The ephemeral pleasure of consistency

Among the many pearls we received from the mountains of Davos, this list of things successful people do in the morning is probably the best one.

Leaving the ridiculous aside, the list points to a growing phenomenon: being it meditation, the five-minute workout, or writing (like in my case), daily rituals are becoming synonymous with living an efficient and successful life.

Since beginning blogging regularly I have struggled with balancing between the painful pleasure of embarking in long posts and the satisfaction in the discipline of daily writing. A couple of months ago I have started my own small ritual: I wake up at 6 am, prepare coffee and start writing. By 6:45, when it is time to wake up the kids, I have to hit "publish". Considering travel, weekends (where I try to focus on longer posts) and the occasional oversleeping, I have done quite well, 32 posts in 60 days.

The original idea was to compartmentalise my writing, short in the morning and long, well, some other time. What seemed to have happened instead is an increase in complacency and a decrease in writing quality. Beyond the natural constraints of time-boxing, imposing a daily habit has given room to a certain complacency that is impacting negatively my ability to embark on longer, more ambitious projects. Is my writing habit - along with all other habits - just another form of instant gratification?

Treacherous pleasure

Daily rituals appeal to our desire to be disciplined and consistent. They also allow us to turn ambitious long-term goals, like getting into better physical shape, into manageable bites. Getting something done every day is a real booster for self-confidence, but the main question remains whether they actually work.

When I started my (semi-)daily writing habit I did it for two reasons. I wanted a place to capture my thoughts and, in turn, develop a better noticing muscle. Twitter is quite good at that but its mechanics make it little rewarding if you don't have a lot of followers. The alternative would be to work through that first, but that's a bigger goal and it will eliminate the purpose of a manageable daily activity. Writing in short form - around 500 words per post - offered me a sweet spot. It is something I can manage do achieve almost every day (discipline) and gives me a strong sense of accomplishment, way more than a tweet. It felt good, for the first few weeks.

Athletes know though that muscles become lazy when you keep repeating the same workout. It is an inevitable drawback of being an amazing learning machine. Every time an exercise is repeated, our body learns how to go through it in a more efficient way. The intensity of the effort diminishes and while the mental benefits persist (you keep patting yourself on then back just for showing up). Progress reaches a plateau.

Writing differs from exercising in that the aim is to create something finite and not "simply" keep the brain active. Sticking to a daily routine is even more treacherous, there is a wide gap between our long-term goals - which might be to use writing for insight generation or more mundanely to create an audience - and the short-term pleasure of hitting "publish" every day. No sequence of short posts can deliver the sort of "insight porn" both readers and writers can attain when pushing the limits of quantity in a non-mechanical way (listicles not allowed).

Ultimately, it is a matter of patience and deferred pleasure. The more we train our brain to its daily shot of accomplishment-induce endorphin, the more we become addicted to it. Daily habits are popular because they deliver on their promise: they make life look simple and us look good, a seven minutes workout is all we need to be in shape. Deeper down, they give us the illusion that we can avoid schlep.

Schlepping through time

All important endeavours have something in common: they involve a lot of schlep. The issue is that most of us (all probably) have an innate tendency to avoid it, to live in the hope that something beautiful can come out by sole act of conceptualising it.

"No one likes schleps, but hackers especially dislike them. Most hackers who start startups wish they could do it by just writing some clever software, putting it on a server somewhere, and watching the money roll in—without ever having to talk to users, or negotiate with other companies, or deal with other people's broken code. Maybe that's possible, but I haven't seen it." Paul Graham

The sad reality is one where no shortcuts exist. You cannot think of a decent long from post by planning it, just in the same way no truly successful startup can be "designed" at the drawing board before actually starting. It is this inevitable uncertainty that blocks us from embarking on long projects. The inability to clearly see the end and defer gratification. It doesn't matter that we have memory of accomplishing something before (although it helps), the fear of wasting time is too strong.

The same is true, in particular, for a lot of complex skills where the learning curve is flat, long and painful. My personal weakness is thinking that I can learn myself out of rookie status, that reading up will make me a better writer, developer (that I have barely started), etc. It is probably an inherited theory-fetish I got from school. "Deliberate practice", the only way to get there, is a much harder and schleppy activity. It's the tedious repetition of sub-skills until you have mastered them and then move to a new one.

How do we then accept "schleppy work"? How do we "defer gratification and accept, even seek out, a degree of pain based on the no-pain-no-gain heuristic."

A random walk in Melee Island

In my case, the answer came from a surprising place: the (almost) forgotten world of adventure games. Adventure games were a big thing in the late 80's and in the 90's but they slowly lost appeal among gratification-starving gamers. Why did it happen?

