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The Rational Flaneur Philosophy

I was gearing up for a particular approach to life for years. However, while I started practising it, I was struggling to put it in words (still struggling!). My ability to express this was handicapped by the lack of a proper term to express it.

 I got introduced to this term in Nassim Taleb’s writings. It immediately struck a chord with me…a coup de foudre! And I got an anchor for my philosophy – The Rational Flaneur. All my principles in life revolves around this core Philosophy.

Let me expound this term. Two words, let’s take ‘Flaneur’ first.

A Flaneur is a traveller, but not like a typical tourist, with a fixed itinerary –

DayItinerary (Complimentary breakfast at the hotel)
Day 1City guide Tour
Day 2Zoological Park & Museum
Day 3Theme Park
Day 4….and so on & so forth
A Tourist’s Itinerary

A Flaneur is a wanderer with a curious backpacker’s attitude. He wanders from place to place, totally driven by curiosity; takes what comes his way. There is no fixed plan. One thing leads to the other; one place leads to the other. He wields a compass, not a map. He is very flexible in what path he takes, how long he stays at a particular place. While a tourist is tethered to his plan, a flaneur tinkers with his schedule everyday, based on his previous day’s experience (new information or feedback or experience).

However, there is a certain element of risky randomness or directionlessness in a flaneur’s approach. There appears to be a fair chance of getting lost in the woods!

…enter the first word – Rational

Rationality is the ability or trait of being logical. This brings an element of purpose in flaneurship. The objective is to travel and see the world with highest weighted average joy w.r.t. resources like time – spending maximum time in the places one enjoys the most, while decreasing the time spent in other places in a descending order of enjoyment. But, even before that, rationality brings an element of risk management – prevention of getting lost in the woods & never finding one’s way again, prevention of ruin….a permanent irrecoverable loss. Here’s the distinction:

TouristFlaneurRational Flaneur
Driven by a deterministic approach – a planDriven by a curiosityDriven by cautious & controlled curiosity
Starts with a fixed planRandomly picks an option which attract the mostRandomly picks an option which attract the most
Has a perfect sense of direction. Sticks with the plan no matter whatMakes a plan on the go. Choses the place & the time spent depending on joy. Plans next move based on experiences.Have a certain general sense of direction. Makes a plan on the go. Choses the place & the time spent depending on joy. Plans next move based on the general sense of direction, but influenced by the recent experiences.
Mixed feelings. Several cases where more time spent on places that were boring at the cost of less time spent on places that were fun.Mixed feelings. Spent more time at places he enjoyed. But got lost in the woods with no overall sense of direction.Achieved maximum weighted average joy trip. Got maximum bang for the buck & time!
Rational Flaneur – Brings best of both worlds!

Let’s put this approach in perspective.

The essence of the philosophy is captured in this Introductory paragraph from Incerto, by Nassim Taleb:

…while there is a high uncertainty (and causal and probabilistic opacity) in the world, what to do about it – which option to take – is always certain. Furthermore, paradoxically, the more uncertain the world’s outcomes are, the more certain the optimal policy. It is the most prudent one with the most convex outcomes, that is, the one that, first is precautionary and insures survival and second, carries the most beneficial second order effects.

There is a storm outside & there is a storm inside.

Life is uncertain. Randomness plays out in random sizes! One needs to make big & small decisions under these big & small uncertainties. But, there is an equally big storm inside, as one deals with behavioural biases under uncertainty. The external and the internal uncertainties interact and create a collective storm which is bigger than the sum of the parts. This approach puts a framework that helps one navigate through this mega-storm of uncertainty.

World is a complex place. It is a multivariate field, where multiple factors interact with one another and create a collective outcome that is bigger than the sum of its parts. This phenomenon is called by various names – Emergence, Matthew Effect or Lollapalooza Effect.

In such a Complex World, it is futile to try to predict the world in a deterministic manner and “travel with a fixed plan”. When you go with that fixed mindset, you are susceptible to make terrible, irreversible mistakes, which can lead to a ruin, leave alone a suboptimal outcome.

“Think of a car driving through the night. The headlights only go a hundred to two hundred feet forward, and you can make it all the way from California to New York driving through the dark, because all you have to see is the next two hundred feet. And that’s how life tends to unfold before us. If we just trust that the next two hundred feet will unfold after that, and the next two hundred feet will unfold after that, your life will keep unfolding. And it will eventually get you to the destination of whatever it is you truly want, because you want it.”

– Jack Canfield

While, it is important to have a general sense of direction when one is headed, but long term planning is a futile exercise, if it makes you rigid. The plan needs to be nimble, with an element of opportunism – an intent & ability to observe and course correct on the go. This gives us an ability to dynamically respond to a dynamically changing Complex environment. The American Philosopher, William James gave a nice Romeo-Juliet allegory to compare blind, fixated, planned head banging against course correcting maneuvering towards a goal.

