Meet Comex, The 19-Year-Old iPhone Uber-Hacker Who Keeps Outsmarting Apple

http://www.forbes.com/sites/andygreenberg/2011/08/01/meet-comex-the-iphone-uber-hacker-who-keeps-outsmarting-apple/

Nicholas Allegra lives with his parents in Chappaqua, New York. The tall, shaggy-haired and bespectacled 19-year old has been on leave from Brown University since last winter, looking for an internship. And in the meantime, he’s been spending his days on a hobby that periodically sends shockwaves through the computer security world: seeking out cracks in the source code of Apple’s iPhone, a device with more software restrictions than practically any computer on the market, and exploiting them to utterly obliterate its defenses against hackers.

“It feels like editing an English paper,” Allegra says simply, his voice croaking as if he just woke up, though we’re speaking at 9:30 pm. “You just go through and look for errors. I don’t know why I seem to be so effective at it.”

To the public, Allegra has been known only by the hacker handle Comex, and keeps a low profile. (He agreed to speak after Forbes‘ poking around Twitter, Facebook and the Brown Directory revealed his name.) But in what’s becoming almost an annual summer tradition, the pseudonymous hacker has twice released a piece of code called JailBreakMe that allows millions of users to strip away in seconds the ultra-strict security measures Apple has placed on its iPhones and iPads, devices that account for more than half the company’s $100 billion in revenues.

The tool isn’t intended for theft or vandalism: It merely lets users install any application they want on their devices. But jailbreaking, as the  practice is called, violates Apple’s obsessive control of its gadgets and demonstrates software holes that could be exploited later by less benevolent hackers.

Apple didn’t respond to requests for comment, but it’s not thrilled about Allegra’s work. When he released JailbreakMe 3 in July, the company rushed to patch the security opening in just nine days. Nonetheless, 1.4 million people used the tool to jailbreak their gadgets in that time, and more than 600,000 more since then. Allegra has become such a thorn in Apple’s side that its stores now block JailbreakMe.com on in-store wifi networks.

“I didn’t think anyone would be able to do what he’s done for years,” says Charlie Miller, a former network exploitation analyst for the National Security Agency who first hacked the iPhone in 2007. “Now it’s been done by some kid we had never even heard of. He’s totally blown me away.”

see photos

Click for full photo gallery: A Brief History of Apple Hacking

To appreciate JailbreakMe’s brilliance, consider how tightly Steve Jobs locks down his devices: Since 2008, Apple has implemented a safeguard called “code-signing” to prevent hackers from running any of their own commands on its mobile operating system. So even after an attacker finds a security bug that gives him access to the system, he can only exploit it by reusing commands that are already in Apple’s software, a process security researcher Dino Dai Zovi has compared to writing a ransom note out of magazine clippings.

After Allegra released JailbreakMe 2 last year, Apple upped its game another notch, randomizing the location of code in memory so that hackers can’t even locate commands to hijack them. That’s like requiring an attacker to assemble a note out of a random magazine he’s never read before, in the dark.

Yet Allegra has managed to find a path around those locks. In JailbreakMe 3, Allegra used a bug in how Apple’s mobile operating system iOS handles PDFs fonts that allows him to both locate and repurpose hidden commands. That critical flaw allowed a series of exploits that not only gains total control of the machine but leaves behind code that jailbreaks it again every time the device reboots –all without ever even crashing the operating system. “I spent a lot of time on the polish,” Allegra says with a hint of pride.

Dino Dai Zovi, co-author of the Mac Hacker’s Handbook, says JailbreakMe’s sophistication is on par with that of Stuxnet, a worm thought to have been designed by the Israeli or U.S. government to infect Iran’s nuclear facilities. He compares Allegra’s skills to the state-sponsored intruders that plague corporations and governments, what the cybersecurity industry calls “advanced-persistent threat” hackers: “He’s probably five years ahead of them,” says Dai Zovi.

Allegra isn’t after profit: his site is free, though it does accept donations. Nor does he criticize Apple for wanting to control what users can install on their devices. He calls himself an Apple “fanboy,” and describes Android’s more open platform as “the enemy.” “I guess it’s just about the challenge, more than anything else,” he says.