One school of thought tends to blame the invincible trend of shortening attention spans. Why should we spend hours wandering through an imagined world with basically no direction, poking around, asking questions and trying to solve puzzles just to get ahead in the game? You can find scores of adventure games fans ranting about this online.

"Today all the games act like you have the attention span of a hamster and if shit isn't shooting and you or exploding for longer than 20 seconds you'll fall asleep".

A better explanation blames adventure games themselves (or better designers of adventure games). Many of them simply took the exercise too far, making a fetish out of the complexity of solving puzzles, forgetting that the actual value for the player is in going through a journey, following the plot to the end.

Great adventure games are open-ended and challenging without being frustrating. In its 1989 manifesto, Ron Gilbert (the mind behind Monkey Island and many other memorable adventure games) listed the principles to make adventures games that don't suck. In the opening paragraph he defines the type of games he set out to make:

"I enjoy games in which the pace is slow and the reward is for thinking and figuring, rather than quick reflexes."

A key aspect of that is keeping the user in a state of suspension of disbelief:

"As designers, our job is to keep people in this state for as long as possible. Every time the player has to restore a saved game, or pound his head on the desk in frustration, the suspension of disbelief is gone. At this time he is most likely to shut off the computer and go watch TV, at which point we all have lost."

When you wander through the street of Melee Island, you have an overall awareness of your goals but the rest you discover by poking around, talking to the different characters, picking up stuff. It is fun to watch someone trying playing the game today (I recently introduced it to my 11 years old daughter), the first reaction is to ask "what am I supposed to do?".

Initially, it will be difficult to measure your progress. You visit the SCUMM bar and notice that the cook often comes out from the kitchen and walks into the main room (leaving the door open behind him), the prisoner at the local jail has a terrible breath and a weird looking individual is trying to sell you obviously fake maps. As you play along, some people will help you (let's call it, the muse). You will learn that you need to distract the dogs guarding the governor house, and you will remember about the piece of meat you have seen in the kitchen. You'll be told that one of your trial consists of digging up the famous treasure of Melee Island(TM) and you'll realise that map wasn't so bad after all. The shopkeeper will offer you some mints, and when you give that to the prisoner you'll make a useful friend for later stages in the game.

In a well-made adventure game, progress is the sum of small, apparently meaningless, discoveries. In Steve Jobs' style, connecting the dots can only happen in hindsight. The key is embracing curiosity, let go of short-term rewards and start exploring. Do it every day, that's the antidote for our daily habit mania.

"You're going to get stuck. You're going to be frustrated. Some puzzles will be hard, but all the puzzles will be fair."

The rudder effect

Sailing metaphors are a much used - and abused - way to describe the act of running a team or a company. A leader is "firmly at the wheel" and "motivates the crew" to "stay on course" while facing "rough waters". It all reminds me of a set of posters I once saw in some office: large pictures of a sailing boat, people working together on at the winches, waves crashing on the sides, a skipper seriously - but calmly - looking at the horizon, a large "TEAMWORK" printed in large letters just below the image. If you find it cheesy, count me in with you. 

There is one thing though that running a team has truly in common with sailing, and that's the concept of correcting. Rubber is controlled directly, you touch the wheel and your car, bike, truck, turns. A rudder, instead, acts by (re)directing the energy created by the propeller or, in the case of a sailing boat, by the wind. The main implication of this difference is a lag between stimulus (your movement on the wheel) and action (the boat actually changing course). Partially because of that, and partially due to a lower sensibility, the change imposed by the rudder ends up having bigger impact than we originally intended. The result is "correcting", a steering style that consists of seamingly contradicting inputs to maintain a steady course.

I find the same applying to the motion of a team. It is natural for a team, at any point of time, to be erring on one particular side. Too much attention to details or too little, too much self criticism or too little, too much dialogue or too little. Nobody has yet invented a mixer for human interaction: you get tempered water by adding first cold then warm, and viceversa. A good team can recognize the erring and correct  it by opening the other faucet. 

Back to sailing. A poor skipper will apply too much force in each direction, causing confusion to the boat and losing wind. A good one will use her sensibility to delicately adjust course.

Finding time for unplanned time

This weekend we held Founders annual offsite. When planning for it, different people made me realise that we had probably underplanned it. "Sounds great", they said as they were telling me about offsites that turn out to be a little more than a long long meeting in a location far from the office. But I started to have my doubts. 

In our busy business life there is a clear bias for efficiency. We want everything to run smoothly, we want to be doers and we want to use every single minute in the most optimised way. Going the opposite direction feels sloppy and it is difficult to kick away that guilty feeling. Then, as the first day unfolds,  you start to see the magic happening. People that would normally barely have time for a quick "good morning" getting together and engaging in deep conversations, lots of side discussions getting to the bottom of past situations not properly closed, plans being made, ambitions being shared. 

