, or to act as though nothing of consequence will happen. On the contrary, when we are playful with each other we relate as free persons, and the relationship is open to surprise; everything that happens is of consequence. It is, in fact, seriousness that closes itself to consequence, for seriousness is a dread of the predictable outcome of open possibility. To be serious is to press for a specified conclusion. To be playful is to allow for possibility whatever the cost to oneself.

We can make a simple distinction between finite and infinite players here. We can say that finite players live life theatrically. They accept roles and scripts. They alleviate anxiety of an uncertain future by focusing on winning titles, awards, and games set up by other people.

On the other hand we can say Infinite players live life dramatically. They choose themselves. Like improv actors, they accept uncertainty as the norm. Thus, they embrace surprises, “no matter the cost to themselves.”

Surprise
If you’re below the age of 35, then you probably were raised by people who grew up in a world that tried to create lots of order. Call it a symptom of industrialization and mass production. From the day Gutenberg invented the printing press to the dawn of the internet, the linear ordering of society has been a foundation of Western culture.

The internet, software eating the world, the digitization of everything, and free movement of information are disruptive because they result in non-linear outcomes. Human society is returning to a tribal-like global village that is more organic and interconnected than the linear world of assembly lines and snail mail.

The result is that uncertainty and surprise are the new norm. The irony of Donald Trump being elected is that a group of marginalized people who typically didn’t vote went out and voted because of technology. We’re going to continue to see technology unlock the energy of underserved populations.

So if surprise is the norm, playing with an infinite strategy, a fluidity of personality and skills, is the best way to navigate in an ambiguous and uncertain world. Because “surprise causes finite play to end, but it’s the reason for infinite play to continue.”

Infinite players live by the principle that “only that which can change can continue.” They realize that the only way to keep the game going is to keep changing it.

[They] prepare themselves to be surprised by the future, they play in complete openness. It is not an openness as in candor, but an openness as in vulnerability. It is not a matter of exposing one’s unchanging identity, the true self that has always been, but a way of exposing one’s ceaseless growth, the dynamic self that has yet to be. The infinite player does not expect only to be amused by surprise, but to be transformed by it, for surprise does not alter some abstract past, but one’s own personal past.

Finite players live in the past: rules are set in the past and titles are attributed to past effort. They build walls and try to make things great again.

The power of the infinite player to be amused by surprise is what helps him/her escape boxes.

Towards The Future
We no longer live in a world where you learn one thing and do that thing your whole life. Governments around the world aren’t providing us a vision for the future. Most of them are trying to retreat to the past.

Rapid change is now our reality. We’re watching, in real-time, the development and convergence of several exponentially, game-changing technologies (Machine Learning, CRISPR, Blockchain, 3D Printing, Augmented Reality and Virtual Reality, Space Travel). A lot of weird shit is going to happen and there will be many surprises.

Those surprises are already changing our political, social, and economic infrastructure and relationships. Using that as a starting point, doesn’t it make sense to be actively aware of what boxes you’re in and be able to fluidly enter and exit them as quickly as possible?

If rapid change is the constant, then we should assume that we’ll be surprised. Thus, going forward, people who play with an infinite mindset/strategy will thrive. As Carse says, “To be prepared against surprise is to be trained. To be prepared for surprise is to be educated.”

We can distill this wisdom into a simple mental algorithm: Take change seriously. Adapt to it playfully. Repeat.

Do so and you’ll see that “the joyfulness of infinite play, its laughter, lies in learning to start something we cannot finish.”

What Box Are You In?

Estimated Reading Time: 6 minutes

“People with dull lives often think that their lives are dull by chance. In reality everyone chooses more or less what kind of events will happen to them by their conscious patterns of blocking and yielding. A student objected to this view by saying, ‘But you don’t choose your life. Sometimes you are at the mercy of people who push you around.’ I said, ‘Do you avoid such people?’ ‘Oh!’ She said, ‘I see what you mean.’” – Keith Johnstone, Impro: Improvisation And The Theater

Our recent posts have focused on psychological freedom and some things you can do to achieve it.

This post focuses on psychological freedom, but from a different perspective. We’ll look at life as a series of boxes. Those boxes influence what we pay attention to. We can stay in the comfortable boxes we know the best, even if they’re not right for us. We can also choose to take a leap of faith by jumping into new, but uncertain, boxes that may help us get closer to what we really want.


