A piece of art is successful (the second part) when the artist’s perspective resonates with an audience in a way that’s understood, even if it differs from the artist’s intention. However, the process of creating art (the first and often less examined part) is selfish: the artist produces to provide himself with a clearer, stronger, deeper perspective of his own life.

As an extreme example of a process-driven artist, consider Henry Darger, a recluse with a negligible public occupation as a hospital janitor who led a secret life as a writer and artist. A custodian during the day, Darger produced a 15,000 page work of fiction, a 5,000 page autobiography, a 10-year weather journal, a 10,000 page novel and a collection of diaries, paintings and illustrations in his spare time. Indifferent to result, Darger’s work did not emerge until after his death. He’s heralded to this day in museums and recognized as a prime example of outsider art.

Art allows for process because it is malleable. An artist can take bits and pieces of life conditions and experiences, often confusing and overbearing to reality, and weave them into a neat, linear narrative on a canvas. The painter chooses from a pallet of colors, patterns, symbols and textures, and arranges them into a painting. The musician uses instruments, samples and production techniques, layering sounds into a song or album. The writer — and this is especially true of the fiction writer — tells a story using language, characters and emotion reflecting pieces of our own lives.

The process of creating art, regardless of its result, can bring us one step closer to understanding our own reality.

Tomorrow: “I’m not sure, but, I think the market will be down.”

This answer is reflective of the current market condition. If the general sentiment — typically what’s portrayed by the mainstream financial media — is pessimistic, the average person will mirror and predict down.

One year from now: “The market will be recovering and probably up by a little bit.”

This answer is often more optimistic because the time period — one year from now — is out of reach. We assume, for one reason or another, that things will “get better by then.” Someone will do something to make it better. This prediction is based on nothing.

Five years from now: “The market will definitely be surging and the economy will be back on track.”

The most illogical and predictable answer of the set results from pushing time parameters out of reality’s grasp. This answer won’t change whether the parameters are five years, ten years or twenty years into the future. The idea is that we can’t fathom what market conditions, let alone our personal conditions, will have in store that far away. We assume that things “will get better,” just because they will.

I don’t think think there is anything wrong, on a personal level, with inherent, unjustified optimism, or what John Cassidy might call rational irrationality. It’s certainly more pleasant than being an unjustified pessimist. But, I do think unjustified, rationality-free optimism can pollute productivity and decision making.

If you assume things (the market, a relationship, hobby, career, etc.) are just going to “get better” without reason, you place yourself in a safety zone, and one of inaction. Unjustified optimism is equipped with mental stagnancy: it assumes natural improvement. It’s as meritless as assuming the stock market will go up if we “keep doing what we are already doing,” just because it will.

I am in favor of, however, justified optimism: things will get better because of this, this and this. Or, because I’m going to do this better or differently. But, unjustified optimism — portrayed by the people that “answer” the stock market questions above — is for fools.

Unjustified optimism allows us to become mentally dormant, permitting cruise control. The solution to any dilemma becomes a quest to amass more of what we are already doing. Ridding ourselves of unjustified optimism creates a natural, inventive realism. It forces us to improve reality, rather than adapting to unreality.

Picasso said, “Even if you are wealthy, act poor.” The same applies to outlook: if you are feeling unnecessarily optimistic, it’s probably a time to become grounded. Focus on reality — things you can touch, feel, change and improve — rather than assuming an externality will accomplish something for you, just because it will.

I can attest to have always floated between various social groups, never really identifying with one particular array of hipsters, artists, punks, jocks, nerds, bloods or crips. It sounds oddly high-schoolish of me to categorize my now post-college social habits in that fashion, but I can assure you nothing has really changed in how I observe everyday social interaction. It’s still rich with cliques, gossip, self-consciousness, and of course, habitual indulgences.

Indulgences are worthwhile to evaluate because the exercise provides deeper insight into an individual’s personality, habits and behavior. They often fall somewhere in between two ends of the following spectrum: quick hitters and long haulers.

