Steve Jobs was one of our generation’s best innovators, if not the best. What he represented was singular and rare: a person in charge of a major company who actually had a strong and socially positive vision. Corporate executives are expected to have some quantity of vision and foresight, but so very few, across the Fortune 1000, ever actually have it that there is a certain surprise associated with learning of one who does. Most corporate executives are mediocrities if not negative in their contribution, meddling with those who are actually getting work done with constant churn and (in the negative sense) disruption. Steve Jobs, on the other hand, was integral to the success of Apple. As Apple’s posthumous tribute to him said, only he could have built that company. Unlike the typical businessman, Jobs was not especially charismatic. He was an effective salesman only because the quality of what he sold was so high; he could sell because he believed in his products. What he was is creative, courageous, disciplined, and effective. He had a sharp aesthetic sense, but also the clarity of vision to ship a real, working product.

Why do people like him appear only a few times in a generation? It’s not that there is a lack of talent. Not to denigrate Steve Jobs, because his talents are in any case uncommon, but I’d bet heavily (on statistical grounds) that there are at least a few hundred or thousand people like him out there, hacking away at long-shot startups, cloistered in academia, or possibly toiling in corporate obscurity. The issue is that people with his level of talent almost never succeed in human organizations such as large corporations. A keen aesthetic sense is a severe liability in most corporate jobs, as the corporate style of “professionalism” requires tolerance of ugliness rather than the pursuit of aesthetic integrity at all costs. Creative talent also becomes a negative in environments that expect years of unfulfilling dues-paying before one gets creative control of anything. People like Jobs can’t stand to waste time and so, in corporate America, they rarely make it. When they are set to boring work, the part of their brains not being used scream at them and that makes it impossible for them to climb the ladder.

That human organizations are poor at selecting leaders is well-known, and startups are an often-cited antidote to this problem. The issue there is that a herd mentality still exists in venture capital and startup press. The herd almost never likes people of high talent, and for every independent thinker in a true king-making role, there are twenty overfed bureaucrats making decisions based on “track record” and similarity to existing successes– a fact not in the favor of a 22-year-old Steve Jobs in 2011. To be honest, I don’t think such a person would have a chance in hell of acquiring venture capital funding on his own, unless born into the necessary connections. Elite incubators such as Y Combinator are solving this problem, and quite well, by connecting young talent with the necessary resources and connections. Are they doing enough? Will they succeed in changing the dynamics of startup funding and traction? I don’t have the foresight to answer that question yet; honestly, I have no idea. Time will tell.

I think a lot of people around my age (28) have spent some time thinking: How can I be more like Steve Jobs? That’s the wrong question to be asking. The perfect storm that enables even a moderately creative person (much less an out-and-out disruptive innovator like Jobs) to overcome the enormous obstacles human organizations throw at them is an event that occurs less often than a $100-million lottery windfall. The right question is closer to this: what can I do that makes people with immense creative talents, like Steve Jobs, more likely to succeed? So this, I believe, is a more reliable path to success and an indirect sort of greatness. It’s great to have dreams and work hard to achieve them, but it’s equally noble (and more often successful) to help others with great ideas realize theirs. Right now, most people with great ideas almost always linger in obscurity, with powerful people and institutions actively working to keep them there. That has been the case for nearly all of human history, but technology can change it.

How? I’m not sure. I spend a lot of time thinking about this issue. How can a world with so much creative talent in it (on account of having nearly 7 billion living people, at least a billion of whom now have the minimum resources to express creativity and at least a few million among those having the talent) be achieving so little? Why is there so much ugliness, inertia and failure? How do we empower people to change it? These questions are too big for me to answer, at least for now. I’m going to focus on one thing: the process of turning talent into greatness, the former being abundant and the latter being desperately uncommon. How do we get people with high talent to such a degree of skill that they can, as individual contributors, contribute to society substantially– so much so as to overcome the general mediocrity of human institutions?

This is an educational problem, but not one solved by traditional schooling. Greatness doesn’t come from completing assignments or acing tests, obviously. It requires personal initiative, a will to innovate, and courage. Then it requires recognition; people who show the desire to achieve great things should be given the resources to try. It doesn’t seem like it, but I’ve exposed an extremely difficult problem, one that I don’t know how to solve. Educational processes that encourage creativity make it extremely difficult to measure performance, and therefore fail to gain the social trust necessary to propel their pupils into positions of creative control in major organizations. On the other hand, those educational processes in which it’s easy to measure performance generally favor conformity and the ability to “game the system” over useful creative talents or skills. Moreover, there’s a variety of grade inflation that exists far beyond academia whose effect is socially pernicious.

