For the longest time, I struggled between deciding how to best be productive. Should I rigorously confine myself to a fixed schedule, or should I give myself maximal freedom to be creative and let serendipity run its course?

Somehow, possibly with laziness as a underlying motivator, I deluded myself into thinking freedom was the way to go. I certainly didn’t want to compromise my ability to be imaginative and stumble upon wondrous new worlds by putting on blinders.

While I know it to not be entirely true, my general feeling is that I failed to get anything done for about a year after making that decision and entering the free world as an entirely autonomous being devoid of any external impositions. Certainly, I failed to accomplish anything tangibly significant.

In my misguided attempt to preserve all opportunities for creativity, I precluded myself from actually creating anything.

...

An email conversation between a few friends and myself on net worth. My thoughts follow.

Began with two of us stating we didn’t really like this article

And then somewhere I noted that my goal was 10 million in net worth for financial security and independence and concluded a long rant (included at the end) with this paragraph:

Ultimately, perhaps: Do what makes you happy. It’s fine if it makes you happy for the standard reasons - as long as you’ve thought it through and are sure it will truly make you happy, do it. Try to maximize happiness both now and in the future. Maximizing happiness in the future gives the greatest returns since there is more of the future than there is of the now…but then again, we are young now and won’t be in the distant future, so there is a strange thing to be said of the particular quality of life and the variant opportunities afforded only in certain...

I’ve seen several people post to this video recently.

This is just a quick response I posted as a Facebook comment somewhere.

TL;DR I want to point out that the ‘rightness’ or ‘wrongness’ of wealth distribution should be in terms of where people are in regards to how much wealth is needed to maintain a good quality of life, not how wealth is distributed in relation to the total amount of wealth.

If the total amount of wealth is $100 under today’s rate of monetary value (e.g. $1 in this scenario buys what $1 today would) with the same amount of people as today, everyone’s doing shit. Doesn’t matter if 10 people own $60…we’re all going to die.

On the other hand, if the total amount of wealth is 100 centillion with the same amount of people, we’re all doing fine and every single one of us can almost certainly buy and do anything we want. The reason for this is just because in this...

A response to recent articles like this and this quora question

I have a different and more straightforward take on why advice won’t make us or break us. There are those of us that read hundreds of self-help books and don’t make it, and there are those of us that haven’t sought out advice and all and get along just fine.

1. Watching Tiger Woods hit a golf ball won’t instantly confer upon you the same capability to swing a ball. This applies just as much to an intellectual or entrepreneurial pursuit. While the right coaching can be indispensable, it’s ultimately sheer work, making mistakes, and our own internal introspection on our specific state that will make us.

2. The last part above segues into my second point: advice is easier given than received. Easier said than done. Ultimately, only we can act on the advice given, and also provide the necessary amount of inner reflection to distill...

It’s 0:48 AM right now. For the past two days I’ve been forced to wake up at 5:30am, a solid three hours before my usual wake-up time, to go hang-gliding with the other fellows. I am beyond tired right now, but I’m going to writing this post because I have to.

I’ve imposed the obligation on myself to pen a new blog post every Monday and every Friday. For the past two iterations of this obligation, I’ve thrown up the posts last minute, due to significant other priorities those days.

Today’s no different. I just came back from our fellow dinner with Peter Thiel, and I haven’t stopped being plugged in all day. There’s nothing more I want to do than sleep right now, and it’s without a shred of uncertainty in my mind that I assert that had I not created the obligation to post today, there would be no way in hell that I wouldn’t be passed out right now and this post would never see the light...

Back in high school I used to run cross country. Either through the summer or when I stopped senior year-I don’t really remember-I kept up my running habit, generally doing a few miles every day.

This isn’t about running however. This is about having epiphanies, and I distinctly remember I literally had at least one every single time I ran.

It didn’t happen during the run. But it always happened right after the run, as I was walking through my cooldown.

This always fascinated me, and there’s probably a very straightforward explanation for it, such as increased blood flow to the brain as a consequence of running. While running, physical exertion likely commands most of the blood flow, but during the cool down, I’m sure the brain gains the privilege of some increased oxygen supply.

The most intriguing thing is how subtle this entire process is. There’s nothing that feels distinctly...

A good friend of mine sent out an email the other day on ‘leadership’ versus ‘salesmanship’.

I wanted to edit this post a little before throwing it up here, but unfortunately it’s 2:30am already so here’s his email verbatim:

Hey friends,

You’re getting this email because we’ve had a intelligent and meaningful conversation at some point about leadership, or some aspect of leadership (e.g., charisma, trust, being a ‘visionary’). I wanted to send this email out to solicit your thoughts regarding a particularly powerful piece of writing on leadership that I recently read and also hopefully kickstart a conversation. I am curious about your answers to two questions:

1. What does being a leader mean, in your opinion?

2. What are some of the most difficult aspects of leadership to learn or develop?

But first, I want to share the piece on leadership. It’s a bit long, but I assure you it’s worth...

This stems from an observation I’ve been gradually building from rock climbing. I’m really getting into this sport, and from my first experiences to my most recent progress one primary theme keeps standing out to me: to break new ground, you must first believe that the ground can be broken. The rest is just follow-through.

My first and only outdoor climbing experience was what really blossomed my fascination with climbing. Two incredibly patient and generous veteran climbers offered another newcomer and me a ride into Connecticut or some other cold New Eastern place while I was at Harvard. We did several routes, and I’m fairly certain that I exhausted the bulk of my physical reserves by the time I was halfway up my first ascent.

But the veteran climbers kept encouraging us to continue and coached us patiently, and I’ll remain forever grateful that they did. The final ascent is the one...

This is a rebuttal to the oft-repeated notion that it’s not what you know, it’s who you know.

I’m going to make the somewhat scandalous point that no, it is in fact what you know. Connections are great. But they’re worthless without certain prerequisites in the skill department.

I’m going to journey through some cliches to prove my case. Sure, it can be argued that if Mark Zuckerberg hadn’t met Sean Parker or managed to get initial seed funding from Peter Thiel Facebook may never have become the behemoth it is today, but the fact of the matter is if Mark Zuckerberg hadn’t been able to build Facebook, it definitely wouldn’t be what it is today.

There are thousands of people who have met Sean Parker and Peter Thiel and none of them managed to build Facebook.

Taking another pithy statement that opportunity is the intersection of serendipity and preparation, we can make this point a...

There are a lot of choices for tech/entrepreneurial hero these days, and broadly it seems the trending fashion is to throw out a name like Steve Jobs or Mark Zuckerberg. “Stay hungry, stay foolish” seems like the battle cry of our generation.

But I remember when things were different. I remember my childhood days where no one had ever heard of Steve Jobs and Zuckerberg hadn’t even started Facebook. There was only one real tech idol back then that was a household name. A person everyone knew – Bill Gates.

The richest man in the world. Everyone talked about Bill Gates. Everyone was going to be like Bill Gates. He was the hero and the villain of tech. He vindicated software, took down IBM, and stole Jobs’ GUI. He was the winner, and the only one.

But Bill Gates is a tired phrase in this new decade. Everyone still knows him, but no one really mentions about him. What happened to him? Why...