Thermodynamics is not usually helpful in understanding racemisation: think mechanisms and kinetics instead
The thing about enantiomers is that, from a thermodynamic point of view, they are the same so any process is not being driven by differences in the energy between the molecules.
What matters, if racemisation is to occur, is that there is some accessible pathway that allows interconversion. For example, in acidic or basic ethanol solution, (3R)-3-phenyl-2-butanone will racemise via the (achiral) enol form of the molecule. There is a small amount of the enol present which interconverts to the (chiral) molecule but without remembering which chiral molecule the enol was formed from. This will, ultimately, give a racemic mixture. If no such mechanism existed the molecule would not interconvert. What matters is that some such pathway exists.
The notorious medicine thalidomide is an interesting example. One enantiomer is a useful therapeutic, the other a dangerous teratogen. But making a pure enantiomer doesn't help as the two forms interconvert in the body (by a complicated mechanism).
These conversions are not driven by the different stabilities of the end products but by the inability of non-chiral intermediate molecules in an equilibrium with the chiral starting materials to remember the chirality of their progenitor. This, in effect, increases entropy. But that entropic force is only possible if there is an available reaction mechanism that passes through a non-chiral form allowing the increased disorder that results from a chiral starting material turning into a racemic mixture.