The quick hitter is dangerously near sighted. He spends his paycheck the day it’s received, proudly pushing bank accounts to zero and credit cards to their maximum. The only future he is concerned with is that night, or maybe the upcoming weekend. The quick hitter is prone to addiction, convincing himself that a short-term high will lead to extended pleasure. He lives for material items, addicted to the rush upon the checkout line when the credit card swipes.

The long hauler saves every dollar he earns, reluctant to spend or act beyond basic necessities. He isn’t saving for anything in particular, besides a distant goal that will never be met. The long hauler lacks spontaneity, with meticulous planning and over-preparation reducing any exposure to serendipity. He doesn’t live for any items besides the uptick in his safety bank account. He denies impulse, mistrusts his own instinct, lacks balls and generally lives a caged, dull existence.

As I write this, I realize the process of indulgence distinction is more than a simple exercise in arm-chair psychology; it’s a tool for how to make relationship decisions:

The advantageous strategy is to commit to relationships that fall somewhere in between the two poles of the indulgence spectrum. As I recall the friendships I’ve lost in the past, and the friendships I’ve made more recently, I attribute indulgence habits as one of the reasons why one started or ended. When two people have similar habits, indulgences become transparent to regular behavior. When they become out of alignment, it tugs on the balance and benefits of the relationship.

Quick hitters are blind to the future, and long haulers are ignorant to the present. Both views are equally destructive in losing focus on the happy, more productive medium. Extreme perspectives are distracting, narrow minded philosophies that accomplish very little besides appealing, at best, to sparing occasions of our own selfish entertainment. Quick hitters and long haulers are best kept at a distance.

At one point in my life, I would have told you Allen Iverson was my role model. While I still respect him for certain accomplishments, a turning point of maturity forced me to realign what a role model was and who was worth having as one.

At the close of adolescence, my role models became within reach. These role models, only an email away, included those doing a more professional, lucrative transformation of what I was doing or wanted to be doing in business.

After a period of time, I realized my role models and I were on the same track, just a few laps ahead. I wondered if I could just run a little faster…

–

What happens when role models become peers?

You could seek new role models. There is something intriguing about constantly admiring someone so out of reach that the opportunity of rubbing shoulders is unlikely. The fairytale distance can be seductive and equally motivational in reaching big, ambitious goals. Within the same argument, others might claim that if a role model can realistically become a peer, you aren’t reaching high enough. Who wants to join the club that will accept them as a member, anyway?

You could remain a disciple to your role model, making him feel comfortably superior. While from an outsider’s perspective it may seem that you’ve reached an intellectual limit, there may be more to gain by appearing less aggressive than him. If you aren’t explicitly running ahead of the role model, his guard is down. The dilemma is that without a power strategy, there is a ceiling. With awareness and manipulation of the superiority complex, you are still controlling the chess board.

Finally, you could ignore the level playing field and approach the situation with your arms swinging. Maybe this is what we’re all fighting for: to box in the same ring as our idols. Fuck making friends, just stiff arm them to the end zone.

Creativity falls into a category of traits often claimed but rarely defined. My observations tell me this happens for three reasons:

One, the word has sex appeal. Similar to “entrepreneur,” it’s become marketable and desirable for someone to claim he is a “creative,” even if he’s not. The second, most authentically, is communicated by someone who creates things while lacking the acuteness to articulate what he is creating. The third is communicated by someone who claims a creative philosophy, but is ignorant to communicating his reasoning.

The distinctions play a role in the unique war occurring between the opposing poles of popular culture: art and marketing. I categorize art as original work derived from the hands and minds of the second and third distinctions. Historically, art has generated new cultural movements. The subsequent mass marketing is a collection of messages recycled from the original art, often developed by individuals in the first distinction.

Both art and marketing can, and do, stand on their own, but are more effective when combined. For instance, for a painting to reach mass appeal and commercial success, it needs to be created by the artist, while most effectively marketed by a second party, such as a museum. Likewise, a marketing campaign will prove influential when its guts have been created by the unique work of an artist.

