Intellectual Empathy and the Orthodox Life
Jesse Roberts, OCAN Board Member
From our first day in law school, we are encouraged, ad nauseum, to ‘think like a lawyer.’ I was surprised to learn that this does not mean to think strategically, or to think analytically, or even to think clearly. Rather, as I took it, to think like a lawyer is to develop a capacity for intellectual empathy; that is to say, to develop an ability to articulate the strengths and weaknesses of both our own position and the opposing party's argument. Indeed, we were presented with cases that challenged our instincts and exposed our biases, often compelling us to reconsider, and in some instances, completely revise our views on the underlying controversy. I submit that to “think like a lawyer” is to engage with our vocations in the same manner that we, as Orthodox Christians, should be living our lives.
“Judge not, that you be not judged. For with what judgment you judge, you will be judged; and with the measure you use, it will be measured back to you. And why do you look at the speck in your brother’s eye, but do not consider the plank in your own eye” (Matthew 7:1-5).
“What is the sign that a man has attained to purity of heart…? When he sees all men as good and none appears to him to be unclean and defiled, then in truth, his heart is pure.” - St. Isaac the Syrian.
To “think like a lawyer,” then, is not merely to argue persuasively or to win cases. It is to cultivate a disciplined mind—one that can hold competing truths in tension, that can examine its own assumptions, and that can extend charity even to the most challenging adversary. This intellectual empathy is not weakness; it is strength. It is the strength to see the humanity in others, even when we disagree. It is the strength to acknowledge that our own reasoning may be flawed, and to seek correction not with shame, but with humility.
In this way, the vocation of law becomes a training ground for the spiritual life. Just as we are called to examine the “plank in our own eye,” we are also called to examine the weaknesses in our own arguments. Just as we are called to see all men as good, we are also called to see the merit in the opposing counsel’s position. This does not mean abandoning truth or justice—it means pursuing them with a heart that is both discerning and merciful.
St. Isaac the Syrian’s words remind us that purity of heart is not achieved through isolation or judgment, but through love and understanding. The legal profession, at its best, offers us daily opportunities to practice this kind of purity: to listen deeply, to speak truthfully, and to advocate justly. And when we do so, we are not only thinking like lawyers—we are living like Christians.
So let us embrace our vocations with reverence, knowing that every case, every client, and every courtroom encounter is a chance to grow in wisdom and grace. Let us think like lawyers and live like saints.
September 9, 2025
© 2025 Jesse Roberts
Jesse Roberts serves as OCAN's Board Secretary and is Of Counsel with the law firm Michael Best & Friedrich. He focuses his practice on a diverse range of tax and corporate matters, assisting both nonprofit and for-profit clients with a variety of tax compliance, tax planning, and tax controversy issues. He attends Ascension of Our Lord Greek Orthodox Parish in Lincolnshire, IL.