We make choices every day, like what to eat for lunch. Once in a while, we make major life choices: where to live, and where to work. 

Life choices feels like we’re ordering from a menu. I’ll have… mm, living in Houston, and a job at NASA please. Obviously, that’s not how it works. Choosing is not always an active thing, and not all choices are available to us. One such life choice happened when I was 18… I “chose” to not go to Cambridge and went to NUS instead for undergrad. 

I was good at maths when I was a teenager, but only certain kinds of maths. Like trigonometry and complex numbers. I was bad at things like number theory, which was essential to do well in a Maths Olympiad. 

My school held a mock Olympiad to select people to train for the Singapore National Maths Olympiad. I placed #47, and was deemed unworthy of investment. This was Raffles Junior College, and I didn’t quite appreciate how smart everyone else was. It was the kind of school that brought back gold medals from the International Maths Olympiad.

Despite this, I filled in “Maths” for the course I wanted to apply for in my application to Cambridge University. An old, white guy flew down to Singapore to interview prospective applicants.

That interview was one of the highlights of my teenage years, because I got really lucky with the question. They cleared out the (usually very busy) library for the interviews. After a very long walk through rows of empty desks and bookshelves, I finally came face to face with the pointy-nosed chap from Cambridge. 

He looked over his half moon spectacles and lobbed me a maths problem that involved solving a cubic equation with complex number roots. There was pen and paper on the desk. I worked through the problem verbally, and solved it in conversation. I don’t remember how long it took because the mind plays tricks… ten seconds?

You keep your pen and paper, sir, I don’t need stationery to do your maths. 

The mouth of Cambridge face went like an O. I don’t remember much after that, and I walked out feeling like I had aced it. This happened before my final A-level exams, so I hadn’t had a “standardized” test or grade yet. I got a conditional offer to join Trinity College, subject to my final A-level results. Step aside Issac Newton, there’s a new kid in town.

Now, between this Cambridge interview and my A-level exams, I met a girl. I was in love, and we spent a lot of time together. My A-levels didn’t go well. 

One day, when I was sitting at home in Hyderabad, I got a letter in the post. After reviewing my grades, Cambridge decided that there wasn’t a place for me after all. I was on the waitlist. My mother was with me when I opened the letter.

Oh well, I said. It doesn’t matter because I can’t afford to pay fees anyway. My grades were not good enough for Singapore government scholarships, which was the only funding source that I knew of. 

My mother was reading a newspaper at the time, and it had an article about Infosys. This was 2002, and now you know how old I am. Narayan Murthy, the founder of Infosys, was a newly minted tech billionaire. 

My mother said: Why don’t you ask Narayan Murthy if he will fund your education?

I thought, what! What an nutty idea. Yeah, maybe, I mean… what would I do? Write a letter? Noooo. Who does that! 

I went to NUS and my life took it’s own path. 

Had any single one of these events not happened, my life would have turned out different. That’s a lot of mouthy words, it’s better represented in a diagram.

The dotted lines are alternative futures that could have happened, but didn’t. They could be regrets, they could be just idle musings. This isn’t about quantum physics and the many-worlds interpretation. I don’t really care if there’s a version of me that did, in fact, write to Narayan Murthy, and I went to Cambridge. That version is not me, it is a theoretical curiosity. 

This other version probably ended up in a bank and is some sort of finance dickhead who drools at market alphas. Dodged a bullet there. I am who I am, because of the choices I did make… and because of the choices that I didn’t. 

Events happen, and choices push us down a specific path. 

The tree of our life 

This set of circumstances happened to be available to me, and some of it was forced i.e. not really a ‘choice’. Cambridge rescinding my offer was a forced choice. We can think of choices as anything that pushes us down a specific path, when multiple paths exist. Choices are not necessarily active. In fact, they can be passive. And we make a lot less active choices than we imagine.

Active and passive are big words, so let’s ground this in feelings. 

When it feels like we’re ordering from a menu, it’s an active choice. If we have two job offers and have to choose one, for example. If it feels like we’re flowing and flitting about in the wind, choices are being made for us. 

Our tree is unique to our life context. We all have different contexts, because we are different people. Where we live, the people we hang out with, how much money we have, whether we have kids, or a mortgage, our political views, whether we are in a fulfilling relationship, the entertainment we consume— all create a unique life context.