Today’s original art is reflective of today’s mass marketing and media, rather than the other way around. Consider the following two examples:

The Banksy-influenced street artist Mr. Brainwash currently has an exhibit displaying colorful pop portraits in a spacious New York warehouse reminiscent in style of Andy Warhol, including quirky prints of Obama, Kate Moss, Keith Haring, a taxi cab in a toy box and broken record outlines of pop figures Slash, Jay-Z, David Bowie and Sid Vicious. Mr. Brainwash leveraged existing, pre-marketed trends, repackaged them and resold his art to an existing culture and new audience.

Or, take the Significant Objects project, where writers develop original stories around insignificant objects, crowning them significant, subsequently selling the items on eBay for more then they are “worth.” The objects, often just everyday items, increase in value because of the original narrative wrapped around them. Similar to the Mr. Brainwash exhibit, an existing culture has been repackaged, redesigned and recycled for a likely new audience.

Art has become so recycled and repetitive that one meme’s high quickly fades until the next hit. Today’s artist isn’t an individual; he’s been reduced to another, for lack of a better word, remixer.

Present culture is faced with a cyclical dilemma: Artists aren’t starting trends, they are repackaging them. Mass marketing, to its benefit, has become so relevant that it’s viewed as inspiration by today’s creatives. With any period of inflection–a loophole exists. There is a rare opportunity to lead a wave of artists that create the culture, rather than simply reflect it.

Who will be part of it?

Being that we are actively selfish, treating actions as investments comes naturally. However, I’d argue that it’s not actively leveraged or thought about by the average person. Ignorance has its pros and cons: The pros allow you to avoid getting drowned in your own ideologies. The cons revolve around wasted inputs of money, time or emotion.

Everyday investments can be sorted based on the situation or occurrence. For simplicity, I’ll outline each with personal context:

The most frequent investment of time I make is allocated to meetings. I’m at a point in my career where meetings–business development, hiring, management–absorb the majority of my day. Is the projected outcome of a meeting, based on outcomes of similar previous¹ meetings, worth the investment of my time? I treat books, blogs, film, art and music the same way.

Disbursement of disposable income is an investment. I’m less hesitant spending money on useful experiences and items than I am with my time, simply because I’m confident I can make more² money, but not more time. What I attempt to calculate is if the net payoff of the experience or item purchased will be greater than the net effort involved in creating the original wealth.

Emotional investments are allocated to relationships. There isn’t much to say about this investment, except that I’ve found it beneficial to take note of how you feel after you’ve spent time with someone. As you might assume, it’s the hardest payoff to calculate: emotions often feel one way but mean something else.

The basis for any investment–time, money and emotion–like a hedge fund, is based on objective and risk. I live by the general rule that the younger one is the more risk they should take. While I’m aware of my investments, I tend to not let the neuroticism involved with quantification become counter-productive to my efforts for profitability.

1. I realize projections based solely on historical context go against Nassim Taleb’s investment philosophy, but I abide to it anyway. People aren’t stocks.
2. Time runs out. Money, technically, doesn’t have to.

A bit of conventional wisdom echoed between traditionalists is “don’t do a job for the money.” This dictates that you shouldn’t chase a career for a paycheck that’s a means to short, material boosts of happiness facilitated by addictive consumerism. The advice implies you should only be pursuing a career for the intellectual stimulation, where the cash is merely a side effect.

The advice is misguiding. The goal of a job should be wealth creation, either for yourself or for your organization. I don’t think the “beware: money!” advice is bad in itself, but it’s taken too literally. The idealist philosophy gets in the way of building a profitable business, which is often a painful endeavor. Convincing yourself money doesn’t matter is the easiest way to justify a failure.

