I am nothing

On a scale of one to ten, how good of a cog are you? How well do you function in your assigned role? How much of a man or woman are you? How do you rate yourself as a son or daughter, father or mother, wife or husband, heterosexual or homosexual, liberal or conservative, black or white, winner or loser, shark or sheep, introvert or extrovert, Christian, Muslim, atheist? How smart are you? How rational? How emotional? Do people like you? Are you getting ahead, or falling behind?

How do you know? Are you keeping an eye on the others in your category, comparing to see how you measure up to your peers? Is it more important for a man to be tall, or to have good hair?

This is, of course, the path of insanity, and not the good kind of insanity.

What will you do if you're too tough to be a good woman, too sensitive to be a good man, too selfish to be a good husband, too lazy to be a good employee, too shy to be a good friend, too caring to be rational, too fat to be pretty, too effeminate to be straight, too introverted to be a good leader, too smart to be kind, too young to be taken seriously, too old to make a difference, or too far behind to even get in the race?

These are all false standards and false dichotomies, but they are so common and so ingrained that we sometimes believe in them without even realizing it. And this leads to a mountain of insecurities, because nobody measures up to these crazy standards (and nobody should). But even if we don't believe in these things, it still matters what other people think, right? What will the neighbors think? Or how about our co-workers, or the people at church? And so everyone works to hide their insecurities, and they look around at their peers for comparison, and maybe they feel bad because everyone else seems to have it easy, to have it all figured out. The truth is, nobody can see the truth anymore. They are all working to hide the truth, because the truth is that they are afraid of who or what they really are. So they all put on a show, and they pretend to be a good whatever. Or maybe they rebel, and make a point of being a bad whatever, but then they are still under the control of that false standard, and they are still not being themselves.

That is all so exhausting. 

I am nothing. It's simple. If I were smart, I might be afraid of looking stupid. If I were successful, I might be afraid of failure. If I were a man, I might be afraid of being weak. If I were a Christian, I might be afraid of losing faith. If I were an atheist, I might be afraid of believing. If I were rational, I might be afraid of my emotions. If I were introverted, I might be afraid of meeting new people. If I were respectable, I might be afraid of looking foolish. If I were an expert, I might be afraid of being wrong.

But I am nothing, and so I am finally free to be myself.

This isn't license to stagnate. Change is inevitable. Change is part of who we are, but if we aren't changing for the better, then we are just slowly decaying. 

By returning to zero expectations, by accepting that I am nothing, it is easier to see the truth. Fear, jealousy, insecurity, unfairness, embarrassment -- these feelings cloud our ability to see what is. The truth is often threatening, and once our defenses are up, it's difficult to be completely honest with anyone, even ourselves. But when I am nothing, when I have no image or identity or ego to protect, I can begin to see and accept things as they really are. That is the beginning of positive change, because we can not change what we do not accept and do not understand. But with understanding, we can finally see the difference between fixing problems, and hiding them, the difference between genuine improvement, and faking it. We discover that many of our weaknesses are actually strengths once we learn how to use them, and that our greatest gifts are often buried beneath our greatest insecurities.

Letting go of your identity can be difficult and takes time, possibly forever, but as with any change, moving in the right direction is all that really matters (which is why you shouldn't compare yourself with others -- you didn't start in the same place or with the same challenges). Fortunately, we have a variety of emotions that can help us: pride, anger, fear, jealousy, insecurity, unfairness, embarrassment, bitterness, etc. These are sometimes portrayed as bad emotions, but there's no such thing as a bad emotion, just bad responses to emotions. (For example, torturing children is a very harmful response to fears about your own sexuality) If we instead use these emotions as a cue to remember, "I am nothing", let go of our identity, and examine why we are feeling the emotion (typically because something has threatened our identity) then these emotions are actually beneficial. They point us towards the buried truth.

