This is an excellent article regarding meditation, or more accurately when prayer and meditation doesn’t seem to work:
That so many who are experienced in prayer go through this difficulty with meditation is a sign of the truth of John’s teaching. The great doctor of the Church gives three signs by which we may discern whether it is time to leave meditation aside in favor of this more direct practicing of the presence of God. And, as we might now suspect, the first sign is “the realization that one cannot make discursive meditation or receive satisfaction from it as before. Dryness is now the outcome of fixing the senses on subjects that formerly provided satisfaction.” Note, however, that John cautions us against getting ahead of ourselves. We are not to give up meditation unless and until this dryness occurs.
The second sign is equally important and must accompany the first. It is “an awareness of a disinclination to fix the imagination or sense faculties on other particular objects, exterior or interior.” The imagination will, of course, wander at times. John is speaking of fixing purposely on extraneous things. If we do deliberately seek to enjoy thinking about extraneous matters, then the inability to meditate which constitutes the first sign is doubtless due to some dissipation. To be a sign that meditation should be given up, there must be a general disinclination to fix the imagination or sense faculties on anything during prayer.
In fact, not just the first two signs but all three must go together, for the third sign is that “a person likes to remain alone in loving awareness of God, without particular considerations, in interior peace and quiet and repose, and without the acts and exercises…of the intellect, memory and will.” Or again, a person at this stage “prefers to remain only in the general loving awareness and knowledge we mentioned, without any particular knowledge or understanding.”
Meditation used to be all the rage during the late 1990’s, when Bhuddism then Catholicism became the new “in” thing to be. Of course, since it was all for style and not for substance most people neglected the sublime undertones of what makes both faiths so beautiful.
Meditation is a lost art in the hustle and bustle of today, and often is confused as prayer. Prayer is something much more active, a conversation between yourself and God. Meditation is much more subtle, enjoying the mere presence of God.
As of yet, the message of St. John of the Cross is helpful, but I haven’t quite mastered the art — or more accurately, my own will has refused for one reason or another to allow God to operate in my life.
If it were easy, it wouldn’t be worthwhile.