The life of a monk ought to be a continuous Lent.The life of the monk, and I would argue the life of every Christian, should be a continuous life of prayer and fasting, a continuous life of confession and repentance. These aren't to be seasonal activities. Thus, during the season of Lent observances are intensified rather than taken up from scratch: "During these days, therefore, we will add to the usual measure of our service something by way of private prayer and abstinence from food and drink."
I like that phrase, "the usual measure of our service." You shouldn't be going from zero to sixty during Lent. You should already be moving down the road.
A. J. Heschel said, "The sense of dignity grows in the ability to say no to oneself". I think this fits well within the thought of your last sentence. Dignity does not come from special times of "No", but from the exercise of traveling the road of which you speak
Yet, the divine irony of this dignity is that it softens us so that when we do fail to say no, the humbling and grounding sense of failure soon turns us gently and tenderly toward others who also follow a desire into the ditch. There is something about struggling out of the ditch with them, as opposed to simply pulling them out, that makes our times of "no" in their sight a whisper of love rather than a proud display of angel wings.