Creativity is one of those undeniably positive words that is reflexively associated with virtue, leadership, intelligence and industry (even though I’ve known some creative people who lack those traits). Yet, 28 years of experience has taught me that people don’t have much patience for creative people. We are like the nautilus, a strange-looking and, some would say, unattractive creature that leaves behind a beautiful shell. Most people are happy to have what we create, but would prefer never to see the marine animal that once lived inside the art. All they want to do is pick it up once left on the shore.

Creativity isn’t in-born and immutable. It’s an attribute of which most people end up using (and, in the long-term, retaining) less than 1 percent of their natural potential. It grows over time as a result of behaviors that most people find strange and potentially unpleasant. Creative people are curious, which means that they often seek information that others consider it inappropriate for them to have. They’re passionate, which means they have strong opinions and will voice them. Neither of these is well-received in the typical conservative corporate environment. Worse yet, creative people are deeply anti-authoritarian, because it’s simply not possible to become and stay creative by just following orders, not when those orders impose compromise over a substantial fraction of one’s waking time. It never has been, and it never will be.

This doesn’t mean that creativity is only about free expression and flouting convention. Creativity has divergent and convergent components. An apprentice painter’s more abstract work may seem like “paint splatter”, but there’s a divergent value in this: she’s getting a sense of what randomness and play “look like”. She might do that in January. In February, she might do a still life, or an imitation of an existing classical piece. (Despite negative connotations of the word, imitation was an essential part of an artist’s education for hundreds of years.) It’s in March that she produces art of the highest value: something original, new, and playful (divergence) that leverages truth and value discovered by her predecessors, trimmed using rules (convergence) they teach. Computationally, one can think of the divergent component as free expansion and the convergent aspect as pruning. The convergent aspect of creativity requires a lot of discipline and work. Novelists refer to this process as “killing your darlings”, because it involves removing from a narrative all of the characters or themes that an artist inserts for personal (often emotional) reasons but that add little merit to the completed work. For technology, Steve Jobs summarized it in three words: “Real artists ship”. It’s intellectually taxing, and many people can’t do it.

Convergent creativity is what our culture’s archetype of “the artist”, for the most part, misses. Youthful “experience chasing”, social climbing, extremes either of fame and wealth or of miserable, impoverished obscurity, all have some divergent value. On the other hand, that type of stock-character artist (or real Williamsburg hipster) has almost no hope of producing anything of artistic value. Divergence alone leads to mutation and insanity, not creation. This also explains why the highest-priced “modern art” is so terrible. We have a culture that worships power, money, and social access for their own sake and so the “brand-name artists” whose connections enable them to be paid for divergence (and divergence only) are treated as high priests by our supposed cultural leaders. The result of this is that terrible art sells for astronomical sums, while real artists often work in obscurity.

Most people, when they think of creative workers, whether we’re talking about writers or game designers or computer programmers, only seem to understand the divergent part. That gives them the impression that we’re a coddled bunch with easy jobs. We “get paid to have fun”. To quote Mad Men from the perspective of an “account man”, we’re “creative crybabies”. Bullshit. Creativity is rewarding and it can be a lot of fun, but it also requires an incredible amount of work, often at inconvenient hours and requiring very high levels of sustained effort. Wake up at 5:00 am with a great idea? Get to work, now. If that idea comes at 10:30 pm instead, stay up. Most of us work a thousand times harder than “executives”, the private-sector bureaucrats whose real jobs are white-collar social climbing.

As with the adiabatic cooling of an expanding gas, and the heating of a compressed one, divergence has a cooling effect while convergence is hot. For the first, free writing tends to calm the nerves and diminish anger. Improvisational art is deeply anxiolytic and invigorating. But if it is taken too far without its counterpart, divergence leads to softness and ennui. A metaphor that programmers will understand is the concept of writing a 100,000-line program on paper, or in a featureless text editor (e.g. NotePad) without an appropriate compiler or interpreter. In the absence of the exacting, brutal convergence imposed by the compiler (which rejects programs that don’t make sense) the programmer is deprived of the rapid and engaging divergence/convergence cycle on which programmers depend. Over time, the hand-written program will accumulate shortcuts and errors, as the programmer loses touch with the substrate on which the program will run. Related to divergence’s cooling effect is convergence’s heating effect. It’s very taxing to hack branches off of one’s “search tree”. It’s painful. As humans, we’re collectors and we don’t like setting things we’ve found out of view, much less discarding them. About two to three hours of this work, per day, is more than most people can reliably perform. Although extremely important, the convergent aspect of creativity is exhausting and leads to frayed nerves and difficult personalities.