A Thought Experiment
One of the things I like to do when I’m caught up in my emotions is to imagine I’m experiencing life from a third-person perspective.

Try it right now for 10 seconds. What do you see?

Most of you probably see yourself, maybe the back of your head, staring at the computer screen reading this blog post. Maybe you’re riding the bus home, reading this post on your smartphone while being squished like a sardine between weary-eyed office zombies.

I find this exercise fascinating because it makes life feel like a video game and the character I’m playing with is Dino. Every day I choose all the things to do with Dino. There are a few things I must do with Dino, like bathe and feed him. Otherwise, the game might end prematurely. But a large number of things are totally up to me to decide: what to dress Dino in, who to have Dino hang out with, what Dino should learn, the places Dino should live, or even when Dino should talk/see his family.

This exercise is useful because it takes us out of our discrete, habitual routines and allows us to see the gestalt.

Seeing the whole of our life helps place things into perspective. We occasionally develop tunnel vision for our current standing in life. We tell ourselves that we have to get that promotion or we have to study a specific subject in order to fit into society. We assume that reaching these end states will give our lives meaning. But how often do we stop to ask ourselves if we truly want that end state? Is it what I want or do I want it because I’m narrowly focused on my environment (i.e. what my peers are doing, what my parents expect, what I think society expects)?

I like to think of this tunnel vision as being stuck in a box. You can think of this box as an identity or a desired identity. It is something that is defined by external factors, but it feels like a part of you.

Examples of boxes could be student, teammate, investor, dancer, investment banker, wife, mother, engineer, or assistant to the regional manager. Those identities can be positive or negative identities. I’m a “good public speaker” or I’m “bad with relationships.” These labels come with a set of internal and external expectations and norms/rules.

Boxes aren’t good or bad. Like almost anything in life, the answer is it depends. The more time we spend in a box, the more we learn about how it works. The goal is to understand how the various emotional, cultural, social, and psychological components of our boxes shape our perception of life. Then we can figure out if a particular box is right for us.

What’s In the Box?
I stole this idea of boxes from a talk by Tobi Lutke, CEO and Co-founder of Shopify (See the bottom of this post for the full video). Tobi uses this box idea to describe his self-development process.

In the talk, Tobi tells a story about being in school and wanting to be popular. He analyzed the situation and came to a conclusion: he needed to buy Air Jordan sneakers. Tobi says he, “was vaguely aware that there was more to the world, but it didn’t truly matter. Within my little world, this school, the most obvious profound thought I had was that I needed Air Jordan sneakers to be a part of the popular kids.”

Tobi is saying that he wasn’t aware of the gestalt. He describes school and the social goal he cared about as “this box I was in and everything I was experiencing could be explained from within this box.” The dynamics of what was going on in his box shaped what he viewed as important. It also veiled him from other rich aspects of life.

It’s funny. I can certainly relate to Tobi’s Air Jordan experience. I bought Ed Hardy clothing in high school to be “cool.” Other times I changed the way I talked to try to fit in with certain groups. And it wasn’t 100% my fault. I was influenced by the boxes I was in!

If you think of a box as your environment, then everything in that environment will influence you: your peers, the titles, the rewards & punishments, and the older people who went through that box and expect you to go through that box the same way. Luckily, life has a way of automatically pushing you into new boxes when you’re young.

The Problem With Getting Older
The problem arises when we get older and it’s up to us to get up and move boxes. We end up like Alice In Wonderland, asking the Cheshire Cat, “Where should I go from here?” The Cheshire Cat responds, “Well that depends a great deal on where you want to get to.” Except we don’t move.

Instead of continuing to play the game of exploring the next box, we develop tunnel vision and linger. We stay in the mediocre job, the shitty relationship, or hang out with people we don’t really like because the certainty of our current box seems to outweigh the uncertainty of exploring the next one.

Life In A Box

Tobi highlights this danger of getting stuck in a box, “There is significant automatic churn in this infinite game. Every time people get comfortable [in a box] some people leave. Everyone has an uncle at some family reunion who has left this process way too early.”

Getting Out Of The Box
Tobi moved on to university and then started working. These next stages became new boxes. Sometime during his first job, Tobi gained a mentor. This mentor was able to operate within the same box Tobi was in, but he could also take events in that box and make sense of them with context from other areas of life. The box that Tobi shared with his mentor was really just a small box within a “much bigger box.”

