While they didn't have Hacker News or leadership RSS feeds a hundred years ago, people were still evidently inundated by stories with "How I Became Successful" narratives.
English essayist G.K. Chesterton, who was a skewer-wielding cultural critic in the Christopher Hitchens mold years earlier, had little use for such studies of success.
"That a thing is successful merely means that it is; a millionaire is successful in being a millionaire and a donkey in being a donkey," he wrote in All Things Considered, published in 1915 and resurfaced on Kottke. And yet books abound with stories about how builders can become better builders, stockbrokers better brokers, and maybe even turn a grocer into a yachtsman. More recently, if learn how Richard Branson lost his Virginity, then so can you.
To Chesterton, business war stories aren't instructive—they're unnecessary.
It is perfectly obvious that in any decent occupation (such as bricklaying or writing books), there are only two ways (in any special sense) of succeeding. One is by doing very good work, the other is by cheating. Both are much too simple to require any literary explanation. If you are in for the high jump, either jump higher than any one else, or manage somehow to pretend that you have done so. If you want to succeed at whist, either be a good whist player or play with marked cards. You may want a book about jumping; you may want a book about whist; you may want a book about cheating at whist. But you cannot want a book about success. Especially you cannot want a book about Success such as those which you can now find scattered by the hundred around the book market. You may want to jump or to play cards; but you do not want to read wandering statements to the effect that jumping is jumping, or that games are won by winners.
Why we fall for the fallacy
That we invest so much in stories of success, Chesterton would argue, is a fallacy. The narrative fallacy to be exact. What's that? Glad you asked. Berkeley statistician David Aldous supplies this excellent account:
When we write the details of some interesting past episode—a three-hour football match or a three-day battle or a three-year war or a 30-year career or a 300-year rise and fall of an empire—we select and recount events sequentially, and within this "narrative" a reader is inclined to assume that one event was caused by the previously described events. Sometimes the writer is explicit about causation (I bet no historian ever wrote "war broke out on the date . . ." without attempting to say why!) and sometimes the writer isn't; but our mental processes tend to lead us unconsciously toward the post hoc, ergo propter hoc assumption (This happened after that, so that caused this). The main point is that even if one can identify proximate causes of particular events within a larger Episode correctly, after the fact, this doesn't contradict the hypothesis that the way the Episode as a whole developed was unpredictable. Seeing the historical details makes us forget it might have just been chance; the Frog might not have been a Prince after all.
In other words, the causes that bring together a successful career or venture are so varied, complex, and mysterious that to capture them in a feel-good memoir is pretty damn difficult. Which was partly why Outliers was such a successful book: Malcolm Gladwell traced the different causes of success that we often overlook—for instance, that instead of hockey players succeeding due to superior skills, they benefited from being born in a certain month.
Okay, so why do we read these things?
This is a big question, but it's probably so that we can become better—at work, love, life. But first we probably have to admit, as geek icon Nate Silver would encourage us to do, that the career game is more like poker than it is like chess: The information we're working with is incomplete, imperfect, and dynamic—meaning that success is a probabilistic kinda thing.
One way to cooperate with that serendipity is with "step-by-step" optionality, a strategy termed by productivity czar Bob Pozen. The idea is this: Instead of mapping out our careers along a straight line, we head off onto multiple branches. The key, he would say, would be to train in in-demand transferable skills, such as management—-or, increasingly, critical thinking.
But the most obvious strategy, to fold back to Chesterton, is to train. You become a successful high jumper by jumping higher.