We should root for people to lose specific jobs by way of those jobs disappearing.

We should not root for people to lose their access to a baseline level of income, or otherwise a basic living standard.

The fundamental problem with modern society is that jobs are prerequisite for acceptable living standards, including access to healthcare, education, housing, food, and social interaction.

In most cases, minimum living standards depend on a minimum income, which is usually obtained by way of a job.

Other times income alone is not the only prerequisite. In the case of healthcare (in the USA), you need a job through a formal employer in order to make healthcare affordable, i.e. without a formal job you need a much higher income in order to obtain healthcare at an acceptable standard.

In my opinion, diminishing or eliminating the dependence of "living standards" on "job" is essential to a high-functioning society. Even if the dependence is only broken temporarily as part of a "social safety net". The USA has a social safety net, but it's frequently insufficient to maintain morally acceptable living standards.