Grade inflation seems like a “feel good” consequence of people being “too nice”, but from a zero-sum economic perspective, it actually reflects a society that stigmatizes failure heavily. If an average performance is rated at 2 (a C grade) on a 0-to-4 scale, then excellence in one course (A, 4.0) cancels out failure (F, 0.0) in another. On the other hand, if the average is 3.2 out of 4, then it takes four excellent grades to cancel out one failure. This makes failing a course substantially more costly. This reflects risk-aversion on the part of the educational system– the student who puts forth a mediocre performance in three courses is superior to one who excels in two but fails the third– and engenders risk-averse behavior on the part of students. That said, I’m not especially concerned with this problem in the educational system, which is far more forgiving of good-faith failure than most human organizations. A failed course can damage one’s average but rarely results in expulsion. I’m more worried about how this mentality plays out in real life.

This style of risk-aversion is reflected in human organizations such as corporations. An employee who has four great years followed by a bad one is likely to be fired for the damaged reputation acquired in that failed fifth year. People are measured according to their worst-case performance (reliability) rather than their best-case capability (talent). This is a problem for a person like Steve Jobs, obviously capable of hitting the highest of the high notes, but liable to show negative contribution (pissing people off) at his worst. It’s also a more general problem that leaves large organizations unable to tap their best people. Why? Those best people tend overwhelmingly to be “high-variance” people– those whose job performance becomes weak if they lose motivation, and who become so passionate about the quality of work that they invariably end up in personality conflicts. Low-variance individuals– generally lacking creativity but capable of sustaining a middling performance for decades, thereby showcasing “professionalism”– tend to win out in their stead. The creatively desolate world we observe in the leadership of major human organizations is a direct result of this.

In some cases, measuring performance at a person’s bottom rather than top makes sense. As Lord Acton said, “Judge talent at its best and character at its worst.” People who behave in a way that is outright unethical have proven themselves not worthy of trust, regardless of their best-case capabilities. On the other hand, a person like Steve Jobs fails in a mainstream corporate environment fails not because he is unethical but because he’s merely difficult. That is what is in error. In general, human organizations develop a toddler-like, black-and-white view in evaluation of their members and thereby lose the ability to discriminate between those who are outright criminal (and should be distrusted, terminated from employment, and possibly punished regardless of their talents) from those who have difficult personalities or who suffer a good-faith failure (a risk one must be able to afford if one wants to achieve anything).

There’s a solution to that problem, but a touchy one. In technology, programmers have taken to the open-source community as a means of building an organization-independent career. This reflects what academia has had for a long time: active encouragement for its members (graduate students and post-docs especially) to build reputations outside of their institutions. This allows people to demonstrate their best-case capabilites to the world at large. Unfortunately, there is an extremely touchy political matter here. Corporations and managers within them would generally prefer that subordinates not dedicate energy to the cultivation of an external reputation, a process that (a) distracts them from their “real work” and dues-paying, and (b) makes them more expensive to retain. Many large companies forbid employees to take consulting work or publish papers for this precise reason.

Now that I’ve laid out a few problems and ideas, I’ve noticed that both time (9:08 am, and I haven’t yet left for work) and word count (1683 and rising) are encouraging me to finish up. For a closing thought, I’ll admit that I don’t have many answers to the “big picture” problems here. I don’t know what it will take to fix the problems of large human organizations that lead to their pervasive mediocrity. I don’t even know if it can be done. Where to focus? Something smaller and tractable, something grass-roots.

Brilliant people, like Steve Jobs, aren’t born fully-fledged like Venus from the sea. Jobs became what he was due to a thousand influences– his friendship with Steve Wozniak, his early successes, later failures, and yet-later successes. That much is obvious. He was always talented but he became great on account of the opportunities he had– the successes and failures that refined his aesthetic sense until (in his later adulthood) it was a finished product. I also believe that there are thousands of people much like him in existence, their talents unexpressed. I don’t think we need to work hard to “find” them. These people are loud and obnoxious enough that this is an easy task. What we need to do, as much as we can, is enable such people to overcome the hurdles imposed by large human organizations more interested in protecting entrenched mediocrity than in pursuing excellence. We need to fight that battle as much as we can. And yet, we must accept that we aren’t likely to get very far. There’s more we need to do.

We need to rethink education. I’m not just talking about schooling. Instead, I’m talking about technology and business and culture. We need to remove from ourselves the notion that education is a “product” to be “consumed” by those rendered economically useless by their youth and inexperience. Education needs to be an ongoing process. It needs to pervade everything we do. Instead of writing code, managing people, or running businesses we need to focus on teaching people what we can, and on learning from them reciprocally. We need to reinvent corporate and organizational cultures outright so that talent is naturally turned into greatness, and so that excellence isn’t a weird, socially counterproductive personality trait but something that all strive toward.