I first came across Nassim Nicholas Taleb’s ‘Antifragile’ over the summer thanks to an epic post by Kyle Eschenroeder. I vividly remember reading the post as I sat outside a pub on a glorious June evening waiting for my meal to arrive. I lost my job in May so uncertainty was high on my agenda. But at that stage, I planned to return to full- time employment. So while the model proposed by Taleb appealed to my inquisitive nature, I didn’t see much scope for applying his heuristics (or rules of thumb) to my circumstances at the time.

Fast forward a couple of months and I still hadn’t found a job. As I contemplated a return the world of freelancing, I bought a copy of the book and devoured it. Fast forward another few months and I’m freelancing once again, this time as an aspiring flâneur- someone who seeks out rational optionality.

Antifragility
But let’s take a step back for a moment to briefly explore the concept of antifragility. I’m going to paraphrase Taleb’s definition from the first page of the book:

‘Antifragile things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder and stressors and love adventure, risk and uncertainty’

To put this definition in perspective, at the start of the book Taleb distinguishes between antifragility and the other states he describes as ‘the triad’. Things are either fragile, robust or antifragile. Fragile things are extremely vulnerable to uncertainty, robust things can withstand uncertainty whereas antifragile things benefit from uncertainty.

In my humble opinion, one word sums up antifragility: flexibility. Flexibility not only allows you to survive periods of uncertainty or adversity but to gain from such circumstances. Taleb prefers the term fundamental asymmetry, where a situation offers more upside than downside.

The lack of control you experience as a freelancer feels both liberating and frightening in equal measures. So fundamental asymmetry sounds like an ideal scenario. As Taleb states in the book, ‘small may be ugly but it is certainly less fragile’. So while I’m more vulnerable to uncertainty, I’m better positioned to gain from it.

I’m not attempting to deconstruct the concept of antifragility here. I don’t want to discourage anyone from reading the book. Instead, I’m going to cherry pick (although not in the antifragile sense) a few of the heuristics that I feel are most relevant to my current circumstances. I will explain how I am attempting to apply these heuristics to my current circumstances and become, as I hinted at earlier, a flâneur.

Barbell strategy
It strikes me that a lot of Taleb’s heuristics are rooted in the world of finance. For someone who spent 20 years as a derivatives trader, I guess you can’t blame him. One such heuristic is a barbell strategy. In an antifragile sense, a barbell strategy involves pursuing a dual strategy made up of two extremes, one safe and one risky.

My safe strategy is writing marketing content. I specialise in the finance sector which pays well and offers little in the way of competition. But I’m not convinced that I want to pursue the content marketing route in the long term. So for my risky strategy, I plan to indulge in some (antifragile) tinkering.

Firstly, I want to explore transitioning into financial journalism. Without meaning to offend my current clients, I consider journalism a more meaningful form of writing. And I’m not interested in writing for any old rag, I’m aiming high (Forbes, Time et al). But I have limited experience and the competition is fierce so I consider journalism as high risk compared to content writing.

I’m also fascinated by the psychology of entrepreneurship. I read ‘Think and Get Rich’ by Napoleon Hill over the summer. Don’t let the title put you off if you haven’t read it, the thirteen rules divulged by Hill are as applicable to your career as generating personal wealth. I’m convinced one rule in particular played an important role in my relative success over the last few months. Hill suggests that to demonstrate a burning desire, you should burn bridges. Not in the sense of damaging relationships, rather to prevent any route of retreat. In my case, burning bridges meant committing to freelancing full time without the safety net of a guaranteed income.

My final option is to specialise in cryptocurrency. One of my biggest clients at the moment works in the crypto industry. Consequently I’m developing expertise in an area with limited competition. I hope to establish my credibility further by launching a new crypto coin for my coworking space or incorporating crypto payments into my ethical shopping project.

By tinkering, I hope to come to a conclusion about which option to pursue in the long term. I intend to rely on content writing to pay the bills while dedicating one day each week to experimenting with these various side projects. I hope such an approach will act as a form of validation. Without dedicating any significant resources (other than my time), I aim to work out which option offers the most upside for my career while also confirming that it will retain my interest.

Skin in the game
I’m attempting to incorporate another aspect of antifragility- what Taleb refers to as skin in the game. Taleb argues that to achieve recognition as an authority, you need direct experience in a field. For example, he rails against a career academic who teaches students about entrepreneurship without any practical experience of actually starting a business.

I strongly believe in the concept of skin in the game. For me, it implies authenticity. I chose to specialise in the trading sector because I am an active trader, not just because I find the relatively high rates attractive. One of the main reasons a client hires a freelancer is to save time. My grasp of the industry (and the jargon) means that I need very little input from a client to complete a brief (to a decent standard too, if I may brag). Several of my clients acknowledged as much.

As I branch out into the other areas mentioned above, I will continue to have skin in the game. The best way of learning about something is by immersing yourself in it. When I started writing about cryptocurrency, I immediately bought some bitcoin. By accepting Bitcoin as a form of payment in my webshop, I develop experience as a merchant.

As for the concept of ‘burning bridges’ I accidently took the full- time route when I started freelancing in August and I’m convinced it contributed to my success so far (compared to the last time I attempted freelancing anyway). I plan to research the premise further by interviewing other entrepreneurs and freelancers but I can still claim direct experience of it.

Redundancy
Taleb uses redundancy to describe a form of insurance. In the book, he uses the example of the human body having two kidneys even though we only need one to survive. The obvious way of interpreting redundancy from a freelance perspective is to create financial flexibility by building up cash reserves.

While most freelancers depend on a reserve to subsidize earnings during periods of uncertain work flow, I want to take advantage of the time and space it allows me to tinker with the options outlined as part of my barbell strategy.

To create redundancy, I applied another antifragile heuristic, via negative, to my spending habits. Taleb defines via negative as a recipe for what to avoid. It involves removing the negative rather than adding positive.

So I try to live a frugal life. I sacrifice countless luxuries that people of my age (just 36) tend to take for granted at a similar stage in life. I moved in with friends (a considerable sacrifice for someone who values his privacy). I try to stick to a meagre weekly spending budget which just about covers the odd trip to the British Film Institute.

I noticed a similar effect several years ago although I didn’t recognise it as redundancy. Once I cleared my student debt, my savings started to grow much quicker. So one of my priorities for 2015 is to clear my credit card balance. Until then, my personal finances retain a degree of fragility.

Redundancy may end up having longer term implications too. A mortgage, especially one that overextends the borrower’s resources, strikes me as a form of financial fragility. As an Irishman (although one that observed Ireland’s financial crisis from a distance), I’m acutely aware of how financial fragility can affect homeowners. As the Irish economy crashed and people lost or suffered a drop in income, mortgages approved at the height of the Celtic Tiger became a serious burden. Until I can afford a significant deposit, I intend to avoid any such burden. In the meantime, I’ll enjoy the flexibility of renting.

Optional rationality
As an aspiring flâneur, optional rationality is my goal. To paraphrase Taleb’s explanation, if I avoid locking myself into a specific course of action, I can change my mind based on new information. I can benefit from uncertainty rather than suffer any negative effects. When and where these opportunities emerge is a mystery. The concept of burning bridges might resonate with a generation of aspiring entrepreneurs. Or maybe I develop a revolutionary new business model based on blockchain technology. As long as I keep applying Antifragile heuristics to my life and career, I’m better positioned to take advantage of whichever option flourishes.