This situation forced Tobi to realize that the boxes he occupied could be constraining him. He started asking himself several questions to understand these constraints: “what is my world? In which ways is the box I’m currently in constricting me? And how is it stifling my thoughts and ambitions? What are the kind of thoughts that will lead me out of this particular box?”

I think Tobi’s questions are useful to pair with the idea of viewing your world in the third-person. When you combine them, it’s like pausing a video game, going to the menu, and looking at the map. Some parts of the map are gray and blurry because you haven’t explored them yet. You may not have even been aware of those parts until you paused to look around. While you won’t know what lies in those gray areas, you give yourself the option to move in those directions.

Near the end of his talk Tobi summarizes this whole process for us:

Life is this really, really interesting series of entering a box, seeing what it is sort of made of, probing at it, analyzing, seeing how things work, seeing what way gravity is pushing you, and then sort of understanding it and feeling familiar. This is the nice part. Every time you reach there it becomes very comfortable. And then you might learn something that isn’t reconcilable with this world you think exists. That is the very thing that cracks it and you get into the next box. And you start it again. Again and again and again.

Fortunately, like the quote at the beginning tells us, the life you end up with is often the life you choose. It’s your choice to stay in your current box or move on to the next one. If you think your life is dull, it’s probably because you haven’t left a box you find comfortable.

You can leave though. You can start to understand your current box by viewing your life in the third-person and asking the same questions as Tobi. Then you can turn any anxiety you have about exploring a new box into an opportunity for personal growth by reframing the situation. Tobi is living proof that “if you’re ambitious and you’re deliberate about [getting out of your box], you can accomplish very great things.”

Our next post will continue with this idea of life as a game. We’ll consider what it means for life to be an infinite game and look at the series of boxes as individual finite games.

Chamath Sees Where The World Is Going

I’m working on a couple of posts related to psychological freedom that I think will be thought provoking. In the meantime I curated an interview that is related to many of the Permissionless Life themes.


The internet pays many dividends. One of them is having access to information and content from some of the smartest people on the planet.

I recently watched an interview of Chamath Palihapitiya that took place in 2013 and I want to share some of my favorite clips with you.

I think Chamath embodies the principles and ideas of Permissionless Life. His story is what makes America great. He was born in Sri Lanka to poor parents. They moved the family to Canada, where Chamath grew up. He studied hard, went to the University of Waterloo and then eventually moved to America.

Chamath worked at AOL in the early 2000s and then became head of growth at Facebook. He took the money he made at Facebook and started a venture capital firm called Social Capital.

Social Capital is focused on investing in the education, healthcare, and financial services. In Chamath’s own words, he wants to build things “that rip power from the middle and give it to people at the edges.”

Here are some of my favorite parts:

The Framework For How Society Assigns Value Is Changing – watch to 38:08 (less than 2 mins)
https://www.youtube.com/watch?v=pDVDWNguPs4&t=36m30s

Empowering Smart Hard Working Individuals – watch to 44:00 (less than 2 mins)
https://www.youtube.com/watch?v=pDVDWNguPs4&t=42m19s

Empowering Individuals Isn’t Perfect, But It’s The Cost of Progress – watch to 54:15 (a little more than 2 mins)
https://www.youtube.com/watch?v=pDVDWNguPs4&t=51m55s

How You Live In The World & Thrive + Unemployment and Jobs – watch to the end (7 mins)
https://www.youtube.com/watch?v=pDVDWNguPs4&t=64m50s

The whole interview is over an hour and it’s worth a watch:

Opportunity Is Abundant… If You Believe It

Estimated Reading Time: 3 minutes

This week we’re going to explore a habit that can help you make progress towards psychological freedom and help you spot alternate paths to take in life.

Illustrations by Asia Noble. She’s incredible. You can find her here: http://asianoble.co/.

Also, many thanks to Bill Ledley for his usual insightful comments.


“Your beliefs become your thoughts,
Your thoughts become your words,
Your words become your actions,
Your actions become your habits,
Your habits become your values,
Your values become your destiny.”
Mohandas Gandhi

Two Questions
We recently discussed psychological freedom and the thoughts that prevent you from achieving it. While writing those posts, I was reminded of something my good friend Miguel suggested I do when facing anxious or uncertain situations. He challenged me to ask two simple questions:

  1. What is the opportunity in this situation?
  2. What can I do now to take advantage of this opportunity?

I was skeptical. What the hell could asking these questions do for me?