“Romeo wants Juliet as the filings want the magnet; and if no obstacles intervene he moves toward her by as straight a line as they. But Romeo and Juliet, if a wall be built between them, do not remain idiotically pressing their faces against its opposite sides like the magnet and the filings with the card. Romeo soon finds a circuitous way, by scaling the wall or otherwise, of touching Juliet’s lips directly. With the filings the path is fixed; whether it reaches the end depends on accidents. With the lover it is the end which is fixed; the path may be modified indefinitely.”

– William James

Three layered Conundrum in Decision Making – Any significant decision making has to break through an iterative three layered P-conundrum.

  1. Possibilities
  2. Probabilities
  3. Pay-offs

As a Decision Maker, it is important to analyse various scenarios that can play out, what are their probabilities, and most importantly what are the payoffs.

The Rational Flaneur Approach to deal with the Conundrum – Survive then Thrive:

  1. Protection against ruin – An RF, first & foremost creates a defence against those possibilities that lead to outcomes of ruin or permanent irrecoverable loss, no matter how small their probability is. If he sees the probabilities of ruin related outcomes increasing, he works on his survival like a paranoid. Life Insurance, car seat belt, Gold Investing, shunning sugar, processed food and cigarettes etc all come under this.
  2. Opportunistically explore possibilities with positive Payoffs – Once, the downside is taken care of, then an RF is driven by curiosity, rather than fear. Life is a perpetual flow of opportunities; an RF explores all possibilities with positive expectancy, without any inhibitions. Reading books, networking with right people, buying stocks, setting up businesses, travel etc comes under this.
  3. Veridical Model of Justified Decisiveness – Some heavy words. In plain english, the RF let’s his future course of action be driven by empirical evidence of his bets playing out. He works with loosely held opinions, which get swayed (weighted) by the actual action on the ground (the feedback loop). He assigns higher probability to things as they occur, than to things that do not occur. The endeavours which show promise in action, get more resources – time, energy, money etc; the endeavours which show dwindling prospects, see diminishing resources.

This is an iterative process. Every success opens new frontiers. The RF evaluates the scope of ruin, and avoids those avenues. He then explores the remaining avenues with the same curiosity and course-corrects based on the feedback from the environment. In other words, this is a simple iterative “If-Then-Else” approach.

I believe that all the successful endeavours have treated their way through uncertainty in this manner. Once, the success is achieved, it all looks very deterministic in hindsight, not just to the external observer, but even to the person himself who has succeeded. We always tend to look back at past achievement as diminutive, determinstic and well though out compared to our current challenges. The 2008 financial crisis looks smaller compared to Covid crisis; The previous job looked simpler than the current one, the skill we are trying to develop today looks far more difficult than the skill we developed a few years back and so on & so forth.

“The illusion that we understand the past, fosters overconfidence in our ability to predict the future.”

Daniel Kahneman, Thinking Fast & Slow

The skill is not in knowing everything beforehand deterministically or planning everything to perfection. The skill is to manoeuvre one’s way through the vagaries of the complex world we deal with. The deterministic ways look great, intelligent and sophisticated; the RF way looks simplistic & unsophisticated. But, this simple looking approach is the foundation stone of all the rigours and successes.

To summarise the Rational Flaneur Philosophy in one statement.If you:

  1. consistently ask questions (right or wrong!),
  2. follow on the leads (feedback loops),
  3. you’re bound to find right answers!

And that is the simple looking “If Then Else” approach I put to work in various domains of life. Through this blog, I intend to write my thoughts on this approach & its applications in so many domains – investing, health, success, learning, relationship etc.

Leonardo da Vinci, the archetype of human potential followed this curiosity driven approach to a multi-faceted life. Michael J. Gelb, in his book, How To Think Like Leonardo da Vinci, draws “The Seven da Vincian Principles”. Here they are:

  1. Curiosita – An insatiably curious approach to life and an unrelenting quest for continuous learning.
  2. Dimostrazione – A commitment to test knowledge through experience, persistence, and a willingness to learn from mistakes.
  3. Sensazione – The continual refinement of the senses, especially sight, as the means to enliven experience.
  4. Sfumato – (literally “Going up in Smoke”)—A willingness to embrace ambiguity, paradox, and uncertainty.
  5. Arte/Scienza – The development of the balance between science and art, logic and imagination. “Whole-brain” thinking.
  6. Corporalità – The cultivation of grace, ambidexterity, fitness, and poise.
  7. Connessione – A recognition of and appreciation for the interconnectedness of all things and phenomena. Systems thinking.

These da Vincian Principles are intuitive & effective illustrations of a rational flaneur approach to life.

I sincerely hope you find my musings thoughtful & useful.

Cheers!