Books I read in 2015 and my Great Unbalancing

At the beginning of 2015 I made a few small commitments to improve myself. Call them new years resolutions if you wish, however internally I veered away from that label as it is synonymous with failure. No one ever keeps new years resolutions it seems to me. We state them and forget them. To get over that tradition of failure I decided to approach my goals with a product management type focus. So I understood what the problem was, I formulated a plan, I tracked my progress and and measured the outcome. In short I felt I wasn’t reading enough, so I set a reading goal and tracked it in Trello. Geeky but effective.

The goal was to read 25 books. This is probably a 100% increase from the 10-12 book average I managed in recent years. It is a meagre goal for some I know, but for me this represented a challenge and one I felt I could hit. And I am delighted to report that I did. So for no other reason than to revel in the achievement, here is what I read:

  1. Waking Up: A Guide to Spirituality Without Religion by Sam Harris
  2. Letters of Note by Shaun Usher
  3. How We Got to Now: Six Innovations That Made the Modern World by Steven Johnson
  4. Zero to One by Peter Thiel
  5. Meditations of Marcus Aurelius
  6. I Am Pilgrim by Terry Hayes
  7. The People’s Platform: Taking Back Power and Culture in the Digital Age by Astra Taylor
  8. Geek Sublime: The Beauty of Code, the Code of Beauty by Vikram Chandra
  9. The Second Machine Age: Work, Progress, and Prosperity in a Time of Brilliant Technologies by Erik Brynjolfsson, Andrew McAfee
  10. HIIT – High Intensity Interval Training Explained by James Driver
  11. Werner Herzog: A Guide for the Perplexed by Paul Cronin
  12. Steve Jobs by Walter Isaacson
  13. Ready Player One by Ernest Cline
  14. Storyteller: The Authorized biography of Roald Dahl by Donald Sturrock
  15. The Girl On The Train by Paula Hawkins
  16. The China Study by T. Colin Campbell and Thomas M. Campbell
  17. The End of Power by Moises Naim
  18. Mr. Mercedes by Stephen King
  19. American Gods by Neil Gaiman
  20. On Balance by Adam Phillips
  21. In The Light Of What We Know by Zia Rahman
  22. Nexus by Ramez Naam
  23. Benjamin Franklin by Edmund Morgan
  24. Digital Gold by Nathaniel Popper
  25. The Thin Man by Dashiell Hammet
  26. On the Move by Oliver Sacks

Some of these books were real gems. I especially enjoyed Letters of Note, Storyteller (the Roald Dahl biography) and The End of Power. The Steve Jobs book was also fascinating, if not entirely stuff I hadn’t already heard. On the fiction side, I ripped through The Girl on the Train, and was mesmerized by American Gods, and intend to read a lot more by Neil Gaiman. Nexus by Ramez Naam was also brilliant and thought-provoking but I didn’t feel the need to read the next two in the series straight away. Maybe I’ll pick them up in 2016.

On the down-side I thought Steven Johnson’s, How We Got To Now, was the weakest of his books I have read. It felt very lightweight compared to those others I have loved such as Emergence and Future Perfect. Digital Gold was also just like reading a long New Yorker article. I wanted more on the impact of Bitcoin. That’s not to say it wasn’t an enjoyable read, just not what I wanted.

But of them all, the one book that has planted something new and foundational in me is On Balance by Adam Phillips. The book in its entirety grew a little wearisome in the later essays as it dwelled on Freudian, psychoanalytical interpretation. But, the Five Short Talks on Excess were truly fantastic. As someone who has spent his whole adult life striving for balance, especially between work and non-work commitments, these early essays shook me to my core with the simple concept that Balance is perhaps not that desirable:

‘There seems to be something singularly captivating in the word balance,’ John Stuart Mill said in a talk to the Mutual Improvement Society in 1834, ‘as if, because anything is called a balance, it must, for that reason, be necessarily good.