We can plan for things, but mostly our context is just there. Invisible. We only feel it through events and our choices. 

Our life context, combined with who we are, makes our tree. Our tree is bigger than the path we take through it; it represents the opportunity space for our lives. There’s the tree itself, and how we traverse it. Choices are how we traverse our life tree. 

Forced choices is the reduction of possibilities. Even though the other paths are available in theory, we cannot take them. We can think of this as narrowing the tree. Take, for example, what happens if we take on mortgage debt to purchase a house.

It is unlikely that we will quit our job and start doing standup comedy gigs, unless we have enough money to cover the mortgage debt. The fact that we have taken on this debt reduces the possibilities available to us. 

Tree templates

Making choices, especially big life-changing ones, is a difficult process. The easiest way to do it is to borrow ideas from someone else’s traversal of their life tree. My father worked his entire working life in a government-owned engineering company, slowly rising through the ranks over forty years. This intuitively felt like a bad idea for me. I had to find my own way to traverse my life tree. 

The least stressful and stable strategy is to go on the path that is well understood and has a template. All of us subscribe to at least some templates. We have to, in order to survive in our social systems. Most of us go to school, open a bank account and agree that killing someone is a bad idea. 

Some templates we can choose to reject. But the rejection of a template comes at a price. Deciding not to get married makes moving countries much more difficult, if one of the partners needs to get a dependent visa. A piece of paper that bestows a legal status on a relationship makes some things easier. 

Spending three months of salary on a diamond engagement ring was the work of a Don Draper-like figure in the advertising machinery of the diamond industry. Such expectations form templates for our choices, and these templates are everywhere. 

Templates are not a bad thing, necessarily, because they reduce existential angst.

Bring Your Own Tree

But, you say… I will create my own path, blaze my own trail through the tree! Great, welcome to free will, or at least the illusion of it. You are also taking on a higher cognitive load to figure out your life. Imagine going through life without a bank account, or a card. It’s harder to do, so it better be worth it.

Actively rejecting templates for traversing the tree of life means that we are faced with greater uncertainty, and are more precarious than those who accept and follow a template. Clouds of uncertainty loom over our choices because we have rejected templates. The clouds remain, no matter how much we think about these choices before we make them. 

Templates result in narrow trees. If we don’t want to follow a template, it would make sense to try to broaden our life tree as much as possible. A broader tree means more available choices, and increases the chance that we traverse a path that does not fit a template. A path that works for us, is unique to us. 

Narrow trees are good, because going through life in a narrow tree means that you don’t have to think about choices so much. The only source of stress and frustration is that the tree is not broad enough i.e. we don’t have more choices.

I eat spaghetti carbonara at Italian restaurants. Every time. There are lots of choices but I ignore them because I am comfortable with a narrow tree.

Broadening a life tree is not necessarily an explicit action to take. Sometimes, we may only need to identify the choices that will narrow our life tree, i.e. result in less choices, and avoid them. If we choose to actively think about how to maximise the choices available to us, we can try to deliberately construct our life context to allow for broadening of our life tree. 

People rent homes despite being able to afford to buy one, because it gives us more flexibility. This is broadening of the tree. Broadening can (and should) be selectively applied to different areas of our lives.

Navigating broad trees 

One way to broaden a tree is to make active, risky choices. 

Risky choices are scary, because why take a risk? Risks are stupid. The riskiest choice is the choice that we know least about, and hence are unable to predict its outcome. We can tell when a choice is risky if we cannot logic our way into clarity.

Risk is the absence of information, not probability of success. 

Traversing the riskiest path allows us to gain more information, because it may put us in different contexts where we meet people, get exposed to new ideas or change our physical environment. A strategy that traverses the riskiest path is a strategy that maximizes new information. Doing this all the time is not a great idea unless we love instability.

There isn’t a right way to traverse our tree. Living with a very broad tree is debilitating, because we are in flux. We are constantly in exploration mode, and not in exploitation mode. We have to find the balance, just like a contextual bandit algorithm does. Sometimes we broaden, then we narrow, then we broaden again. 

Broadening can be uncomfortable; we are operating out of our comfort zone. But we feel alive, because information-heavy experiences are richer. If done right, we have a better chance to reject templates for traversing the tree of life. 