True self improvement requires becoming a better version of our selves, not a lesser version of someone else. But without self acceptance and understanding, how can we even know what that looks like or whether we're headed in the right direction? It would be like putting the final touches on the Mona Lisa while picturing some celebrity you saw on the cover of People magazine -- the result would be a mess. Until we let go of our mental images of who we are or who we should be, our vision remains clouded by expectation. But when we let go of everything, open ourselves to any truth, and see the world without fear or judgement, then we are finally able to begin the process of peeling off the shell of false identity that prevents our true self from growing and shining in to the world. And it starts with nothing.

The two paths to success

The recent WSJ article on the supposedly Chinese style of parenting has generated a lot of interesting discussion. The most amusing commentary comes from The Last Psychiatrist, who also points out that Amy Chua, the "Chinese" mother, was actually born in America. There were also claims that the WSJ misrepresented her views, which may or may not be true, but is ultimately irrelevant since it's the ideas that are being debated.

Here's the part of the article that interests me:

What Chinese parents understand is that nothing is fun until you're good at it. To get good at anything you have to work, and children on their own never want to work, which is why it is crucial to override their preferences. This often requires fortitude on the part of the parents because the child will resist; things are always hardest at the beginning, which is where Western parents tend to give up. But if done properly, the Chinese strategy produces a virtuous circle. Tenacious practice, practice, practice is crucial for excellence; rote repetition is underrated in America. Once a child starts to excel at something -- whether it's math, piano, pitching or ballet -- he or she gets praise, admiration and satisfaction. This builds confidence and makes the once not-fun activity fun. This in turn makes it easier for the parent to get the child to work even more.

She has two main points here: 1) Learning is not fun and 2) It's important to make kids dependent on praise and admiration.

One of the problems I've faced throughout life is that I'm kind of lazy, or maybe I lack will power or discipline or something. Either way, it's very difficult for me to do anything that I don't feel like doing. If I try to force it, my energy disappears, and I hate life. Furthermore, not only were my parents not Chinese, but they had five kids, so there wasn't time for Amy Chua's style of parenting. I kind of had to figure it out on my own.

My strategy can be reduced to two rules: 1) Find a way to make it fun and 2) If that fails, find a way to do something else.

For example, I didn't really like school, and I especially hated homework, so I turned it into a game to see how little time and effort I could possibly waste on it while still getting "good enough" grades. I barely made it into the top 10% of my public high school class, so I probably wouldn't be accepted into whatever college Amy Chua has picked out for her kids, but I find that I really don't care. Instead, I went to a "good enough" college, slept through most of my classes, then got a "good enough" job after graduation. Meanwhile, I taught myself how to program and build all kinds of things, which to me was much more fun than school.

I'm not going to claim that my approach is superior to Amy Chua's, or that it will work for everyone, but I do think it provides an interesting contrast.

Amy Chua's approach is based on extrinsic motivation. Children must do exactly what they are told to do, and they must not be happy unless an external authority gives them praise and admiration. They must learn that their own internal motivations and judgement are worthless and not to be trusted. They are successful when an external authority, such as an Ivy League school, tells them that they are successful.

The extrinsic path to success is to focus on being the person you are told to be, and put all of your energy and drive into fitting that mold.

The approach I stumbled into is based on intrinsic motivation. To the greatest extent possible, do whatever is most fun, interesting, and personally rewarding (and not evil). External constraints, such as the need to go to school or make money are simply obstacles to be hacked. Be skeptical of external authorities, as they are often manipulating you for their own benefit, or for the benefit of the institutions they represent (often unknowingly, as they were already captured by the same systems which are attempted to ensnare you). Your identity comes from within -- external recognition such as degrees and awards are only of tactical importance -- don't allow them to define who you are.

The intrinsic path to success is to focus on being the person that you are, and put all of your energy and drive into being the best possible version of yourself.

Of course this leads to the question, "What is success?" Someone who spent his life working 80 hour weeks, living in hotels, and fighting his way up the corporate ladder to become VP of toilet paper marketing would probably consider himself more successful than a sandwich shop owner who spends his nights and weekends playing with his kids and working on hobby projects, but maybe the sandwich shop owner would be happier and healthier. Ultimately, it is up to each person to decide what success means to them, but I think it's important that everyone be mindful of the decision they are making. 