This obvious statement, that balance is not inherently good, was transformative for me. Phillips goes on to show that those “singularly captivating” aspects of our life, those things that are described using excessive, but fundamentally positive, adjectives (captivating, exciting, desirable), unbalance us. Of course it works to the negative side also. But the key is that a life of balance strives to smooth out the very things that make life interesting and progressive. Those things that stir up our passions and drive us forward. When those things that unbalance us enter our lives, it is a sign that something truly matters to us. It is a clue to what makes us tick. So I leave you with this quote, which I read again and again, and is something I now carry with me every day.

It is of some significance that when we talk about many of the things that matter most to us – as the essays in this book on excess, on fundamentalism and on schooling suggest – we soon lose our so-called balanced views. So we should not, perhaps, underestimate our wish to lose our balance, even though it’s often easier to get up than to fall over. Indeed, the sign that something does matter to us is that we lose our steadiness.

Happy new year!

On Antifragility and why we need a National Entrepreneur Day

Antifragility. It’s an awkward word but one that sinks in to your consciousness as you read “Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb. As a big fan of The Black Swan by the same author, I eagerly devoured this book. It takes the findings of the Black Swan and projects it outwards in to a philosophical and pragmatic outlook on modern life. Taleb is a divisive, opinionated, funny and passionate writer and this book, like his last, seems to have settled in to place at the base of my spine where I will carry it forever.

So what does antifragile mean? Well if you have a linear scale with “fragile” on the left, the common thought is that “robust” sits opposite to that on the far right. However what Taleb introduced with the notion of the Black Swan and expands upon now, is that robust doesn’t exist as this polar opposite state to fragility. Instead, a robust system is one that protects itself against known dangers, but as a consequence is hugely vulnerable to Black Swan, or unpredictable, events. Taleb instead proposes the notion of antifragility as it represents both preparation for known fragility whilst also allowing for the unknown. Whether they be small, large or Black Swan sized setbacks, the antifragile person or organization is set up to roll with the punches and still come out fighting.

If you work in an agile software development environment, or are an entrepreneur, or work in an entrepreneurial environment, then you are probably seeing some key familiarities with your daily work-life. The much discussed innovators burden is that they need to accept failure more than success, because every setback propels you forwards in the end, so long as you learn from your mistakes and can keep going. Failures should be bumps on the road to success, not big gaping pot-holes from which you will never emerge. Taleb himself sees this correlation between antifragility and start-up, Agile business culture, so I wanted to share some of his nuggets of wisdom.

On Entrepreneurs & Start-Ups

To answer the question of where Taleb sits on the scales of opinion regarding entrepreneurs, I present exhibit A:

My dream—the solution—is that we would have a National Entrepreneur Day, with the following message: Most of you will fail, disrespected, impoverished, but we are grateful for the risks you are taking and the sacrifices you are making for the sake of the economic growth of the planet and pulling others out of poverty. You are at the source of our antifragility. Our nation thanks you.

His impassioned view of entrepreneurs and scrappy start-ups ties very closely to his views on education. He believes in trial and error, and people who forge a path with nothing or little to lose and a lot to gain.

No one at present dares to state the obvious: growth in society may not come from raising the average the Asian way, but from increasing the number of people in the “tails,” that small, very small number of risk takers crazy enough to have ideas of their own, those endowed with that very rare ability called imagination, that rarer quality called courage, and who make things happen.

Also that start-ups fertilize the soil on which the economy will continue to grow:

The fragility of every startup is necessary for the economy to be antifragile, and that’s what makes, among other things, entrepreneurship work: the fragility of individual entrepreneurs and their necessarily high failure rate.

Whilst also forging the path towards greater knowledge:

Entrepreneurship is a risky and heroic activity, necessary for growth or even the mere survival of the economy. It is also necessarily collective on epistemological grounds—to facilitate the development of expertise.

So foster that pursuit of trying new things and learning from your mistakes and failures:

my characterization of a loser is someone who, after making a mistake, doesn’t introspect, doesn’t exploit it, feels embarrassed and defensive rather than enriched with a new piece of information, and tries to explain why he made the mistake rather than moving on. These types often consider themselves the “victims” of some large plot, a bad boss, or bad weather.

