Contradicting conventional wisdom: Resist starting and fear failure

If you read enough books and blogs and listen to enough of entrepreneurs and investors, you will eventually build a bank of conventional wisdom about startups and building new companies from scratch. There seems to be a set of “rules of thumb” that is recited and repeated and rarely challenged. I like it when conventional wisdom is not taken for granted, so it’s been refreshing to see at least a couple of these challenged recently.

Resist starting: “Just get going.” It’s a piece of advice I’ve heard and personally doled out at conferences and training sessions for would-be entrepreneurs.  Heck, I probably said this to the audience in Portland just last week. It seems so simple that in order to create something, one must first get started on the creation process. Not so, according to Cal Newport, whose post on Lifehacker this weekend sparked an interesting conversation on Quora and forced many entrepreneurs to consider whether they started too soon (or not soon enough).

I think an instinct for getting started cripples your chance at long-term success. And I suggest that, on the contrary, you should develop rigorous thresholds that any pursuit must overcome before it can induce action.

Newport’s point is really that aspiring entrepreneurs should be careful to not start too soon, not that they shouldn’t ever start. His advice: “Spend lots of time learning about different pursuits, but put off action until an idea begins to haunt your daydreams and refuses to be dislodged from your aspirational psyche. Then, and only then, should you reluctantly take that first step, one of what’s sure to be many, many more before you get to where you want.”

Fail early, fail often: The notion of failure is often discussed in entrepreneurial circles and the acceptance of failure, even the pursuit of it, has become de rigeur. ““Failure is inevitable; 
it happens all the time 
in a complex economy,” says Tim Harford, author of Adapt: Why Success Always Starts with Failure.

But just how comfortable should one be with the possibility of failure? During a discussion about entrepreneurial journalism a couple of weeks ago at Arizona State University, Dan Gillmor suggested that being too comfortable with failure might actually be a liability, not a strength. Citing a blog post by Dave Winer, Embracing failure is a good way to fail, Gillmor said that having a full-force faith in one’s idea is a powerful agent and one that should be cultivated.

Believing that your idea will succeed, no matter the odds, is certainly how many entrepreneurs have succeeded. But it’s also how many failed. I think what’s most important is to learn from failure, and try to “fail forward” if at all possible. Embracing failure is only necessary once you’ve actually failed since you’ll have to pick yourself up, dust yourself off, and get on with your next idea. Just don’t start too soon.

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