In The True Believer Eric Hoffer makes the case that freedom and equality are opposites: thesis and antithesis. The true believer is drawn to a mass movement precisely because it offers him equality, an escape from freedom into an environment where his worth and value is established without regard to his individual characteristics. His individual self has decisively failed him; the true believer thus must search outside himself for value and worth. This ideal is the antithesis of the the ideal of freedom, that each individual ought to be judged on his individual characteristics.
The problem is that judgments are always relative: We pick out the top 10% (or some small fraction) on some measure as "successful" and judge the bottom 90% as "failures". Self-esteem is, I think, best seen as a dialectical relationship between the individual's own conception of herself and her peers' social regard; the concept of freedom thus ineluctably consigns a substantial portion of the population to the negative regard of society and the corrosive effects such a negative regard has on their self-esteem.
It is both the power and the downfall of capitalism that the precise characteristic that distinguishes the capitalist ruling class — their ruthless economic competitiveness — tends to destroy the institutions that give meaning and purpose to those who fail the judgment of freedom. By elevating freedom to the highest or even the only virtue, they hold each individual up to merciless scrutiny, and offer no escape to those who must necessarily fail that scrutiny. But human beings are not so easily thwarted. The frustrated and disaffected individual does not simply lie down and die; she seeks some alternative means to create a dialectic that will generate positive self-esteem. Freedom has failed her — as freedom must necessarily fail most — so she seeks equality. The only way to combat this tendency under the paradigm of freedom is to force those who fail the judgment of freedom into a daily struggle for life and death.
On the other hand, people are not actually equal. So long as people can be led, leaders will select themselves. They will then label some set of characteristics they happen to posses as "superior" to justify their position as leaders. Equality also must be somehow enforced. Even if all that's required is that one say the prayers; the prayers must still be said, with the appearance of sincerely and without irony. Those who do not say the prayers, those who do not sound or act sincere, must be excluded. But enforcement implies some privileged to actually perform the enforcement, to determine compliance, sincerity and authenticity; those so privileged are manifestly not equal.
It is not enough to say that at some stage of human development people can maintain equality "on their own", that the vast majority of people ever will be actually equal, and small deviations can be corrected without some minority privileged to correct them. Such an attitude is not precisely unrealistic — we can definitely observe social organisms that have near-total equality; even the queen bee is subservient to the hive and her life bound entirely to duty — but such equality seems to lose something ineluctably human.
It is perhaps possible that self-esteem could become independent of social regard, that each person's evaluation of her own self simply did not take into account the judgment of her peers. If one ignores Ayn Rand's hostility and contempt for those she considers sub-human, and her delight in their ruin, the human progression to true socially-independent autonomy is probably her most admirable idea. But I think our evolutionary history works against this idea. More importantly I think the tasks an immense and complex universe affords us require a high degree of social cooperation for even the longest-term foreseeable future. It might be the case that some, even many, individuals will develop socially-independent autonomy, but I suspect those individuals will simply remove themselves from the narrative of history and human development.
I have to say I'm a proponent of neither absolute freedom nor absolute equality. I have to see freedom and equality as existing in a dialectical relationship, both affecting the other with complicated and impossible-to-predict feedback effects.