Saturday 26 January 2002

Build or demolish

While I was sleeping, the Dave/WinerLog contretemps boiled over at Burningbird. “Should I comment?” I asked myself. After all, there seems little point in picking at the scab of a wound that might best be left to heal (or fester) on its own. On the other hand, the synergy between these three sites gave me a much-appreciated boost at the beginning of my blogging career. It didn’t feel right to ignore the issue so I went with my gut.

I am by nature a bit of a smartarse. At school I was in constant trouble for making “inappropriate remarks” in class. Because it was a Catholic school, many of my witty ripostes sprang from what I saw as the gap between theory and practice, between the dogmas the Marist Brothers espoused and their everyday behavior. It strikes me that WinerLog arises from a similar impulse. It wouldn’t surprise me at all if one or two of the Wiener Boys were recovering Catholics.

On arriving at Sydney University I found, to my great delight, that my talent was as widely appreciated there as it had been by my high school classmates. I only learned upon entering adult society that “adolescent” and “undergraduate” are used to describe a particular kind of humor. As I grew older and began to curb this instinct, I discovered that I got along with all kinds of people, many of whom would have been disconcerted or even offended by the former me. As one of my close friends put it last New Year’s Eve, “You’re a lot less angry than you were when I met you in 1979.”

It’s a widely remarked aspect of online life that people write things in email they’d never dream of saying face-to-face. I suspect that the immediacy of blogging also encourages the expression of thoughtless or malicious remarks. Dave seems to be making the same point here.

Some history: I posted some (what I thought were) lighthearted comments about disappearing items from Scripting News; Dave ripped me a new arsehole in a post that quickly disappeared; WinerLog picked up on it; I wrote another post about how tough it must be to have to listen to people criticizing you with the tools you built. Finally — and this is the really important part — Dave did something incredibly sweet and generous. He posted an item about my site looking beautiful that drove a ton of traffic here; an act that opened up a space for me in the blogging firmament, pointed me towards finding a better tone for my blog, and taught me the importance of displaying grace under pressure.

Burningbird notes the value of the Roman belief that “one’s ultimate enemy is, in actuality, one’s most powerful friend. Your enemy spends more time thinking about you than your friends do. Your enemy points out all your weaknesses, allowing you to learn how to become stronger. Your enemy will be honest when others, fearing to offend, will lie.” She’s right; though I suspect that this, as with a lot of advice, is easier to dispense than to swallow.

In a sense, Dave created an uncomfortable situation for himself by taking on two seemingly incompatible roles: building software as well as writing essays and a weblog. Most people do one or the other. Dan Bricklin also does both, but — for me anyway — his weblog lacks the spark of Dave’s. I believe that other CEOs will follow in their footsteps, finding an authentic voice with which to replace the bland platitudes of their marketing departments and PR flacks. Those who succeed will owe a debt of gratitude to Dave.

Burningbird may also be correct in telling Dave that he needs a sense of humor. But even if Dave wasn’t “a little irony-challenged” as Brent Simmons pointed out in a Wired profile, that’s still a really hard ask. The editor of the Sydney Morning Herald might print articles or letters critical of the newspaper’s stance on a given issue, but he doesn’t have to devote space every day to a column whose sole purpose is to draw attention to real or imagined deficiencies in his business and personal behavior.

Irony is certainly a sharper, more entertaining tool than sarcasm but, like any other tool, irony rapidly becomes blunted with overuse. That, ultimately, is the problem with WinerLog. There’s no light to temper the shade. Though I’ll probably continue to read it. Partly from a libertarian conviction that every voice, no matter how offensive, should be heard (listening is obviously a matter of individual choice); mainly because it gives me an occasional chuckle by appealing to the less generous side of my nature.

Dave, on the other hand, might be inconsistent or occasionally obnoxious but he’s possessed of a huge heart. In giving me a tool and a space in which to use it, he’s supported and encouraged my desire to do what I love most: to write. And he’s made me more aware that building things takes a lot more skill, love, energy, passion, and commitment than demolishing them.

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