The young hacker taught himself to code in the programming language Visual Basic at the age of nine, gleaning tricks from Web forums. “By the time I took a computer science class in high school, I already knew everything,” he says. When he found that he couldn’t save a screenshot from the Nintendo Wii video game Super Smash Brothers to his computer, he spent hours deciphering the file, and later worked on other Wii hacks, getting a feel for its obscure operating system.

“I didn’t come out of the same background as the rest of the security community,” he says. “So to them I seem to have come out of nowhere.”

Allegra argues that his jailbreaking work is legal. The U.S. Copyright Officecreated an exemption last summer in the Digital Millenium Copyright Act for users to jailbreak their own cell phones, despite’s Apple objections that the ruling could open phones to dastardly hackers and even lead to “catastrophic” attacks that crash cell phone towers.

Whether it’s acceptable to release tools for others to jailbreak their devices, however, has yet to be decided. Three courts have ruled the practice is legal, while another said it could violate the DMCA. In January, Sony used that law and others to sue George Hotz, one of Allegra’s fellow iPhone hackers, for reverse engineering the Playstation 3. The suit was settled, but not before it touched off a wave of retaliatory cyberattacks on Sony by hackers around the world.

Allegra admits that technically, there’s little difference between jailbreaking phones and hacking them for more malicious ends. “It’s scary,” he says. “I use the same phone as everyone else, and it’s totally insecure.”

But at least in the case of JailbreakMe 3, Allegra also created a patch for the PDF vulnerability he exploited, allowing users to cover their tracks so that other hackers couldn’t exploit the same bug. In the period before Apple released an official patch, users who had jailbroken their iPads and iPhones were in some sense more secure than those who hadn’t.

A postscript to Apple: Perhaps your security team could use another intern.

How to Deal With Crappy People - James Altucher!

Ugh, I’m disgusted with my brain.  I see people walking down the street and there’s like this killer inside me providing running nasty commentary about each person. Do you do this also?

I have to stop myself often: “you don’t know this person who is randomly crossing the street. You can’t possibly know that he’s a cheating lying rich Hamptons-worshipping whoremongering obnoxious trust fund baby with a 17 year old mistress on the side who doesn’t wipe, who doesn’t wash, who would wish nothing better than to see you die”. You can’t know that! So why do I think it? Most people crossing the street probably think that about me also. Who is that freak? Is he homeless? Why can’t he comb his hair? Why is his fly open? Is he a child molesting pervert?

Most people are pretty crappy. But not all. And even the ones who are no good and not worthy of your time need a system for you to use so YOU can be happier and leave this lecherous gossipy crack addict thats in your head on the road and kick him or her to the curb.

I was talking about this with Penelope Trunk and Melissa Sconyers who works with Penelope. Penelope has an excellent blog I recommend. She also has Asperger’s Syndrome which, from what I can gather, means she can’t read social cues on people so has trouble knowing how to respond to people. So she told me her technique what she does.

(Penelope Trunk)

I came up with a better technique for her. But first, her trick:

She uses something called Myers-Briggs to determines someone’s personality type. Then, in advance of meeting that person, she looks up the personality type and figures out how she needs to respond and interact with that person.

Forget that. There’s a billion personality types on that thing. I’m about to make it easy for Penelope.

There are only four types of people. If you understand in advance how to deal with each of these four types you will be infinitely happier. Ultimately, interacting with the four types in the way I describe below will make one fit firmly into the first type, however difficult it is. That’s the goal. You don’t want to go through life unhappy.

In an earlier article I gave the Daily Practice that has helped me out of every tough situation in my life for the past 15 years (when I’ve been disciplined enough to apply it). It has 4 legs. Many of us focus in our daily lives on only one of the legs (Physical, Emotional, Mental, or Spiritual) but we need all the legs in balance to really sit down at the dinner table without falling.

The Practice works and brings one from the brink to success and then more success. I believe in it more than I’ve ever believed in any hocus-pocus anything ever.

But to develop the emotional leg of that practice takes a lot of work and I’ve written nothing on this. Probably because it’s the hardest. In my talks people ask about the Mental side, the idea muscle. But the Emotional side, equally as important, is much harder.

