The phrase suggests an expectation of bad outcome, usually due to poor decisions or actions. Ignoring the warning signs, he was riding for a fall with his reckless investments.
Pro Tip 2/3
Idiomatic Usage
This is an idiomatic expression, meaning its true meaning can't be derived from the individual words. She’s ignoring all advice and is really riding for a fall.
Pro Tip 3/3
Negative Forecast
Use this phrase to predict future trouble, not to describe a current failure. If they keep overspending, they're definitely riding for a fall.