Be ready to be constantly uncomfortable. Be comfortable with uncertainty. 

I first wrote this three years ago (late 2019), to explain my approach to choices to a friend. I think I go through life with the broadest possible tree that I can handle at any given time. It’s not fun. And then I find myself wanting a narrow tree. And then I feel like life is boring. Then I want to broaden the tree. Then I feel like I need to ‘grow up’

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Games are constructed universes. 

When we say universe, we think of The Universe, with all the dark matter, stars and galaxies that the Hubble Telescope shows us. The Universe is huge, and we are a tiny part. The Universe may not be The Universe, but a part of a multiverse. Many multiverses, even. Types I, II, III and IV. A Type IV multiverse is a mathematical structure. My head hurts, just like yours does.

The Universe feels theoretical because it is not what we perceive and generate in our brains every day. Our inner universe has feelings, emotions and human connections. In my teens, my universe consisted of going to school, my family and immediate friends. I grew up in a factory township 30 km from Hyderabad. People from the city were different, they went to parties. There was no way I could understand what their universe was like, because I had no access to it. Our inner universe is heavily influenced by what we’re exposed to.

Games are constructed universes. Someone sets up the rules, and we play. The game acquires meaning when players have feelings and emotions. Monopoly, for example, evokes strong emotions every time I think about it. A constructed universe is only valid if we accept the construct. Age of Empires asks us to imagine that we’re a small tribe wanting to build an empire. If we don’t believe in this mission, or don’t like it, we’re not going to play the game. 

There can be an infinite number of constructed universes but only a finite number of them exist, and some work better than others. Why is that?

Now is a good time to define a game. There isn’t a standard definition but we all know what a game is, right? I offer you a working definition for the next few minutes. Games are patterns of repeated behaviour. Loops. 

Improvisers talk about finding the game in a scene. In improv, the game is a repeating pattern of fun. In this improv scene, Stephen Colbert is an old black woman, back in her hometown after a very long time. Steve Carrell is the unknown companion who is ignored by everyone else. That’s funny, so that’s the game. All the characters that show up after that have figured out the game, so everyone only talks to Colbert and ignores Carrell, acknowledging him only in passing oh, very nice meeting you, sir. Steve Carrell has figured out the game, too. He “plays” by standing in a corner and looking incredulous. Improv players know what to do because of this loop structure.

Loops of repeated behaviour happen at different time intervals in games. Candy Crush has a repetitive core action that happens every second: swapping candies. 

A core loop happens every few minutes. Candy Crush players really care about what level they are on, because the core loop is driven by accomplishment.

“Meta loops” are loops that aren’t the core loop. Running out of lives in Candy Crush is one such loop. This enables two loops, one that brings the player back to the game in a few hours, and one that encourages the player to spend money. The money loop is driven by impatience.

Loops are built to encourage players to behave in specific ways. There is no reason to pay for five extra lives in Candy Crush when you can change the time on your phone, or wait for two and a half hours. The rational consumer would wait.

Someone designs a loop and we, the people, bring our humanness to the table. Humanness drives us through these loops. Evolution has shaped our core drives, and designers exploit them to build loops of repeating behaviour. 

Everyone outside the games industry marvels at this mysterious power. They want gamification, which is a horrible concept. Imagine an entire creative field reduced to a -ification. TikTok is social filmification of songs, duude. That’s how ridiculous gamification sounds to games people.

Gamification implies that you can take a thing, slap some magic on it and suddenly, people’s behaviour will change. Games take something that is already within us: our core drives, and tap into them. We’ve encountered two so far: impatience and accomplishment. 

We are also driven by scarcity; a word beloved by NFT projects. Just make them scarce, give it exclusive feels and people will buy them. But where’s the utility!?

Ten years ago, we wanted to gamify everything. Today, we want to add utility to NFTs. Same poo, different smell.

Why do NFTs exist?

NFTs are smart contracts that live on a blockchain. We should ask every NFT creator: why are you on the blockchain/ web3? Why can’t this be done in web2, a good old website or an app? NFTs give us two new capabilities: provenance (proving who owns what, and a trail of transactions), and the ability to encode a creator cut.

