Poor in Spirit

St. John Chrysostom’s fourth century sermon on the beatitudes insists that to be poor in spirit is to be “humble and contrite in mind.” The Saint also suggests, “He blesses them first, who by choice are humble and contract themselves.” Self-righteousness is avoided through purposefully cultivated humility.

Humility is not a virtue that immediately leaps to mind when considering most business leaders. Partly this is an artifact of media coverage. There is a tendency to focus on the flamboyant, such as Donald Trump or Larry Ellison. We probably hear the most about those who are accused of serious wrong-doing, such as Bernard Madoff or Dennis Kozlowski. Excessive humility seldom seems to be the charge.

Psychometric studies of a broad range of business managers find that, in fact, introverts are much more common in the executive suite than in the population at large. Humility is a very pragmatic virtue for business leadership. The humble person is inclined to ask more and listen better. Humility encourages self-reflection and self-correction. Admitting mistakes is important in building trust with others, especially those who may be dependent on you.

When I was in my twenties and thirties I often envied those peers who seemed free of self-doubt. There are certainly situations where this kind of confidence can be helpful. Start-ups – when something has to be created from nothing – can especially benefit from an impervious sense of personal destiny.

But by the time I was in my forties, most of my doubt-free colleagues had either burned-out or seemed to be churning through one “sure bet” after another. A few who got in early on the dot.com bubble took home a great deal of cash, but that experience, if anything, seemed to encourage humility rather than confirm confidence.

Despite my own tendency toward self-doubt, I have spent most of my professional life in start-ups. By the time I was working on my third or fourth business plan I had become very thankful for my tendency toward doubt. Doubt is realistic. Doubt is a good discipline.

A start-up, like many aspects of business-life, involves stepping off into the unknown. You can very seldom be sure what is coming next. To be strategic means engaging in an explicit process of attempting to anticipate what is most likely to be coming at you and what you want to do about it. This involves listening to others, reflecting on your own experiences, and asking questions of yourself and others. Doubt, uncertainty, and humility stimulate helpful questions.

When someone announces, “failure is not an option,” doubt is an appropriate response. Not only is failure an option, it is – at some level – almost assured. This kind of impervious confidence is a suspension of reality.

No great enterprise can be constructed entirely on the foundation of an individual’s tsedaq. No matter how profound the individual gift, it requires being worked out in community. The greater the individual gift, the greater the need for humility.

St. Chrysostom claims, “For as pride is the foundation of all wickedness, so is humility the principle of self-command.”

(The eight principles for strategic insight can be found in the Gospel of Matthew, chapter five, verses one to twelve.)