The internet, especially in the entrepreneurial blogosphere, seems to have an order of magnitude more people producing literature about success (i.e. “success crack”) than actually succeeding. Every day I see the peddlers of reckless optimism swarming Hacker News with dangerous naivete about entrepreneurial pursuits. Don’t get me wrong: startups and self-employment are great, but people should be aware of the risks and pitfalls, which too many people gloss over. This isn’t limited to startups; every sector of business has its own cottage industry of how-to manuals for breakout success, usually chock full of unrealistic promises (which, I guess, lends credence to their authors being successful in business, such promises being the currency of their world). Is this “fake it till you make it” syndrome on the part of the “crack” peddlers? I’m not so cynical as to suspect that. Blog posts and books about “success” are written by well-intended people who want to share insights they’ve had about life and about their own successes. The problem is that their insights are rarely very deep. You have to lose in order to get a sense of what’s really happening in the world.

I’ve designed games before, and when I play-test, I strongly prefer to lose. Why? No one likes losing, not even me (and I play so many board and card games that I ought to be used to it). When I lose at my own game, it’s even more harsh. But it’s the (very mild) embarrassment and emotional unpleasantness associated with losing that gives me insight into design flaws that I would overlook as a happy-go-lucky, full-of-himself winner. For a game designer, it’s a blessing to lose. If I feel like I deserved to lose, I know the rules that contributed to my loss are good. If I lose because of a bad rule, it’s a double-loss (I lost the game, and my rule sucks) but the “bug” in my design gets squashed before the next release. Every game is fun for the winning player, but if it’s not fun for the losing player– or if not “fun”, at least enticing enough to make her want to improve her skill and become better– it’s a mediocre game. Thus, losing is a boon for the insight it provides to a game’s designer. It’s the only way the designer can develop certain insights into the character of the game. The same’s true of life.

A very small set of people, just on account of the planet’s immense size, have untarnished track records of success and never develop the desire to look deeper into the processes that led to their outcomes. With six billion people in the world, the existence of champion coin-flippers is a statistical guarantee. Many people desperately want to be like those perennial winners, which is why such peoples’ optimism is so appealing, even inspiring, to others. Far more people than that (in fact, almost everyone, including most of the “success crack” vendors) get a fair mix of failures and successes. The problem is that failures are embarrassing and under-reported, while the successes are magnified to outlandish proportions. In 1999, at the height of the technology boom when “everyone” was getting rich, how many technology companies actually did IPOs? 5,000? 100,000? Two in every garage? Nope. A few hundred, with the precise number varying depending on how one defines “technology company” but uncontroversially under 1,000. Also, many recent years had less than 100.

Success crack is harmful, because it leads both to ill-considered efforts and too-early discouragement. It makes success look easy, but not in the conventional sense, because aside from Tim Ferriss, few of its peddlers actually argue that their success comes without hard work. The problem with success crack is that it seems to believe “work hard” and “work smart” are enough, as if being intelligent and putting in 10 hours a day, six days per week, suffice to lead to break-out success. That’s not true. People have to prepare for adversity, uncertainty, discouragement, and a high likelihood that, even if they do everything right, they’ll fail. These dangers are virtually guaranteed to a person undertaking anything interesting. That’s not a pleasant thing to hear, but it’s reality.

One observation I’ll make is that, when the locus of control is internal, one generally learns more from one’s successes than from one’s failures. An example is music practice: playing an instrument incorrectly is damaging to one’s long-term performance, because it reinforces bad habits. Playing it correctly, and experiencing the “click” when it sounds perfect, is when learning occurs. The same pattern I noticed in high school with contest math (e.g. AMC, USAMO): I would learn more when I solved a problem, even if I couldn’t solve it within the alloted time or made a mistake and got the wrong answer, than when I failed to solve it and had to read the solution. In these arenas, success teaches more than failure, and consequently, the best thing one can do when one wants to become better at the craft is to find the most successful people and learn from them.

When the locus of control is largely external, such as in most workplaces where one’s success or failure is largely a function of how one’s work and ability are perceived, not what they actually are, the opposite becomes true. More is learned through failure than through success, as those who succeed rarely peer into a system’s dysfunctions and discover the pitfalls. This is why, whenever I take a new job, I always make sure to quietly befriend the person at the bottom of the social hierarchy. This is only mildly motivated by an altruistic sense of wanting to help the omega pup, and there’s a purely selfish reason for my doing this: in terms of office politics, he actually knows what’s going on. And if you befriend him, he’ll tell you. His report may be biased and bitter, if not unduly negative, but it’s also the most insightful and, if not always accurate, the most precise. Apply appropriate filters, but listen to what he has to say. In any organization, the least popular person is the most knowledgeable about its character. Learn from him.

Most of the notions of achievement we develop in childhood come from a time in which success is largely objective and one’s success is derived from an internal locus of control: music practice, athletics, contest math. Even in schools, with their often-decried (and greatly exaggerated, since even high schools are utopian compared to the average corporate workplace) emphasis on obedience at the expense of creativity, a student’s success is primarily a function of intellectual talent and his or her work ethic. Deadlines are well-tested, people are working on similar projects, and people in authority (e.g. teachers) are required to grade fairly and can lose their jobs if they don’t. There are, of course, some students who get bad grades because they run afoul of professors’ idiosyncratic prejudices but, by far, the most common cause of bad grades (I say this having earned a few, and having deserved almost all of them) is mediocre work. Therefore, in childhood and adolescence, learning from the most successful is an excellent strategy in order to become better.

However, the “real world” is far more interdependent and capricious, and it’s nearly impossible to succeed without convincing others that one deserves the resources necessary to try– and competence and the ability to sell oneself to others rarely occur in the same person. This is what no one wants to tell bright-eyed college students: that they’re about to enter a world where their success is likely to depend, in a serious way, on being given resources and opportunity by others, and that working hard and being smart are only marginally important. In fact, at the overkill levels seen in the best students at elite schools, intelligence and a strong work ethic can easily become social liabilities. Because the locus of control is so often external in the “real world”, peoples’ failures have more to teach us than their successes.

The fundamental problem with success crack is that, while it makes for engaging light reading, it’s written either by those who know the least about the world, having never been down in the muck, or (more commonly) by those who have suffered, but still wish to mimic the wide-eyed optimism of those who haven’t– it’s somewhat of a status symbol to believe, as an extremely fortunate person might, the world to be better than it actually is– and therefore censor out the unpleasant but important details they know but have expelled from consideration. Thus, we have a slew of terrible advice floating about such as “Do what you love, and the money will follow” that is accepted because it seems appealing in spite of being utterly untrue. Like some charismatic religions, it sounds pretty, and half of that is because the author is trying to convince him- or herself that he or she actually believes it: that desire to believe the incredible and wrong is a powerful force capable of motivating some of the world’s beautiful, but also utterly untrue, prose.

In this light, I hope to see more attention given to pitfalls and patterns to avoid, so that true learning may occur, and far less in the way of vague, feel-good directives about “success”.