4 things I learned from Breaking Smart about the future of work • Dan Fries

4 things I learned from Breaking Smart about the future of work

Every once in a while, I read something that massively changes my perspective and world view.

These moments are uncommon, so it’s easy to recognize the Aha! moment when it actually happens. These are often books, less often podcasts, and on very rare occasions, conversations with a friend or colleague.

This week, I was fortunate enough to have one of those satori moments, thanks to a collection of essays called Breaking Smart by Venkat Rao.

Breaking Smart is part of a project with the VC firm Andreesen Howitz that aims to explain how technology will evolve in the future. Structured like a TV show (the name is a play on Breaking Bad), Season 1 gives a detailed explanation of Marc Andreesen’s claim that, “software is eating the world.” In doing so, Venkat makes a convincing argument that hacker ethos – “the belief that being open to possibilities and embracing uncertainty is necessary for the actual future to unfold in positive ways” – will be the driving force which brings technology to dormant industries and changes the world for the better.

4 Lessons from Breaking Smart

1. View the game as something you’ll play forever

“Concerns that the game might end should not lead us to limit ourselves to what philosopher James Carse called finite game views of the world, based on “winning” and arriving at a changeless, pure and utopian state as a prize. As we will argue in the next essay, the appropriate mindset is what Carse called an infinite game view, based on the desire to continue playing the game in increasingly generative ways. From an infinite game perspective, software eating the world is in fact the best thing that can happen to the world.”[source]

What is an infinite game? It’s a game you play, forever. Why would you continue playing a game forever? Because your desire to simply enjoy the process of playing the game outweighs any specific result you could achieve from the game itself. The simple joy of creative play is the end you seek, and so you seek for ways to just keep playing.

Rather than play the game to achieve a result, ie win and horde resources from your competitors, focus on just playing the game. This is a central concept in Zen Buddhist philosophy.

Take, for example, the tale of Buddha and Mara.

On the morning before his enlightenment, Buddha was attacked by the demon god Mara. Rather than running or fighting back, Buddha simply acknowledges Mara and invites him for tea. Again and again, Mara attacks and each time, Buddha calmly acknowledges his presence. Buddha is playing an infinite game. Not once does he try to strategize nor build a defense against Mara’s attack (a short-term finite game where he would “win” the battle).

This same archetype can be seen in business. Personal development blogger Steve Pavlina explains his shift from a “resource-gaining” mindset to an “infinite game” mindset in his essay, How to Defeat KorlamiPavlina explains how he failed in business for 5 years, and that his failures ultimately were the result of him chasing wealth (trying to horde resources, a zero-sum finite game). It wasn’t until he shifted his perspective to an infinite game strategy that he was able to achieve success (and massive success):

I saw each business negotiation partly as a competition. If I got more money out of a deal, it meant that the other party got less. The more I succeeded in setting things up to maximize my financial score, the more I had to diminish the scores of others. In order to maximally win, someone else had to lose, at least a little bit. The harder I tried to win, the more friction I created that would ultimately cause me to lose.

Maybe some people are good at playing this kind of game. I wasn’t. Someone always had more resources, more time, or more expensive lawyers. The more I pressed for gains, the more I felt an opposing force pushing back against me. This led to many problems such as delays and cancellations. I could blame others for it, but the truth is that I was responsible for creating that reality.


Instead of trying to win, I began to play for a draw. I bypassed what seemed like obvious avenues for financial advancement, recognizing that it was exactly what Kolrami expected me to do. If I made those self-maximizing moves, he would simply knock me back, and I’d be worse off than when I started. Again, I had 5 years of experience to drill this lesson into me.

In practice what this meant was that I stopped trying to maximize revenue or profits. In each business transaction, I opted to give more than I received in return. I always sought to leave extra value on the table.

The game went from finite from infinite when Pavlina stopped trying to get some finite value, and instead focused on giving value, of which there is an infinite amount to give. I can certainly relate to this mindset, and it’s not an easy shift to make. However, once I’ve made the shift, it actually alleviates any anxiety about a single transaction or interaction, because I’m focused on just playing the game of giving, and nothing more.

He concludes:

You see… I don’t run my business to optimize revenue or profits. When I tried to do that, my real-world results were the exact opposite of what I wanted. So these days I deliberately make business decisions that leave significant value on the table, untapped and unextracted. Kolrami cannot make sense of these moves, and therefore he cannot counter them. Consequently, any potential competition with him remains in a state of perpetual stalemate. He cannot defeat me, and theoretically I can keep playing indefinitely.

2. Take small steps toward things of maximal interestingness

Breaking Smart lays out a novel three-step process for effective problem solving:

“[The networked world-approach to problem solving] begins with open-ended, pragmatic tinkering that thrives on the unexpected. The process is not even recognizable as a problem-solving mechanism at first glance:

  1. Immersion in relevant streams of ideas, people and free capabilities
  2. Experimentation to uncover new possibilities through trial and error
  3. Leverage to double down on whatever works unexpectedly well

Where the politician’s syllogism focuses on repairing things that look broken in relation to an ideal of changeless perfection, the tinkerer’s way focuses on possibilities for deliberate change.”

The first approach to “solving a problem” is immersion — but immersion in what? If a problem doesn’t look like a problem, then where should our attention be given? The answer: whatever is most interesting. Choose what excites you, even if it looks inconsequential to the your longer term goals.

In my own life, this was a very clear decision to quit a traditional, safe path in medicine for a far less traditional, but infinitely more exciting life of travel, business and self-development. Still experimenting with what’s working and what’s not, I’ve at least gained the ability to leverage one key aspect of my life: my time.

