There are mistakes, and there is a process of mistakes. The difference between them is the difference between a one-time failure and an ongoing pattern.
Almost every executive can recall a single decision that turned out to be wrong. That is a natural part of business and entrepreneurial activity. The real question is not whether we made a mistake, but what happened afterward—did we stop, learn and correct course, or did we continue out of inertia, hoping reality would sort itself out?
Mistakes happen to smart people, experienced managers, and excellent companies. What distinguishes an isolated setback from a crisis that brings down an entire system is the ability to stop in time. The moment an organization stops examining itself and begins justifying its decisions, the decline begins.
It is precisely here, in this week’s Torah portion, Mishpatim, that a particularly sharp management insight emerges. The Torah states that a thief who steals an ox must pay double, but if he slaughters or sells it, the penalty increases fivefold. Not because of the value of the ox, but because of the continuation. The issue is not the initial act, but the multiplication of actions.
Rabbi Isaac Arama, author of Akeidat Yitzchak, offers a far deeper reading: the severity does not stem merely from repetition, but from the fact that each stage constitutes a renewed decision. The theft may have been a momentary impulse, but the concealment, the sale and the escalation are conscious choices. Responsibility does not accumulate in a straight line—it multiplies. Each continuation increases both the moral and practical cost. A mistake is an event; continuation is a policy.
2 View gallery
The Torah states that a thief who steals an ox must pay double, but if he slaughters or sells it, the penalty increases fivefold; Musk Ox taken at the Pavillon de la Faune, Stratford, Quebec
(Photo: Circeus/Wikimedia Commons)
Similarly, Aristotle explained that ethos—character—is formed through habit. It is not a single action that defines a person or an organization, but what is repeated. Repetition builds identity. Arama adds another layer: repetition not only shapes character; it increases responsibility. It is not only about who you become, but about how accountable you are. This concept of moral proportionality is highly relevant to leadership.
In the organizational world, most crises are not born of one bad decision, but of a familiar inertia: “We’ve already started, so let’s keep going.” The first misrepresentation is made under pressure, the second to salvage the situation, the third to avoid appearing weak and, at some point, the mistake becomes the norm.
I witnessed this firsthand during an investment due diligence process. Early warning signs appeared at the outset, but inertia and the desire to believe that everything would work out kept the process moving. You convince yourself that you have already invested too much time and resources to retreat. It took time to understand that true courage lies in stopping—and in the end, we did. In retrospect, that was the most important managerial decision in the entire process.
The same pattern can be seen in the public and economic arena. The Epstein affair and its repercussions in Britain illustrate how poor judgment at the outset is not necessarily fatal, but a sequence of endorsements and denials can turn it into a systemic risk. Very quickly, the issue ceases to be moral and becomes economic: volatility in the British pound, pressure in the bond market, and rising risk premiums demanded by investors. Markets do not punish the first mistake—they punish leadership that refuses to stop.
The same mechanism is familiar in the security sphere. A single flawed assessment can still be corrected, but when a system continues to justify it instead of pausing to reassess, the cost grows exponentially. Whether in investment, public policy, or operational decisions, the pattern of self-justification operates in the same way.
True leadership is not measured by the ability to push forward at any cost, but by the courage to stop in time.
In the end, organizations do not collapse because of one mistake—they collapse when the mistake becomes a habit, and the habit becomes culture.