The key is to identify the FOUR types of people and discipline yourself on how you should approach these people.

The Four Types of People

#1 Happy. There are people who are genuinely happy in the world. Sure they have their suffering. Everyone does. But a lot of people really are pretty satisfied with their lives at this very moment.

A natural reflex (not for everyone, but certainly for some people) is to resent people for being happy. Who doesn’t do that some of the time? Raise your hand!

Let’s say someone lives in 20,000 square foot house in Connecticut, has a sexy wife (or sexy husband), and is genuinely happy. It’s hard not to resent such a person. This resentment will block the Daily Practice from having beneficial outcomes in your life.  In 2002 when I was pitching hedge fund managers to invest money with me I often ran into the exact person described above. And their families. The sexy wives in short shorts. The hedge fund managers served gourmet meals for lunchtime by loving cooks.

(Stevie Cohen’s house. Here’s How Stevie Cohen Changed My Life)

You can’t fake resentment. You can’t put on a mask. If someone is at a costume ball, you can easily see they are wearing a mask. You have to genuinely be happy for these people.

It’s so hard to grab a single ounce of happiness in this world, please be happy for the ones who are happy today. Train your mind to be sincerely happy for their happiness. Catch your resentments and jealousies before they turn into monsters.

Carrie Fisher once said, “nobody wants to read about a good looking happy person”. She was making a commentary on comedy screenwriting and she’s probably right about that. But for you to go from success to success you must first be sincerely happy for the people who are happy around you. Like attracts. Picture all the people you might resent. Spend five minutes a day training your brain to be happy for them. You’ll die lonely in the jungle if you don’t do this and everyone will forget you ever existed.

#2 People in pain. I’ve been unhappy often. Particularly in the past decade. Sometimes things just don’t work out. Sometimes people die. I think the level of unhappiness and pain I’ve had in the past decade (versus prior decades) has taught me compassion towards others in a similar boat. Try to cultivate that compassion. It doesn’t mean you have to drain yourself to help those less fortunate.

But even showing compassion and doing what you can goes a long way. If you can share what you have, all the better. If you can give a word of advice, do it.

Unhappy person can easily turn into category #4 below. You always have to protect yourself first. Be compassionate but keep your boundaries. Your goal is your own peace of mind throughout the day, so you can focus on your own success. The fastest way to do that is show compassion to those less fortunate. What you give, comes back tenfold. Try this exercise: picture everyone in your life who is unhappy or in pain, spend five minutes picturing them in a happier state. This trains your mind.

#3 Good people. This is different from “Happy”. Good people don’t always have ulterior motives. Some people legitimately want to help others. There’s an initial impulse (at least with me) to suspect them. To resent them. Maybe even to envy them. I envy Bill Gates being able to donate $100 billion to charity. But the best thing for me is to catch myself doing that (almost a meditation in itself) and say, “this guy is good. I wish I could be as good as him. I hope I can help him in any way I can.” Be grateful for all the people good to you. Five minutes a day. Doesn’t have to be with incense burning and in the lotus position. On a bus, smile and think of the people you are grateful for.

(i'm starting to believe Gates has become a genuinely good guy)

And finally, the most important category of all. The category that wastes a quadrillion brain cycles a day around the world. What man can say he is Jesus and not fall prey to the ongoing anger and pain of dealing with this next category:

#4  Crappy people: People who will do you harm, no matter what you do, for no reason at all. They never will get it. They will say and do things to you and they will never ever understand how evil they are.

And you will hate them. HATE THEM. And they knock on the door of your brain at three in the morning and they want to yell at you. And you yell back. And they yell back. And on and on. All day. All afternoon. The ongoing conversation with the shittiest people in the world. They will torture you, kill you, rape your wife and slit the thoughts out of your mind and not even care because they think they are doing the right thing. You know who I’m talking about. Because you have a good 20 or 30 of these in your life just like I do. They might even be former friends, relatives, neighbors, bureaucrats, whatever, whoever, whenever. They swoop down on your life and are just plain crappy and they won’t even know it.