Part II

George Soros cringes when he’s called a hedge fund manager, financier, speculator, trader, banker, entrepreneur and probably even an investor. Soros, above all, is a philosopher who applies his world views to capitalistic endeavors.¹

This illustrates my bigger point: Soros prefers the title of a philosopher because he enjoys the implications of philosophizing more so than money managing. For example, take his view of credit default swaps, referred to as “buy[ing] insurance on someone else’s life and then hav[ing] a license to kill them.” If you talk to any trader on Wall Street, they call it a hedge, not a death certificate like Soros.

Soros does what he does–his craft–for wealth creation. His profit and loss statement is the major measure of success. He is, after all, a top-tier investor. However, he uses his interest in philosophy to make investing sound and feel, specifically to him, like a glorified hobby.

Part III

If you really would do a job for free, the job is either completely worthless or someone smarter than you is absorbing the value creation. Every time I hear someone say, specifically an eager young person, that “they aren’t doing it for the money,” I hear someone being foolishly naive about business and avoiding the ultimate judgment of a potential failure. Money is the market’s way of signaling value. If you aren’t making any, or slated to make any, you’re doing it wrong.²

I’d be willing to bet the most popular jobs are those most difficult to measure, simply because they make hiding behind failure easy. I blame the marketers, simply because they are the easiest target. They’ve convinced a whole class of aspiring creatives that you can base a career on building relationships, community evangelizing and blogging. These descriptions may sound productive in text, but they are skills people say they are good at because there is not an easy way to measure financial results. They aren’t quantifiable, measurable or testable. These skills are valuable if you can determine their ROI (and the talented, versatile marketers can), but if you can’t measure, you’re just overhead.³

Part IV

The more I dive into my career, craft, path, journey or whatever you want to call it, the more I realize that I’m absolutely doing it for the money. I love what I’m doing, no doubt, but I inevitably know that the measure of success will be judged by how much wealth I create for my organization and its stakeholders. Going into business without the intent to make money is like crossing a busy highway without looking both ways.

Do it all for the money. Not necessarily to spend it–but to make it and measure it. Long-term wealth creation proves economic tangibility. To pursue anything else besides money will put you out of business.

1. Like Soros, Charlie Munger was keen on “philosophizing,” rather than just “investing,” even though he did the latter. Many entrepreneurs, especially Marc Andreessen, live by his almanac.
2. An interview strategy relevant to this point would be to proclaim you will make an organization more money than they are slated to pay you. From the employer’s stand point, this is obviously their the goal.
3. Stock traders are a good example of the ultimately measurable career, although the majority of the ones I know hate their job. It’s possible that too close of an association between P&L and the job can be mentally counter-productive.

When my foot hits the solid pavement outside of the front doorway, I spend a few seconds absorbing the surroundings: the New York people, the New York air, the New York noise, the New York smell¹ –the entire New York pill swallowed at once is an inspiring drug.

The average person’s morning priority is to begin moving their legs into a walking pattern towards their destination. But for me, walking becomes secondary to my music fixation. With my legs locked into the ground, stiff and rigid, I pull out out my iPod and browse to the day’s first song. I usually pick something loud and soulful–the only way to compliment a New York morning. It’s the grease to my wheels.

Music: begin.

The bass kicks. The treble screams. The lyrics bring the sonics together. Like a sedative, my legs loosen, the buildings around me melt and the surrounding passersbys become lost, ghostly silhouettes. I begin walking, moving closer to my destination, which is different every day. I like this city. But, I love this city–on music.

I move quickly. No one is timing me, but I still attempt to arrive early, just to feel ahead of schedule.

Where am I going? The destination is completely meaningless. Sometimes I have no destination in mind; other times, I do. But, it’s always one foot in front of the other, knowing I want to be one step ahead, two steps from there and ten steps from there. Ad infinitum.

The beauty of the situation is trapped inside own narrative, expressed here, that means nothing to anyone but me.

1. I was going to add the New York dirt, but there is none. This city, especially on the west side, is immaculate.

And, uh, the doctor says, “Well, why don’t you turn him in?”