The creator cut is important if an NFT creator thinks like this: 

1. I create digital assets that people want
2. I make awesome/useful stuff, so people will want to trade my assets. I deserve a cut of every transaction
3. It is impossible to get a creator cut for digital assets traded in web2. Web3 has smart contracts that allow me to get a cut whenever my asset is traded

The creator cut is unique tech here, and it has spawned a gold rush to create digital assets in web3. 

Most of us think NFTs are useless, and people who buy them are idiots. We thought virtual currencies and microtransactions in games were stupid in 2007. We laughed at the poor souls who bought purple trees for $1 on Farmville, while Mark Pincus and Facebook were laughing for other reasons. Zynga unleashed a revolution in Facebook games that carried on to mobile and didn’t stop. By 2017, virtual currencies and microtransactions in games had gone from laughing stock to the dominant business model in the games industry. This happened simply because the capability for microtransactions at scale existed for the first time, and people built products that exploited this new capability. 

The new capability that exists now is the ability to enforce a creator cut.

Our ability to understand something is not a predictor of its success. If anything, there’s a negative correlation that increases with age because we don’t get these damn kids. smh.

To infinity and beyond

NFTs have a price, and can be traded, so we can think of them as assets. Assets have value. Talking about the value of NFTs tends to start Twitter feuds, so let’s express it with unbiased mathematics. I present you… an equation. 

Creator revenue from an NFT

=

Mint price (the price paid for the first sale)

+

Creator cut x Number of trading loops x Average value of each transaction

There’s four ways to maximize the money one makes from creating an NFT. Have a high mint price, take a big creator cut, have a lot of trading loops or ensure that the price keeps going up with each trade. 

NFTs that made the news, like the Beeple artwork that sold for $69 million, were NFTs where an auction mechanic drove up the mint price. Auctions are great at upping the mint price, but they don’t necessarily enable a trading loop.

The first trading loop happens when the holder of the minted NFT sells it to someone else. At some point, this person would sell it on to someone else, and that would be the second trading loop. 

Creator cuts only become important if there are a lot of trading loops, or the price skyrockets. To begin making more money from secondary market sales than the initial mint, you would need 40 trades at a 2.5% creator cut. This assumes that the NFT is sold 40 times for the mint price, which is unlikely. But we’re looking for a high number of trading loops, not like… five. 

We’re on web3 because of the creator cut, so we’d want to make assets that can be traded a lot. There’s no reason to limit the number of trading loops. We might as well go for infinity.

This is not I create digital assets that people want to buy 

It is I create digital assets that people want to keep buying and selling

HODLing an NFT in the hope that someone will want it later does not enable a trading loop. We are thinking that the price will keep going up. This isn’t just a hope, the community might take action to ensure that this happens e.g. by buying up NFTs available on the secondary market to drive up the floor price; sweeping the floor.

Infinite trading loops are really important because they create continuous conditions that bring in new NFT traders. To enter the trading loop in the first place, we have to believe that the loop will continue to exist forever. At least until we want to sell it to the next sucker who believes that the loop will go on. For NFTs to be mainstream, this would need to work for everyone beyond crypto bros and NFT enthusiasts. The loop really does have to exist forever. It can’t be a Ponzi scheme. Successful NFT projects should look like stock markets with high trading volumes. But that isn’t happening.

One reason is that most NFT projects are on Ethereum. High gas fees means high transaction costs. NFTs are expensive and less trades happen. NFT projects need to have low trading costs to even have a shot at enabling trading loops. 

NFT projects and marketplaces love talking trading volume. About 500k ETH ($1.5 billion) worth of Bored Ape Yacht Club NFTs have been traded so far. It’s the hottest NFT project in the past year. Trade volume numbers are sexy, but they don’t measure trading loops.

The trading loop in Bored Ape Yacht Club (BAYC) is driven by belonging. The NFT is an entry ticket to the Club, and the club will do these awesome things. That’s vague because it is. The utility doesn’t matter, because the trading loop is broken.

Once you belong, you don’t want to un-belong. The only reason to un-belong is if the NFT stops being useful to you. It’s the most buzzy NFT project in the past year, and the number of trading loops the entire collection has gone through is less than 1, which means that 10,000 BAYC NFTs have been traded less than 10,000 times. In the last 120 days (November 2021 to March 2022), there have been 3,303 BAYC NFT trades. (Thanks to the team at cryptoscores for this data)

Lowering transaction costs has a dramatic effect on the number of trading loops. Boss Cat Rocket Club, on the Cardano blockchain, is a project similar to BAYC and every NFT in the 9,999 cats collection has been traded at least 25 times. 