It's often said that people become entrepreneurs because they can't handle a regular job. Perhaps these people are simply too "defective" to fit into any mold, or maybe they lack the extrinsic motivation necessary to care about bosses, performance reviews, and other things which are so important for success in the corporate environment. However, what they do have is the creativity and natural sense of direction necessary to run their own business. I doubt that this is a coincidence.

As explained in this TED talk by Dan Pink, extrinsic motivation is a great way to get people to do boring and repetitive tasks, but it actually harms performance on more creative tasks. Creativity is a surprisingly fragile thing. It comes from deep inside, and external concerns (most especially, "What will people think?") seem to scare it away. But that's a topic for another time.

Of course, intrinsic vs extrinsic motivation isn't a completely black and white distinction, and we probably can't survive entirely on one or the other (I aim for 90% intrinsic). I also doubt it's possible to simply "switch" from extrinsic to intrinsic motivation. It's a skill like anything else. It takes time to find your internal voice, learn when to trust it, and stop fearing outside opinion (closely related: ego-fear).

Amy Chua's book was about parenting. Her style is based on extrinsic motivation. How do we raise successful, intrinsically motivated children? I'm sure someone will leave book recommendations in the comments -- Alfie Kohn comes to mind. However, I suspect that one of the most important factors is how we live our own lives. If we demonstrate that work and creativity can actually be fun and enjoyable, that at least sets an example. If we first solve the puzzle for ourselves, we have a better chance of helping others to find their answer.

Angel investing, my first three years

I started investing in startups with the assumption that I don't know what I'm doing (which is always true), but that the only way to actually learn anything is through experience. Therefore, my goal was to invest in a variety of startups, learn from the experience, help some startups, and hopefully not lose too much money while doing so. I don't have any single criterion for investing. Sometimes, the idea seems good, sometimes the people seem good, and other times I'm just curious to see what will happen. No matter what though, I want to be helpful and learn something interesting from the experience.

I've definitely learned a lot, but the recent Heroku acquisition (for a reported $212 million) made me wonder if I've also reached the point of "not losing too much money", so I did the math. From 2006 (when I started investing) through 2008, I invested about $1.21 million in 32 different companies. About half of those companies were either acquired or are dead/mostly-dead. The other half are still alive and seem to be doing well. The current acquisitions total about $1.34 million, only about a 10% gain, which isn't great, but at least I'm not losing too much. Fortunately, the "still alive" category includes a number of very promising investments, such as Meraki, Weebly, and Wufoo, so I expect the final return will be much better than 10% (which is all gravy anyway, since my primary goal was to learn more and be helpful).

Of the current acquisitions, only two have yielded a greater than 10x return: Heroku and Mint. Unfortunately they were also two of the smaller investments, proving that I don't know what I'm doing, or at least showing that I need to make a point of investing more money into the best companies (Mint was oversubscribed, but I don't remember why I didn't put more into Heroku -- edit: apparently it was also oversubscribed).

It's worth noting that the highest return was from a Y Combinator company (Heroku, winter 2008). I've been investing in the YC companies almost from the start (Wufoo was winter 2006), and they keep getting better. YC is attracting the best founders, and Heroku is just the tip of the iceberg. The more great YC companies there are, the more reasons there are for other smart founders to join YC, and I find myself asking non-YC companies why they aren't yet in YC. This trend definitely contributed to my decision to join YC as a partner.

There were also a couple of medium-sized acquisitions (AppJet/Etherpad and 280North) and several smaller but still nice (2x-3x) exits such as Auctomatic, Parakey, and Zenter. Sometimes people complain about these deals, but as much as I'd like to get a nice 10,000x exit, I'm certainly not going to complain when someone doubles my money!

