I don’t think you can find an enlightened person that still doesn’t have at least a few identifications / attachments. I followed Osho for a long time and I would not have characterized him, at any point in his life, as completely free of attachment. He may not have had the same attachments to things as you are used to seeing in people, but he did have strong opinions on things that wouldn’t respond to reason. That’s an attachment in my book.
Of course some people don’t think of Osho as having been enlightened but I would accuse those people of No True Scotsman and only give half an ear to anything they say further. Moral failings cannot disqualify you from enlightenment because morality is external judgment and external judgment can never be fully aware of the facts.
Dr. David R. Hawkins has a scale of consciousness, from 1 to 1000. Anywhere above 600, he calls enlightenment. I don’t subscribe to the scale itself, but I do find the idea of progressive stages of enlightenment useful.
I consider myself as having been enlightened since birth. It took me many years of spiritual study and introspection before I could take the idea seriously and many more before I became comfortable describing myself as such.
For me, finding a place in the world has always been difficult. It wasn’t until long after I found spiritual ‘peace’ with myself and what I was that I could turn my attention to worldly accomplishment. I put ‘peace’ in quotes because while I never would have characterized my existential explorations as anything other than satisfying curiosity, it did prevent me from building a life for myself, more out of lack of focus than anything.
I never had much trouble finding jobs or sustaining myself, but the finer aspects of career and accomplishment couldn’t be front-burner concerns. I had to get ‘finished’ with the lion’s share of my philosophical and spiritual wanderings before I could take career seriously.
But once I did, I found starting and maintaining a career ridiculously, almost absurdly easy. I already had the necessary skills to make it happen, I only needed to just apply for a few jobs.
Now I treat my career like you might treat a pet. A very valuable part of my life, but not something that can or ever could require 100% or even 20% of my time and effort. As a function of time spent, my 40 hour a week job consumes maybe 6–10 hours a week. I accomplish a lot of my tasks subconsciously, leaving my conscious mind to roam and muse on things.