• Josh Lewis

Episode 54 – The Art of Losing


Let us begin with some unsettling facts:

  • You will die someday.

  • It is quite possible your death will be painful and frightening.

  • For some, death comes tragically early and unexpectedly.

  • For some, death comes much later and is fully expected, after years of the body and mind steadily deteriorating to the point vital organs no longer function.

  • If you live long enough, everyone you care about now will die.

I’m not trying to be macabre here; I’m simply trying to frame things in a certain context before we proceed.


Our society is obsessed with success, winning, reaching our goals, being our all, “arriving”, self-help, and self-actualization. Trump promised his supporters we’d be winning so much they’d get tired of winning. We love winning. Shelves are dedicated to self-help books in bookstores and there’s no end to podcasts offering advice on how to get rich, be successful, and reach whatever goal you have in mind.


Failure is temporary. If it manages to truly set us back or keep us from our goals that’s only because something or someone—God? The lifeforce? The Universe?—has set in motion something even better for us than we had imagined. Death, if it enters our minds at all, is some distant threat that won’t come knocking until after a long life of success and a solid legacy that will ensure our life’s impact is felt for generations to come.


Conservative thinkers have had a lot to say about loss and failure. And their words can be a great comfort when our shallow world of "winning" falls apart.


British philosopher Roger Scruton observed in his book, How to be a Conservative: “The loss of religion makes real loss more difficult to bear; hence people begin to flee from loss, to make light of it, or to expel from themselves the feelings that make it inevitable…The Western response to loss is not to turn your back on the world. It is to bear each loss as a loss. The Christian religion enables us to do this, not because it promises to offset our losses with some compensating gain, but because it sees them as sacrifices. That which is lost is thereby consecrated to something higher than itself.”


“There has been a decline in the belief in an afterlife in whatever form—the belief that, somehow or other, the ‘unfairness’ of this life in this world is somewhere remedied and that accounts are made even,” wrote Irving Kristol in his book Neoconservatism, “As more and more people cease to believe any such thing, they demand that the injustice and unfairness of life be coped with here and now.” What if the faith of our ancestors that taught life everlasting is awaiting us after death wasn’t an antiquated superstition that we’ve evolved out of, but the very glue that held people together when everything else around them looked meaningless in an eternal sense?


“I am a conservative. Quite possibly I am on the losing side; often I think so,” wrote Russell Kirk several generations ago, “Yet, out of a curious perversity I had rather lose with Socrates, let us say, than win with Lenin.” Can Millennial conservatives muster the strength of mind to say the same today? Once again, a new generation of conservatives faces the very real possibility of the movement fading into oblivion. The only thing that has prevented that in the past were those brave men and women willing to choose the prospect of losing over meaningless victory. Let us pray that we can find the same courage. Because when all we’re about is winning, we’ve already lost.



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