On Innovation

In turn, innovation evolves out of this entrepreneurial, trial and error, antifragile spirit:

How do you innovate? First, try to get in trouble. I mean serious, but not terminal, trouble. I hold—it is beyond speculation, rather a conviction—that innovation and sophistication spark from initial situations of necessity, in ways that go far beyond the satisfaction of such necessity (from the unintended side effects of, say, an initial invention or attempt at invention) … The excess energy released from overreaction to setbacks is what innovates!

Also an interesting outcome of the antifragile thinking is that the best ideas should come via negativa:

we know a lot more what is wrong than what is right, or, phrased according to the fragile/robust classification, negative knowledge (what is wrong, what does not work) is more robust to error than positive knowledge (what is right, what works). So knowledge grows by subtraction much more than by addition—given that what we know today might turn out to be wrong but what we know to be wrong cannot turn out to be right, at least not easily.

And just like a good writer or programmer who enjoys removing words and code to reach a more elegant solution, Taleb quotes one of my favorite Jobs-ism’s:

Finally, consider this … saying from Steve Jobs: “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying no to 1,000 things.

On Risk Taking 

Risk taking is where the spirit of antifragility meets reality. There must be an acceptance of asymmetric payoffs:

To see why asymmetric payoffs like volatility, just consider that if you have less to lose than to gain, more upside than downside, then you like volatility (it will, on balance, bring benefits), and you are also antifragile.

As a product manager in software development, this quote rang so true about decisions our product team make daily:

In other words, if something is fragile, its risk of breaking makes anything you do to improve it or make it “efficient” inconsequential unless you first reduce that risk of breaking.

Taleb also proposes a heuristic against which to validate your ideas by using extremity of opinion, both positive and negative (of course):

consider this simple heuristic: your work and ideas, whether in politics, the arts, or other domains, are antifragile if, instead of having one hundred percent of the people finding your mission acceptable or mildly commendable, you are better off having a high percentage of people disliking you and your message (even intensely), combined with a low percentage of extremely loyal and enthusiastic supporters. Options like dispersion of outcomes and don’t care about the average too much.

It is also not about being right most of the time but instead being wrong with impunity and right that one time when it matters:

The frequency, i.e., how often someone is right is largely irrelevant in the real world, but alas, one needs to be a practitioner, not a talker, to figure it out. On paper, the frequency of being right matters, but only on paper—typically, fragile payoffs have little (sometimes no) upside, and antifragile payoffs have little downside. This means that one makes pennies to lose dollars in the fragile case; makes dollars to lose pennies in the antifragile one. So the antifragile can lose for a long time with impunity, so long as he happens to be right once; for the fragile, a single loss can be terminal.

On Education

Taleb is unforgiving in his assessment of the education system in the modern first world. The most powerful idea he presents is an assessment of the relationship of between education and wealth:

The implication is nontrivial. For if you think that education causes wealth, rather than being a result of wealth, or that intelligent actions and discoveries are the result of intelligent ideas, you will be in for a surprise. Let us see what kind of surprise.

I fully agree with this, now I read it, but I had never reviewed the relationship objectively in this way. Once you do, you see that entrepreneurialism and risk-taking in the US are the bases of future growth and wealth and it is this spirit that we should be fostering along with core STEM fields:

Many people keep deploring the low level of formal education in the United States (as defined by, say, math grades). Yet these fail to realize that the new comes from here and gets imitated elsewhere. And it is not thanks to universities, which obviously claim a lot more credit than their accomplishments warrant. Like Britain in the Industrial Revolution, America’s asset is, simply, risk taking and the use of optionality, this remarkable ability to engage in rational forms of trial and error, with no comparative shame in failing, starting again, and repeating failure.

And once again, what we see in software development so often now, is that some of the best developers are those passionate “amateurs” without the formal training:

Amateurs in any discipline are the best, if you can connect with them. Unlike dilettantes, career professionals are to knowledge what prostitutes are to love.

I just love that last line!