But then I had an insight. Our thoughts and beliefs are like gravity. You can’t see gravity, but it shapes reality. Likewise, you can’t see your thoughts and beliefs, but they shape your perception of reality.

If you believe the world is scary, that people are untrustworthy, or that you are worthless, you will attract events that confirm these beliefs. You’ll end up noticing and focusing on all the things that can go wrong, the negatives in life, and the ways you aren’t perfect. Then your behavior will follow. You probably won’t meet new people, or travel, or try to learn something new.

Those actions reinforce your thoughts and beliefs and you create a self-fulfilling prophesy. If you don’t trust people, they won’t trust you. If you don’t share your knowledge, people won’t share with you. Those events will then reinforce your beliefs and a stronger, viscous cycle begins.

Humans are wired to seek out information that confirms their beliefs. It’s called confirmation bias. Your mind will seek out information that aligns with your beliefs. So if you have negative beliefs, your mind adapts a mental filter that is primed to focus on negative events. We all know people in our life who act in this way. They aren’t fun to be around.

Some People Can Be Sweet

I don’t think we should all join a happy-go-lucky cult of positivity where everyone receives a gold medal. This isn’t Lake Wobegon. That would be ridiculous.

The Universe is supposed to have problems. Entropy is a property of creation. Life isn’t supposed to be easy. How could we learn without making mistakes? How could we appreciate the harvest without the hard work that went into planting the seeds?

What I’m suggesting is taking responsibility for your reactions and becoming proactive with your life. There are no negative or positive events. There are just events. Nothing is happening to you. Rather, things are just happening.

To remind myself of these facts, I started asking myself the two questions whenever I was feeling anxious, scared, upset, or stuck. They’re great questions to ask if you ever feel like, “I’m falling behind” or “I should be at a certain point by now.”

At a basic level, these questions give you an alternative frame for viewing the events currently happening in your life. If you experience a negative bias, then they give you the space to see the positive.

They offer you the opportunity (see what I did there?) to manage your emotions. It’s really difficult to be both anxious and excited about something at the same time. So, if you can see an opportunity and turn that insight into action, then you can switch your negative mood into excitement.

Getting Into The Habit
To get into the habit, Miguel and I would play a game. One of us would make up scenarios and the other one would shout out the opportunity. If one of us were talking about a problem in our life then the other would burst into how it was really an opportunity. At first I thought this was some woo-woo hippy shit. However, I gave it a chance and over time I realized it really worked for me.

  • Stuck in traffic. Opportunity to practice being patient.
  • Stub your toe. Opportunity to practice resilience.
  • Break up with the person you’re dating. Opportunity to rediscover independence or meet new people.
  • Get fired. Opportunity to travel. Opportunity to go back to school. Opportunity to volunteer.
  • You see a good looking person on the street. Opportunity to practice talking to strangers.
  • You get sick. Opportunity to appreciate life and take care of your health.

Getting Too Excited

Why They Work
Asking yourself those two questions works for a couple reasons.

First, I find that thinking of how to turn negative events into opportunity can be really funny. It adds an element of humor into life. It gives us room for the acceptance of negative events and a chance to move on. When you look at it from that angle, the questions are a form of catharsis that is severely lacking for many of us living in the 21st century.

Second, they turn your focus away from outcomes and onto processes. Seeing opportunities isn’t an outcome, it’s a process. And when you get into that process you throw yourself into the ocean of life and force yourself to swim. You become a participant rather than a spectator.

We live in a rapidly changing and uncertain world. No one is going to tell you what to do. But if you can see opportunity, you can take action. And taking action will get you closer to wherever it is you want to go.

Interview – Podstel’s Chief of Community Jason Gastaldo

I recently spent two weeks in Bucharest, Romania at Podstel HQ. My friend Jason was kind enough to sit down for an interview. Jason is an inspiring person who has little formal education. At the age of 16, Jason decided to try college out. He went to a community college, transferred to the University of Santa Cruz, then dropped out to travel and learn languages.

Jason has a passion for languages. He’s fluent in 6 languages and has taught English in Brazil and China. He is an adventurer and has extensively traveled across four continents over nine years. During that time, Jason hitchhiked over 100,000 kilometers in over 1,500 vehicles. He says, “It was beautiful to be concerned with little more than where to eat and sleep every day, to understand just how little I needed to be happy, and to live completely in the moment.”

