Three cases to set up my conundrum:

1. In October 2012, Italian courts sentenced seven earthquake experts—mostly seismologists and geologists--to six years in prison for failing to give adequate notice of an impending earthquake that killed more than three hundred people. (I learned the news from "Italy Orders Jail Terms for 7 Who Didn't Warn of Deadly Earthquake" by Elizabetta Povoledo and Henry Fountain in The New York Times.)

2. A few years ago, the owner of a painting sued the Andy Warhol Foundation for damages after the organization's scholars expressed doubt that the work is a self portrait of the artist. Defending itself cost the Foundation $7 million. (For a fantastic article about the commerce of art that mentions this case, read Rachel Cohen’s "Priceless" in The New Yorker.)

3. In May 2004, the family of a patient who died from aggressive colon cancer sued Joan Savitsky for medical malpractice. Four and a half years and over $150,000 later, the family dropped the case at the advice of their lawyers, who argued that they could not win. (Read Dr. Savitsky's column in The New Yorker, "A Patient Dies, and Then the Anguish of Litigation," for the full story.)

Perhaps these experts were grossly negligent in their determinations and practice. In cases of complete incompetence, courts should impose penalty for possible damages. Yet here's the rub: How do we define gross negligence? When is something simply an honest human mistake and when is it neglectful harm?

Yes, there are cases where it's painfully obvious. Yet there are many more cases where it's not clear at all. In the latter, larger category, how can we truly know?

You can't ask other experts to weigh in: With the benefit of knowing the outcome, they know what to seek in the data. And even if their opinions aren't biased by the benefit of 20-20 hindsight, or hindsight isn't a factor, what professional wants to risk his reputation by stating that he would make the same determination?

Not punishing gross negligence has consequences that allow unethical practitioners to run rampant. Punishing what we think is gross negligence and may not be gross negligence—in other words, the gray area—has additional negative consequences.

In the three cases listed above,

1. experts who could save lives or help society will not offer their expertise to do so, for fear of liability;

2. researchers in all fields will not undertake studies for fear of lawsuits; and

3. physicians will order unnecessary tests to cover every base and the companies that insure them will charge exorbitant rates, driving up the cost of health care.

Sound familiar?

How do we fairly define the gray area between doing your best and willful negligence? Or can we define it?