On Data

I found it very refreshing to read Taleb’s perspective on data, and particularly the dangers of big data. Working on the web you are constantly made-aware of the need to gather and use data to guide your decision-making. This is not something I disagree with per se, but something I am wary of, and Taleb captured my wariness in three words:

data increases intervention

Like a doctor who feels he must prescribe a pill in order to have a sense of agency in an uncertain situation, a product team will feel the need to constantly tinker with their product as a result of data, which is not bad in itself, but is compounded by the very quantity of data available:

In business and economic decision making, reliance on data causes severe side effects—data is now plentiful thanks to connectivity, and the proportion of spuriousness in the data increases as one gets more immersed in it. A very rarely discussed property of data: it is toxic in large quantities—even in moderate quantities.

So amid this large quantity of data, the real information can be lost, skewed or overlooked altogether:

Modernity provides too many variables (but too little data per variable), and the spurious relationships grow much, much faster than real information, as noise is convex and information is concave.

Going back to innovation via negativa, data should be used likewise:

Increasingly, data can only truly deliver via negativa–style knowledge—it can be effectively used to debunk, not confirm.

On Life

I will end with a more general quote, but one that demonstrates the underpinning of Taleb’s whole outlook and why this book just sang to me. The fact that life is about ups-and-downs. About failures and successes, and risks and rewards. To try and level everything out is to set yourself up for a bigger and more inevitable fall, like the economists who thought modern financial life had evolved beyond the boom-bust cycle just before the greatest depression in 60 years. There is no flat line through life, but if you are ready for the troughs and protected against the unknown, then the peaks will be all the sweeter and more lucrative:

The best way to verify that you are alive is by checking if you like variations. Remember that food would not have a taste if it weren’t for hunger; results are meaningless without effort, joy without sadness, convictions without uncertainty, and an ethical life isn’t so when stripped of personal risks


Managers as Curators

The dilemma of a fast growing company is one that needs little introduction. To grow is to add more of everything. More people. More projects. More customers. More money.

What is not clear to me is whether there must, and always will be, more layers. More hierarchy. More planning. More meetings. More stress.

Undoubtedly, to grow is to add complexity. If there are more moving parts then there more possible results from every action (and inaction). So much so that you cannot take all of them in to account with every decision, and some decisions will have unexpected outcomes. However some of these other items seem debatable. In fact, more than debatable. I think they naturally arise as a product of inertia rather than from any real management decision-making.

The core premise of Steven Johnson’s excellent “Future Perfect” book has been rattling around my head recently, which this quote nicely summarizes:

Increasingly, we are choosing another path, one predicated on the power of networks. Not digital networks, necessarily, but instead the more general sense of the word: webs of human collaboration and exchange

This quote broadly describes and accepts two fundamental points. Firstly that networks, not hierarchies, are the way to go. Secondly that the real intellectual horsepower in a company or any organization of people exists in the corners and at the edges of the network. The history of humanity is replete with examples of figureheads who drove through their vision despite the doubters, and so seeming to nullifying this second point. But I would counter that no person works in a bubble and there are no examples of these figureheads working alone. Always they are surrounded by a network or networks, small or large, that significantly help shape the vision. What the figurehead does is show great determination and foresight in seeing something through to the end. Either that or they are stubborn and lucky. The result is the same.

So what is being discussed here is not a suggestion we all pack up and move in to a small commune of common ideals, with no management and no leaders. I believe that strong or visionary managers and leaders can be a positive not negative force. Instead, I propose that we embrace the power of the networks as a management technique. By pushing sufficient power to the edges management can then act as a guide for the networks focus by defining the constraints within which the network operates. By constraints I mean defining what problems need to be solved and, most importantly, why. Networks are messy and noisy. Embracing it and letting the power of emergent and self-organizing behavior thrive is the opening chapter, but not the full story. It should be directed emergent behavior. How much direction is needed will be network specific, but leaders can be used to think at a broader level of abstraction than the more near-term parameters within which those in the trenches are normally restricted. Managers and leaders work to ground those problems and projects in a broader strategic context. Leadership in this sense doesn’t have to mean hierarchical oversight.

Importantly, there should not be just one big network either. There should be multiple overlapping networks, with all the hidden layers and complexity that comes with it. As Johnson says:

the power of the system comes not just from the individual peer networks, but from the way the different networks layer on top of one another.