Podstel was founded 3 years ago, when childhood friends Dan & Sam travelled the world with a dream to set up a hostel. During that journey, they visited 400+ hostels and interviewed 100s of backpackers to work out what made a great hostel.

After all the research, Dan & Sam developed a vision for Podstel to create a place that was built on principles of community, learning, & exchange, offering fun activities and inspiring workshops that empower people to grow as they travel around the world.

The first Podstel was set up in Bucharest in 2016, with plans to expand to some exciting locations across Europe in the next few years.

If you’re traveling to Bucharest, book your stay at Podstel. They also have a great tea room where you can meet cool locals while enjoying some of the best tea in the world. I promise you will have an incredible experience.

I’m grateful for being able to share this interview with you and I hope you enjoy it.

Note: Resources mentioned in the interview are linked at the bottom.

Resources & Links:

Founder’s Letter

Welcome. I wrote a letter to potential readers because I view you as stakeholders in this endeavor. You invest your time. You deserve to have a roadmap as to what you’re investing in and a North Star by which to hold me accountable.


Dear Reader,

I started Permissionless Life because I think it’s one of the greatest times to be alive. I also think things are going to continue to get a lot better. The problem is that my opinion doesn’t seem to be the current consensus. The narrative in the mainstream media and on social media is one of anxiety, uncertainty, fear, and divisiveness.

My goal is simple. I want to use this site to counter the fear narrative and replace it with a narrative of opportunity and self-empowerment. I’m not trying to be optimistic for the sake of being optimistic. I think I’m actually being a realist. As a society, we are collectively focusing on the negatives while undermining the positives to a dangerous degree. It is a group-think driven thought distortion. If we want to take advantage of opportunity we need to have the right mindset. I want to help us do that.

My optimism comes from the following underlying realizations and personal beliefs about the world:

    1. You have a lot of control over your life. If you don’t realize it yet, you can rewire your brain.
    2. Once you figure out #1, you’ll realize the average individual is more powerful than ever.
    3. Knowledge is cheap and easily accessible.
    4. For many people, the cost of experimenting with life is low.
    5. It’s cheaper and easier to start businesses than ever before.
    6. It’s easier to find people who have similar interest than ever before (and they don’t bite! …but monkeys do!).

I intend to accomplish my goal through personal writings, content curation from around the web, interviews with inspiring people, guest posts, and live chats. My posts will seek to revolve around or include these six beliefs.

The last 16 or so years have been characterized by the rise of giant tech companies that have “disrupted” multiple industries — and their success has created the reality that underscores these six beliefs. Some of these companies will be familiar: Google, Amazon, AirBnB, Shopify, WordPress, Instagram, YouTube, Udacity, Coursera, Wikipedia, Stripe, Etsy, Kickstarter, Alibaba, and Squarespace to name a few.  Dan Rosensweig, CEO of Chegg, believes those companies succeeded because they “acknowledged that the organizing principle for their industries should be around the actual consumer, not the channels built to reach them.”

That organizing principle based on the consumer is why I am so excited. Not all of us are going to become technologists and start tech companies (I hope some of you do). But many of us can leverage the tools that these companies have invented to create meaningful lives. I’m using several of them right now to provide this content to you.

All of us have a choice. We can sit around waiting for the government, some giant corporation, religion, or someone else to create structure for us or we can start to utilize these tools and empower ourselves.

I’ve been at a job I didn’t like, afraid to quit because I was terrified of not having a steady paycheck. I was afraid to travel by myself. I was afraid to have faith in myself.

This site is for those of you who sit at your desk at work bored as hell wondering how the hell you can do something more interesting. It’s for the college student who doesn’t know what to study or is anxious about getting that first job. It’s for the person who wants to travel and doesn’t know how. It’s for baby boomers who want to understand young people.

The journey isn’t easy. In order to create our own destiny, we need to accept uncertainty as normal. Every time we take a step and become comfortable, we’ll take the next step and become uncomfortable again. We’ll start by examining our psychology and how we can develop the appropriate mindsets for our current reality. From there we’ll examine the content and tools available to create our lives and meet people who are doing this today.

The title Permissionless Life is a play on a popular term in tech circles, Permissionless Innovation. Permissionless Innovation is one of the philosophies that underlies the internet. It means that no one has to give you permission to create things on the internet. There is no gatekeeper. The irony is that life can be that way too and it’s easier than ever in our current reality.

All the best,

Dino