I think now that feeling comfortable with unplanned time takes courage and experience. Falling back to filling every moment with an agenda item is the easy thing. Controlling for efficiency can guarantee a safe outcome, but it will never be like optimising for serendipity. It's like engaging in a long dialogue and feeling comfortable with keeping silent. Try it. 

Starting is irrational, continuing is delusional, succeeding is obvious

I came across an old post from Sam Gerstenzang which summarises pretty well what I have learnt in four years of starting companies through Founders. 

"Silicon Valley loves the mission-based startup and retroactively constructs a founder mythology. But big companies get started because someone takes the leap, she listens to encouragement, and ignores the haters until the company reaches product-market fit. That part is always the same."

It reminded me of a chapter in "Thinking, fast and slow", dedicated to entrepreneurs' innate, and illogical, optimism. It also reminded me of Indiana Jones and the last Crusade, when Indi is facing the second trial and has to take the "leap of faith" to reach the Graal. Imagine if he had simply fallen down, ending his quest, and the movie, in the most unglamorous way. Celebrating faith is easy when it turned out to be the right choice, yet any rational person should not have attempted that in the first place. 

There are a couple of ways to overcome rationality and take the leap. The first one is to be blind to the challenge, either because we believe so much in ourselves or because we are naive and wholly unprepared. The other one is to trick our mind and push any true probability assessment to a later moment. This is Paul Graham's "questions", and it still the best trick I know to get started. 

Each startup is a journey against sound thinking and probability. It begins with the irrational decision to attempt something that is doomed to fail and it continues through the delusion of persevering when any sane person would quit and do something better with their life. Until one day you make it, and it all becomes obvious.

False consciousness in the freelancer age

Every time I walk into a WeWork I can't help thinking about Marx. What do a modern, hipster, co-working space and Das Kapital have in common? After all, WeWork is a symbol of today's entrepreneurial renaissance: scruffy startups and hustling freelancers breaking the yoke of salaried labour to realise their dream. All true. But there is more under the surface. Behind the cosy vintage-looking furniture, the coloured coffee-table books and the free beer, I see an army of hard-working people struggling to make ends meet while happily handing over a large chunk of their income to a multi-billion dollar real estate company in exchange for what is basically a Dilbert-style cubicle. Don't get me wrong here: everybody is just doing their job, no scam, no forcing of anybody to take up the deal. It reminds me, tough, of the discussion around positive externalities and consumer surplus which we are receiving from our ads-driven internet giant. True, we get a lot of stuff for free, but at what real cost? Let's call a spade a spade, free beer and cosy furniture have a price. A certain German philosopher would have a name for that: false consciousness.  

My vision or yours

I have opinions on most topics. At time quite strong, often - at least I hope - weekly held. Given that what I do consists in large part in thinking about product ideas, I also have a lot of opinions about what would work, and wouldn't, in a wide range of markets. 

It's both a blessing and a sin. Every time I meet an entrepreneur working on a new product, I fall inevitably in the confirmation trap. Is she working on the angle I think would work? It's a terrible way of judging other people's ideas, and yet a very human one. I understand much better now the difference between a good investor and a rookie: the rookie will pretend - consciously or not - to know more than the entrepreneurs and seek teams that fit in his or her frame, the good one instead will remain objective, and open-minded, and let the entrepreneur show the way. Entrepreneurs are the ones creating the future. 

There is a consequence to this. A good investor will inevitably tend to be sceptical and will try to underpin her judgment by looking for facts. The team's track record, usage metrics, growth, etc. Investors are patient and often prefer to wait precisely because they understand that their judgment - everyone's judgement - is easily biased. 

But what to do when you can't wait? If you are a founder, or a co-founder, or an investor that wants to get in before any solid fact reaches the table, the only thing you have left is vision. Conscious of my bias, I will be happy taking a risk if it means following my vision. Right or wrong, it is at least mine. The only alternative is to buy into someone else's - and thus make it mine. 

So this is my decision criteria in these situations: it's either my vision or yours, in all other cases I'd rather wait. 


Here is a new challenge. I normally write in the morning, before waking up the kids. I never have more than thirty, maybe forty, minutes. Sit down, look at some notes I have typed the day before, anything new on my mind after the night? The clock races. If I am not done by 6:50 we'll be late again. Writing more than 500 words is a painful process, I published something yesterday I wasn't happy about. I should be better at throwing out an entire draft and start from scratch when it just doesn't work. Writing short is different. Open the editor, even the phone is just good enough. The cursor is blinking, what time is it already? Today I wanted to write about visions and narratives. I had this conversation the other night and I realised something about how I tend to make decisions, it would make for a good short post. Not today though. As I am typing these words, my laptop tells me I running out of battery, the charger at work - thank you apple. I will push "save and publish" now, it's 6:42, I am on time, for once. 

