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The Lucilius Parables, Volume I


February 22nd, 2020


When considering an opportunity, there’s perhaps one quality above all else that we should look for.

We might at first think about how big the pay off is if the opportunity goes as hoped, and we’ll probably wonder what the likelihood of success is.  We compare and contrast different opportunities in accordance to how good they might potentially be, and ‘good’ in this case involves a few variables.


But an overlooked variable is to sort opportunities by what a failed outcome looks like.  Just as not all successes have equal results, so to with failure.  Betting everything on the roll of a die has a pretty clear negative outcome if things don’t go well, but working for a start up that fails gives you an insider’s look at how such a machine works, or in this case doesn’t work.  Success is hard to pin down in terms of why it happened.  All the variables are probably involved and there’s no way to tell which ones were more salient.  But with a failed attempt, the reason why something fails often lends itself to a much higher degree of precision. 


The benefits of a failed opportunity can be far greater.  For example, any project that requires you to learn something.  Even if the project is a failure or doesn’t take off, you emerge with a new skill set, one that can potentially be leveraged in countless new ways.  This sort of failed opportunity has a counter-intuitive upside. 


This might be the most important aspect of opportunity selection.  By constantly sorting for opportunities that have a pay off no matter how bad things go, you constantly hedge your bets against catastrophic failure.


It’s one thing to start from scratch.


It’s quite another to land in that position with a new power in hand.

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Podcast Ep. 678: Upside Fail

Tinkered Thinking

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