A few companies (such as ScanScout) were acquired by other private companies, so I include those in the "still alive and doing well" category, since it was not an exit from the investor perspective (no liquidity). Only two companies are officially dead, but there are at least four "zombies" that still exist, but in a minimal form and are almost certainly worthless.

The two bits of advice that I always give to people looking to get started with angel investing are: 1) Assume you'll lose your money and 2) Plan on investing in a large number of companies. (my third bit of advice is to attend YC demo day) I think my experience so far validates this advice. It's important that investors have the right motivations (helping out startups and learning how to be a better investor) and the right expectations. Anyone doing it with the idea that they can simply find the next Google, invest a bunch of money, and then get super-rich is going to be very disappointed. That said, finding the next Google and buying a 1% stake is my current billion dollar plan :)

Four reasons Google is still Awesome

My recent predictions about which Google products will succeed (and which won't) are causing people to think that I'm anti-Google, which makes me sad since Google is probably still the best company of its size, and I really enjoyed my time there. 

Unfortunately, positive stories are never as popular as negative ones, but regardless, it's worth highlighting some of the things that continue to differentiate Google as one of the best companies in tech.

1 - They take big risks. People often point to projects such as Wave as evidence that Google has "lost its magic" or something. To me, it's evidence that they are still willing to take risks on new ideas and new ways of doing things (Wave was run as a completely autonomous project in Australia). If everything you do works, then you're not taking many risks and probably aren't innovating either. Obviously, if everything you do fails, that's not good either, but there's a sweet-spot somewhere in the middle. Google has enough big successes, such as Chrome and Android, to show that they are somewhere near that sweet-spot.

2 - They are willing to build new technology seemingly unrelated to the core business. When we started work on Gmail, many people said it was a distraction and that Google should focus on web search. Now nobody questions email, but they wonder why Google is developing self-driving cars. From a market perspective, this looks like a lack of focus, but that's a rather narrow way of viewing things. From a broader perspective, it can be seen as a focus on using technology to improve the world. Did people criticize Edison or Tesla for inventing too many different things?

From an employee perspective these non-core projects are also an opportunity for greater autonomy. Part of what made the Gmail project so fun was that we had a lot of independence and could pursue ideas that other people inside Google thought were "the wrong way to do it". Most other tech companies do not offer that kind of freedom.

3 - They compete in positive ways. Many companies compete in ways that actually destroy value, such as using patent lawsuits to slow down or kill competitors. Google's weapon of choice is more often open source and open standards. There's no question that projects such as Android and Chrome have strategic value and work to weaken Microsoft and others, but they also happen to be good for the world. Google has managed to keep their interests surprisingly well aligned with the interests of their users.

4 - They don't seem to mind honest criticism. I'm currently reading a draft of a forthcoming Google book, and was amused to find that it includes an email that I sent back in 2000 trashing our then most recent product launch. It's painful for me to not tell people what I think, so for the most part I try to find people who don't mind hearing the truth (or my take on it, rather). Much of my interaction with startups consists of me telling them everything that I don't like about their product (and then they thank me!). I've worked for a lot of different companies, and Google was the only one where me speaking my mind never seemed to cause a problem. I'm not claiming that I'm always right, because obviously I'm not, but systems (or individuals) that don't welcome negative feedback are doomed. Cultures that don't laugh at themselves are cults.

Talking about Google is always a little tricky for me given my background, but they continue to be a fascinating company and a great source interesting lessons, so I'm going to keep trying. Hopefully I don't come off as a hater or a fan boy, but simply an honest observer.

The Cloud OS

My recent remark about the future of ChromeOS generated a surprisingly passionate response. Some said that my prediction was obvious and boring, but others disagreed, arguing instead that I am ugly and "don't get it". I won't disagree with either side, but I also noticed that my prediction was sometimes inaccurately characterized as me "hating" ChromeOS, Google, or The Cloud, all of which is false. Since there seems to be so much interest in this topic, and because people keep emailing me about it, I should probably explain my actual thoughts a little better.

