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What could go wrong?  

Leo Widrich:

"What could go wrong?", is the one line that brought us to where we are today. It is the one sentence that helped us to outsmart any enemy, as we could pre-empt their attacks, built caves with better protection and make sure our children and theirs will make it through many summers.

(...)

On behalf of "Yes!" and on behalf of daring, it is my sincere belief that thinking "What could go wrong?" can't bring us any good (anymore).

Instead, I think it is of the highest importance to learn (and learning this I think we must, as none of us are born with it) to start asking ourselves and everyone else "What could go right today?". And then, go do that right thing.

While the sentiment of this article is right, I have to pick a nit about this "discarding 'what could go wrong?'" business.

"What could go wrong?" is still incredibly useful, because it is a risk exploration question. Successful entrepreneurs don't ignore risk, they minimise and embrace it. To do that, they need to be very aware of the risks - i.e. of what could go wrong.

We can never be aware of all the risks (and that is a risk, or meta-risk, in itself). However, we can make a decent effort to think about the risks and come up with ways to mitigate or minimise them so that "what could go wrong?" is no longer unknown and unlimited.

Smart entrepreneurs knowingly take risks with small potential downsides and large potential upsides. For example, in starting Buffer, Leo took the risk that it might not work and waste some of his time (unlimited downside), minimised that into "it might not work but we'll focus on proving that it works as quickly as possible" (small downside), and therefore reaped the large upside of a successful, rapidly growing startup.

Ignoring risks would have meant building Buffer with no validation to a full-featured version 1 before launching it, and then perhaps finding out that nobody wants it.

More from the library:
The Noun Project: Large collection of free symbols
Metrics for social startups
Why VCs lie