Rules Posted by Matt Little on 1st Oct 2025 "I am free, no matter what rules surround me. If I find them tolerable, I tolerate them; if I find them too obnoxious, I break them. I am free because I know that I alone am morally responsible for everything I do." - Robert A. Heinlein The day I wrote this The New York Times published a four part article series entitled “America’s Vigilantes” about accusations of war crimes committed by U.S. Army Special Forces soldiers in Afghanistan. These articles were politically slanted to be sure, but they started a train of thought about ethics and rules. Ethics and rules, contrary to popular opinion, are not even remotely the same thing. There are situations where following the rules can be unethical. How do we ensure that our moral compass is guiding us correctly if following the rules can’t give us ethical certainty? I have always pushed the envelope in order to accomplish things. There’s some truth to my often said joke that claims you know you’ve made it in your career when they have to make a new rule because of your actions. There’s also some truth to my claim that I’ve done just that in two careers and two sports. I laugh at myself for it, but I don’t regret any of it. My choices may have pushed the edges of what was organizationally acceptable but I’ve never benefited at others’ expense. This character trait was reinforced and rewarded during my time in special forces. The SF regiment intentionally seeks out soldiers who understand which rules to follow, which to bend in order to accomplish the mission, and which to outright break. They tested us for this without our knowledge in the way our training was run. If you were caught cheating in the SF pipeline you would be removed for cause, never to return. The paradox however is that there were events that could not be passed if you strictly followed the rules. This conflict was intentional. They were looking for individuals with a strong moral compass who were also pragmatic. Soldiers who understood the very real difference between illegal and immoral. Soldiers who were able to navigate that ethical minefield with sound judgement and unwavering commitment. By way of example, speeding while driving, at least within certain limits, is generally understood to be illegal without being unethical. No one feels like a villain for being issued a speeding ticket for driving ten miles over the speed limit if weather and traffic conditions don’t make that unsafe. Nor should they. By contrast, I think all decent people view certain business practices as immoral even if they are legal. Unethical can be within the rules, and the ethical action may violate the rules. Understanding that distinction and doing what is right independent of its legality is a hallmark of ethical maturity. The ability to break the rules ethically without being held accountable for that breach is a hallmark of competence and decision making. And that competence and decision making ability is foundational for someone who has to operate “in the gray” like an SF soldier does. Not all decisions are black and white. The same is true for law enforcement. Being a good cop in any proactive assignment requires the same ability to navigate the winding and razor thin line separating unethical but effective from lawful but ineffective. Good cops, like good special forces soldiers, live in the grey. The danger of course lies in losing your way amidst the uncertainty of the grey. And sometimes, good and moral soldiers and police officers can lose their way amidst the uncertainty and chaos that working in the grey entails. It’s a fine and winding line that has to be walked, like Somerset Maugham’s metaphorical razor’s edge. Step off even slightly in either direction and you fall. There’s a powerful lesson in all of this that applies throughout life when the stakes are high and the course unclear. Life isn’t always black and white. The intersection of legality and ethicality, the border between self interest and social contract, these are seldom clean straight lines. To navigate these we have to learn to live in the grey…