The Tail of the Serpent

Be careful and attentive

until you see that you are strongly determined

not to offend the Lord,

that you would lose a thousand lives

rather than commit venial sins . . .

for otherwise, who can go without committing many?

St. Teresa of Avila

I’ve never been to a funeral where the matter of where the deceased ended up in the afterlife was in question. In my experience, it is uniformly proclaimed that, without a doubt, the dearly beloved now beholds the beatific vision. Similarly, not once have I ever heard anyone speak of someone who has passed without quickly following it up with some version of “but at least they’re in a better place now.” My anecdotal evidence isn’t an aberration. In fact, research shows that decade after decade, of those Americans who believe in Heaven, the vast majority72-77% in fact!imagine they will end up there.

There are several reasons for this, of course, not the least of which being that it is painful to think about death. To the extent we do think of it, it is far more comforting to think of ourselves and our loved ones in eternal bliss rather than damnation. We avoid the topic of death so thoroughly, in fact, that nearly 70% of Americans die without any type of will despite the fact that each one of us has a 100% mortality rate. The response to the current pandemic has merely served to underscore the extremes people are willing to undergo to avoid the inevitable.

As Daniel Defoe observed in The Political History of the Devil, however, only two things in life are certain: death and taxes. Death, and more importantly, where we are headed once we begin that “next great adventure,” is something we all must seriously consider at some point in our lives. And despite our wishful thinking, the idea that most of us will end up in Heaven once we do cross that final threshold is directly contrary to Church teaching (see Matt. 7:13-14, 21-23; CCC nos. 1033-1037). The cold, hard fact is that most of us aren’t going to Heaven, and we have only ourselves to blame.

The problem is that most of us think of hell as reserved only for really evil people. People who do things we would never do. People like Hitler or pedophiles. Bad people who do the kinds of things that everyone, regardless of political persuasion, uniformly label as evil. And each of us is convinced that we could never do something like that! We’re mostly good people, after all. We don’t steal or kill. We don’t do anything truly evil.

That’s the thing about evil, though. All sin is evil to one degree or another. More often than not, the small sins [that lead to greater sins] that eventually cut us off from God aren’t very obvious. Evil “look[s] fairer and feel[s] fouler,” as Frodo says in The Fellowship of the Ring. It’s subtle. No one wakes up one day and decides out of the blue to commit a mortal sin. Instead, we get there little by little and suddenly all at once. And the consequences, even if we don’t see them immediately, always follow.

“Be careful and attentive,” St. Teresa of Avila cautions us, “until you see that you are strongly determined not to offend the Lord, that you would lose a thousand lives rather than commit venial sins . . .; for otherwise, who can go without committing many?” Unfortunately for us, however, maintaining this constant vigilance against sin is harder than one might think because of the very subtle nature of sin and temptation itself.

In fact, Adam and Evewho first opened that door to the chaos of suffering and deathare perfect examples of this subtlety. They didn’t set out with the intent to disobey God. Moreover, the Devil, disguised as a serpent, didn’t do anything so obvious as to directly tempt them to disobey God. The temptation started out as most temptations dowith a question, and a response containing a grain of truth with a twist.

We learn in Genesis 2:16-17 that God gave Adam one commandment: “You are free to eat from any of the trees of the garden except the tree of knowledge of good and evil. From that tree you shall not eat; when you eat from it you shall die.” Later, when the serpentthe most cunning of all the wild animalsapproached Eve, he launched his attack with a simple question: “Did God really say, ‘You shall not eat from any of the trees in the garden’?” Then Eve answered him: “We may eat of the fruit of the trees in the garden; it is only the fruit of the tree in the middle of the garden that God said, ‘You shall not eat of it or even touch it, or else you will die.” (Gen. 3:1-3).

Did you catch it? The serpent initiated the temptation with a questiona question that in and of itself, isn’t necessarily problematic. But by responding to the question, Eve falls into his trap. One of my mentors calls this trick of the Devil the “tail of the serpent.” Temptations don’t usually begin as obvious challenges to God’s authority. The Devil doesn’t usually reveal himself at first as the great fire-breathing dragon that he is, roaring into our lives. Instead, he begins quietlythe very tail of the serpent slipping through an otherwise good intention, so smoothly that you might not even catch it at first.

The Devil is not creativehe can only twist and pervert that which is true, good, and beautiful. Eve, in responding to the Devil, answers mostly in truth, but also in a lie. The truththat Adam and Eve are forbidden to eat of the treeis perverted by Eve’s addition that God forbade even touching the tree under pain of death.

It’s a small addition, to be suremerely the tail of the serpent. But Eve’s response coupled with that small addition set off a chain reaction that ended in mankind’s expulsion from paradise. Her lie impugned God’s integrity, planting the seed in her mind that perhaps God was not good, truthful, or honorable. It opened the door for doubt to creep in.

It’s a bit like those small acts of disobedience we do every single day. St. Teresa of Avila confessed in her autobiography that her neglect of rooting out small sins blocked her from progress at the beginning of her spiritual journey: “As for venial sins, I paid little attention; and that is what destroyed me.” So, too, it is with each of us, and that road leads not to Heaven, but to the fiery pit of Gehenna.

As we head into the Lenten season, I will leave you with one last word of advice from St. Teresa of Avila: “Remember that you have only one soul; that you have only one death to die; that you have only one life, which is short and has to be lived by you alone; and there is only one Glory, which is eternal.” Watch carefully for the tail of the serpent in your own life. When you glimpse it or hear that artful hiss, don’t deign to answer it. Instead, throw yourself at the foot of the cross, and place all your confidence in Him instead.

Lauren is a Catholic convert, wife, and mother of three, ages 7, 4, and 2. After practicing law for 7 years, she “retired” in March 2020 to become a full-time homemaker and homeschooler. She is also pursuing a master's in spiritual theology through the Avila Institute. In her spare time she enjoys coffee, running, and reading (though not necessarily all at the same time). You can find out more about Lauren at