If a trading loop is finite, then once the loop reaches its limit, NFTs don’t get traded. That means there’s no continuing benefit for the creator and the community, and the project dies. NFT projects have to keep the trading loops going. 

Most NFT projects are driven by scarcity, belonging and ownership, which tend to result in HODLing and finite trading loops. This is why they need seasons, or collaborations with other projects, while they’re trying to figure out utility. We can’t just add utility later, we’ve got to bake it in. Counterintuitively, we have to bake it in such a way that it incentivizes trading, not HODLing.

Mobile games do seasons as a last resort, only when the core loop stops being effective, and needs some help. Seasons create a months-long meta loop. 

Problem is, seasons and new NFT drops don’t always create reasons to trade existing NFTs in a collection. They don’t spin the same trading loops, they create new ones. That’s not a bad strategy, because it works. But it’s much less effective and scalable than if the core trading loop is powerful enough that people will do it naturally anyway. At best, seasons scale linearly and have a diminished effect over time.

If everyone’s doing this, NFTs are not scarce anymore.

Projects where trading the NFTs is a game are very interesting because there’s a high chance of finding infinite trading loops.  Games lend themselves naturally to loops because… games are loops.  

Cryptokitties is one of the first successful game NFT projects, even before art NFTs were a thing. Kitties are bred, evolved and traded in Kittyverse. In theory, it has an infinite trading loop. It was built by Dapper, the same company that did NBA Top Shot, where iconic moments of NBA history are minted as NFTs.

Is NBA Top Shot a game with an infinite trading loop? You decide.

Constructed Universes, not metaverse

We’re building the “metaverse”, and the tech community is excited because the building blocks are coming together. AR, VR, cryptocurrencies and NFTs are already here.  Brain-computer interfaces are not consumer-grade yet but when that happens, we won’t need haptic suits and VR glasses. We can do full immersion through sensory substitution. 

Builders are excited about building the metaverse but no one is really asking people why they would want to be in the metaverse. This is build it and they will come. 

We see this mindset every time there’s a new way of doing things in the world. Eventually, we need to build things that users want. 

Okay, so what do users want? No one’s going to tell us, we have to try things and see what sticks. 

Okay, so what’s going to stick? That’s a slightly easier question to answer because the last fifteen years of consumer tech products and games have been a battle for user acquisition and retention, and we have learnt quite a bit. 

Sticky products means that we’re trying to build loops of repeating behavior that tap into a human’s core drive.

All the things that drive loops

Understanding human motivation is big business (and research area), so everyone has an opinion. If you ask Bollywood films from the 1970s; money, power and revenge drives people.

The OCEAN model identifies five big personality traits: Openness, Conscientiousness, Extraversion, Agreeableness, and Neuroticism. It is the bestest, most researched and  backed-up-with-data model. 

This stuff feels incomplete because it is focused on interaction between people. We’re building universes, so we need something that captures the complexity of interacting with the universe itself.

Constructed universes share three design features with The Universe. 

1. There are other people in the universe
2. The universe is meaningful to the people in it 
3. The universe has resources

This allows us to ask specific questions about what drives us in The Universe. How do we interact with other people? How do we find meaning? What is our attitude to resources?

When we interact with other people, we are driven by belonging, pride/envy, competition and cooperation. 

We find meaning in the universe by accomplishing things, overcoming barriers, expressing our creativity, feeding our curiosity and by participating in stories. 

Our attitude to resources is driven by scarcity, impatience, ownership and unpredictability.

When I was a PM in games, I learnt how to spot loops in other games. When I see loops, I see the designer’s intent, so I can no longer play a game with the innocence of a player. I see loops everywhere. Not at all loops are good or effective, but everything wants to be a loop.

Where’s money, power, love, sex? Laughter? This is my take, from being in the gaming industry, and building on lots of existing work on core drives. I formalized it during my work with Activision building training material for their product managers.

Every digital product has a behavioural loop that is driven by one of the things on this list. Money, you will notice, is not on this list. That’s because something else drives us to seek out money. For example, we want to buy a bigger house because we feel envy of other people’s houses, and pride for the ownership of our own house. Mobile games taught us that one loop may not be enough, you need many loops working at different time intervals to build a successful, sticky, constructed universe.

