Once you've resolved upon your Lenten penances, there are two ways you can go through Lent.
The first is to try to keep those penances and stumble once or twice along the way. The disadvantage of this is it demonstrates quite clearly your weakness and attachment to the things you have striven to renounce and thus how far you still fall short of the law of freedom and love of Christ. On the other hand, this is also an advantage because, even if I now know how faintly the love of God burns in my heart and how grossly addicted I am to corruptible things or, worse, to the objects of my vices, the fact that, having made a firm intention and then having broken it, this is brought home to me is a great cause of humiliation and thus an incentive to humility. And, furthermore, to dependence on God's grace rather than my own efforts.
The second is more dangerous. I may resolve upon certain penances and remain firm in them for the entirety of Lent. On one hand, this does show that I have at least the rudiments of spiritual discipline. It may or may not show that my love of earthly things is not inordinate or excessive. It may or may not show that I am beginning to learn what it is to seek hard after the Lord and to seek after things to the extent that they lead me to Him. But on the other hand, there are perilous dangers here. It is very easy for me to focus on the penances as ends rather than means, so that they become an exercise in spiritual or mental discipline for its own sake, not as a training course in becoming and loving like Christ, as avenues leading onto the Via Dolorosa. It is likewise easy for me- terrifyingly easy- to ascribe the results of my penances to my own efforts. To be glad that certain unhelpful or sinful habits have been broken and to subconsciously congratulate myself on having overcome them, rather than acknowledging that His grace alone has been sufficient to do it, and if my efforts have achieved anything it has been only to clear the way to allow that grace room to work, not so much doing something as ceasing to do something.
These dangers are almost like reflexes. We fall into them without even realising, then catch ourselves, horrified at our own thoughts. One expects that the further one goes in the spiritual life, the easier and safer it will get. In fact, the opposite is the truth. The highest are able to fall the farthest. The great saints are the ones in the greatest danger at any particular moment. Or perhaps it is only they that perceive the danger, and we who are not so far along are in precisely as much danger but our vision is too clouded to perceive it.
In either case, as I myself plug along and Lent begins its final ascent before the great Abyss of Good Friday and Holy Saturday and the great Pinnacle of Easter Sunday, I find one or two things which I, at any rate, find helpful in face of these dangers.
1) Coming face to face with the saints is always a worthwhile reality check. Dante has a beautiful passage in the Purgatorio when he gazes into the face of Beatrice and sees reflected in her eyes the face of Christ. There is a profound truth in that. The saints are precisely those who, in this life, followed Christ most earnestly and stubbornly, and who were thus more completely transformed into His image before they died (of course, the life they enjoy now is that of full sanctification, but it is hidden in Christ and we cannot see it yet). In seeing them, we catch a glimpse of the road ahead, where we are supposed to be going. We also realise how far there is yet to go.
There are times in our lives when we have successfully battled against particular besetting sins and vices. We think with a certain legitimate joy, "Oh, I can't really think of anything I need to confess this week." And we entertain the thought that we are coming along alright in our spiritual walk.
When such moods come upon me, I find a powerful antidote (although one I confess I do not always take) in reading a passage or two from Augustine's Confessions or a letter of my patron, Ignatius of Antioch. These serve as a kind of map, reminding me that things that look close may actually be very far away indeed. And above all, to remind me that this journey is one of relationship, not personal accomplishment or fulfillment. To read Ignatius' heart-wrenching cry as he is transported ever closer to the place of his martyrdom that he still knows and loves Christ too little, sobers me every time I read it, and invariably compels me to pray.
Which brings me to the most important thing of all.
2) Prayer. The whole purpose of penance is that we might diminish our love of earthly things so as to increase our love of Almighty God. To wrench our affections from that which perishes so to give them to Him Who is eternal. Our inclination is to focus on the negative, to reflect on what we are refraining from or, worse, to look forward to the day after Easter when we can take thes things back up. Every time our thoughts look like this, the whole good of Lent is lost. Like the Law, it has only served to demonstrate where our true affections lie, but it has not changed them. Penance, difficult as it is, is only a negative thing, not giving virtue but rather uncovering vice. When I give something up and spend days and weeks longing for it, I have only shown how addicted and attached to that particular thing I am. Something more is needed.
That thing is to use the penance as an opportunity to turn my eyes to that to which my affections should be attached. For a husband who loves his work more than his wife, it is not sufficient for him to take two weeks off if he sits around home wishing he was at work. He must spend time with his wife, talk to her, learn what it is to love her. We have the same object in Lent. We must spend time with Jesus, talk to Him, and learn what it is to love Him. That is the object, and without that our penances are less than worthless (may even be positively dangerous). Prayer therefore is of the utmost importance.
For my own part, I am striving for an even balance between personal prayer and liturgical prayer. In the former, I am (or try to be) ruthlessly honest, and speak what is on my heart. In the latter, I learn to mold my heart to my words, to learn how and for what I should be praying, like a person learning a foreign language by imitating the pronunciation and expressions of their teacher, or an apprentice watchmaker or metalsmith, learning by imitating. In the one I express what love there is in me now. In the other, I begin to perceive what that love looks like fully grown, and try to put my whole person in sync with that. In the one I pray what I mean. In the other, I learn to mean what I pray. Both are necessary in my relationship with Christ.
That is the key, however. All of Lent (and indeed every season of the Church year) is a walk with a Person. Regular prayer is vital to keeping Him before my eyes (for I am always before His) and keeping that relationship alive, and for learning the intimacy with Him in which alone is my salvation and ultimate happiness.
Know the truth and the truth will make you … an idolator? - My friend Fr Gerald Murray has a very good essay at The Catholic Thing. He posted it a couple days ago, so you may already have seen it. It deserves some...
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