Sometimes, in a weak moment, I think to myself: What if I run into them again? How badly I will hurt and destroy them. Maybe just casually walk up to them and smash a glass over their head so their nose is broken, glasses broken on the floor, blood all over their face. Arm broken after I hold the elbow and stomp on it.

STOP!

Similarly, I was talking to someone the other day who couldn’t stop talking about someone who had wronged her fourteen years ago. Stop! You are an idiot. And it’s boring already. It was your fault anyway!

This is the worst category. I’ll tell you one more anecdote. Two seconds ago someone posted a horrible comment on my blog. I won’t repeat it. Racist, mean, rude to me, whatever. I deleted the post, blocked the user, blocked his IP address. And then I was going to send him an email telling him what I thought of him. I was angry. Then I stopped myself. You have to stop yourself.

Remember this:

When you get in the mud with a pig, you get dirty and the pig gets happy.

There is only ONE only way to deal with these people in a way that will make you happier instead of sadder. ONE WAY. And it always works. This is the most important part of the Emotional leg of theDaily Practice. COMPLETELY IGNORE THE EVIL PEOPLE:

• Completely ignore them.
• Don’t think about them.
• Don’t talk to them.
• Don’t write them.
• Most important: Don’t give them advice. They will NEVER listen to your advice. It’s arrogant and stupid to think they will. It will only lead to  more cycles of pain for you. The goal for me is to stop all cycles that cause me any pain at all. Giving advice to crappy people will only result in more pain for you. That’s the only possible result. Much better to be happy than to flush knotted up brown advice down a toilet that caused you agony to push out. This is hard.
• Most important: Never gossip about them behind their backs. Just completely disregard. We don’t care about their happiness or how evil they are. We only care about you. Its hard to do. Never ever talk about them behind their backs. Repeat this 500 times. This is hard also. Because it’s an addiction.

This isn’t easy. It’s a daily discipline. Much easier to do a 1000 pushups. I had an article recently on the Wall St Journal site that had 971 comments. No exaggeration when I say 950 of the smartest anonymous trolls on the internet called me an idiot moron and worse. I ignored all the comments. Great. I could care less. I was the winner there.

Then I put another article up on a supposedly peaceful site about Buddhism and yoga, the Elephant Journal. Great site. I post there regularly. The topic of my post was that 18 year olds should basically not be sent into war. I like peace. Better to send 40 year olds. They are closer to death anyway. The most hateful responses popped up. People comparing me to Hitler. I was so shocked I wasted one whole night until 2 in the morning responding to these people but ignoring the many emails I get that genuinely support me and that I want to be friends with. Why did I do that? I wanted my haters to like me. I wanted them to agree with me and love me. Its like putting a gun to your head and saying, “unless you do what I say, I will kill myself”. You’re going to end up firing that gun.

I lost my discipline for a whole night and then I slept late and it took at least 36 hours to get back on track. What a waste. For nothing! Its hard to keep up this practice. But you fail and die unhappy if you don’t.

And did I win a trophy for doing this? Was it a huge trophy made of gold? For responding to all of those comments? Did everyone/anyone write back and say, “you’re right. I’m sorry. Now I LOVE you! Let’s all be lovers!” Of course not! They just want to fight. I got in the mud with pigs. I got dirty.

If someone says, “what do you think of so-and-so”, your worst enemy, you say back, “So-and-so who?” And that’s it. No explanation. Nothing more. “So and so who?” Change subject right then. This is the emotional leg of the Daily Practice and must be balanced with the other three legs. Any deviation will set you back. Any addiction to the opposite of the above behaviors will eat you alive like cockroaches feasting on your heart. Have a good night.

7 Things I Learned from the First Blogger - James Altucher

I was first called “Charlie Brown” in 8^th grade. I refused to stand up and say the Pledge of Allegiance with the other kids. I didn’t like being forced to do anything. Afterwards some kids came up to me.

“Hey Charlie Brown,” one of them said, “you a commie?”

“No,” I said, “I just don’t like being forced to do something.”

“He’s more like a Linus,” Larry Sorbino said. Having stayed back a grade or so he was having more sex than anyone else in junior high school. I was definitely jealous of him. Everyone laughed because he was the leader of the roost. “Linus, hahaha.” And then for the next few months people would pass me in the hallway and sneer, “Hey Linus, haha” or, when they forgot who Linus was, “Hey Charlie Brown, haha!”