So think of the managers and leaders as a network incorporated within lots of other networks that are self-organizing and collaborating around problems, topics, projects and interests. The information flow between the management network(s) and the others should be bi-directional. They need to feed equally off of one another. The managers must fold-in information from the internal networks as much as they do their own personal beliefs, opinions of other managers, actions by competitors and trends in the market.

This is how management changes from a job of hierarchical oversight in to that of being the teacher, the pupil, the scientist and the curator at the same time. The same statement applies in-fact to every member of all the networks. The only difference may be that their perspectives are either primarily tactical or strategic. The networks must be recursive in structure, meaning they are identical at all levels. Because I strongly believe that the Small can and must still exist within the Large.

So to reel this back in to the fast growing company issues, lets translate those initial problems using this idea of networks and managers as curators:

More people = More networks
More layers & hierarchy = Layers of networks not hierarchical oversight
More planning = Empowering the network to deliver what is best within strategic constraints
More meetings = More collaboration. If that means more meetings then fine.
More money = More money and more fulfillment from making that money

To lead in today’s societies or companies is not to construct a plan and get buy-in from below. Instead it is to be a scientist (think peer reviews and empirical evidence) and a curator. To promote network style collaboration and openly hypothesize to those networks on strategies, possibilities, scenarios and challenges. To then comb through the resulting cacophony of information for themes and threads that form the solid basis of what to do next and letting that inform what should be the next project to tackle.

This I believe can help enable companies to grow fast and grow happy.

Mental Model Mis-steps

Traveling is a wonderful way to bring in to focus just how much of your daily life is beholden to a mental model of how things work. On a recent trip back to the UK, a country from which I moved some 7 years ago, I picked up on a series of UK specific cues that my brain mis-interpreted as it varied from what I am now used to in America.

As I was driving round a small town, I turned on to street seemingly only wide enough for one car. On the left side of the road was a car parked facing me. I panicked, thinking I was going the wrong way up a one-way street (remember, they drive on the left in Blighty). It was in fact a two-way street, but it reminded me that in the UK you do not have to park facing the same way as the traffic is moving. Subconsciously my brain had established a shortcut to determining if a street was one-way that wasn’t by looking at the road signs. Instead I was subconsciously taking note of the direction of the parked cars. I had a mental model of what a one-way street looked like.

Another interesting example was how UK services, particularly web services, advertised in the mass media. The trend in the UK is for services to use a very conversational tone, along with slang and regional vernacular. Services such as and have an almost purposefully scruffy look and tone to their brand. UK audiences seem to react well to this, and I would gamble that part of the reason why is as a reaction against many years of BBC-style, regionally agnostic Queens English that most everyone north of the Watford Gap saw as ‘posh’ and ‘southern’. Having been Americanized over the last 7 years, that goes against my mental model for what a trustworthy service looks and sounds like. Services are advertised with a higher degree of slick and polish in the US, and for the most part are still regionally agnostic in tone so as to achieve the broadest appeal without falling into stereotypes. I had a mental model for what a trustworthy service should look and sound like, and my immediate reaction against this opposite tone in the UK was negative.

I characterize these jolts to my subconscious understanding of the world as a ‘mental model mis-step’. They are short-sharp shocks to your perception. They unsettle you, sometimes just for a split second, but noticeably nonetheless. It’s like tripping on an uneven sidewalk (pavement). It throws you off your stride and you lose your cool. You may even look around to see if anyone noticed. It can be distinctly unsettling. This reiterated to me how important a well designed user engagement flow is for online interactions. To interrupt a user in pursuit of their goal, even to possibly help them, is to present an opportunity when the user may lose their cool and temporarily feel insecure in their convictions. You must clear and smooth that sidewalk. Understand who is walking down it and where they want to go, and the number of people who succeed should increase.

Breaking free from learning determinism

I have been watching with interest as education becomes disrupted by a wave of online innovations, startups and visionary individuals. In particular Code School and Treehouse have caught my eye. These services have attacked the problem of professional education with a user experience / web designers eye. Using creative course structures and themes (Code School in particular), video, audio, text and presentation slides, they bring to life pragmatic and relevant topics around web development and design.

