The Holy Spirit teaches you the difference between pain and joy. This is the same as saying He teaches you the difference between imprisonment and freedom.
(A Course in Miracles)
God in Neale Walsch's "Conversations with God", often said that there is no "wrong" or "right", there is is only useful and less so, judged from the perspective of what you want to achieve. Some want status and power, while others want love and freedom. Freedom was Buddha's stated goal and he was uncompromising in his approach to get there. I remember a scene in Deepak Chopra's "Buddha", where Lord Krishna visited Buddha after a long meditation session. Buddha said to Lord Krishna, "You have no idea how much I have longed Thee!", to which Lord Krishna responded, "I know!". But then Buddha closed his eyes again and said, "Please leave now I have work to do." That is indeed the mindset of someone who is on a mission. You keep on going until your goal reached. In Buddha's case it was a mission to be completely free from all mind-driven illusions.
It is in fact possible to be "free". Not in the way that you can cut yourself completely off from the subconscious processes that run below the surface, but in the way that you can really live your life completely detached from the longings of the ego. There is a Way that somehow always knows best and all you have to do is to follow Her. Sometimes it is external signs that guide you, while sometimes it is your intuition. There always will be a few missed steps but mostly you can be connected every step of the Way. You can see and feel the Way just as a scientist would and you learn as much from your mistakes as you do from your blissful moments. Along the Way, the longings of the "I" simply melt into nothingness and in those moments you get a taste for true freedom, just as the Course in Miracles claims.
It is pretty meaningless to strive for enlightenment just because this gift a higher authority has to grant you. What you can do though, you can cut out interferences to the best of your abilities by just holding on to the Way. Joy and freedom follow you where you go. Never mind if there are still a couple of dimensions in your life where people or positions seemingly still hold you back. This just means that you aren't quite ready for the big jump. Serve willingly as a free master and true freedom will be yours before you know it.