(the first Charlie Brown strip)

Since I was about 4 years old I had been buying the Charlie Brown collected strips. Usually after a doctor’s visit my mom would get me a book of the strips. I was thinking this the other day because I took my kids to Friendly’s. The waitress came over and said, “what would you guys like?”

“Well,” I said, “first off, about 38 years ago I left a Charlie Brown book in a Friendly’s by accident and when my mom and I came back to look for it it was already gone and I’m wondering if since then anyone has reported it lost or if it’s maybe in the lost and foud.”

“Uhh,” the waitress said, “I’ll check.”

“Daddy!” both my daughters said and they were embarrassed. Why’d they have to have a daddy like me? Even Claudia said, “oh no.”

“But,” I said, “I’m serious. I really wanted to read that book and my mom had just gotten it for me. We were coming from the doctor’s office. I had a vaccine shot then. I needed Charlie Brown.”

Charles Schulz, the creator of Charlie Brown, wrote the strip from 1950 to 2000, just about every day. He was basically a blogger. I don’t even know if he missed a single day.

It’s hard to come up with ideas that are meaningful every day. But he did. Here’s 7 things I learned by reading his various biographies and also by probably reading every strip he every produced.

1)      He made over a billion dollars in his lifetime.  Nowadays when we think of a billion dollars we think of a guy like Mark Zuckerberg or the Groupon guys, who seem to have made a billion dollars overnight. We get jealous (I do) and think, “I could’ve done that. These guys got lucky.” But Charles Schulz showed that through recessions, stagflation, wars, high taxes, low taxes, whatever -  persistence and making sure you’re creative every single day so each day you outshine yourself and your peers a little bit more, will get you a billion dollars. Creativity every day is the key part.

(the blanket is almost like an archetype. Everyone has a version of Linus's security blanket)

2)      He had a creative process. I may have mentioned my own process before.

-          My process:  I wake up around 5am, give or take. I drink 3 cups of coffee and by the third cup I’m at the computer writing.  I read for about an hour – only strong autobiographical voices (fiction or non-fiction) [See, My Summer Reading List], then I write a blog post. I write at least a post a day even if I don’t post every day. It takes me anywhere from a half hour to eight hours to write a post. A typical post is 800 – 2000 words.

-          Charles Schulz’s process: He woke up and ate a jelly donut. Then he’d try to come up with an idea, a process he said took him between a few minutes to 3 hours. Then he would draw and ink up the strip, which would take up to another three hours. He “posted” every day, 7 days a week.

I think creativity doesn’t happen spontaneously. I think the key is persistent exercise of the creative muscle. Doing the same process every day so your brain and body expect it and know what to do once you are “in process”. That makes the possibility of having spontaneous GREAT ideas come out during those hours much more natural and easy. [See, Nine ways to light your creativity ON FIRE]

3)      Success happens over decades. I said this in #1. But it’s a specific point also. Charles Bukowski wrote for three decades before he was able to make a living at it. Charles Schulz built Charlie Brown into a powerhouse over the course of five decades. For the first two decades of Warren Buffett’s investing career, nobody knew who he was. Now he’s the richest man in the world. [See, 8 Unusual Things I Learned From Warren Buffett]

This is a hard thing for me to learn. I’ve been on and off writing for two decades, writing professionally for one, but only blogging for less than one year. And sometimes I’m really impatient for traffic, etc. But I don’t even quite know what it is I want yet. I’m very confused on this point. The only thing I know I want to do is write / post every day and build community around the posts. Schulz ultimately drew 17,897 strips. One critic said that its arguably “the longest story ever told by one person”.

4)      He loved what he did. I don’t think real success could come any other way. It seems like the formula is passion + creativity + persistence + process. When sickness was forcing him to retire (about a year before his death) he said to Al Roker on the Today Show: “”I never dreamed that this would happen to me. I always had the feeling that I would stay with the strip until I was in my early eighties, or something like that. But all of sudden it’s gone. I did not take it away. This has been taken away from me.””