Business executives’ jobs are social climbing, internal and external. Their jobs are intentionally made extremely easy to minimize the probability of social hiccups, for which tolerance is often zero. They’re paid five times as much as any person could possibly need, to eliminate the possibility of financial worry and allow them to purchase ample domestic services. They’re given personal assistants to remove pollution and stress from their communication channels. This makes sense in the context of what companies need from their executives. He only needs to have average intelligence and social skill, but he needs to sustain this level reliably, 24/7, under a wide range of unpredictable circumstances. Rare moments (“outlier events”) are where creative people earn their keep, but where executives set themselves on fire. To be an executive, one needs to be reliable. Executives may have the authority to set working hours, but they have to be on time, all the time, every day.

For a contrast, the creative person often “needs a walk” at 3:00 in the afternoon and has no qualms about leaving work for an hour to enjoy an autumn day. After all, he does his best work at 7:00 am (or 11:30 pm) anyway. Creative people earn their keep in their best hours, and are wasting time in the mediocre ones. From an executive perspective, however, this behavior is undesirable. Why’d he up-and-leave at 3:00? There could have been a crisis! What risk! By definition, creative people are full of risk, socially gauche on account of their tendency to mentally exhaust themselves in their desire to produce something great, and therefore not reliable. Clearly “not executive material”, right? I disagree, because I think the discrepancy is more of role than of constitution. Most creative people could become tight-laced executives if they needed to do so. Creatively inclined entrepreneurs often do find themselves in this role, and many play it well. There is, however, an either/or dynamic going on. It’s necessary to choose one role and play it well, rather than attempting both and being very likely to fail. Someone who is exhausted on a daily basis by the demands of high-level creativity (and I don’t mean to say that creative work isn’t rewarding; it is, but it’s hard) can’t be a reliable people-pleaser in the same week, any more than a clay jar that just came out of a 1000-degree oven shouldn’t be used, until it cools, to store ice cream.

For this reason, business executives tend to look at their most creative underlings and see them as “not executive material”. Well, I agree this far: not now. That perception alone wouldn’t be such a problem, except for the fact that people tend to judge others’ merit on a “just like me” basis, especially as they acquire power (ego confirmation). They tend to be blind to the possibility that people very different from them can be just as valuable. Executives tend, for example, to favor mediocre programmers who don’t exert themselves at work, and who therefore retain enough mental energy for social polish. The technical mediocrity that sets in over most software companies is the long-term result of this. It’s not that companies go out of their way to “promote idiots”; it’s that they are designed to favor reliable career politicians over “risky” hard workers whose average performance is much higher, but whose lows are lower.

Would a creative person make a good business executive? I believe so, but with a specific variety of mentoring. Creative people given management positions generally find themselves still wanting to do the non-managerial work they did before the promotion. The problem here is that the manager can easily end up hogging the “fun work” and giving the slag to his subordinates. This will make him despised by those below him, and his team will be ineffective. That’s the major obstacle. Creative people tapped for management need to be given a specific ultimatum: you can go back to [software programming | game design | writing] full-time in 6 months and keep the pay increase and job title, but for now your only job is leadership and the success of your team. Good managers often find themselves taking on the least desired work in order to keep the underlings engaged in their work. It’s unpleasant, but leadership isn’t always fun.

I’ll go further and say that creative discipline is good practice for business leadership. Business leaders can’t afford to be creative at the fringe like artists or computer programmers, because the always-on, reliable social acumen they require precludes this kind of intellectual exhaustion, but the processes they need to manage are like an externalized version of the self-management that creative people need to develop in order to succeed. They must to encourage their subordinates to grow and test new ideas (divergence) but they also need to direct efforts toward useful deliverables (convergence). Many managers who fail do so because they only understand one half of this cycle. Those who focus only on convergence become the micromanagers who complain that their subordinates “can never do anything right” and who rule by intimidation. They fail because the only people who stay with them are those who actually can’t do anything right. The too-nice bosses who focus solely on divergence will either (a) fail to deliver, and be moved aside, or (b) are unprepared when young-wolf conflicts tear apart their organization. So, although the creative personality appears unsuited for managerial roles in large organizations, I’d argue that creative experience and discipline are highly valuable, so long as the manager is prepared to temporarily sacrifice the creative lifestyle hor professional purposes.

The results of creativity are highly valued, although sometimes only after an exhausting campaign of persuasion. The creative process is deeply misunderstood, creative roles are targets of misplaced envy because of their perceived “easiness”, and the people who have the most creativity (the top 0.1%) are rarely well-liked. People want our ideas, but not us and our “attitudes”. The shells, not the gnarly creatures. I invoke Paul Graham’s explanation for why “nerds” are rarely popular in high school. His explanation is that most high schoolers make a full-time job of being popular, while the nerds are too busy learning how to do hard things, such as programming computers or playing musical instruments. We see the same thing (the high-school social dynamic) in the slow-motion cultural and moral terrorist attack that we call “Corporate America”. People can invest themselves into working really hard in pursuit of the chance (and it’s far from a certainty) of producing something truly great. Or they can throw themselves wholesale into office politics and grab the gold. The world is run by those who chose the latter, and the cultural, artistic and moral impoverishment of our society is a direct result of that.