How To Thrive on Discomfort, Even if You Think You’re A Wuss: On Becoming Antifragile

“If you put the scallops in a cold pan next time, I’ll shove it up your arse!” – My cooking mentor.

“Fuck sake, just listen and do exactly what I tell you!” – My sailing mentor.

I love these memories. They’re in the same category as going in for the first kiss, winning a triathlon after months of hard training, nailing a speech, and being honest with a friend.

It might seem strange. That among my memories, these two get the call-up. They weren’t particularly enjoyable in the moment. But they’re symbolic of the journey I’ve been on for the past five years.

In highschool, I was fragile. I avoided uncomfortable situations and attention like the plague. Getting shouted at was the ultimate embarassment. The collective attention of my peers felt like the Eye of Sauron.

Now, I feel like a bad-ass. Once a primary school kid who would be on the verge of tears everytime a teacher shouted at me, I can now get threatened with a luke-warm pan up my arse, take it on the chin, and come back 10x stronger and more determined than ever.

If you’re like me, maybe you’re wondering: how the hell did this happen?

They say every man’s life is changed by a beautiful woman and an older mentor. I’ll add to that a terrifying Greek monster, a violin virtuoso, and stacking the deck of life along the way.

So, How to Thrive in Discomfort: On Becoming Antrifragile.

Let’s do this.

Inspiring Dissatisfaction &The Beautiful Woman

Man is very well defended against himself, against being reconnoitred and besieged by himself, he is usually able to perceive of himself only his outer walls. The actual fortress is inaccessible, even invisible to him, unless his friends and enemies play the traitor and conduct him in by a secret path.” – Nietzsche

Inspiring dissatisfaction is a powerful thing. Instead of being depressed by your situation, it’s a much needed shot of motivation that jump-starts a change. For me, inspiring dissatisfaction came in the form of a girl I fancied in Spanish class.

One day, we were tasked with writing and reading out loud an essay about ourselves, using a bank of spanish phrases.

The phrases were generic, so I was given a Hobson’s choice. A phrase which here means reading: “Hi, I’m Iain, I like going out with my friends, having a drink and dancing” instead of “Hi, I’m Iain, and I love avoiding social encounters of any variety”.

I read it out, and said pretty girl laughed in my face. Iain! That is not you!

(Maybe she just laughed. I’ll put “in my face” down to the sting of young love.)

I was angry.. I’d been led into my fortress, to a place I never wanted to see. But I was there, and I realised I’d become a person and was a living a life that I’d never consciously chosen. I was the shy, unconfident, serious guy. I never wanted to be like that. But, through lack of effort, I’d slipped into it, until I’d become something I hated.

I had shackled myself in high school with my thoughts, behaviours and beliefs. As a man who could not dance, I was a man who was not free.

Inspiring dissatisfaction. The force that girded my loins for the uncomfortable situations to come.

We all need some inspiring dissatisfaction from time to time. Sometimes, it takes a friend or an enemy to show you the potential you’re sacrificing by living how you are at that moment.


The Older Mentor

Looking for weight-lifting advice in second year, I stumble across Elliott Hulse. He changed my life, because for the first time, I was told the uncomfortable truth:

Nothing great was ever achieved in a comfort zone. No virtue is developed in a vacuum. Ralph Waldo Emerson: You do the thing to have the power, not the opposite.

His advice was in the limbo between scary and liberating. To become the strongest version of yourself, you need to get uncomfortable. You have to not just accept it, but embrace it. You need to take the leap of faith.

All growth needs stress. Whether this is mental growth, or building some guns under a barbell. It’s IMPOSSIBLE to grow inside your comfort zone. It’s impossible.

(What about reading? Aren’t you growing, whilst being comfortable?

No. We don’t grow by reading. Explicit knowledge dunt count for shit. It’s the tacit knowledge that counts. And tacit knowledge is only aqcuired in The Arena, where the only garauntee is a face marred in sweat and dust and blood.)

Thanks to Elliott, what had been a vague concept (socialising will be good for you!) turned into a concrete goal. Hey Iain, dude, you know that thing you’re really, really scared of doing? Yeah, that. Go do it. 

The idea of using fear as a compass to guide us towards what we need to do revolutionised my thinking.


You might not need a mentor to tell you this, but you need to appreciate the fact that there is no growth without discomfort. That nothing worth having can be obtained without effort. It’s the law of the universe, and the Price for being in The Arena.