First, what is a "cloud OS" and why should I want one? Actually, I don't even know if anyone calls it a "cloud OS", but I couldn't find a better generic term for something like ChromeOS. The basic idea is that apps and data all live on the Internet, which is has been renamed "The Cloud" since that sounds cooler, and your laptop or whatever is basically just a window into that cloud. If your laptop is stolen or catches fire or something, it's not a big deal, because you can just buy another one and nothing has been lost (except your money). Many people characterize this approach as using a "dumb terminal", but that's wrong. Your local computer can still do all kinds of smart computation and data manipulation -- it's just no longer the single point of failure.

To me, the defining characteristic of cloud based apps is "information without location". For example, in the bad old days, you would install a copy Outlook or other email software on your PC, it would download all of your email to your computer, and then the email would live on that computer until Outlook corrupted its PST file and everything was lost. If you accidentally left your computer at home, or it was stolen, then you simply couldn't get to your email. Information behaved much like a physical object -- it was always in one place. That's an unnecessary and annoying limitation. By moving my email into "the cloud", I can escape the limitations of physical location and am able to reach it from any number of computers, phones, televisions, or whatever else connects to the Internet. For performance and coverage reasons, those devices will usually cache some of my email, but the canonical version always lives online. The Gmail client on Android phones provides a great example of this. It stores copies of recent messages so that I can access them even when there is no Internet access, and also saves any recent changes (such as new messages or changes to read state), but as soon as possible it sends those changes to the Gmail servers so that they can be reflected everywhere else (such as my home computer). To the greatest extent possible, the information all "lives" in the cloud, and all other copies are simply caches which may be discarded at any time. (BTW, Apple is lame for not allowing a native Gmail app on the iPhone -- email is the one place where Android really outshines the iPhone for me)

Continuing with the Gmail example, it's not just your data that resides in the cloud -- the entire application lives there. This is the part that causes people to erroneously describe cloud based apps as a "return to dumb terminals". Just because an application "lives" in the cloud doesn't mean that your local computer isn't still doing work. When you use Gmail from your web browser, it downloads large chunks of Javascript code to run on your computer doing things such as rendering your inbox, handling keyboard and mouse events, pre-fetching messages, etc. The advantage of having this code run on your computer is that it can respond to your actions within a few milliseconds instead of the hundreds of milliseconds it could take to reach Google's servers (thanks to the relatively low speed of light). Which parts of the application run on your computer and which run on Google's computers? Ultimately, it does not matter, and can change over time (and in fact the split is different for different interfaces -- the basic html interface does not need any Javascript) As an end-user, you simply use the app, and let Google worry about making it all work, keeping it up to date, etc.

Because we're now treating the executable code and system configuration as data that lives in the cloud and is only cached locally, it also makes sense to do away with the old notions of installing and administering applications on your computer. And of course we also need a security and sandboxing system that prevents the code from breaking your computer (as is so common in the Windows world). In the web/Javascript world, this happened somewhat automatically because web apps evolved from simple web pages, and obviously you don't have to install or uninstall web pages -- your browser simply fetches what it needs to display, optionally caches parts of it for improved performance, and discards resources that it no longer needs (since it can always re-fetch them later on).

Cloud-based apps don't necessarily have to be written in Javascript and run in your web browser however. iPhone and Android apps behave in much the same way. Although they can be "installed" or "uninstalled", from a user perspective, that process isn't substantially different from adding or removing a bookmark, and in fact many of those apps are little more than a thin wrapper around an embedded web browser. A combination of technical and review policies prevent those apps from doing anything dangerous to your computer (unlike a Windows app, which could install a new device driver, replace a core system library, install a root-kit, etc). 

One way of understanding this new architecture is to view the entire Internet as a single computer. This computer is a massively distributed system with billions of processors, billions of displays, exabytes of storage, and it's spread across the entire planet. Your phone or laptop is just one part of this global computer, and its primarily purpose is to provide a convenient interface. The actual computation and data storage is distributed in surprisingly complex and dynamic ways, but that complexity is mostly hidden from the end user. For example, interacting with my FriendFeed page involves the coordination of thousands of individual processors and disks owned by a dozen different entities, including you, Facebook, Amazon, Google, your ISP, and many intermediate ISPs. The same is true of the services provided by thousands of other web apps.