There’s no such thing as a good drive, bad drive, powerful drive or weak drive. It depends on the context, and what we’re trying to build. We don’t get to choose the drive we want as designers, the drive already exists in people. What matters is that we identify the drive accurately and tap into it.

It’s all a game, you say

People in constructed universes are real

They live, laugh and play in them

They have meaningful experiences, that makes the universe real

All universes equally valid

All universes equally real

So what? 

I work with a team to trade NFTs in projects with low transaction costs. We operate like a fund, in the sense that we want to make money in a repeatable way, following an investment thesis. We find ways to bet on projects that have infinite trading loops.

We want the entire NFT space to succeed. All these words about universes, core drives and infinite trading loops need to actually turn into great products that people want. 

But first, a crash is coming. 2021 was the year when NFT projects launched with the promise of building trading loops in the future. 2022 will be the year of dead loops, and we’re going to declare NFTs a fad, especially on Ethereum mainnet. The people who focus on building long-term, sustainable, effective trading loops will rise through this noise.

We’ve made a loop designer tool to help people making NFTs, or any loop, really. You can find it here. 

————————

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We are creative, i.e. we are capable of making creations— building products in the broadest sense of the word. We are product producing machines. We are not like the machines we might see in a Tesla factory, ruthlessly efficient and cranking out products in an assembly line (and still missing production targets heh). We are not soulless, metallic and clangy. We break down a lot and need constant maintenance. We’re the worst kind of machine there is. 

The language we use to talk about our lives, our world, frames how we see it. 

One way to think about a full-time job is that you rent your body and mind to someone for 40 hours a week. In return for the use of the asset that is you — thank you for signing the contract, by the way — that someone pays you a monthly rent. They understand that there will be physical damage to your body over time. They have a comprehensive health plan. Mental damage, what’s that?

When I was growing up, my father would talk about his job. I just finished 25 years of service. I have 15 years of service left. He was a servant, he served the company. The government-owned company rewarded loyalty, happy to play the role of benevolent master, by not asking people to do too much. It was possible to have a work-life balance and tons of benefits without the danger of being fired. This was the dream of the industrial age, and public sector jobs.

We are better than that now, yes? We no longer serve a company, we play a role in the company. Joining a company is like auditioning for a play. We are actors that wish to play a role in a shiny, new production. If we don’t like our play, we audition for the happier-looking, better-paying production next door.

Some of us desire to be more than actors in a play, we want to be the directors and scriptwriters in the Great Drama of Our Life. 

This desire led me to stop working full time and spend more time on creative projects. The most pressing project was (is!) a Sci-Fi novel about merging brains. The first question on my mind was— do I expect to make money from this? Er, no. That’s a lot of pressure. 

Was it a side hustle? It started as one, and quickly demanded more time from me. A full-time job took up all my time and energy, so a side hustle would remain exactly that: a side hustle.

Ni hao ma, do you speak English?

When I was making the transition, I struggled to find the right language to describe what I was trying to do. Finding the right language was important so I could describe my life to myself. If I did that, I could explain myself to other people. As much as I wanted to say I don’t care what anyone else thinks, the reality was that I needed the support of the people around me, and I had responsibilities, so I had to externalize my thoughts and make sense of them. 

I am burnt out, and I cannot work any more. No, no. That’s not the narrative. I want to spend more time writing, and I’m going to reduce the amount of time I work for money. Ah! That’s my narrative. 

I am a writer now. No, no. That’s not the narrative. One can’t call themselves a writer unless one is trying to publish. And I wasn’t trying to publish any time soon. I was just focused on buying creative time in a sustainable way. 

Someone said— why don’t you find a contract gig for 6 months, bank enough money for a year, and write your book?

This felt wrong, because it wasn’t sustainable. What if it took longer than a year to write the book? What if I wanted to write more things? The book is not going to make money, so then what? Do I go back to working full time? I don’t need that kind of pressure.

I was looking for a new way to structure life, not for the next year or even five years. A sustainable solution is one that could work for the rest of my life, until I die.

I also wanted to protect my creations from monetary pressures. I could take my time, and write whatever I wanted. I was buying creative freedom. I was also trying to buy time to work on creative projects. 

