I think there may always be too much socioeconomic pressure against it in modern industrial society for it to become normalized.
As technology gets better at eliminating jobs, we may see a socioeconomic pressure towards remaining pivot-ready by constantly broadening one's capabilities... A world where as soon as you have a job you start training for your next one on the side because they just don't last that long. Making such a lifestyle broadly accessible would mean some significant changes from where we are now, but in the long run paying for all that school and tolerating all that time-off to attend it might end up being cheaper than the cost of the unrest associated with resisting change.
If this isn't already a line out of a dystopic speculative fiction short story someone should crib it for that purpose.
It sounds outlandish but I think the path away from scarcity based economics must eventually traverse a zone where the only scarcity-driven careers left aren't substantial enough to commit a lifetime to, so being dual- or triple-specialized will be a necessity.
And as much of a hassle that may be, letting scarcity continue to drive despite its inability to avoid hazards seems much worse.