I find this particular notion of gradual/ intentional, transition problematic at best. 'Transition' connotes movement, however, the way progressivist ideologies use this term is completely abstract, dead, since it never lived at all. Transitioning relates and speaks of continuous re-placing; ever-shifting qualities, tones, textures, contours, conditions; incessantly fluctuating, dynamic, ephemeral, and thus always perspectival. You know, living. This perspectivity can probably be better spoken of in terms of 'where' rather than 'what' in our clunky, thing-oriented, language ('English'). So, when we speak of transitioning, we may first wish to ask: 'From where to where?'
In my experience at least two unspoken presuppositions are often hard at work from the get-go. One, is that the two 'wheres,' the present/now and a future 'place' are somehow equivalent; the 'concrete' and the ideal no-place-as-of-yet are presented as equally perceptible and thus comparable according to some meta-schematic.
Another, and more subtle, presumption is the belief that one may indeed 'get there from here.' This, in turn, poses more problems. 1) It assumes a unified 'nature' or 'world' through which each of us makes our journey and 2) this world has no 'say' and we carve out each of these states from this silent cadaver. 3) That 'here' and 'there' represent two states (as in 'static,' 'stasis'), and thus for a progressivist ideology; beginning/end, cause/effect, means/ends.
Another story: Perhaps our lives are better spoken of in terms of 'near' and 'far' from where we live now; our perspective now. Can one sense such an idealized 'there' from this lived 'here'? I remain skeptical to say the least.
Yet one more count against this type of progressivist worldview lies in a totalitarian demand for general consent in order to exist at all. For the ideal to become reality, everyone must think what I think so as to be considered an 'anarchist,' one who's capable of envisioning 'true anarchy,' and thus able to reach 'real anarchy' someday or at least provide a map to it. Of course, embedded in this are many further implications, given the humanistic pedigree at work, but I'll leave off for now...
edit for quick fix and clarity