Here’s the last Charlie Brown strip that appeared. It came out on February 13, 2000 (the day after Schulz’s death)

5)      He had a stance and wasn’t afraid to state it. I’ve seen over and over in my blog posts that people are afraid to even remotely THINK anything that’s outside the box that society has built for us and put us in. Schultz was always trying to step out of that box and because he did it under the guise of sweet looking children, hardly anyone noticed.

For instance, 50 years before our constant worries about Google and Facebook privacy Schultz introduced a minor character named “5” (who had sisters “3” and “4”) whose last name was his zipcode. Apparently “5”’s father was protesting that everyone now is being boiled down to just a number, taking away our individuality and privacy. Here’s the first strip with 5:

6)      Losers win.

Charlie Brown is not a bad guy. He’s a very sweet little boy. He tries to do good things. He wants to kick the ball, to get advice on how he can be better, to have more friends, to even have a girl (“Heather, the little red-headed girl”) love him. But he rarely gets what he wants. And yet, with 350 million readers worldwide at his peak, he’s one of the most beloved characters of all time. Nobody wants to read about the kid who wins every game. We all relate deep down in our hearts to the person who is isolated, a little lonely, who wants something better out of life than the cards that have been dealt him. Not that everyone is depressed. Charlie Brown is not depressed. He just loses. And so do I. And so do you. We’re all in it together to try to be a little happier in a world that’s just a little too tough on us.

Focusing on these darker elements in life, and examining them in almost 18,000 strips, is how Schulz defined his characters and shaped his stories. Don’t brag to us. Tell us how you tried to kick the ball and failed. Ultimately, Charlie Brown’s innate kindness is what caused the other kids to rally around his choice of a sickly tree in the Charlie Brown Christmas Special. Being kind against all struggles creates art, friends, beauty, happiness.

7)      He worked 100% of the time. Even when he wasn’t actively engaged in his process of drawing, he was constantly thinking of ideas and thinking of new ways to draw. This, despite the fact that on the surface the strip seems relatively simple to draw. In Schulz’s own words:

“While I am carrying on a conversation with someone, I find that I am drawing with my eyes. I find myself observing how his shirt collar comes around from behind his neck and perhaps casts a slight shadow on one side. I observe how the wrinkles in his sleeve form and how his arm may be resting on the edge of the chair. I observe how the features on his face move back and forth in perspective as he rotates his head. It actually is a form of sketching and I believe that it is the next best thing to drawing itself. I sometimes feel it is obsessive, but at least it accomplishes something for me.”

I look at his lifetime and I’m jealous even though he’s dead and I’m alive. He did the only thing he ever wanted to do, he had an audience for it, he made a lot of money doing it, he never got burnt out, he said what he wanted to say, and he said it every single day. I hope I’m so lucky

When I was a kid I would be really upset at the other kids who called me “Charlie Brown”.  But now I’m thinking it wasn’t so bad after all.

You are not running out of time - Rahul Bijlani

You are not running out of time

or How I Learned to Stop Worrying and Began Enjoying Infinity

Rahul Bijlani, October 2010

Tale of two conquerors

Early in his political career, Julius Caesar is said to have wept upon reading a biography of Alexander the Great. When asked why, he apparently said, “Do you think, I have not just cause to weep, when I consider that Alexander at my age had conquered so many nations, and I have all this time done nothing that is memorable!”

This story was seared in my memory when I read it in high school, because it spoke to my own search for achievement: I had read that at 17, Bill Gates had already created his first successful business venture. At the same age, I hadn’t even figured out where to start. It didn’t make me weep, but it did make me worry.

And so, incredibly, at 17 I genuinely wondered:

was I running out of time?

It seems amusing now – but back then I was deadly serious.

The game
You know the feeling – the feeling of being left behind in the race for achievement. Of falling back in ‘the game’. For some people, the game is keeping up with the Joneses: marrying a good catch, living in a nice house, driving the right car, having a good job, kids that do well at school. For others, it is enjoying life’s pleasures – the best vacations, the most enjoyable parties, with the most exciting partiers. Then there are people who are forever pursuing harmony and peace in their lives, resolving the discordant threads one by one, and for some the game is living up to their personally defined objective definition of personal development.