This global super-computer enables us to do things that would have been impossible not long ago, such as instantly search billions of documents, access our email and other info from almost anywhere, easily share ideas with thousands or millions of people, collaboratively edit documents with people spread around the world, leak embarrassing diplomatic cables, etc. It also makes it easy to launch new services and applications with almost zero money, which has created a new generation of low-budget startups and expanded the world of high-tech entrepreneurship to many more people.

Inevitable, some curmudgeonly types will say this is all bad, and indeed it is not without some downsides and complications, but overall I believe the development of this global super-computer is one of the most important technological advances in history.

And what about ChromeOS? If my laptop is just one part of a much larger computer, what is the ideal design for my local node? It should be relatively cheap and reliable, secure (no viruses or anything), zero-administration (I don't want to be a sys-admin), easy to use, and fast. I believe this is roughly the design target of ChromeOS. They are building laptops that run the Chrome web browser and approximately nothing else.

I actually like the idea of ChromeOS, so why did I predict its demise? The answer is that we already have millions of devices that almost meet the same ideal, and they are running iOS and Android. In the 1.5 years since ChromeOS was announced, Apple launched the iPad, which quickly became one of the fastest selling new devices ever. Google will necessarily respond by building Android tablets, which means Android will be running on larger, more powerful devices. All of the benefits of ChromeOS (security, instant-on, etc) should apply to Android as well, and I expect that any new Chrome features (mostly under the umbrella of HTML5, but perhaps Native Client as well) will also be added to the Android browser, since platforms succeed by being as large as possible. Once Android has all the benefits of ChromeOS, the most obvious difference will be that ChromeOS lacks the thousands of native apps which are popular on Android. Android apps are closer to web apps than Windows apps in terms of security and manageability, so eliminating them doesn't seem like much of an advantage for ChromeOS. 

The other obvious difference between ChromeOS and Android is that ChromeOS assumes a mouse/track-pad while Android currently assumes a touch interface (many Android devices already have a keyboard). If my prediction is wrong and both OSs stick around, this will probably be the reason. However, I doubt that's enough of a difference to justify maintaining two separate OSs, and ultimately everything may end up with a touch screen anyway. Perhaps the tablet / laptop convertible will make a comeback.

Put another way, the ChromeOS laptops are awkwardly positioned between the established Mac/Windows laptop market, which isn't going away anytime soon, and the rapidly growing Tablet market, and it has approximately zero users. That's not a great place for a new platform to get traction and establish itself. But if it does, I will be happy for it. And even if it doesn't, it may still be a worthwhile experiment.

The quest for freedom and safety: Why I donated $100,000 to YesOn19

The common theme uniting most of my efforts is the desire to be free. One of the reasons I'm so interested in startups is that they give people the freedom to create, independent of the institutional limitations found in large companies. This is why unexpected new ideas and techniques (such as new languages or development practices) often appear first in startups. Of course the startups don't always succeed, but at least I'm free to pursue my own ideas, even if others don't believe in them. And when a startup is successful, it can provide a great deal of financial freedom to the people who built it.

Internal freedom is also very important, though often less obvious. If we are always held back by our own fears and self-limiting beliefs, then we aren't really free. That is why my previous post on serendipity is largely about escaping ego-fear and other negative limitations.

Benjamin Franklin once wrote, "Those who would give up essential liberty to purchase a little temporary safety, deserve neither liberty nor safety."

Philosophically, I agree with that. However, if we don't feel safe, if we can't go out in public without fearing for our lives and the lives of our family, then we aren't really free. Since becoming a parent, I've come to understand why parents often seem especially fearful. Our children are so precious to us, and we must keep them safe. I can understand the impulse to simply make more rules, to build taller walls, and to lockup anyone who seems scary.

