Prepare to WIN in 2017


At the end of every year, I take some time to look back at the previous year and look forward to the next. It is an exercise that is not uncommon and I use the time to evaluate and make a plan is several areas of my life. So, in the couple weeks after Christmas and to start the new year, I spent a significant amount of time reflecting and planning.

When working with coaching clients, I find that many people are attracted to the though of doing this, but lack a framework that allows them to safely evaluate. Hence, for many, such an exercise becomes one of comparison, shame and making a commitment to try harder.

What I wanted to do in this first blog of the year is give you a simple framework that you can add to or subtract from as is appropriate for the context of your life. It is a great tool to examine yourself spiritually, relationally, physically, financially, professionally, as a parent, or in numerous other areas.

The acronym is simple: W. I. N.

Click here to get 33 clarifying questions to help you make a discipleship plan.

W is a prompt to look at what you did well in the area you are examining. Too often our tendency is to start an examination with where we fell short. My own tendency is to want to press on before celebrating what has been done. Here are a few sample questions:

  • What did I do well in the area being examine?
  • How have I celebrated these milestones?
  • How will what I did well impact this next season of life?
  • What can I learn from the obstacles that I experienced?

I represents the aspects of this area that need improvement. Note of caution: avoid comparing your results with others. This is not an exercise in building shame, but being honest in order to make progress. Sample questions include:

  • How did I fall short of my expectations in this area?
  • What obstacles am I presently experiencing in this area?
  • Are my expectations healthy? Why or why not?
  • In what ways am I depending upon this area to sustain my sense of self?
  • With what negative symptoms – fear, anxiety, anger, busyness, perfectionism, etc. – do I struggle in this area?
  • What sins am I committing in this area of life?
  • How can I invite the presence of God in this area more fully?

Click here to get 33 clarifying questions to help you make a discipleship plan.

Finally, N stands for what comes next. This is the place where you set course and look honestly at the next season. Here are some key questions:

  • What goals do I have in this area for the next (3, 6, or 12) months?
  • Why are these goals important?
  • How do these reflect my life’s mission?
  • What do I need to prune in this area?
  • How is God important to this goal?

I would love to hear any questions you would add in these areas of examination. Or how often you take time to examine and evaluate the direction of these areas of your life. Send me an email letting me know.


I am an author, discipleship coach, and speaker who helps followers of Jesus gain perspective on their identities so they can experience transformation in their decisions, behaviors and relationships and live in freedom. My book Tree of Lies: Transforming Decisions, Behaviors, and Relationships By Gaining Perspective On Your Identity in Christ available on Amazon ( or Barnes and Noble ( Visit for free resources.

Services I offer are one-on-one coaching, group coaching,  speaking at organizations/churches, workshops on marriage/discipleship/leadership, and church retreats. For more info, click here to contact me.

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