For most, it is a combination with a common thread: Am I moving up in the world at an acceptable pace, or am I running out of time? Am I maximizing my potential?

What that quickly meant to me was that wasting time and opportunities were criminal, with my own potential achievements as victims that needed to be rescued from the assault of lost hours and non-productivity. It meant becoming a workaholic. Bill Gates probably felt that way once – looking back at his teenage years and his own obsessive time spent with computers, he said,

“it was hard to tear myself away from a machine at which I could so unambiguously demonstrate success.”

I thought I was on the right track.

A moving target
Ironically, when I started to cross some of my own personal benchmarks, I discovered that something was very wrong – I kept moving the goalposts.

One counter-intuitive handicap of playing the game is that with every step you move forward, two things happen:

1. You discover that its possible to go further than you previously knew, and
2. The people you are left playing with are better at the game than people left behind. In other words, distinguishing yourself from your peers gets tougher as your definition of your peer group gets upgraded. It must have been easy for Bill Gates to stand out at Harvard, not so much in Silicon Valley, where he has constantly competed with Steve Jobs, Larry Ellison and others master games-men.

Thats why the ‘acceptable pace’ aspect of moving up in the world keeps evolving as you discover greater and greater opportunities. When Bill Gates made his first million, it probably felt extraordinary to him and a landmark achievement. How about his 2nd? His 20th? His 100th? How did he know he wasn’t running out of time to achieve his true potential when he made his first billion? If he was measuring himself on market domination, where would he go after 95% market share was secured?

The questions I had got crazier, but they seemed logical progressions of understanding the game. For example, geneticists say that one in 12 Asian men is descended from Genghis Khan. How did Julius Caesar feel about not leaving behind his empire to his progeny? Or Alexander for not having any children at all? Does that mean Genghis Khan played the game better? What does that make Bill Gates feel about marriage and kids? Does it make sense for him to have a harem, for example? Would it make sense for me to have one? And one child showered with attention, or the risk spread over a couple hundred?

If you keep asking these questions, how can you not keep moving the goalposts? How can you not get exhausted, overwhelmed, anxious?

The journey
Eventually, I came across a thought from ‘Zen and the Art of Motorcycle Maintenance’. In the story, Pirsig, a young man, goes mountain-climbing with some elderly monks. He struggles throughout, and eventually gives up, while the monks easily continue to the peak. What is apparent is that Pirsig, focussed as he is on the peak, is overwhelmed by the climb, and continues to lose his desire and strength with every step. The monks, on the other hand, used the peak only as a guide to mark the direction of their climb; they were more focused on the journey and its enjoyment, and made it to the top with ease.

This offered a valuable insight. Maybe Bill Gates doesn’t sit and ponder these definitions of success: maybe he keeps it simple – to maximize his fortune and have a small loving family – and simply enjoys programming. Maybe Alexander simply enjoyed battles, and Stephen Hawking loves physics. It would appear that they would still be active in those pursuits regardless of the relation of their endeavors to material success.

This would also suggest that the game – i.e. maximizing your potential, and what you can achieve with your time and resources – is best played if you enjoy the pursuit of your goals. In other words – if you are journey based, rather than destination driven. Pirsig’s monks probably just liked walking in the mountains, maybe they were as not wedded to the idea of standing on a peak as they were to enjoying nature.

Earlier, to me the game meant maximizing your time and potential to get somewhere, now it meant maximizing those things to enjoy the trip. That would mean that Bill Gates measure of success is how much he enjoyed his day, not how much code he wrote, or how much his businesses expanded.

A revolutionary thought! The point of my life was to enjoy it to its potential, with goals to set the direction in which I was headed.

This was my new definition of the game.

And it meant it was impossible to run out of time, because every day was a brand new opportunity to play and win.

But that still begged the question: how do you pick your destination? Doesn’t it keep moving, every time you re-evaluate the meaning of success? The monks had a fixed peak in the mountains they were climbing, most of us don’t have the luxury.

The right question
The answer to these questions occurred to me somewhat unexpectedly, through the best line in an otherwise unremarkable movie.

