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Keep Your Head to the Sky: Five Day Devotional

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Here are a few additional resources to guide your quiet time this week:


Day 1: Letting Go to Move Forward

Based on the Message: "Keep Your Head to the Sky" by Pastor Dexter B. Upshaw Jr.


"Then it came to pass, when Pharaoh had let the people go, that God did not lead them by way of the land of the Philistines, although that was near; for God said, “Lest perhaps the people change their minds when they see war, and return to Egypt.” - Exodus 13:17

Devotional: Change is inevitable, yet we often resist it with all our might. We cling to the familiar, even when God is calling us to something greater. Why? Because we crave control. We want to dictate every aspect of our lives, forgetting that our perspective is limited while God's is infinite. Think about the Israelites leaving Egypt. After 400 years of slavery, freedom should have been welcomed with open arms. Instead, many longed for the predictability of captivity when faced with the uncertainty of the wilderness. They couldn't see that what felt like sudden upheaval was actually the culmination of God's long-prepared plan. In our own lives, transitions that seem abrupt have often been in divine preparation for months or years. God works behind the scenes, orchestrating circumstances and preparing our hearts long before we recognize the shift occurring. The question isn't whether change will come—it's whether we'll trust God enough to embrace it.


Quote: "We must be led by the Holy Spirit, not nostalgia. Sometimes we get stuck in the good old days, failing to embrace a better future." - Pastor Dexter B. Upshaw Jr.

Question: What familiar but limiting situation are you clinging to that God might be asking you to release in order to receive something greater?


Prayer: Lord, give me the courage to open my hands and release what You're asking me to let go of. Help me trust that Your plans for me are greater than anything I can imagine or control. Prepare my heart for the transitions ahead, knowing that You've been working long before I recognized it. Amen.


Day 2: Embracing the Ending

Based on the Message: "Keep Your Head to the Sky" by Pastor Dexter B. Upshaw Jr.


"The LORD had said to Abram, 'Go from your country, your people and your father's household to the land I will show you.'" - Genesis 12:1

Devotional: The first phase of any transition is acknowledging that something is ending. This sounds simple, but it's where many of us get stuck. We enter denial, pretending change isn't happening. We reminisce about "the good old days," allowing nostalgia to anchor us to the past instead of propelling us toward God's future. Moses faced this challenge when God called him to confront Pharaoh. He had to accept that his quiet shepherd life was ending. Abraham encountered it when God called him to leave his homeland. Each biblical hero had to consciously release what was familiar before they could embrace God's next chapter. Endings require grieving. It's appropriate to honor what was valuable about the past season while recognizing it can no longer continue. The danger comes when we refuse to acknowledge the ending, creating an unhealthy attachment that prevents us from moving forward. God's instruction to Abram in Genesis 12 is profound: "Leave your country, your people and your father's household." Before mentioning the destination, God emphasized what needed to be released. Sometimes we're so focused on asking God where we're going that we miss His instruction about what we need to let go of first.


Quote: "The first step in transition is acknowledging that something is ending and letting go of it. We can't be in denial about change and pretend like it's not happening. In order to embrace a new beginning, we have to let go of the past." - Pastor Dexter B. Upshaw Jr.

Question: What ending in your life have you been resisting or denying that you need to acknowledge and process before you can move forward?


Prayer: Heavenly Father, give me the courage to face the endings in my life honestly. Help me grieve what needs to be grieved and release what needs to be released. Guard me against unhealthy nostalgia and denial. Lead me by Your Spirit, not by my attachment to the past. In Jesus' name, amen.


Day 3: Navigating the Neutral Zone

Based on the Message: "Keep Your Head to the Sky" by Pastor Dexter B. Upshaw Jr.

"By day the LORD went ahead of them in a pillar of cloud to guide them on their way and by night in a pillar of fire to give them light, so that they could travel by day or night." - Exodus 13:21-22

Devotional: Between every ending and new beginning lies what transition experts call "the neutral zone"—a disorienting middle space where the old has gone but the new hasn't fully arrived. It's the wilderness between Egypt and the Promised Land, the three days in the tomb before resurrection. This in-between time often feels uncomfortable. We're tempted to rush through it, seeking quick resolution to our uncertainty. Yet Scripture repeatedly shows God doing His deepest work in these neutral spaces. David was anointed king long before he took the throne. Jesus spent 40 days in the wilderness before beginning His ministry. Paul experienced three years of preparation after his Damascus Road encounter. The neutral zone, while challenging, holds tremendous potential. It's where innovation emerges, creativity flourishes, and true commitment is revealed. When we embrace this uncertain middle rather than fighting against it, we position ourselves for transformation. In Exodus, God led Israel with a pillar of cloud by day and fire by night. He provided exactly what they needed for each stage of the journey. Similarly, God gives us what we need in our neutral zones—not necessarily what we want, but what will prepare us for what lies ahead.

