The economist Thomas Hazlett once told a story about the father of his high-school girlfriend. “I must say,” the man boasted, “that in my dating days, I never once asked a girl out who didn’t say ‘yes.'”

Hazlett figured the brag was calculated to make him feel insecure. But it didn’t really work. “Even as a callow youth,” said Hazlett, “I knew the answer to his hollow boast: He simply hadn’t asked out enough girls.”

Hazlett’s observation about his girlfriend’s dad jumps past economics and teenage angst to our spirituality. We can see it displayed in Lent, the penitential season leading up to Easter. Eastern Christians just completed this season and and Western Christians not long ago, but its lessons have no expiration date.

Charlie Sheen spirituality

When recently discussing Lent, Patrick Henry Reardon underscored the common feeling of failure during its annual observance. The rigorous demands of self-denial and repentance often trip us up. “[A]rguably,” he said, “most Christians fail to observe all of [the Lenten disciplines].”

For Americans this is particularly tough, said Reardon, because we feel like we always have to win. Losing is, after all, for losers. It’s a kind of Charlie Sheen spirituality. We can’t stand the thought of being rejected by the girl.

But this sort of self-confidence is misleading, even dangerous to the soul. The failures are real and they are important. In fact, said Reardon, “I don’t believe that it will be possible to become a saint at all, unless we find some way of dealing with the sense of failure, incorporating the sense of failure into our experience of the Christian life.”

Entire groups of Christians reject this understanding. The Christian life is about victory, they say, about overcoming, about standing on that other shore. And it is, just as Easter shows us, but not before we hang on the cross.

Embracing failure

We can be like the man in Hazlett’s story, but such victories — especially in the spiritual world — are cheap. We’re playing it safe for fear of failing. But spiritual rigors like fasting, lengthy prayers, and other traditional disciplines can be very useful. To play it safe could mean missing the benefits.

Of course the more we try to do, the greater chance we’ll blow it. But opening ourselves up to the possibility of failure on the other hand means opening ourselves up to the possibility of gain.

That gain only comes with toil. We recall Paul’s language about the strain of training, the athletic discipline he undertakes. Spirituality isn’t easy, nor should we expect it to be so.

Publicans, Pharisees, and pride

Reardon couched his comments on failure in the larger discussion of Christ’s story of the publican and the Pharisee. His point was that our failures do not keep us from heaven. Only our pride can do that.

We put our trust in our own efforts but then stack the deck for an easy win. We risk nothing so we can manage the outcome, so that we can brag that we’ve never been turned down, so that we can stand with our head held high. But that’s the fatal trap.

The Pharisee insisted on placing his trust in his own efforts, and he went away unjustified. Meanwhile, the publican relied totally on God because he knew his failings. He cried, “Have mercy” and left justified.

The trick with fixating on avoiding failure is that we become tempted to think that we can do it all on our own, particularly if we rig the game for an easy win that doesn’t ask too much of us. As a consolation prize, we get all the smugness and self-satisfaction we can muster. But we also walk away unjustified.