The Re-Entry Vacation

When you say you need a break, this is probably what you actually need


You have been telling everyone how much you need this vacation. Your spouse has heard it. Your assistant has heard it. You have heard yourself say it in the car, out loud, more than once. The year took everything, and you are going to rest if it kills you.

Three days in, you are answering email by the pool.

There is a quiet truth in that moment. If you are leaving on vacation talking about how badly you need it, a break is not going to be enough. You do not need time off. You need a re-entry vacation. The difference between the two decides which version of you walks back through the school doors in August.

So ask the honest question before you go. When you said you needed a vacation, did you want rest, or did you want to re-enter your calling refreshed and refocused? They are not the same thing, and only one of them requires a plan.

Rest is where most leaders stop

A depleted leader reaches for rest, and reaching for it is right. The trouble is that rest alone returns you to the same tank you left on empty. Your body recovers, and nothing else does. The staffing decisions you deferred are stacked on your desk, waiting for a leader with nothing left to give them. Depleted leaders make bad decisions, and the hiring calls waiting for you in July are some of the highest-stakes decisions you will make all year.

Rest is step one. It was never meant to be the whole trip.

RE-ENTRY: a recovery framework for leaders coming off a hard season

Three movements, in order. You cannot skip one and reach the next.

01. Rest

Sleep without an alarm. This is not laziness, and it is not indulgence. Physical recovery is what creates the capacity to receive everything after it. It is also harder than it sounds. You cannot rest well while you are still carrying the school, still answering the poolside email, still lying awake running the list. Settle the body first. Nothing else works until you do.

02. Reorient

Once you are rested enough to think clearly, open a journal and walk through every domain of your life. Work. Your marriage. Your friendships. Your kids. Look at each one through a single question. What is God already doing here that I have been too depleted to see?

Depleted, you become the center of your own universe. You see from your own angle only, because fatigue shrinks the world down to you and your survival. Reorienting is where that breaks open. It is where you begin to see yourself, and the people around you, from God's perspective instead of your own. Paul told the Corinthians what this looks like: "So from now on we regard no one from a worldly point of view." That is reorientation. Same people, new eyes.

Let me tell you this one from the inside. Last month I took a vacation with my wife after a season that had emptied me. Had I not stopped long enough to reorient, I would have spent the whole week looking at her, at my work, at everyone, from my own point of view, because that is what depletion does. It makes you the center of your own universe. Reorienting is what let me see the people around me the way God sees them, not the way my tired eyes had reduced them to.

03. Re-Enter

Then, and only then, you re-enter. Not with a strategy. Not with a request for direction. With an act of availability.

I am back. I am yours. Put me where you need me.

This is the posture the whole framework exists to recover. You are an ambassador. "We are therefore Christ's ambassadors," Paul wrote, "as though God were making his appeal through us." An ambassador shows up, rested and reoriented, and represents the One who does. Your school was never a story you were writing alone. It is a story God is already authoring, and re-entry is how you offer yourself back into it.

The same desk, two different leaders

Now look again at the decisions waiting on your desk. A principal who only rested walks in and fills the roles from anxiety, settling for whoever is nearest so the pressure lifts. A principal who re-entered walks in settled, clear about what God is already doing in the building, and available to be used in it. Same empty offices. Two very different leaders making the call.

Come back to your calling, not just your calendar

The vacation is coming, and you have earned it. The only question is what you do with it. You can use it to stop, and come back in August as the same leader who limped across the June finish line. Or you can rest, reorient, and re-enter, and come back to your calling instead of just your calendar.

So before you leave, answer the question honestly. Did you want rest, or did you want to re-enter? Then take the vacation that gives you what you actually came for.

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The Better Question Beats the Right Answer