Libertarianism only seems likely to work in two cases:
1. Small societies where everyone has skills or resources that are essential to the others, or
2. Societies where everyone has resources to be self-sufficient.
There may also be a requirement that the society not be in competition with outside, non-libertarian societies for necessary resources, because libertarianism is poor at handling negative externalities. A non-libertarian society has the option of careful government regulation which allows better utilization of important natural resources.
You need to define your terms, namely "libertarianism" and "work." I assume you mean right-libertarianism, something like anarcho-capitalism or perhaps minarchism. By a society "working," you could mean scores of things, from maximizing personal happiness, to raising the minimum personal happiness, to maximizing average income, to maximizing socioeconomic equality, etc. Do you consider any modern or past society as "working?"
1. Small societies where everyone has skills or resources that are essential to the others, or
2. Societies where everyone has resources to be self-sufficient.
There may also be a requirement that the society not be in competition with outside, non-libertarian societies for necessary resources, because libertarianism is poor at handling negative externalities. A non-libertarian society has the option of careful government regulation which allows better utilization of important natural resources.