The way to break smart is: don’t plan a long-term vision for action before taking action. Rather, take the clear and immediate first step. Had I waited for all the answers, “what will you do if?” / “what will happen when?” / “how will you know about?” And a long list of others that could have stopped me in my tracks. I still get these kinds of questions, from myself and from others. But I’ve learned to just ignore them and take that first step.

That long journey will always be unpredictable and not always end where we expected. As Steve Jobs said, “you can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.” We can’t create a grand plan that leads to a wonderfully determinate and perfect future; but we can take that first initial step in the right direction – the direction of maximal interestingness.

The top options come from 2 different places: 1) scarcity and 2) abundance. Let’s look at the decision processes:

  1. Scarcity-based decision making: fear of not-having-enough resources, coupled with a desire to horde resources, leads to anxiety. Anxiety seeks some soothing salve to make it go away. The ego comes in and makes a grand plan that says, “if we reach this perfect future, we don’t have to worry about all these uncomfortable feelings.”
  2. Abundance-based decision-making: not concerned with resource gathering, but rather with creative play. There is an abundance of opportunities that allow for the game to be played infinitely, and any one of those works as a definite next step. The next step that we choose is based on whatever roughly looks like the most interesting option. The result is constant fun work that is “indistinguishable from play.”

There is always a “most interesting thing” and therefore there is always a next step that will be fun to take.

3. Problem solving will not look like problem solving.

My mental software is outdated, handed down from now-dated cultural norms and practices. Chief among these is a goal-setting approach to problem solving. As Venkat explains:

“In the last century, the most common outcome of goal-directed problem solving in complex cases has been failure.

The networked world approach is based on a very different idea. It does not begin with utopian goals or resources captured through specific promises or threats. Instead it begins with open-ended, pragmatic tinkering that thrives on the unexpected. The process is not even recognizable as a problem-solving mechanism at first glance:

  1. Immersion in relevant streams of ideas, people and free capabilities
  2. Experimentation to uncover new possibilities through trial and error
  3. Leverage to double down on whatever works unexpectedly well

This is the key difference between the two problem-solving processes: in goal-driven problem-solving, open-ended ideation is fundamentally viewed as a negative. In tinkering, it is a positive.”

That last sentence is telling: the difference in mindset shift is evident by how we view open-ended ideation. Think about times in your life, whether at school, business, in relationships, or wherever, where you’ve sought closure.

I can certainly think of many examples in my own life. Now try to think of examples where you haven’t sought closure. Or, perhaps, think of someone you know who excels despite having thousands of open loops in their life (I’m looking at you, Eduardo).

It’s a much tougher exercise, because your lack of closure-seeking is a side effect of something deeper: an optimistic focus on the future. Seeking closure or resolve is a means to reduce anxiety; optimistically moving toward the future is a way of delving into processes that are maximally interesting.

You can’t connect the dots looking forward. 

4. It’s a good thing that software is eating the world.

In the effort to clarify the concepts put forth by Venkat in this first season, I’ve been bouncing ideas off fellow entrepreneurs. This morning at breakfast, I made an attempt at summing up one of the main arguments in Season 1: the fact that software is eating the world is a good thing. We were discussing Uber, and how the app has already upended the taxi cab industry and will soon replace drivers altogether. He bemoaned: “but what will happen to all those jobs?” (somewhere between 5-10% of the entire US workforce are drivers).

This question is addressed in Breaking Smart:

Viewed through any given pastoral lens, any unplanned development is more likely to subtract rather than add value. In an imagined world where cars fly, but driving is still a central rather than peripheral function, ridesharing can only be seen as subtracting taxi drivers from a complete vision. Driverless cars — the name is revealing, like “horseless carriage” — can only be seen as subtracting all drivers from the vision. And with such apparent subtraction, values and humans can only be seen as degenerating (never mind that we still ride horses for fun, and will likely continue driving cars for fun).

This tendency to view adaptation as degeneracy is perhaps why cultural elites are startlingly prone to the Luddite fallacy. This is the idea that technology-driven unemployment is a real concern, an idea that arises from the more basic assumption that there is a fixed amount of work (“lump of labor”) to be done. By this logic, if a machine does more, then there is less for people to do.

History of course, has shown that the idea of technological unemployment is not just wrong, it is wildly wrong. Contemporary fears of software eating jobs is just the latest version of the argument that “people cannot change” and that this time, the true limits of human adaptability have been discovered.

The question itself is based on a faulty assumption: that there should be a clear plan for all these “jobless drivers” before we let software eat the driver-ful transportation industry. As mentioned early, a yearning for such a plan is just a means to soothe the anxiety we feel about a hypothetical future. By doing so, we miss out on the abundant, maximally interesting short steps to take right under our noses.

What my friend missed, as many other Uber-alarmists fail to recognize, is that new technology creates more opportunities for maximally interesting next steps:

“John Maynard Keynes was too astute to succumb to the Luddite fallacy in this naive form. In his 1930 conception of the leisure society, he noted that the economy could arbitrarily expand to create and satisfy new needs, and with a lag, absorb labor as fast as automation freed it up. But Keynes too failed to recognize that with new lifestyles come new priorities, new lived values and new reasons to want to work.”

That is the missing piece that Luddites cannot grasp: creative work is incredibly fun. If work is viewed as pain rather than pleasure, then of course minimizing work seems like an effective strategy. Why would anyone pursue work that creates more work?

The real question is: why wouldn’t they? Perhaps because work, to many people, is horribly un-fun, a major source of stress. When we make the transition to creating value – work no longer is something to be minimized but rather maximized.

How do we maximize work? By playing infinite games.