Quote: "If managed well, the in between time, the neutral zone, can provide opportunity for innovation and creativity. It unlocks genius." - Pastor Dexter B. Upshaw Jr.

Question: How might God be using your current "neutral zone" to develop new skills, perspectives, or character qualities you'll need for the next season?


Prayer: Lord, I confess my discomfort with uncertainty and my desire to rush through this in-between time. Help me recognize the value in this neutral zone. Open my eyes to see how You're working even when progress isn't visible. Develop in me the patience and trust to embrace this season of preparation. Amen.


Day 4: Releasing the Penny

Based on the Message: "Keep Your Head to the Sky" by Pastor Dexter B. Upshaw Jr.


"Then the whole congregation of the children of Israel complained against Moses and Aaron in the wilderness. And the children of Israel said to them, “Oh, that we had died by the hand of the Lord in the land of Egypt, when we sat by the pots of meat and when we ate bread to the full! For you have brought us out into this wilderness to kill this whole assembly with hunger.” - Exodus 16:2-3

Devotional: On Sunday, Pastor Dexter shared the story of a little boy whose hand was stuck in a vase because he was holding on to a shiny penny. Just like that little boy, we pray for God's blessings while holding tightly to things that prevent us from receiving them. We want new opportunities but won't release old habits. We desire healing relationships but hold onto bitterness. We seek God's direction but refuse to surrender our plans. The Israelites faced this challenge repeatedly. Even as God provided manna, they craved Egypt's leeks and cucumbers. Even as He led them to freedom, they yearned for the familiarity of slavery. They couldn't embrace the Promised Land while clinging to Egypt in their hearts. God often asks us to open our hands—not because He wants to take something valuable, but because He can't give us what's next while we're clutching what's in the past. The penny seems valuable when it's all you have, but it's preventing you from receiving the treasure God has prepared.


Quote: "God wants to set you free without breaking you, but you got to be willing to let go of the penny. It’s hard to embrace big, when little’s got you." - Pastor Dexter B. Upshaw Jr.

Question: What "penny" might you be holding onto that's preventing you from receiving the greater blessing God wants to give you?


Prayer: Father, show me what I need to release. Give me the courage to open my hands completely, trusting that what You want to give is far greater than what I'm holding onto. Forgive me for the times I've chosen the familiar over Your best. I surrender my pennies to receive Your treasure. In Jesus' name, amen.


Day 5: God's Presence in Transition

Based on the Message: "Keep Your Head to the Sky" by Pastor Dexter B. Upshaw Jr.


"The LORD will fight for you; you need only to be still." - Exodus 14:14

Devotional: When facing life's transitions, we often focus so intently on the destination that we miss God's most precious promise: His presence with us throughout the journey. The Israelites' exodus from Egypt reveals three powerful ways God manifests during our transitions. First, God remains constantly with us, though His manifestation may change. For Israel, the same God appeared as a cloud by day and fire by night—different expressions of the same faithful presence. In our lives, God's methods may shift, but His commitment never wavers. Second, God goes before us, preparing the way. Before Israel faced each challenge, God had already gone ahead to make provision. He doesn't send us anywhere He hasn't already been, working behind the scenes to prepare hearts, circumstances, and solutions. Third, God positions Himself as our protection. When Pharaoh's army pursued Israel, God moved between His people and their enemies. The same presence that guided them forward became their defense against what threatened from behind. When transitions feel overwhelming, remember: you never walk alone. The God who called you to this journey walks beside you, goes before you, and guards behind you. His presence is not just comfort—it's your greatest advantage in navigating change.


Quote: "The presence of God was more than a navigational system; it was a buffer between Israel and it’s enemies. We serve a God who fights for us!" - Pastor Dexter B. Upshaw Jr.

Question: In what specific ways have you experienced God's presence as guidance, preparation, or protection during your current transition?


Prayer: Lord, thank You for the promise of Your presence in every transition. When change feels overwhelming, help me sense You walking beside me, going before me, and protecting me from behind. Give me eyes to recognize Your work even when the path seems uncertain. I choose to keep my head to the sky, trusting Your guidance every step of the way. Amen.

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