Success through failure in Lent

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All of the great spiritual insight of the holy fathers and mothers of the Church must be accepted with discernment.  The insight into the human psyche (soul) is eternal—human beings are human beings whether it is the fourth century or the twenty-first.  However, the specific acetic practices and disciplines that work very well in one context might not work well at all in another.  This applies not merely to the differences between monastic life and family life, but it applies also to the differences of culture and lifestyle among people who live in the world
For example, I know someone who lived in a city in the southern U.S. and ate as a vegan all year around.  She did this for no reason other than it seemed a more globally sustainable life-choice and she didn’t like the idea of killing animals unnecessarily (and, perhaps—and this may just be my cynicism—also because it was a socially cool choice that also helped her keep her weight under control).  However, when she married a farmer and moved to the Canadian prairies things changed.  Fresh vegetables and fruit were pretty expensive a lot of the year, and meat and eggs were basically free (at least on her farm).  Now when this woman was in her vegan stage, lenten fasting was almost no sacrifice whatsoever.  Fresh fruits and vegetables were cheap and easily available all winter, so there was basically no change in her diet during the fast.  However, on the Canadian prairies, keeping a lenten fast costs quite a bit more.  First, it represents a radical change of diet.  Those of us who have kept a strict lenten fast and then feasted on the paschal lamb know what kind of suffering one can undergo switching from a diet high in animal protein to a diet high in plant-based protein, and back again. Second, it cost a lot more money to buy fresh fruits and vegetables imported from halfway around the globe, and consequently, there is much more reliance on high carbohydrate (read: fattening) foods.  Thus it becomes very hard to keep from gaining several pounds during the still very cold days of lent on the Canadian prairies.  
The lifestyle of a person in a city with a Mediterranean climate is quite different from that of  Canadian prairie farmer, and thus for the spiritual benefits of the Great Fast to accrue, the fasting provisions need to be adjusted to the situation.  I am not saying that the fasting regimen of the Church should be ignored.  If one asks what the Church fasts from during lent (or on any fasting day), the answer can be easily given.  That does not change.  However, what does change is people and their circumstances.  A vegan city dweller might be deluded in thinking herself quite an ascetic because she experiences no struggle whatsoever in keeping the lenten fast, while the prairie farmer may be equally deluded in thinking she is a complete ascetic failure because she calls chicken “prairie fish” and eggs “early spring apples.”
But this is just an example.  I don’t really want to talk about food.  I want to talk about something a bit harder to see.  I want to talk about cultural expectations for success.  A goat herder in nineteenth century Greece, for example, had very little future expectation other than to live and die as a goat herder.  There was no expectation nor any need for him to push himself beyond the expectations of a goat herder because there was no opportunity for him beyond herding goats.  Why go to school (even if schooling were available and could be afforded)?  Why learn to read?  Why work really, really hard to acquire a little more wealth when it would only attract the attention of envious Turks who could easily steal it from him?  Consequently, such a goat herder had, on the one hand, a lot of discretionary  time (no electric lights and lots of long walks); but on the other hand, he had very little motivation attain anything more.  In such a context (a context that reflects, perhaps, the reality of most of the people of the world for most of history), The practical teaching of the Church for these people would have sought to motivate these people to strive harder in their personal religious practices, either by means of promises of blessings or threats of possible torments to come.
However, in my pastoral experience dealing with mostly highly-educated American and Canadian people, the cultural expectations for success are very different.  From Kindergarten, children are told that they can grow up to become whatever they want to be: an astronaut, a doctor, Prime Minister, you name it.  Drilled into these children, not only at school, but by the media and by their parents, is the expectation that if they work hard enough, if they try very hard, they can attain to whatever they dream to be.  This expectation of success is, I think, one of the big causes for the very hush hush epidemic of depression sweeping North America (no one wants to talk about the fact that a huge percentage of the adults of North America—and a good percentage of the children too—are taking some kind of mood-enhancing drug).
For these people with a high expectation of success based on their hard work, traditional Orthodox ascetical disciplines are a minefield leading many to delusion, both of pride because they think they have succeeded in meeting the ascetical “requirements”; or of despondency because, no matter how hard they try, they fail miserably at keeping the “rules.”  Unfortunately, I have met with very little success helping those in the former camp (although [and may God forgive me if I sinned, but I think I did the right thing at the time] I did once recommend to someone who seemed a little too happy about his success halfway through Great Lent that he go and eat a cheese burger to free himself from the delusion that he was somehow succeeding).  Maybe I can’t help high achievers because I’ve never been one.  I don’t know.  I seem to do better with those who know they can’t meet the expectations.  I’m not talking about those who haven’t tried.  I’m talking about those who have tried and failed, tried and failed, and tried and failed again.  I fit in quite comfortably with this crowd.  
I was talking to someone recently who was telling me about their failures in keeping a disciplined prayer life.  This person lives in a large Canadian city and works more than fifty hours a week in a high-stress job that they spent many years training for and working to attain.  However, their prayer life is dead (not that they don’t say prayers, but that nothing is moving in their heart) and although it is relatively easy to keep the lenten fast, it means nothing.  They can make themselves go through the motions, but their heart is cold; and thatis driving them toward despair.  What do you do about that?  How do you help someone who has been conditioned to succeed, but who has discovered that their many serious attempts to succeed in standard Orthodox Christian piety have resulted repeatedly in failure?  How do you help someone who almost never stands still, to still their heart?  Is it possible for such a one to be saved?
Yes, of course it is.  But certainly the spiritual tools that worked very well with the goat herder will need to be adapted for this success-oriented city dweller.  
I recommended to this person that they embrace their failure.  I suggested that their prayer be continually that of the prodigal son: “I am unworthy to be called your son.”  I suggested that several times though out the day, whenever they felt their cold heart or realized that they had completely forgotten about God, again, or had treated someone poorly, that they say in their heart/mind, “I am not worthy to be called your son.”  This person responded to my suggestion with the following question, “Are you allowed to be a prodigal more than once?”  I assured this person that it is a grace of the Holy Spirit if we can spend our whole life continually seeing ourselves as a prodigal.
It may seem counter intuitive to recommend to someone who is despondent about their apparent failure in the spiritual life to embrace the failure.  It seems that such a recommendation might run the risk of sending the person into a depressive tailspin.  It is a risk, I admit.  It could indeed do that.  However, if we learn anything from the hymns and readings of Great Lent it is this: it is the prodigal, the harlot and the publican who are saved, not the religiously successful Pharisee.  Salvation comes to those who need it, not to those who (think they) don’t.  
It seems to me that this approach is no different from St. Silouan’s famous dictum, “Keep your mind in hell and despair not.”  And for the twenty-first century, for those of us trapped in a culture of success, who have very little time without distraction, I do not think there is any other viable path but the path of failure, the hell of not meeting even the minimal religious expectations.  This is the hell in which our minds must remain without despair.  Like the prodigal and the harlot and the publican, we bring nothing except failure and a strong sense that we are not worthy to be received.  But we come nonetheless.  We come because the greatness of our Father’s love extends to the lowest hell of our misery.  We come expecting nothing, but asking our merciful God for mercy.  We come knowing that we are a compete mess, but that we are God’s nonetheless.  We are God’s, mess and all.
And this very act of coming to God (again and again) as one completely unworthy creates in us a thin sliver of humility.  And that very thin sliver of humility attracts the grace of the Holy Spirit.  And the Holy Spirt is the Lord and Giver of Life.

"Go ye therefore, and make disciples of all the nations, baptizing them in the name of the Father and of the Son and of the Holy Spirit"

Mathew 28:19