The Greek Monster

In third year, I stumbled across an article on the Art of Manliness blog, titled “Beyond Sissy Resilience: On Becoming Antifragile”, exploring Nassim Taleb’s book, Antifragility.

Here’s the core idea.

Anything in life, – objects, companies, countries, people – are in one of three categories. Fragile, resilient, or antifragile. Each has a story illustrating them.

  • Fragile

Myth: Sword of Damocles.

Damocles is a jeded servant of the king, Dionysius. How come the king gets his every whim catered for?! How great it must be to be king…

Hearing this, the king offers to switch places. Damocles eagerly accepts, and sits upon the mighty throne. There’s just one caveat. To represent the perils of great power, Dionysius hangs a sword by a single horse hair above his throne.

The situation is extremely fragile. The slightest tremor or a rogue breath of wind would cause the sword to fall. Damocles realises that there’s more to being a king than just meets the eye, and humbly returned the throne to Dionysius.

Fragile people are Damocles on the throne. They rely on external conditions to be perfect. With the slightest of hiccups, a slight detour into the world of discomfort leaves them dead or dying.

  • Resilient

Myth: The Phoenix.

For those of you without a Hogwarts education, the phoenix is a bird of fire. When it dies, it bursts into flame, and is reborn from the ashes. In other words, the phoenix is resilient. You can’t hurt it, you can’t break it. If you kill it, it comes back.

Resilient people are like the phoenix. The steady eddies. Nothing phases them. They’ll be there come rain or shine. In uncomfortable situations, they take it on the chin and keep ploughing on.

This is where most people stop. Trying to become resilient. Sissy resilience? Taleb says there’s something far more powerful to set in our sights…

  • Antifragile

Myth: The Hydra.

The Hydra is a multi-headed serpentine monster in Greek mythology. It lives in the lake of Lena, entrance to the Underworld.

Warriors can’t kill the Hydra. When you slice off one of its heads, two grow back in its place. By trying to kill it, you make it stronger. In discomfort, the Hydra doesn’t just revert back to the norm. It becomes deadlier than before. It’s an absolute beast.

The Hydra is eventually killed by Heracles, who learns that when he cautarises the chopped off heads with fire, they can’t grow back.

The Hydra is what we want to aim for. We want to become post-traumatic growth machines. When we take a beating in The Arena, we come out tougher and more muscular than before.

It’s like Nietzsche said, “That which does not kill us makes us stronger.”

Reading this, my mind was blown. Once again, a vague destination (strongest version of myself) became a concrete vision (the Hydra). But still, the AoM article had few actionables. I still didn’t know how to become the Hydra.


Stacking The Deck in Your Favour

Even if I didn’t know how to become the Hydra, I could still throw myself into uncomfortable situations and hope for the best. So that’s what I did. I booked a flight four months in advance to Madrid, and on returning to Scotland I said yes to speaking opportunities, paid to go to an entrepreuner conference in London, and signed up on tough adventures.

Stacking the deck in your favour means signing up for discomfort in advance, preventing you from backing out. It’s human nature – if there’s discomfort, we avoid it. Stacking the deck gives us the push we need.

Surrounding yourself with hydras or hydras-to-be is another way of stacking the deck.

You are the average of the five people you spend the most time with.” ~ Jim Rohn

If the people around you are courageous, you will become more courageous. Seek out those people.

Hanging out with my friend Patrick inspired me to become more courageous, and less inhibited by the expectations of others. Plus, reading the biographies of Theodore Roosevelt, Alexander the Great and Churchill redefines what you think courage and discomfort truly are.


Focus on the Journey, and Who You Are Becoming.

Violinist virtuoso Fritz Kriesler was due to play a gig in the fabled Carnegie Hall in New York with legendary pianist Sergei Rachmaninoff.

Kriesler wanted to try something new. “Hey Sergie, why don’t we do this performance without rehearsing? It’ll be fun. Let’s try it.

Rachmaninoff, a man of the Soviet Union, is a little worried. “I don’t know… But for you, Fritz, I’ll do it.”

So they’re playing in Carnegie Hall, and about half way through the perfomance, Kriesler gets hopelessly lost. He walks back slowly, playing the violin, and whispers “Sergei, where are we?

