Are we coloring outside the lines?

The women in New York amaze me. Every day on the subway, I observe women of all income levels, ages, and walks of life. They all have one thing in common: they are remarkably well put together.

For years I have analyzed this question: how do New York women present themselves to the world so effectively?  What exactly do they do to develop this “core competency”?

New Yorkers will almost always wear one item that is either more formal or more casual than the rest of the outfit, and will often wear one color that slightly collides with the rest of the outfit.  A New Yorker will fearlessly pair high heels with shorts, and boldly mix orange and pink.

New York women color outside the lines.

In the past few years, three groundbreaking cases have changed bankruptcy law in far-reaching ways: Enron. Lehman. General Motors. In each case, Harvey Miller advocated positions that departed greatly from established precedent and practice.  He colored not just outside the lines but on the walls.

The United States Bankruptcy Court for the Southern District of New York in each case took pains to say that the decisions were driven by extreme necessity – in each case, to avoid consequences of epic proportions – and not to be considered precedent in future cases. This is a bit like a fashionable woman in New York who says she wants to be “under the radar.”  Every decision in this bellwether jurisdiction impacts future cases – particularly an uprecedented decision in one of the largest cases in history.

Last night’s annual Judge Conrad Duberstein dinner was attended by over a thousand bankruptcy professionals. What separates the luminaries is their willingness to break new ground.  They are bold, fearless, and sometimes even discordant.

I fearlessly pair a t-shirt with a suit, and boldly wear high heels with jeans. But could I argue boldly for a departure from the most fundamental of bankruptcy principles? Were I a judge, could I fearlessly approve such a departure in one of the most significant chapter 11 cases in history?

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