But this is the cutting edge. The education system on the whole is, and remains, hierarchical, highly structured, rigid, and slow to evolve. To imagine that a UX type approach could come to mainstream K-12 education in the near future, is far from the mark, and by no means what I am advocating for. However we are seeing the development of purely online university courses at distinguished institutions, with enrollments in the hundreds of thousands, and this a giant leap forward. It is a natural reaction to an era of crushing university debt, living with parents or bankruptcy, simply because a decision made at age 18 didn’t turn out to be how you wanted to spend your working life (if you can believe that some people are so stupid, personally I knew exactly what I wanted to do from the age of 5!). It is no coincidence that cheaper, more fluid online alternatives are gaining traction. However there are competing business models and motives at work with these university courses. They are not motivated primarily by the need to expand education to those students who cannot afford the in-person version of their course. Instead they are fighting against becoming an anachronism, like studying Latin or the classics at Oxford. The result may seem to be the same, broader access to quality education, but it is still within a rigid university learning structure, and driven by a defensive rather than progressive posture.

It is time to break free of this learning determinism.

What services like Code School, Treehouse, Cousera and Khan Academy are doing is showing a new way to learn outside of these traditional education networks. It is about the pursuit of life-long learning in an age when evolutionary leaps forward in science and technology are happening multiple times a generation. The old model of learn until you are 18 or 22 then work until you retire is already looking, if you’ll pardon the pun, old skool. As a professional worker in today’s environment, to stop learning at 22 or even 24 / 5 following a Masters, is to doom yourself to a struggle for job security come middle-age. To stay relevant and more importantly engaged and motivated, you must stay on top of developments in technology, business, society and culture, and strive to understand the broader impact in your space. Be an admin clerk, market researcher or a project manager, if you do the minimum and don’t strive to keep learning, you will will wake up one day wondering where your job went.

But, learning is not a constant pursuit. It ebbs and flows. Your interest in subjects peaks, troughs and then levels out. It’s like a Gartner Hype Cycle for your brain.

Learning Hype Cycle

The Learning Hype Cycle

This is where the existing education system breaks down. To take a course at a college, apart from the expense, you also need to join at the beginning of a semester, and the course will be designed to run long enough to justify hiring a teacher and devoting classroom space and resources. The topic is molded to the needs of the educational structure. After bending to this structure, by say starting the months after the interest peaked, the student may then arrive at the end of the course unenthused, or perhaps realize it is not exactly what they thought. It will still be a valuable experience no doubt, but you committed a lot up front, in time and money, for a mixed bag of results at the end. Online services such as Treehouse show us the potential to dip your toe in to subjects, gather enough knowledge to see it’s relevance or otherwise, and understand if you want to dig in deeper. All for $20-30 a month and a few stolen lunch breaks or hours in the evening, starting whenever works best for you. The traditional structured learning can come in after this period if required.

I arrived at this conclusion after personally realizing how you can match or get beyond 80% of the population competing in your job market through the consistent reading of one good blog or magazine, or 2-3 good books a year. Even reading and understanding a full wikipedia entry, along with clicking a few links for context, can get you a long way down the path to a level of comprehension that is beyond a majority of your competition. But here’s what’s interesting. Whether you then immediately use that knowledge in your day-to-day job is not really the point. Learning opens the doors to serendipity and and increased perception of the world around you. Our brain does an excellent job of focusing on words and concepts we already know something about. We are constantly screening out more than we know. Through targeted, semi-deep learning, you are adding to that bank of knowledge just enough that your brain will now latch on to related concepts and phrases you hear which will in turn fire off more connections and thoughts related to other topics you know. This is when interesting ideas arise, and that’s where things get more fun. If you are excited by the result, you will naturally want to learn more. You can now take that idea, and do a little more research. Run down the rabbit hole and see what’s there. If that is achieved by taking a traditional classroom based course, then great, at least you are going in to it with your idea validated by earlier learning. The advent of true online education means you are free to follow that flow of interest and see where it leads with little financial or time repercussions should it be the wrong choice.

Online courses allow us to follow our natural rhythm of learning. For some it is a more constant pursuit. Others can choose to dip in and out sporadically. But most importantly, cost, structure and tradition no longer dictate when and how you want to learn.