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Drawing Outside the Lines

by | 13 February 2026

My sister is an artist and a brilliant teacher. For thirty years, she’s been educating young people not only about the history and foundations of art, but she has inspired and enabled two generations of children and teenagers to find their creative voice and express themselves in ways that simply stun their parents. The exhibitions of her students’ work amaze me as they demonstrate their skill and inventiveness in drawing, painting, ceramics, and print making. The works that make it to those exhibitions are far more than demonstrations of technique, but of real creativity.

This Christmas, along with a number of supplies for drawing and painting, she gifted me with a drawing lesson, hoping to help me rediscover this old pastime that I enjoyed so much as a kid.

She began by teaching me shading techniques with pencil, and then how to take perspective of an object that I might want to draw. I hate to admit it, but I was a little frustrated with the lesson. I wanted to jump in and start drawing ā€œfreehand,ā€ instead of learning these rules and moving step by step. But as a good teacher, she was so patient with me and asked me if I really wanted to make progress beyond my simple childhood scribbles. She asked whether I was willing to first ā€œlearn the rules in order to also know why, when, and how to bend the rules.ā€ A wise and skillful teacher, my sister.

In our readings today from the scriptures each of these passages refers to not only the importance of knowing and following God’s law, but also discerning the ā€œspiritā€ of those laws. The Book of Sirach and the Psalms belong to the Wisdom Literature of the Old Testament, because each of their authors go beyond simply describing the rules and precepts of God for the Israelites, but also exploring the intention, purpose, and meaning of God’s law. These authors suggest that for God, following the rules was only a beginning.

ā€œBetween good and evil… life and death,ā€ we hear the Sage in the Book of Sirach recommending that we choose carefully, because there are always consequences for our choices. In the Psalm, we are encouraged to not only live in a morally correct and ā€œblamelessā€ way, but also to seek God with all our hearts, so that we might discern and observe his commandments and keep them faithfully, more than fearfully. In Paul’s first letter to the Corinthians, he goes even further to say that the full wisdom of God, which had been mysterious and hidden, was now revealed to us through the Holy Spirit in Jesus. So while the Law had been essential as a foundation for understanding what kind of behavior was in and out of bounds, it was surpassed by Jesus, who often drew ā€œoutside the lines,ā€ and appealed to the higher law of love.

Jesus embodies and expresses this Wisdom and the Law of God, not by enforcing blind observances of rules, but by discerning whether the way our relationship to God’s laws are fulfilling God’s intention. Revelation teaches us that God’s desire is to lead us into a deeper relationship with him and to live in right relationship with one another. This requires us to enhance our freedom from attachments and to mature our desires for a more abundant life. However, Jesus met religious leaders who consistently held to the letter of the Law without understanding that true spirit and intention, and who enforced religious codes in ways that created blind obedience, oppression, and alienation. These leaders somehow ā€œlost the forest through the treesā€ and by obsessing about dogmatic obedience and purity, they missed the mercy, tenderness, and compassion that God desired.

Jesus himself teaches that obedience to the Law is necessary, but it is not sufficient. Obedience to the Ten Commandments will keep us from doing harm, but it will not fulfill God’s desire for us to mature in the Spirit, and to discern how to seek and follow what will bring about the more abundant life that is our proper end. To extend the parallel with my sister’s instruction, following the guidelines and rules will help me master technique, but it won’t help me create real art.

Now, lest anyone think that I’m suggesting Jesus was lenient and soft in his moral instruction, this Gospel suggests that Jesus was in fact more rigorous and demanding than the Scribes and Pharisees in a very particular way. He didn’t want people to assume that by complying with the Law, they would discover the fulfillment, joy, and inner peace that most of us seek. Instead, he includes and transcends the Law. Jesus taught that beyond not actively doing harm, or living unfaithfully in our actions with others, that we are called to a higher standard of spiritual maturity, of freedom from even the impulses that would lead us astray. He wanted us to learn how to choose what it is that God desires for us… life and life to the full.

This spiritual maturity requires an inner path of growth and development that is more challenging than simply complying with rules and avoiding wrongdoing out of fear. It involves a paradoxical path of surrender to God’s unconditional love, which in turn inspires us to want to be a better person in response to that love: more compassionate, more just, more generous, more humble, more free to enter into the messiness and complexity of life with joy and courage.

As leaders, how do we help people to learn the basic foundations and essential rules for what to do and not do in the service of living and working together, but not to stop there?  How do we also help people mature in ways that really count in life: in their emotional and social intelligence, in their discretion and conscience, in their capacity to meet the challenges that life throws at them with wisdom and resilience?

God does not want us to blindly follow his Law, but through his Law and his Love, God liberates us to ā€œdraw outside of the linesā€ as co-creators. If we as leaders follow Jesus’ way, it is not by imposing more rules, but rather, by helping liberate people’s gifts and cultivating their maturity, conscience, and capacity to thrive. Of course, this begins by humbly modeling this wisdom and these behaviors ourselves, and by giving people space and freedom to grow, experiment, make mistakes, and learn along with us…  that we might become artists in this one precious life that we’ve been given.

With you on the road,

Tags in the article: On the Road Reflections
Executive Director of the Program for Discerning Leadership

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