Shockingly Happy

I’m fascinated by Nassim Taleb's concept of “antifragility,” that the opposite of “fragile,” something that breaks easily under stress, isn't something that is strong; rather, it is something that heals and learns quickly in response to stress.

Ever since I learned about this concept, the more I see it in everyday life and the more I believe that it is a fundamental part of success and happiness.

Antifragile Entrepreneurship

For example, in entrepreneurship, this is the idea behind the trial-by-fire, learn-by-doing approach of entrepreneurship. The prototypical entrepreneur is highly risk-seeking to the point of irrationality. A simple cost-benefit analysis would dissuade most people from traveling down this path; yet, the entrepreneur is an entrepreneur because of the risk involved.

The entrepreneur runs through walls they don’t know exist. The same unknown unknowns that can doom the entrepreneur to failure are the same unknown unknowns that create the outsized successes of the entrepreneur.

When you look at the decision tree from that perspective, it seems not so bad: failure is always the same, a zero, while the return (however you define it: monetary, happiness, utility, etc.) is astronomical, and worth it.

"The Entitlement Generation" is Fragile

My generation is an obnoxious one. The author Ron Alsop calls us the Entitlement Generation. We are a generation of Millennials, trophy kids of doting parents who went through immense sacrifice to ensure our success, praising our accomplishments and padding our failures to avoid hurting our self-esteem. The losing team of a soccer game gets ice cream, too. They get an E for Effort.

I’ve met people in my generation who are surprised when they don’t have things laid out in front of them. And they perpetuate the problem because they expect something to be done for them. Many times they’ll wait for a long time for something that won’t come. It is this idea of entitlement that prohibits them from being antifragile. Rather than learn from the roadblock, they stagnate. “Many flounder without precise guidelines but thrive in structured situations that provide clearly defined rules and the order that they crave…” Because everything was given to them, “those basics aren’t necessarily apparent to many millennials.”

I think entrepreneurship is the greatest equalizer. Everyone is treated the same. If you don’t perform, you don’t succeed. You alone are responsible for your success.

You don’t have to come from a rich family to be subject to antifragility of entitlement. I come from a middle class family. My dad is an environmental engineer who designs landfills and makes sure that the runoff from the landfill when it rains doesn’t get into our drinking water. My mom stays at home to take care of now 6 (six!) kids, the equivalent of 6 most important jobs in the world. Arguably more important than anything that I’ll do in my lifetime.

Dad immigrated alone to the USA from Taiwan, leaving his wife and 2 kids, ages 1 and 3, to pursue his dream of getting a masters in engineering from a top school, and ultimately of building a solid foundation for his family and his children to stand on the shoulders of giants.

So they did (and still do) everything in their power to make sure that my siblings and I are in the best position to succeed. It is the greatest luxury of all to not have to worry where your next meal is coming from, whether your life is going to be in mortal danger from exogenous forces. We can concentrate all of our efforts towards our own self-gain. This is the greatest gift that my parents gave me.

And it takes all of my power of self-awareness to remember that. I will not squander this opportunity. It takes all of my power to remember that I am not entitled to anything. While my parents did everything in their power to make sure that everything was lined up for me and that I got a good education and went to a good college, they made sure to instill values in me of appreciation. This is the intangible that cannot be recorded in grades that I will forever be grateful for.

Expect nothing. Earn everything.

Happiness and Shocks

The eternal cliche of all cliches is to enjoy the journey, not the destination. But I believe that cliches are cliches because they are true. And the biggest cliches are the most difficult to internalize. I believe this King of Cliches is core to antifragile happiness.

There are two main types of mindsets that separate the fragile and antifragile. Stanford psychology professor Carol Dweck categorizes them as “fixed” and “growth,” respectively.1

Those with a fixed mindset believe that abilities are innate, a given, whereas those with a growth mindset believe that abilities are learned.

When those with a fixed mindset are faced with a system shock, they stand in place. They are too focused on the end result, and shocks to the system seem daunting and maybe even annoying. “Why can’t we just get along with the show?” They constantly look for the shortcut to success because that’s what they’re used to; they believe that success and happiness is innate. They look upon the goal with longing, but aren’t willing to put in the effort to get there:

"If only I were rich."

"If only I knew how to code."

"If only I had the perfect girlfriend."

On the other hand, those with a growth mindset embrace the inevitability of these shocks. Rather than try to account for every possible outcome, they embrace the immutability of unknown unknowns. For example, the most successful people I know are skeptical in shockingly great outcomes and optimistic in shockingly bad ones. And when a shock occurs, they know that they alone are responsible for their own change and their own happiness.

This is the core idea behind antifragility, shocks, and happiness. These shocks are inevitable, and they don’t matter as much as you think. They’re just part of the process.


  1. If you’re interested in learning more about this idea of resilience, this Quora post is a good start.