The guy says, “I would, but I need the eggs.”

Well, I guess that’s pretty much now how I feel about relationships; y’know, they’re totally irrational, and crazy, and absurd, and… but, uh, I guess we keep goin’ through it because, uh, most of us… need the eggs.

- Woody Allen, Annie Hall, 1977

The technology culture in the Bay Area is saturated. The justification for working on a startup requires little explanation because the person you are talking to is probably working on one as well. In New York, it parallels the density of the financial industry. Many of the professionals living in the city work on Wall Street. And if they don’t, they probably want to, even if they won’t admit it. In Los Angeles, I’d assume it’s similar with the entertainment industry.

Cultures cause a tunnel vision, and the result, if you stand back, can be laughably absurd. For example, the nuances of the technology culture in the Bay Area drag along the pettiness of social media counting. If you’ve been to a technology conference, I guarantee you’ve overheard a conversation as ridiculous as this:

Geek #1 in a “If you were coding Ruby, you’d be home by now” shirt:

“Dude, my follower count dropped from 147 to 143 yesterday after I sent out that NSFW link without warning.”

Geek #2 in a “I’m huge on Twitter” shirt:

“Ah, that stinks. At least you’re still not trying to break 100. I’ll just follow a few hundred people until they follow me back, then drop them all!”

I’d interject, in reference to what Howard wrote, that you have to be willing to be unfollowed or unread if you want to be followed or read at all. It’s similar to investing; you need to be willing to lose money to make money. Any progression has its waves in and out, up and down, happy and sad.

But seriously, now taking another step back. The conversation I referenced, which happens more often than you might think, is about losing Twitter followers. These are people you probably don’t really know. What does it mean?

The irony is that I’m taking the time to write about it and fight about it. It’s as ridiculous as the guy with a brother that’s a chicken: maybe I’m the crazy one. For jobs or hobbies, including mine, the bullshit just might be part of the opportunity cost. My criticism is stale, but to me, it feels warranted.

Conversations like the one I described aren’t about the love of technology, fascination with social media, or about the group-think the two cause together; they are about being in love with the tragedy of it all.

And, if you can’t laugh at it, everyone else will for you. Or, at least I will.

The decision revolved around my move to San Francisco to work on my venture full-time, or to move on to new projects. When that thing you’ve been seeking is finally in the grasp of your hand, closing your fingers around it can be daunting. I knew what I had to do, but was I ready?

I had a term sheet; do I scribble my name on it? I just graduated college; is this supposed to happen? The two thoughts seemed to be stuck together.

As I paced aimlessly around Harvard Square one afternoon, frustrated and nostalgic as the eager college students moved into their dorms, I called Derek:

Derek. What the fuck should I do?

He didn’t tell me what to do; he never does. But, he did reply to my question with a story that I’ve thought about every day since:

I never wanted to sell CD Baby, but I was noticing that I was less enthusiastic about the company, and losing interest.  Around this time I had three different companies wanting to buy it, but had always said no.  I asked my friend Seth for advice and he said:

“If you care, sell it.”

Derek’s interpretation, and mine as well, was that if he was even considering selling CD Baby, he would be doing the company little justice by continuing to run it. The thought alone was unfair to the organization he not only managed, but built from the ground up. It required dedicated attention.

The answer to Derek’s dilemma was apparent in the decision-process alone. Meaning, if he truly cared about the company, it was best to pass it on to someone who didn’t have the intent to sell.

The result? Derek sold.

In my situation, I knew I cared enough to stick with my own company. I wasn’t actively considering other opportunities, even though they existed. And even if I was, I knew I’d add little progress to someone else’s project with my own startup nagging me in the back of my mind. How could I not give it a try?

The reality of my situation was that I cared so much, I was having difficulty dealing it.

There was only one way to resolve it. I signed.

The decision making process can be more telling than a decision itself, even if the most obvious choice is the hardest one to make.