
The What-If Demon
If there’s one thing that can be said for the demons, it’s that they are persistent. They never rest from their attempts to get us sidetracked from the Way, and they’re relentless in bombarding us with distractions of every type, anything to keep us from focusing on Christ in our hearts. If we’ve been decently formed by the Church and are earnest in our pursuit of Christ, we’re often quick to notice the big temptations they hurl at us, even if sometimes in our weakness we still fall prey to them. So, of course, the demons get all the more tricky (have you read The Screwtape Letters?), and find ways to worm their way into our hearts and minds disguising their nonsense as “normal” thoughts or even “godly” thoughts.

Image from Wikimedia Commons
One of these demons I noticed running around at College Conference this year was what I like to call the “What-If” demon. This annoying beast spends his time making us ask ourselves, “What if this thing I want to have happen never happens in my life?” “What if I had done this one thing differently?” “What am I going to do if some-thing-in-the-future-that-hasn’t-happened-but-could happens to me?” It seems he especially likes to pester young Orthodox Christians with all sorts of what-if’s about dating, relationships, marriage, and monasticism. Illustrative to this point are some of the questions we received from students in our question box:
What if we do not come to the realization to be married or enter the monastic life?
What if I don’t know by the time I’m 25 if I should get married or be a monastic? Does that mean I should automatically become a monastic if there is no one I can marry by 25?
Likewise, many young people who do feel called to marriage wonder, “What if I don’t meet the right person? What if I never get married?” Now, this is not to say that it’s not important to answer questions of how one should go about discerning one’s vocation. But the nasty What-If demon twists this necessary and spiritual undertaking into an anxiety-ridden, paralyzing question filling us with guilt, worry, and fear.
The What-If demon does his best to keep us looking anxiously to the future or mulling over the past, and this murky cloud of what-has-been and what-might-be is his greatest weapon. It swirls around us, becoming so encompassing, dark, and ominous that we can’t see clearly–we can’t see the present moment. And it is only in the present moment that we can meet Christ, hear His calling, and answer obediently.
In fact, C.S. Lewis in The Screwtape Letters (really, you should read it) says it perfectly. Coaching his nephew on the ways of temptation, the demon Screwtape writes:
The humans live in time, but our Enemy destines them to eternity. He therefore, I believe, wants them to attend chiefly to two things, to eternity itself and to that point of time which they call the Present. For the Present is the point at which time touches eternity. Of the present moment, and of it only, humans have an experience analogous to the experience which our Enemy has of reality as a whole; in it alone, freedom and actuality are offered them. He would therefore have them continually concerned either with eternity (which means being concerned with Him), or with the Present–either meditating on their eternal union with, or separation from, Himself, or else obeying the present voice of conscience, bearing the present cross, receiving the present grace, giving thanks for the present pleasure.
The present moment is the place where time and eternity meet and where God enters into our lives. In an important way, the present moment is the only moment for the Christian. Do you say “yes” to Christ in this moment with this breath? Are you listening for His call in your heart right now? Can you see Him in the person or situation that’s right in front of you?
We must do battle with the What-If demon as we do with all temptations. First, we have to recognize him for what he is. We can’t confuse his what-if’s with repentance for the past or discernment about the future. Don’t let him convince you that his imaginary situations where he replays your past with anguishing regret are the same as contrition or the images he throws before you with terrorizing anxiety of futures that haven’t happened need to be addressed to find God’s will.
His cloud is just that: a cloud. A cloud that is blown away by the Holy Spirit when we call upon the name of Jesus Christ. And once we have recognized the What-If demon for who he is and called upon Christ to banish him away, we can be free to see clearly the present moment in which Christ dwells.

Icon by the hand of Dn. Matthew Garrett. Used with Permission.
If the What-If demon becomes too strong in our lives, he can wreak all sorts of havoc on our hearts, giving rise to anxiety, fear, and depression. If he is pulling too strongly, it’s important that we bring to light this struggle in the sacrament of confession. Confession is a time to be open and honest about the demons that pester us, especially when we feel convinced by their nonsense.
And watch out because just as you start to name the What-If demon and try to escape from his distractions, he’ll send in his cousin the Don’t-Repent demon who will try to convince you that you should feel shame for your anxiety, you are helpless, and you don’t deserve God’s love and forgiveness. Don’t listen. He’s lying.
The best thing we can do when we are tempted by the What-If demon is to remember that he is actually powerless as long as we refuse to give him any of our time and energy. When he comes to distract us, instead of letting him drag us away from Christ in the now, we can answer with the Prophet,
Behold, God is my Savior and Lord. I will trust in Him and be saved by Him. I will not be afraid, for the Lord is my glory and my praise. He has become my salvation. –Isaiah 12:2, OSB