Six months ago, I found myself walking away from a coffee meeting at a cafe at the National University of Singapore feeling like a bit of a douche.

The day before, I had been sitting in my apartment in Saigon, Vietnam scrolling down my Facebook feed when I saw that Nassim Taleb, author of Antifragile and The Black Swan, was going to be in Singapore. He had invited anyone in town to meet up for coffee.

Twenty minutes later, I bought a ticket from Tiger Air for a $120 round trip to Singapore. An hour later, I had thrown my weekend gear into a backpack, hopped in a Mai Linh Taxi and was on my way to the airport.

I’d just finished reading his latest book, Antifragile, and I was fixated on how I could apply the concepts in the book to be successful.

The theory behind Antifragile is that certain things actually benefit from disorder and that as the world grows more complex, it’s those Antifragile things that will benefit.

Taleb developed the theory through his work as an options trader. He systematically made very improbable bets with even higher pay offs. Most were wrong, but if he was right, the rewards were so huge as to make up for all the mistakes.

Basically, he used Stoic philosophy (to keep from going insane) and the volatility of modern markets to get rich. He did extremely well during the 2008 collapse by shorting a lot of the players in the mortgage market.

Sitting outside the cafe with a mix of students, traders and entrepreneurs, I hopped in and asked him the question that I’d been fixating on –

“How can entrepreneurs use the concepts in Antifragile to make sure they become financially wealthy – to make sure they’re successful?”

His response crushed me.

He told me that I’d entirely missed the point of the whole book. That a life well lived does not mean assuring financial success, it means having what he calls “Soul in the Game.” It means living with integrity, taking risks and exposing yourself not just to downside for yourself, but for others.

And this is why I was feeling like a bit of a douche, which was, as it turns out, a good thing in the long run.

Taleb praises entrepreneurship not because of its ability to make a few people wealthy but because of the systemic benefit of having a segment of society commit to working on stuff that is highly likely to fail – understanding that the overall systemic benefit was positive.

And I’ve come to see that is what I find inspiring about entrepreneurship. The vast majority of it on a day-to-day level is just a repeating cycle of failing and learning. It’s just a lot of struggle and hustle.

And that’s what Antifragile people do. They accept that most of what they do will fail. Most of what they say, think and believe will be wrong. And yet they keep going – doing, saying , believing, and being wrong.

 

 

The Antifragile Person: Good Criticism

I was talking to some other attendees after the meetup and one of his old friends from Lebanon said something about Taleb that’s stuck with me –

“Nassim doesn’t care about normal people. Normal people don’t get it.”

And that’s true. None of his writing makes sense unless you’ve been through “some shit.”

For Taleb it was his father being shot, his country falling apart, and the collapse of financial markets as a trader.

I’ve found it to be an extremely effective heuristic for figuring out if a relationship is worth pursuing.

How long into a conversation does a person go before they call you out on your bullshit?

The Antifragile person both appreciates being called out and aren’t afraid to do it to others. They aren’t so insecure.

Antifragile people take failure, criticism and feedback and actually get stronger.

I’ve always felt that one of my problems is that I’m non-confrontational and agreeable. Besides having a nasty habit of showing up 5 minutes late for all my meetings, I’m pretty easy to get along with.

However, a lot of people that I respect tend to be more polarizing than I am.

Not polarizing in an attentions seeking way but in the sense that they have strong convictions and express them confidently. By the nature of social dynamics, that turns off most people.

I was talking to a friend recently and he did something I would normally never do. He cut me off and said “Taylor – It sounds like you’re using this as a rationalization for a decision you’ve already made for entirely different reasons. Which is fine and may be a convenient excuse, but realize that it’s a rationalization.”

I stopped and thought about it for a couple seconds before I realized that he was absolutely right.

It was an extremely valuable insight.

One of the characteristics that people I really connect with is that they’re exceptionally good at calling me out on my bullshit.

It’s hard to find people that will do that because most people are insecure. They’re afraid that if they call people out then those people won’t like them.

And for the most part, they’re right. Most people don’t like getting called out on their BS.

And those people are fragile. If you can’t see criticism and failure and stress as an opportunity for growth then you have no ability to improve.

I’ve started being more openly critical of people lately.

You might say that’s not fair of me that I have tons of things wrong with me too.

That it’s not fair to be critical of other people when I’m just as messed up as they are.

And you’d be right. And that’s the point.

I do have tons of things wrong with me that I’m overwhelmingly blind to it. You don’t know what you don’t know.

 

“You Suck at First Impressions”

When I was living in Vietnam, a friend came to stay with me for a week.

I had met him at a conference a month earlier and invited him to stay at my apartment if he was ever in Saigon.

He took me up on it, dropped me an email, and came to stay at my place.

One of the last days he was there we went to a Vietnamese cafe and talked about people’s trajectories, futures and what we wanted out of life.

During that conversation – he told me that after he had met me at the conference that first time and we’d talked that he thought I wasn’t very interesting or intelligent, that I sucked at first impressions.

The only reason he had emailed me to stay with me was that he happened to run across my website and realized I had at least a bit more depth than he’d first thought.

Two things happened – the first was that our relationship got a lot stronger, a lot faster. For the people that do take being called out, I find that the relationships gets much deeper much faster. I feel closer to people I’ve known for much less time just because of that level openness.  You both accept that you’re human and vulnerable and mess up and trust builds much faster.

The second is that I’ve become dramatically better at first impressions. Primarily because I’ve actually known to work on it actively.

I’m actively seeking to call people out sooner after I meet them. And I’m looking for people that do the same to me.

I suspect at least 95%+ of people are offended by this.

That’s perfect. Because those people aren’t going to help you move your life forward.

I have a friend that sends me email updates once a week. He’s got this great narrative, flowy writing style that matches his personality and he shares a lot of actionable and helpful stuff.

I’ve told him before that I think he should blog instead of just send an email out. He’s an in-the-trenches practitioner and there aren’t enough practitioners out there blogging – there are way too many gurus.

And so I wrote a reply to his email where I actually gave him the same feedback Sebastian Marshall gave me. The breadth and depth of him as a human being once I got to know him was astounding. But it didn’t really come across until I’d hung around him for a while.

I thought blogging had helped me make some connections and clarify thoughts so I thought he should do it too.

I got nervous about sending the email, that he’d be offended, but sent it anyway.

He sent back an email saying he’d been in a slump lately and needed someone to push back and we started talking about getting things set up and action steps to get something going.

Don’t go out and start trying to offend people, but do reframe criticism not as a bad thing but as a good trigger for growth. Focus both on becoming more Antifragile yourself and surrounding yourself with more of those kinds of people. It’s the Antifragile people that have the power to move both you and the world forward.