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Apprenticeship to Jesus Diagnostic | Part Three

By Derick Sherfey | Director of Content Strategy

This year my family- along with a couple dozen others- made the thousand+ mile trek West to the Rocky Mountains to begin our journey of planting churches in the beautiful, but broken urban core of Denver, Colorado. Entering into a new city as a leadership team necessitates a lot of skills in these early formative days as we seek to enjoy Jesus and live for the joy of others. We set out mapping our neighborhood, exegeting culture, engaging tribes, and looking for people of peace using tools like the Tradecraft Workbook and First 30 Daze.

These are exciting days filled with dependence on the Spirit and watching God answer audacious, specific prayers, but throughout this year’s experience of starting over as missionaries in a new context, we’ve continually had to come face-to-face with a daunting reality:


“Umm, Duh!”, you may be saying. I agree, but I wish I was past having “duh” moments in my attempts at following Jesus and helping lead his church on mission. There’s grace for our failures, and there’s grace to free us to ask really honest questions about our obedience and, by his grace, do something about it.

I’ve had to be honest with myself: sometimes I dream/strategize/whiteboard mission as “spiritual novocaine” to numb my soul from actually stepping out in mission. I’m tempted to love the idea of “neighboring” but rarely find time to actually walk across the street. I’m all for the idea of engaging the nations God has brought into our backyard or to be a church among the poor, but often my dinner table is filled with people who are a lot like me. My heart is compelled by the way of Jesus- to see the church caught up in the holistic vision of the kingdom of God breaking through in every nook & cranny (you can take the boy out of the South, but you can’t take the South out of the boy…) of culture, but we’re fighting the drift to settle for structures of ‘doing church’ in ways that are comfortable, manageable, and safe.

It would do us all well to slow down from time to time and ‘evaluate’ our pursuits. Are we being faithful to do what Jesus has told us to do? Are we still growing in listening to God and his call on our lives for the next season? What are our metrics of success? How will we know if we’re doing it?

Below is the last post of a three part mini-series of a personal discipleship diagnostic flowing out of 10 convictions of a balanced pursuit of apprenticeship to the way of Jesus we’ve developed at The Oaks Church that’s meant to be worked out in the context of community. If you missed them, go back and grab Part One & Part Two.

Maybe spend a half day away working through some of these questions and ask the Spirit to deepen us in faithful obedience as His Church on His mission in the world.


MULTI-CULTURAL || We align everything strategically for the global glory of God by pursuing unity in diversity

Have I been tangibly involved in making disciples among the nations over the past few months? Have I devoted time to staying informed of God’s activity among the global Church and among the unreached/unengaged people groups? Am I strategically, specifically, and passionately praying and fasting for the worship of the nations, the salvation of the lost, and the calling and obedience of workers into the harvest? How is God calling me to go deeper in this next season of life?

Am I enjoying the blessings God has given me to be a blessing to all nations? Am I being obedient to leverage my resources in ways that are sacrificially aligned with global need? Or is the way I have been spending my money recently more shaped by selfishness or the culture around me? Is there anything I should give up to share in the dark places of the world?

Am I joining God’s global activity that He has brought to our own city? How have I been living a diverse lifestyle with people of other cultures and ethnicities? Am I seeing, loving, and befriending the refugees and immigrants locally? How might the Spirit be leading me to engage the nations here in this next season? What is my plan to spend time personally in a cross-cultural context with one of our strategic partners in this next season? What do I need to do to prepare spiritually and practically for this trip? Who am I taking with me? How am I using my global involvement to strengthen our church in sending to the nations? Is my “yes” still on the table? Am I honestly and sincerely willing to follow Jesus wherever He calls me? Is God calling me to relocate cross-culturally mid or long term during this next season?

EQUIPPING || We release everyday people and develop leaders to see the kingdom expand in every corner of culture

Have I been taking my growth and development as an influencer/leader seriously? In what ways have I been equipped and how have I grown during this last season? What are one/two areas of growth in leadership that I need to become more competent in? What resources (books, trainings, events, etc.) do I need to pursue during this next season?

How have I been leveraging my passions, privileges, and positions of influence God has given me to cause other people to become who God has called them to be? What needs to change?

Am I asking good questions and developing a good plan to learn, serve, and see the Kingdom come in my neighborhood (location), work (vocation), and the things I do for fun (recreation)? Am I joining God in what He is doing in these areas or just merely existing? What do I need to take the next step in pursuing restoration in these arenas?

Have I been submitting to the leadership God has placed in my life? Am I praying for, speaking life, and respecting those in positions of authority over me?

JUSTICE || We enter into brokenness to see all things set right

Has this last season of my life been insulated from the brokenness and pain around me? Have I been bold and humble enough to ask God and others who know me to help me identify my blind spots? Is there any racism, apathy, superiority, calloused indifference, or even overt hate that exists in my heart toward individuals or groups that I haven’t been dealing with?

Have I been allowing space for lament of the evil and devastating effects of sin in me and in the world during this last season of life? Is my heart still broken and aching over injustice in our world and the pain it causes others? Have I become too cynical, bitter, or begun to loose hope in what God is doing to make all things new?

Am I genuinely entering into the pain of others by listening with genuine desire for understanding, compassion, and solidarity? Am I staying informed about what is happening in the broken and forgotten places of our city and across the globe? Have I been interceding and believing with vision and hope for our neighborhood, city, country, and world- or have I lost vision for what God wants to do to restore all things? What are the specific areas of brokenness, injustice, strongholds, and worldviews am I engaged in and what would the Kingdom of God look like in living color?

Have I been going out of my way to walk through my proverbial “Samaria” like Jesus? What needs to change in the way I am living to be more of a faithful presence? Am I actively seeking shalom by engaging with local/global partner organizations? What are the names of the people I am advocating/interceding for and how can I embody the Kingdom in their life in this next season?

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