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.

That’s right, I was just an intern. It feels so funny to say this now, because I always felt above the deprecating title. I suppose this was how they wanted you to feel, even as an intern: delusionally elevated.

Hubris is what makes Wall Street everything it is and isn’t: a mechanism of the functioning world markets while contributing to the dysfunctional perils of political and economic evil. And, the over-achieving, mostly Ivy League interns are all competing for the same end-of-summer “prize”: a high paying banking or trading position to continue the roles of the men (and all two, maybe three women) who came before them.

I beat myself up mentally during the time I was trying to break into Wall Street. So much that I when I look back, my actions do not feel like me and my words do not sound like me. Eventually, a few smart people and pieces of literature snapped me out of it, but the crowded memories still linger.

The following cringe-worthy recollections seemed appropriate, serious and even prideful at the time they occurred during my short stint on Wall Street. Now, they are telling, reflective and even funny.

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1. During an interview, an interviewer told me I was “intense,” and proceeded to recommend that I “relax.” I grinned, thinking honestly to myself “Yes. I fucking nailed this.”

2. I opened an interview proclaiming, before giving the two colleagues interviewing me a chance to speak, that I had just walked around the block listening to Rage Against The Machine’s “Killing In The Name of.” I then gave them permission to “begin the interview.”

3. I attempted to convince a group of high-frequency traders to use Google Reader for their media intake because it was “faster” than the tools they were already using in their terminals. This clearly wasn’t the case, but I thought it was because I was “internet savvy” and, oh yeah, they were writing advanced algorithms to trade 300 shares-per-second.

4. Barely a few months into my nascent Wall Street career, I wrote a how-to piece for college students eager to compete in finance. Upon publication, I immediately emailed the editor begging to take it down because the comments shit on me worse than I had already shit myself.

5. I signed all thank-you emails “Appreciatively” or what should have read “I hope you appreciate me sounding like a douche in the attempt of writing something different than ‘thanks.’”

6. I would openly tell my managers I was a masochist in hopes that they would assign me more work, while ironically complaining to myself all day how uncomfortable my shoes were.

7. I’d strategically place one “fuck” or “shit” in my enthusiastic “why I want to work here” pitch to the senior male managers. If I was pitching a women or minority, I’d always mention the “great diversity” the organization offered.

8. I used to wake up to so early for the train that the last-shift of b-squad prostitutes were still lounging on my street. I would shake my head in disgust, only realizing now that I should have said: ”You and I — maybe-a-lady possibly-a-dude in the five-inch heels and smeared lipstick — our jobs are not that different!”

9. An actual email written back to me once said “try to use ‘please’ and ‘thanks’ in your emails, otherwise they seem a bit arrogant. I don’t care really, but lots of ppl on the street dont like that.” Thanks, asshole.

10. I wrote Michael Lewis a long, self-aggrandizing email and closed with quite possibly the worst question ever. While I won’t reprint my question, Michael’s single-line classic response was “Alex: There’s no good or even useful answer to this question. Best, ML.”

11. This was one of my favorite movie scenes. Okay, it still is.

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I started writing, mostly as therapy, in notebooks during my summers on Wall Street. The reason being wasn’t clear at the time, but it is now: a pen and paper was the only time I could be myself.

As much as I can laugh, mock and narrate my previous, often ridiculous behavior, what bothers me is that it really wasn’t me, not even at the time. It was me being someone else attempting to meet the expectations of a culture where there is no such thing as enough.

Sure, there are plenty of intelligent, rational people that work on Wall Street who enjoy their jobs, make a good living and manage perfectly stable lives outside of work. But for the most part, I found it a difficult culture and career to keep up with where the monetary rewards aren’t in line with the personal job satisfaction, and the only measure of success is a P&L statement.

My jump post-Wall Street to entrepreneurship-land was a selfish decision: I wanted to take the wheel. No bullshit, no acting and no playing dress up. I wanted to be in control, good or bad, of my own fate and monetary outcome.

I had just gotten off of the phone with the seasoned CEO and founder of a startup I was doing a gig for a little less than a year ago. I loved what the company was attempting to accomplish, but I believed the legal fees necessary to scale the company would absorb their cash reserves before a marketable product was ready to ship. The ecstatic screaming about the income statement was in response to my worrisome, while less experienced, remarks about their business model.

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The CEO was analyzing the accounting documents of public companies with similar business models and infrastructure. He realized, and I would also eventually, that just because the legal fees had the potential to barricade the company’s goal and marketability in the short run, it didn’t mean they couldn’t generate revenue concurrently by bootstrapping what they did have, rather than what they planned to have in the future.

It’s important to consider that businesses often appear as if they generate one revenue stream, but actually generate numerous, concurrent revenue streams behind the public eye. For example, UPS isn’t just a shipping company and Amazon isn’t just a retailer. Some of these unique practices are so obscure you’d never know the company was profiting from them unless you looked at their financial statements.

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When the phone call winded down, the CEO spit out a few examples from the complimentary companies he was analyzing. I remember the example he provided dealt with one of the few successful music startups at the time. The company was not only providing a consumer subscription service, but behind the scenes was licensing music to other platforms, selling ring tones and even providing anonymous user data to advertisers.

Consider these two models of concurrent revenue streams:

1. Moby has the best selling electronica album of all time, Play. While the album dominated the charts for a few years, Moby found success by commercializing his creativity to less obvious (at least in 1999) markets: licensing. According to Wired, the tracks on Play have been “sold hundreds of times for commercials, movies, and TV shows – a licensing venture so staggeringly lucrative that the album was a financial success months before it reached its multi-platinum sales total.” Listen to the album. Even if you’ve never heard of Moby, you will probably recognize a handful of tracks just from being alive during its prominence.

2. Google is now hiring bond traders. While most major corporations utilize financial analysts to hedge foreign cash flows, it’s rumored Google may be using their vast data sets to build and run a hedge fund. Legalities aside, they have the valuable data to pull it off, as would a company like Facebook

These are examples of concurrent engineering applied to sales and marketing. It’s similar to flipping the stick, except you aren’t flipping anything; you’re just being resourceful with your stick. Moby is a musician, but he’s also a brand and advertiser. Google is a search engine, but they are also a hedge fund and hundreds of other things.

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Since the original phone call, I’ve dispersed the concurrent engineering advice to not only my own company, but to numerous artists, musicians and brands. Just because the thing you eventually want to sell isn’t ready, it doesn’t mean what you do have, right now, isn’t marketable.

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.