I think the real point of Benjamin Franklin's quote is that when we destroy freedom, we are ultimately destroying safety as well. This is most apparent when we examine the disastrous effects of drug prohibition.

Not only is prohibition an attack on our basic right to control our own bodies and minds (a philosophical point which most people probably don't care about), but prohibition also provides a multi-billion dollar subsidy to violent criminal organizations that threaten our physical safety and security, something everyone cares about.

The drug cartels have already overrun much of Mexico, and that violence will inevitably spill over in to the United States if we continue subsidising them with one of the world's most lucrative monopolies.

The alternative path is to begin restoring individual freedom and responsibility, defund the drug cartels, and instead shift those dollars towards roads, parks, public safety, and other beneficial causes. This is the solution offered by California's proposition 19, the "Regulate, Control and Tax Cannabis Act of 2010".

Some politicians have argued that proposition 19 is "flawed". To me, this seems like a weak defense of the status quo from politicians afraid to stand out on a controversial issue. Of course it's not perfect -- no law is perfect. However, the current system of drug prohibition is much, much worse. "Perfect" is not one of the options offered on Tuesday's ballot. We can either choose "much better" (Yes on 19), or "keep the current, disastrously bad, system" (No on 19). 

If proposition 19 passes, the immediate effect may not be that significant due to federal challenges and such. However, I believe the long-term effects will be enormous. Prohibition is a disaster. Many politicians will admit to this fact, however most of them have been too timid to actually do anything about it, to lead the country towards safer, saner policies. In this case, the voters must lead, and the politicians will follow. Even if 19 does not pass (Nate Silver of FiveThirtyEight gives it "even odds" of passing), it will still mark an important shift in the debate over drugs, especially if YOU vote for it.

And that's why I decided to donate $100,000 towards the Yes on 19 campaign. It's tempting to wait for the "perfect" solution to the drug issue, but meanwhile millions of lives are being destroyed by the current system. That's evil.

Here are a few more thoughts on the issue:

• Nicholas Kristof in the NY Times
• The success of drug decriminalization in Portugal (from the Kristof article)
• George Soros in the Wall Street Journal 
• San Jose Police Chief Joseph McNamara

If you would like to be part of the solution, please share this or other articles, and encourage your friends and family to show up at the polls on Tuesday and vote "YES on 19" (assuming they live in California). Also, donate to YesOn19 -- it's not too late (ads are still being purchased).

Serendipity finds you

Here is an interesting comment from Hacker News, on a story about someone turning down an early Google offer:

Similar thing happened to me in 1999. I realized Google was way cooler than alta vista and better at finding unknown things rather than Yahoo's directory. Truly the future, I thought. I sent in a resume to do some kind of work not development related; data center & sys admin stuff. They called me twice but I convinced myself that they would not have hired me anyways so I never called back.

Whether or not ignoring Google's calls was the right decision for him, his reason for not taking the call (fear of rejection) isn't great.

I don't have many positive memories from high school, but the one that has stayed with me more than any other comes from the first day of my 11th grade English class. My teacher (I believe his name was "Mr. May") shared a brief anecdote from the prior evening. He was driving home in the rain, and noticed two people on bicycles along the side of the road. He stopped to ask if they needed any help, and ended up driving them back to his house, where they dried off and had dinner with him and his wife. During dinner, the couple shared the stories from their ongoing bike ride across the country.

It's not a very dramatic story, but I loved the serendipitous nature of it, both on the part of the couple having adventures biking across the country, and my teacher who saw people along the road and invited them into his home. None of it was planned -- they simply allowed it to happen. It was inspirational to me because it felt like the right way to live, the fun way to live. I don't think that's how most people operate though.

My own story of how I ended up at Google in 1999 is rather boring. I was interested both in startups, and Linux (which was still somewhat fringe at the time), so I sent my resume to a few companies that I had seen mentioned on Slashdot (a rather lazy job search, in hindsight). Fortunately, most of them never even responded, and only one actually offered me a job, Google. I was skeptical of their business and didn't expect it to last long, but it seemed like it could be fun and educational, so I accepted.

