Why I will attend Nassim Taleb’s Real World Risk Institute workshop in New York City

In February I will attend a 5-days workshop held by the Real World Risk Institute, to get a full immersion training on risk taking, management and analysis with Nassim Taleb and a few other risk practitioners.

Anyone having even the least relationship with me, the stuff I post and the books I write knows how much I care about navigating reality on the solid ground of what we can tell and what we cannot. I have built a whole professional profile on this, since the day I started developing my knowledge and skills in agile software development back in 2003 — phew! Fifteen years next May practicing agile and lean thinking! — up to Extreme Contracts, through the first-person full-skin-in-the-game investigation of better governance models.

During these years I have been influenced by many authors, especially from the negotiation point of view, but one above all has had the deepest impact on the way I conceive my business, my management style and, to tell the truth, my whole life. This person is Nassim N. Taleb. His book “The Black Swan” unlocked a whole new mindset when I read it and his following “Antifragile” helped me connect what I had already learned on my own with new concepts about risk and the way we should cope with it.

Next February I will attend his workshop on risk management. Why?

Straight from the source

Back in the summer of 2004, after years of reading, discussing and enjoying his books, I decided to attend a five-days full immersion workshop held among the Alps by the mythical Douglas Hofstadter, author of books like “Gödel, Escher & Bach: An Eternal Golden Braid” and an undisputed authority on artificial intelligence research and philosophy in times when computing power was definitely too weak to make the best of it.

Those five days allowed me to reach four goals: I understood very deeply the key concepts behind Hofstadter’s fine theories; I managed to leave some of those theories behind, making myself aware of their true limits; I had the chance to understand the person behind the author; last, but not least, I came to share time, know and eventually become friends with a few like-minded and super interesting people who are now among the best friends of mine — no matter if they wrote a few of the best novels I’ve read or if they had the strongest influence on my will to fly.

A photo of me playing together with Douglas Hofstadter and a few friends.
Making “strange loops” with Douglas Hofstadter in Antholz, 2004

Now, in 2018, I want to do the same. I want to expose myself to this experience-pattern again.

Understanding antifragility

The most powerful concept I’ve heard about since years: antifragility. A system which thrives and gets stronger when subjected to negative stress is antifragile. A system may be robust if it can cope with negative stress, but antifragility is another step in this direction. Think of immune system to grasp the idea.

I used this idea a lot in my work in knowledge work management, trying to address the inherent risks which come along any project led in the complex, turbulent markets of present society: software development, organisations governance, negotiation, publishing, advertising, show business and communication to name a few.

Me and Lorenzo Massacci during the last Avanscoperta retreat.

I have read. I have practiced. Now I need to give it a twist and listen about risk managed this way from Taleb himself. The workshop will provide me with some analytical insight along with the chance to… well, just ask questions!

Deeper awareness of risks in negotiation

Despite the concept being only mentioned a few times in the Italian edition of my book “Extreme Contracts: il knowledge work dalla negoziazione alla collaborazione“, my whole negotiation framework is based on antifragility. Since I started experimenting with new contracts for software development in 2012 and still in my recently re-designed workshop about Extreme Contracts, I primarily cared about creating less fragility or even antifragility in my agreements and in contracts used by knowledge workers.

I have the strongest feeling that by attending next Real World Risk Institute’s workshop in New York City, I will get fresh hints and maybe even re-model parts of my negotiation framework.

This is important because I am about to start writing the English edition of my book on negotiation and I want to re-discuss everything I learned so far, relentlessly.

Meet Taleb and other people interested in risk-taking

Being confined 5 days long in a building in Manhattan together with Nassim Taleb and a few other fellow attendees will allow me to get in direct contact with one of the most influential — if not the most influential — author of my recent life. Making this happen was a key turning point in 2004 with Douglas Hofstadter, it is going to be again in two weeks, poco ma sicuro.

Will any next friend of mine be among the workshop attendees? Who knows? Maybe. One thing I am sure about though: there are very high chances that I will be the dumbest in the room, which has always been an amazingly rewarding experience on its own. I am grateful in advance to my classmates for the stress they are about to bring to my comfort zone — the antifragile system I love to exercise the most.

What is it going to happen during the workshop?

The workshop will be held by Robert Frey, Raphael Douady along with Nassim Taleb, with support by practitioners delivering real world case history on risk management, a few of them having even attended the workshop in past editions.

The mission of the Real World Risk Institute is expressed as

We are about risk taking (front office) not just something called “risk management” (back office), which should never be separated from decision-making. Some academo-bureaucrats with something to prove have an incentive to make things look complicated, while real world risk takers with skin in the game do not have such insecurity; they are not ashamed of making those things that are simple simple! The real world require vastly more rigor than textbooks and it is a different type of rigor. Most of all risk requires maximal clarity of mind.

The first aim of the institute is to foster a so-called real world rigor in decision making and codify a clean way to approach risk. Enough for me to attend the two parts of the workshop: two days about risk management and three advanced days with a more technical and analytical layout.

A web log about the whole experience

I will be glad to tell the whole story as a guest author on the Avanscoperta blog with a daily post, sharing my experiences, feelings and learnings every night. It will force myself to tidy my brain up on a regular basis and hopefully will inspire some of you readers.

See you in two weeks or so then! Definitely. I. Can’t. Wait.

[Credits: photo by Joshua Sortino on Unsplash]