Have you ever been “caught napping”? The expression is more than 400 years old. By Shakespeare’s day, it was being used to refer to someone who should have been ready for a situation but was caught unprepared. In sports, it is associated with embarrassment. Think of the distracted goalie who lets the ball into the net. Militarily, it can only mean total disaster. Think of examples like Pearl Harbor, the 1940 Battle of France, Israel’s destruction of the Egyptian, and the 1967 Six-Day War. And who can forget 9/11?
Jesus makes it clear that the same kind of high-stakes, all-or-nothing risk is associated with our own lives. We are all at risk of our own Pearl Harbor. This risk is spiritual, moral, and especially eschatological. We are in danger of being unready for history’s goal and climax: the return of Jesus Himself. “Stay awake, for you do not know on what day your Lord is coming” (Matthew 24:42, ESV).
However, one may say, “I’ve heard that all before” or “We’ve been saying that for 180 years”, and the idea of watchfulness and expectancy is wearing thin. We’re just crying wolf. Have we misread this? Sometimes, we have. A major earthquake, false prophet or another war is not a sign that the second coming is about to take place. It’s a sign of a fallen reality this side of the second coming—a disturbing reality that suddenly escalates and peaks at terrible moments in history (such as the fall of Jerusalem, Luke 21:5–7, 20, 21) and will escalate beyond all others before the second coming.
In view of this, Jesus helpfully tells His disciples how to stay grounded and connected to Him amid deception, political or military conflict, natural disaster, persecution, and social chaos. What Jesus emphasises is we need to be morally and spiritually watchful, awake, and alert.
This alertness is not only vital to being ready for the second coming but for life’s many crises and challenges. Peter outlined the challenges of enduring suffering, taking up leadership, being humble, and dealing with anxiety and counseled us to be watchful amid all these things because the devil is a prowling lion, always seeking a victim (see 1 Peter 5:8). If he can’t devour us, he is seeking to knock us over. In any code of football, being tackled on the blindside is devastating.
You can’t prepare for what you can’t see. Spiritually, there are many potential blindsides. That’s why only the watchful are able to stand firm in the faith (see 1 Corinthians 16:13). Being watchful is relational as well. When Jesus was about to go through the anguish of Gethsemane, He asked His disciples to “watch with me” (Matthew 26:38). Sadly, the disciples fell asleep. Jesus had to face His eschatological trial alone. What a missed opportunity! Watchfulness is not just about ourselves; it also involves being aware of the suffering of others.
Interestingly, Scripture likens being watchful with being sober-minded (see 1 Thessalonians 5:6). Unwatchful disciples are more like groggy, sleepy drunks. They are incapable of clear, firm decisions in the religious, ethical, or spiritual realm.
However, don’t think watchfulness is all about your mental agility. It is most closely connected to prayer. We are to “continue steadfastly in prayer, being watchful in it with thanksgiving” (Colossians 4:2). That is the essence of watchfulness: constant, thankful prayer.
Lastly, all the talk of watching and praying does not imply inactivity. Watchful disciples are not stationary meerkats, simply scanning the heavens and earth for signs of eagles or snakes. Jesus makes clear that the watchful one is an active servant who serves God and others (see Matthew 24:36–25:46; Luke 12:35–49).