https://blog.franklinplanner.com/failing-forward/
https://context.reverso.net/translation/english-russian/fail+forward

generational wealth ~ богатство, созданное предыдущими поколениями

Падать по направлению к успеху?)

failing, not falling

Ну, в переносном смысле)

Косячить в направлении успеха?))

In this context, "failing forward" implies the idea that some people, often those with privilege or generational wealth, are allowed to make mistakes or fail but still continue to advance or succeed. They are given multiple chances to recover and move forward despite their failures.

When Obama says that Harris "understands that most of us will never be afforded the grace of failing forward," it highlights the disparity between those who can recover from failures with little consequence and those who can’t. For many, particularly those without wealth or privilege, failure can have lasting consequences, and they are not given the same opportunities to rebound or succeed after a setback.

Thank you, Uly

👍🏼🤩