In Wall Street 2, right after he has cheated his own daughter out of her trust fund, Gordon Gekko, Hollywood’s favorite bad guy, is confronted by his future son-in-law, who chastises him for his seemingly slavish devotion to money. Gordon hears him out, and responds,

“You never did get it, did you? Its never been about the money – its about the game!”.

While the audience shook its head in disapproval, a lifetimes worth of questions were answered for me in a flash, and I wanted to jump up and cheer: I had the answer – Gordon was playing the game exactly right, and thats why he was exactly wrong!

He wasn’t running out of time, and he genuinely enjoyed every day of playing the game. He didn’t even care about the money, which he made and lost and made back. And yet, he was unhappy and it was clear that something was very, very wrong.

What I realized was that playing the game the right way isn’t good enough – it needs to be played for the right reason: it has to be played to build something, to see something grow. Gordon wasn’t building anything at all, not even a family, and his emptiness showed dramatically.

The destination
The answer to how you pick the destination: by asking yourself, what do I want to see grow? What do I want to build?

Even Bill Gates seems to have an opinion on this. “I’m a great believer that any tool that enhances communication has profound effects in terms of how people can learn from each other, and how they can achieve the kind of freedoms that they’re interested in.” And sure enough, he’s been building these tools all his life. All the money he made doing it? He’s giving it away. And he’s enjoying that process too!

Einstein wanted to build a theory that unified the physics of very large objects, like planets and the physics of very small objects, like atoms. Did he complete his project, before he died? No – but he left a legacy and a foundation for generations of future scientists to keep building on. I doubt he felt like he had run out of time.

A couple years ago, Steve Jobs built a phone that he wanted to see exist, and changed the world forever. Did he really need the money? Or the influence? Or the acclaim? Or was he simply trying to create something, and enjoying the process of seeing his vision come to life?

All of these examples suffered numerous setbacks as well as many opportunities to retire early in life, but chose to keep moving, because of what they wanted to build. The examples that they offer suggest that if you know what you want to build, and play the game to enjoy the journey, you are probably on your way to the good life. All of a sudden, the ‘Am I running out of time?’ question becomes meaningless.

Imagine building a house – would you really want to rush it? Lets imagine you faced an interruption – perhaps a snowstorm halted construction for a week. Would it make sense, or even be safe or wise to continue at the same pace during the storm? You wouldn’t feel bad about the delay, you’d just wait till you could resume. Or lets imagine you ran out of funds. Would you abandon the project because it was running behind time? Or find a way to continue in the future? If the foundations were poured and then you were diverted for a year, would you consider the construction to have moved backwards, or merely paused?

Now imagine building a family, or a skillset, or any object or business. Is it more important to do it rapidly and compare it to others or to build something that will last, and bring your vision to life?

A recipe for life
These questions are also why comparisons don’t really make any sense. Julius Caesar was weeping for all the wrong reasons. Alexander and he had different visions, they were looking to build different things in different times. Similarly, it was meaningless for my 17 year old self to measure myself against a very different person’s desires at a completely different time and place. In doing so, I was denying my own dreams, and trying to live someone else’s – and that too, dreams I imagined that person to have, without knowing what their dreams really were. Maybe all Bill Gates was trying to do at 17 was impress his high school crush. Maybe Alexander was trying to live up to the dreams of his father. The reality is that nobody will ever know!

Work, spouse, kids and family are not items to be checked off a list – they are directly based on the vision of the life you are trying to build, and settling based on a clock is merely a guarantee that the vision is being compromised. On the other hand, realizing what you want to build, as opposed to solely playing the game, may dramatically impact the choices you make.

In fact, answering the ‘what do I want to see grow’ question impacts all decisions, from what to do on a Saturday afternoon, to whether you should move to a different city for your work. It makes near term and long term destinations clear, and then all that is left is to play the game, or maximize your potential, to enjoy the journey of getting there. It also explains why the Gordon Gekkos and Julius Caesars of the world, who play the game just for its own sake, are generally unhappy and unsuccessful in their own eyes, even though they appear to be doing everything right.

A wise man once said happiness is the ultimate currency. The phrase resonated with me, but ‘the game’ didn’t help me maximize the currency that mattered most. Now however, at 30, I think I have the ultimate business plan, and nobody is running out of time any time soon.