Rachmaninoff replies, “In Carnegie Hall.

Take risks, put yourself out there, but completely detach yourself from the outcome. Do the thing not for what you’re going to get, but for who you’re going to become.

For example, ask the cute guy/girl out not because of the date, but the courage you’ll build by asking. (But obviously, if you don’t want to go on a date with them, don’t ask in the first place.)

This is far easier said than done, and it’s something I constantly have to focus on. The Carnegie Hall story reminds me to do just that.


Two Years Later..

I’m on an archaic sailing boat, battling the Pacific ocean. I’m at the bow, and the captain shouts to me to adjust a sail. I adjust the sail, but adjust another rope too.

“Fuck sake, just do exactly what I tell you to do!”

It was an intense moment. On a sailing boat in rough seas, the margin for error is small, and tiny mistakes compound into catastrophy. The stakes can’t get higher. If a man falls overboard, there’s no turning back – the wind is pushing you in the opposite direction.

Years earlier, I would’ve taken this personally. I would’ve got offended and upset. Instead, I took it in, and a few seconds later, smiled. I recognised it as an opportunity to become a better sailor. I took it on the chin, re-adjusted the rope, and from then on, listened more carefully. I was happy. One head chopped off, two heads grew back.

A couple of weeks earlier, quite the opposite happened to another of the crew. We were sailing into a pontoon berth, and one of the crew pushed us off the pontoon way too soon, completely messing up the careful line the captain had been steering.

Again, somethin like “Fuck sake, you’ve just totally fucked me up.” But instead of seeing for what it was: a mistake at the end of a long journey, the guy took it personally. Afterwards, he lamented at his abilities, saying “I’m an idiot.” He was visibly down for the rest of the day. It was the opposite of antifragile.

When I looked back at the two incidents, I realised I’d got much closer to becoming the Hydra version of Iain than I’d thought.


Summary: How To Thrive in Discomfort and Become Antifragile

To sum up, here’s what you need to become the Hydra.

  1. Inspiring Dissatisfaction

“My name is Melchizedek,” said the old man. “How many sheep do you have?” 

“Enough,” said the boy. He could see that the old man wanted to know more about his life. 

“Well, then, we’ve got a problem. I can’t help you if you feel you’ve got enough sheep.”

This doesn’t mean hate what you have. It means accept where you are, and accept that you’re not living up to your full potential. Accepting is not resignation. It means saying “I can become who I want to become.”

Inspiring dissatisfaction steels yourself for the process to come.

May require beautiful woman. Alernatively, an Alec Baldwin pep-talk.

       2. Recognise That No Growth Occurs Inside Your Comfort Zone

You can’t fight an invisible enemy. So unveil your comfort zone for what it is: your enemy – a cushy place that thrives on immediate gratification and mediocrity, that slowly suffocates your dreams until it’s too late.

Your comfort zone is the enemy. Discomfort is your friend.

Recognising this, and knowing your aim to become a Hydra is essential. It’ll reframe you’re “problems” into opportunities.

3. Know The Price for Being In the Arena

It’s not easy being the Hydra. It’s not easy being The Man in the Arena. If it was, everyone would do it.

Realise that there’s a price to be paid – discomfort. The price is feeling awkward, of feeling that maybe you’ve gone a bit too far, sweaty palms, and being OK with failure and rejection.

Are you willing to pay that price?

4. Stack the Deck in Your Favour.

Human nature is tough to counter. When the opportunity arises to ask the beautiful woman out, to stand up against injustice, to punch the bad guy in the face, to speak up in a packed lecture hall, it’s easy to pick the comfy option. Too easy.

To counter this, you’ve got to stack the deck and force yourself into the uncomfortable situation. Sign up for uncomfortable situations that you can’t back out on. Sign up for giving a speech 3 months in advance, or call the girl and say you want to speak to her about something important. Sign up on the trip of a lifetime, book yourself that flight.

5. Detach yourself from the outcome.

This is much, much easier said than done. I struggle with it, but I know that it’s essential, so I’m gonna stick it in here. Remember Fritz and Sergei in Carnegie Hall.

6. It’s about the journey.

Don’t do the thing for what you’re going to get. Do it for who you’re going to become.



So.. Damocles, Phoenix or Hydra? Where are you, and which are you going to become?


As Always,

Dream Big Start Small!

Mucho amor,