Obviously that's an example of rather extreme luck, but I've noticed that most of the good things that happen to me follow that general pattern, and aren't part of any "plan". The story of how I met my wife is remarkably similar. Shortly after moving to California, I signed up for match.com, read a bunch of profiles, emailed three of them, and only one responded. I was very much not looking for someone to marry, but that's what happened anyway. As they say, "Life is what happens to you while you're busy making other plans."

My plans rarely work (unless they are boringly simple), but serendipity has been good to me, so over time I've tried to make the most of that. My theory of serendipity is still evolving, but from what I've seen, it's better to think in terms of "allowing" serendipity rather than "seeking" it or "creating" it. Opportunity is all around us, but we have beliefs and habits that block it.

The two biggest blocks to serendipity seem to be ego-fear and "other plans".

I'm using the term "ego-fear" to describe fears that go beyond rational concern. For example, you wouldn't run out into the middle of a freeway thanks to a healthy fear of getting run over by a car -- that's not ego-fear. However, the fear that often keeps people from public speaking, talking to strangers, interviewing for jobs, etc is typically driven by fear of embarrassment, humiliation, rejection, criticism, etc -- that's ego-fear. Sometimes it can be difficult to separate the two types of fear because ego-fear will rationalize itself as healthy fear, e.g. "I don't want to talk to that stranger because they could attack me, or waste my time."

The HN commenter quoted above who never accepted Google's calls because, in his words, "they would not have hired me anyways", seems to be experiencing quite a bit of ego-fear, fear of rejection and humiliation. That fear is probably blocking a lot of great opportunities.

It's tempting to try and think your way out of ego-fear, but I suspect that only makes the problem worse by generating a more complex tangle of rationalizations for the fear. Fear is defeated by confrontation -- avoidance only makes it stronger.

"You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face. You must do the thing which you think you cannot do." - Eleanor Roosevelt

The program for eliminating ego-fear and unblocking serendipity is very simple: seek ego-fear. Hunt it down and soak in it. Steal its energy. This is, by definition, scary. That's good.

The other big serendipity block seems to be "the plan". Serendipity and luck are by their very nature unpredictable, and therefore not part of any good plan. When something unexpected happens, things are no longer "going according to plan", and there is a tendency to view the unexpected event either as a distraction, or as a frustrating obstacle to success.

The difference between a life full of frustrating obstacles, and a life full of serendipity, is largely a matter of interpretation. It can be difficult, but the most beneficial response to unexpected events is a sense of gratitude. Even seemingly adverse events can lead to something great. Accept what is given. (see Yes Man for a cute caricature of this mindset)

"Plans are worthless. Planning is essential." - Dwight D. Eisenhower

Planning in itself is not a bad thing, but picking a single plan and obsessively sticking to it doesn't allow for much serendipity. The world is very complicated, and we humans are very stupid, so it's good to be flexible and open minded about things. Instead of having one plan, have one thousand plans, and revise them as necessary. 

The desire to have "a plan" can also cause "paralysis of analysis" -- we put all of our energy into formulating the perfect plan, and consequently never actually do anything. The more effective approach is to simply pick a plan with the knowledge that it's flawed, set the plan in action, and then adapt, revise, or switch plans as the world unfolds.

I suspect the desire to have a definite plan is also partially rooted in fear. Uncertainty can be scary, and having a plan helps create the illusion of predictability in a very unpredictable world. However, if we actually manage to reduce risk and unpredictability, then we are also reducing serendipity. This is one reason why large organizations often have trouble producing innovation -- they want it to be planned and scheduled, but that just kills it.

The whole notion that plans are something that we should "stick to" makes them distracting enough that I prefer to call them "ideas" or "rough sketches" instead. Personally, I try to avoid having plans for my life, but I have many ideas. Which ones actually happen will be a surprise to me. It's more fun that way.