I have to pause here and say that this was my approach, and unique to my context. YMMV. No, your mileage will vary.

This gave me some language to start. I was trying to lead a dual-track life. Both tracks were equally important. 

Each track had a different goal. The goal of the work for money track was to make enough money to live while staying within the bounds of 40% working time. What was the goal of the writing track? Publish a book? Write a book? I needed to learn to write better first. This was my goal: be a better writer.

Buying creative time sounds really good in theory, but I quickly ran into two problems. One, there is no easy way to work 40% of the time and make enough money to survive. Two, there is no structure to creative time. I could do nothing for days and it was okay. Being a better writer is nice to say, but not exactly measurable because there are no outcomes to measure.

I began to get very anxious that I wasn’t making money, or any progress even, on making money. I had all these ideas. That gives them an air of importance they don’t deserve— musings are more appropriate. Maybe I could start an online shop? Oh, can I write online for money? What about affiliate links? I used to be a product manager. Can I be a freelance product manager working two days a week? Is that a thing? Apparently not, it is inherently a full-time job.

Opportunities grow on trees

I needed to figure out this money thing because it was an enabler for my creative time. This was a problem that needed solving. Luckily, my time as a product manager trained my brain to work through messy situations like this. 

Opportunity solution trees are used by (some) tech product teams to help make sense of the chaos and randomness of their world. When we build new products, we are trying to address someone’s needs. It doesn’t matter what we can do, all that matters is that we meet the need. 

What the hell is an opportunity solution tree? Let’s say we own a brunch restaurant. By some miracle, we’ve survived the pandemic but now we need to make serious monies to stay in business. We call a management meeting, sit down in front of a whiteboard and say… right, people! Welcome to the Greatest Brunch Restaurant Brainstorm. How might we double our revenue?

A confident voice pops up from the back. We double the prices! 

Ah yes, a grand idea! Let’s write that down. 

What else? Any other ideas?

Emboldened by the charismatic back-bencher, another voice: We double our customers!

After trying really hard to not roll our eyes, because this is a brainstorm and we want to encourage all ideas, and yes-and everything… we say, yes! And… maybe we could get more families. Ooh oooh, let’s sell booze!

Wow this brainstorm is really going places. Let’s write these down before we forget. 

Then the head chef says: I can make a breakfast version of Spaghetti Bolognese?! This time, we actually roll our eyes. How is that going to double our revenue, Chef Pierre? We’re about to move on to the next idea, because what the hell does a chef know about business, when the immovable Chef Pierre interrupts: I think people will like it

No they won’t

Yes they will. It’s insta-worthy

No they won’t

People want to take photos of food, monsieur

No, they don’t. We are not that kind of place

And so on. Eventually, we compromise and say okay! Let’s try it.

This is a different type of idea, because it attempts to address a user’s needs. It’s testable, so it is possible to iterate towards success. The other ideas are solutions. We try them once, and we get stuck if they don’t work. 

A few years of building these trees has taught me that: 

1. We jump to solutions instinctively
2. Opportunities and user needs exist in the world, we just have to notice them
3. We can imagine many possible solutions to address an opportunity
4. We can design an experiment to test if this is the right solution for the opportunity, and to see if the opportunity really exists.

I started making an opportunity solution tree for my work for money track. Starting with the goal of making enough money to survive. 

Everything that looked like ‘get a job’ was a solution with no opportunities attached to it. I was trying to find ways to pinch money out of companies without having to actually work there. It took me a long time to realize that a job hunting mindset (please please hire me) is the wrong way to approach this. 

So I had to dig deeper to find opportunities that I was uniquely positioned to take advantage of.

The opportunity that actually led to a gig was “CPOs need a minion”. CPOs are Chief Product Officers. I hounded all the CPOs I knew and asked if they needed a minion. One of them did, and that got me started. Phew!

It is important to say that this was my opportunity-solution tree, for my context. Your tree will look different, because you have different goals and you are good at things that I am not. 

It’s true what they say: anything new is gonna be twice as hard and take twice as long as you think. Thankfully, I had banked 18 months of savings before quitting full time work in November 2019. In my case, it felt ten times harder and took four times longer. I thought I’d figure out the money-making in three months, but it took me more than a year. The pandemic didn’t help.

