Design a system so that you’d have to actively avoid success in order to fail.

The definition of the Pit of Success is taken from Jeff Atwood’s blog:

The Pit of Success: in stark contrast to a summit, a peak, or a journey across a desert to find victory through many trials and surprises, we want our customers to simply fall into winning practices by using our platform and frameworks. To the extent that we make it easy to get into trouble we fail.


Source

what does “falling into the pit of success” mean?