The Trouble with Optionality

The shortest distance between two points is reliably a straight line. If your dreams are apparent to you, pursue them. Creating optionality and buying lottery tickets are not way stations on the road to pursuing your dreamy outcomes. They are dangerous diversions that will change you.

By emphasizing optionality, these students ignore the most important life lesson from finance: the pursuit of alpha. Alpha is the macho finance shorthand for an exemplary life. It is the excess return earned beyond the return required given risks assumed. It is finance nirvana.

But what do we know about alpha? In short, it is very hard to attain in a sustainable way and the only path to alpha is hard work and a disciplined dedication to a core set of beliefs. Given the ambiguity over the correct risk-adjusted benchmark, one never even knows if one has attained alpha. It is the golden ring just beyond your reach—and, one must enjoy the pursuit of alpha, given its fleeting and distant nature.

Ultimately, finding a pursuit that can sustain that illusion of alpha is all we can ask for in a life’s work.


Make Fewer Things Matter: My Epiphany From Cutting A Pineapple

The first emphasis in Make Fewer Things Matter is “make.” Things don’t stop mattering on their own. You don’t just ignore them. You do something to make them not matter.

The next emphasis is “fewer.” Some things will still matter, but you reduce the number of them. Make a big list of things you think are important. Look at each item and look for ways to make it not matter.

After you go through everything and you try to make them not matter, you’re left with a few things that truly matter.


Stop Keeping Score

Instead of checking items off a list, the Buddha suggests shining a light on yourself and others. “Dwell as a lamp unto yourself,” he advised his disciple Ananda. He meant that happiness comes from the illumination of your greatest virtues, thus showing the way for other people, and making visible to yourself your true purpose.


Your Thinking Rate Is Fixed

Here’s a secret that might sound obvious but can actually transform the way you work: you can’t force yourself to think faster. Our brains just don’t work that way. The rate at which you make mental discernments is fixed.


Positive Feedback Loops

Notice also that many of these examples will have negative feedback built into them as well: I get a bad grade, my habit app streak ends, I feel embarrassed that my friends know I haven’t exercised for a week, my task list is neverending and makes me feel overwhelmed, my coach might criticize what I did today, I forgot to do the language lesson and feel bad about it.

So if most systems have both positive and negative feedback built in … what can we do?

We have to design a better system.

Essentially, you should start rewarding yourself when things are going well, and have compassion for yourself when they are not. Then, the next day, give yourself a micro-task to accomplish. Reward yourself accordingly and get back on track.


How to Do the Things You Keep Avoiding

Tasks you’re avoiding never leave your consciousness for long. They hang there like clouds, some distance away, watching you.

They’re big and looming, but they don’t move very quickly, so you can always just move a bit further away. You still feel their presence though, and it feels bad.

This metaphor is super helpful for me right now.



How to Free Your Mind From Fear

The thing is when you focus all of your attention on the worst thing that could possibly happen – your body listens.

When you’re pulled out of your comfort zone your hands shake, your voice quivers, not because anything, in particular, IS going wrong, but because you believe it will.

Because if you tell yourself that the world is coming to an end and everything is a disaster, your body doesn’t know the difference.

But what if instead of always mentally preparing for what could go wrong, you focus on what could go right instead?


How People Learn To Be Resilient

Human beings are capable of worry and rumination: we can take a minor thing, blow it up in our heads, run through it over and over, and drive ourselves crazy until we feel like that minor thing is the biggest thing that ever happened.

In a sense, it’s a self-fulfilling prophecy. Frame adversity as a challenge, and you become more flexible and able to deal with it, move on, learn from it, and grow.


Legalize It All

John Ehrlichman, the co-conspirator behind Watergate:

"The Nixon campaign in 1968, and the Nixon White House after that, had two enemies: the antiwar left and black people. You understand what I’m saying? We knew we couldn’t make it illegal to be either against the war or black, but by getting the public to associate the hippies with marijuana and blacks with heroin, and then criminalizing both heavily, we could disrupt those communities. We could arrest their leaders, raid their homes, break up their meetings, and vilify them night after night on the evening news. Did we know we were lying about the drugs? Of course we did."

Criminey. I didn't even make it past the first two paragraphs before thinking this article was an instant share, just for that quote alone.