Tracking creativity

I had freed up time to write but I didn’t know how to make use of all this time that I had created for myself. There was no clear goal. I was anxious and worried a lot about the future. It was hard to focus. I was constantly stressed, and everyone — including me ,  was wondering why the hell I couldn’t get anything done.

A badly managed product team feels exactly the same. I know how to fix this! I spent 15 years as a product manager trying to avoid this catastrophe. I needed to think in terms of objectives. I needed OKRs — Objectives and Key Results.

If someone tells me they do OKRs for their personal life, I mock them to the moon and back. Silently, in my head of course. When I first did OKRs in October 2020 — for Q4, gawd, I shared it with a PM friend of mine and was promptly, and rightly, laughed at. I would have done the same.

If you already know how OKRs work, skip ahead. Don’t forget to laugh first.

We start with the objectives. They are strategic in nature and broad AF. For example: be the top video destination for kids.

Wow! How do we do that? We come up with KRs, Key Results, that we can measure ourselves by. The key thing, ahem, is that key results are not things to do. It is the results that we want to measure. We could say that launching a product is a key result. It’s done, woo! Party! Launching is a binary thing. Either we have done it, or haven’t. It’s pass/fail. Who’s administering this exam?

Or we could get a 1000 kids using the product. Building the thing is not enough. What we really want is for people to use the thing so that we can get feedback, and build a better thing. Wording a key result like this means that we have to find the 1000 kids. We can’t just build the product, we must also figure out growth. 

This is not pass/fail. It’s okay if we only get to 500 kids. Or 800. Or 100. We are going in the right direction, we are not at zero. The only disagreement is about the speed of progress, not on whether we are making progress.

Writing a good KR is an art form. Especially in a team setting where everyone has different worldviews. And this is where a product manager comes in. They bring everyone together and tread that fine line of listening to everyone, getting it done, and not wasting people’s time in hours of ‘OKR sessions’. Come on, again? We have real work to do.

So I drafted some OKRs for my life, and was promptly laughed at. These are my OKRs from earlier this year.

I don’t achieve most of my OKRs. These KRs were not supposed to be hittable, they were meant to push me in the right direction. 

You are not a product

OKRs and opportunity solution trees are part of a product manager’s toolkit in tech companies. So this begs the question— why does a product manager approach help to structure a creative life? Is it simply because I was a product manager, so this is the only way I know how to do things? It’s certainly a part of it.

But am I a product? 

We are not products, we are creative people. We are capable of making products— we are product producing machines. The difference is that if we are a product, we must figure out how to sell ourselves. Product producing machines make things, work out what to put out in the world and think of each product separately, with different goals. 

After two years of going down this path, I now have four tracks. This is my ‘future of work’: multiple tracks.

In the time that it took to make this diagram, and publish this post… my work-for-money gig ended. A brutal reminder that this sort of structure is very, very precarious. Multiple tracks is not an end state, it is a constant work in progress.

We are product managers, because we must manage this product producing machine that is us. We have limited time, money and energy and yet we have this immutable drive to create new things. Bad product managers don’t set realistic expectations, have no plans and are constantly stressed. Good product managers are realistic, have a clear vision and are kind to themselves.

Wanting to work on creative projects and needing a steady paycheck at the same time is hard. Giving up a steady paycheck means there is constant worry and anxiety about what is going to come next. It is extremely destabilizing, especially if it becomes existential. Do you need to buy a house? Good luck with that.

This is the trap of uncertainty and it is hard to escape from it to pursue our dreams. So how to be creative in constant uncertainty? We figure out how to live with it. It doesn’t go away. It’s the price we pay for trying to live life as a creative person. If we don’t want to pay this price, or can’t pay this price, we get a job. Most of the time, our circumstances don’t even allow us to think about living a creative life. Every week, I almost give up and find a job.

When I stopped working full time to write more, I thought writing would be the hardest thing. No, the hardest thing was figuring out how to enable the writing.

We are all trying to enable ourselves. In the passion economy, we are all product managers. We get to manage our product producing machines, and the hardest thing is to choose our own objectives, independent of what the world thinks.

We get to choose our objectives. We get to choose the language to describe our lives, which gives us power over our narratives. If we don’t control our narrative, someone else will give us one.

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