In Defense of Reason

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Yesterday Umair Haque tweeted several bits of counterintuitive advice that I’d encourage nobody other than my competition to follow. Among them:

One of them in particular got under my skin —- a recitation of the the counterintuitive idea that success is the enemy:

Most celebrate success, and criticize failure. That’s 100% backwards. Do the opposite, and your edge will be 100x sharper.

Quotes like these get lots of attention in the startup world because they are shockingly contrarian and counterintuitive. Paul Krugman explains this method of distinguishing oneself:

For a long time, there’s been an accepted way for commentators on politics and to some extent economics to distinguish themselves: by shocking the bourgeoisie, in ways that of course aren’t really dangerous. Ann Coulter is making sense! Bush is good for the environment! You get the idea.

The problem is that eventually, it does get dangerous. He continues:

Clever snark like this can get you a long way in career terms — but the trick is knowing when to stop. It’s one thing to do this on relatively inconsequential media or cultural issues. But if you’re going to get into issues that are both important and the subject of serious study, like the fate of the planet, you’d better be very careful not to stray over the line between being counterintuitive and being just plain, unforgivably wrong.

The “celebrate failure” contrarianism may not be “fate of the planet” bad, but it’s dangerous for startups because it trivializes setbacks to their goals and ambitions, which are already overwhelmingly difficult to achieve. If you’re running a startup, you will fail plenty. You needn’t obsess over it, let alone strive for it, or – worst of all, as Umair asks us to do – “criticize” yourself when you avert it.

Entrepreneurs far more accomplished than myself have made this point. At SXSWi 2010, Jason Fried concluded his speech with “‘Fail often’ is probably the worst advice I’ve ever heard.” (I don’t have a link to that, but here’s a similar tweet). His sentiment is highly reflective of my experience. All of my successes (and partial successes) in life have come from drive and determination. Whether it’s as big an undertaking as climbing Denali or as small an undertaking as writing this blog post, I’ve succeeded by thinking about what success looks like and aiming straight for it. I’ve never found dwelling on or romanticizing failure to be a useful compass for navigating hard problems.

Certainly there are valuable lessons in failure. Josh Bokardo points out that rather than “celebrating failure,” we should “celebrate learning.” Brad Feld has written several astute posts on improving on failure, covering his own experiences and arguing that it’s better to fail quickly than slowly and that failure is often worthy of introspection. These are all excellent points, none of which advocate the bizarre philosophy of striving to fail repeatedly.

Contrarian thinking, by definition, implies that conventional wisdom is wrong. If you’re going to challenge the status quo, you should use more than a pithy expression to do so. Otherwise you may as well be telling us to look west to find sunrise, or to saltwater to quench our thirst. If you’re going to talk about the virtues of failure or any other counterintuitive concept, please follow the Brad Feld strategy of thorough reason, and avoid the Umair Haque strategy of shocking contrarianism.

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