Netflix and the intermediate step

We see a lot of attempts these days to take us through a new technological leap. Voice computing and AR are two noticeable examples. In these moments, it is easy to follow a linear path: first, something doesn't exist, then you get a crappy version of it, then a better one and then it works. 

From a pure technology point of view this makes sense, nothing is born in its perfect version. Things, however, gets more complicated from a user - or usage - point of view. We are sold dreams that don't exist, and that annoys us. A good example is a few attempts I have seen recently to capture meeting notes by listening to conversations. We are too far today from a sufficiently good version of this, and I am also asking myself whether this is something I would ever want. 

But this is not the point. If we imagine the perfect experience as being one where: you meet with your colleagues, you start talking through the agenda, you agree on next steps, you stand up and leave the room and, magic, all notes are perfectly there - what is then the intermediate step? 

To find the answer, we need to look at Netflix. In its early days they already had a clear idea that streaming would be the future, but where did they start? The didn't offer a crappy streaming product, the sent DVD's to people. Here is what Reed Hastings says about that: 

"We always viewed the DVD by mail as a digital distribution network, and then we knew eventually... that's why we called the company Netflix and not 'DVD by mail'" 

This is the perfect intermediate step. 

Digital is getting physical

I look forward to a future where digital and physical mix and where we go back to have a mostly physical life, but digitally enhanced. 

There are a lot of good reasons to worry about that, and I have listed some in a previous post. Leaving this aside for a moment, there are also many reasons why we should be happy that our inescapable digital future that has so far sucked us into two-dimensional glassware will finally spit us back to the three-dimensional world where we belong. The future that awaits us is one where we freely utilise data generated by living in a world of bits to make choices in a world of atoms. 

An interesting example comes, not surprisingly, from Amazon whose CEO is on record saying that there is nothing "new" about opening physical stores and that the focus of the company will always be delighting customers and if customers want - also - physical stores then this is what Amazon will do. 

This recent tweet with photos taken from one of the first Amazon bookstores shows where the potential lies.

Data tracked from our digital interaction with amazon and kindle is used to create innovative classifications and smart in-store signage. Just judging from these photos it seems already a better way than "history", "politics", "fiction" or simple alphabetical sorting. It is worth noticing that Amazon can do this because we have now been buying books on its website for a long time and that, since introducing kindle, it has been also able to track what we read, what we highlight, what we finish and what we don't (and where we stop in those cases). 

Again, forget about how creepy this all sounds when we really think about that - this part will have to be solved, at least I hope [1] - and think about a future where the same level of tracking can be embedded in our physical world. The optimistic view is to see that as the time where digital loses its advantage against physical. I want to be optimistic. 

[1] Every time I think about this I see no alternative to a system where we have private ownership of data combined with the ability to give third parties access to it. 

A cultural history of...

There is a type of book or study that I often look for but seldom find. In my imagination it's called "a cultural history of.." and it's a kind of travel guide to the mentality of a place. 

Countries, large regions and even cities, have a distinct mentality. It is more than "traditions" or "cultural events" and it goes beyond a collection of ethnicities, religions and sub-cultures. A place's mentality is a persistent yet invisible fabric that guides the people living there toward a certain type of recognisable macro-behaviour. It transcends individual beliefs and political views, and it applies to the newly settled just as much as to those who have been inhabiting a place for generations. 

When I wrote about California as the "land of dreams" in my previous post, I meant the distinctive DNA that ties together Hollywood with Silicon Valley, going back to the Gold Rush and passing through surfing culture of the South and counterculture of the North. A mentality is the product of a place's history and the history of the people who lived there. However, a traditional history book will only give you the input to understand a mentality. These books are normally a sequence of events and don't spend too much time trying to understand how each event is related to the next (beyond a strict causality) and how they stratify and ossify to produce a place's mentality. 

If you move to Rome today, you will see Roman ruins next to baroque fountains next to churches dating to the beginning of Christianity next to the balcony where Mussolini declared war next to a monument erected for a Piedmontese king which is also the tomb of the "unknown soldier" from the first world war. The innate sensibility of its people, their invincible cynicism, their allergy towards authority, and the sense of tragedy mixed with comedy that pervades every conversation, cannot be grasped without understanding this past. 

I wish there were more books and travel guides that could help the foreign visitor and the occasional expat to a better understanding of this "mentality". You cannot understand a place without grasping how its people think, even when they don't know they think like this.