It is strange that there should be a Flag Day, which is today June 14. That’s in the United States. I don’t know of another country in the (more or less) free world where such a day exists, although governments have many other ways to inspire national pride and obedience.
A flag can represent a group or an abstract ideal. If it identifies a private group, like an association or a company, it is innocuous. It is different when it represents a public group of which some members are forced to belong. Except for the rulers of the group and their favorites, the flag then represents a forced identity and some service obligations. Nazi flags at official events or official flags in the old American South were examples. An individualist would despise this sort of flag.
Flag Day was proclaimed by the progressive Woodrow Wilson in 1916, a bit like the Pledge of Allegiance was invented in 1892 by Francis Bellamy, a socialist who preached that Jesus was too. Schoolchildren were long obliged to salute the flag and recite the pledge of allegiance: American exceptionalism, at least in the Western world. A couple of decades after Woodrow Wilson’s proclamation, the Supreme Court fortunately ruled that the First Amendment prohibited American governments from imposing such professions of faith.
A flag attached to a territory, typically a national flag, can also symbolize an ideal. Many Americans look at their flag that way. Woodrow Wilson believed that the Stars and Stripes represented “liberty and justice.” His conception of liberty of justice was obviously not shared by everybody, including the victims of eugenics, which was first legislated under his governorship in New Jersey. The only way an official flag can be truly representative of everybody in a territory is to represent a common ideal, shared by everybody. A common ideal necessarily excludes victims of public discrimination or exploitation. From a libertarian or classical liberal perspective, a national or territorial flag can be respectable only if it symbolizes an ideal of equal liberty.
We should not expect people exploited or discriminated against by their government to sheepishly worship the latter’s flag. But many do, which points to what Bertrand de Jouvenel called “the mystery of civil obedience” (see his On Power). A number of hypotheses have been proposed to solve this mystery, from a habit of a species (probably genetically wired) to government propaganda and resistance as a problem of collective action.
The ideal of equal liberty for everyone is not easy to achieve. In his Why I, Too, Am Not a Conservative, James Buchanan presents this ideal as a hope and a faith, even if we know since Adam Smith that an autoregulated social order of equally free individuals is possible and conducive to general prosperity. One danger is nationalism, which is what most territorial flags try to fuel. At the other extreme, too much diversity can exclude the possibility of common values necessary for the maintenance of a liberal society. For example, imagine two religious sub-groups of individuals who worship respectively god A and god B, and believe that their god wants them to kill infidels. The set of common values would be the null set, and equal liberty impossible.
There is in America and in many Western countries a memory of, or a hope for, the ideal of individual liberty (and property), which alone can efficiently prevent a continuing clash between individuals and their beliefs, preferences, and lifestyles. Finding a national or territorial flag that unambiguously conveys this ideal is not an easy quest.
******************************