Prompted by the financial crisis, the latest New York Times magazine has a long article "Risk Mismanagement" by Joe Nocera
A risk measure called "expected shortfall" is defined to be the expected loss for a specified time horizon and quantile (such as 1 month and 1%). Unlike VaR, it does depend on the magnitude of the losses in the left tail. The Wikipedia article
Risk measure are relevant to individual investors as well as investment banks. Given a method of simulating returns (either drawing from historical returns or using a parametric distribution such as the normal), one can estimate the expected shortfall of an investment strategy in meeting some liability. For example, one could estimate the expected shortfall from investing a $50K lump sum in the stock market for 10 years and selling 25% of the portfolio over each of the next 4 years in order to pay annual college expenses of $25 K. One would need a distribution of stock market returns, perhaps normally distributed with annualized mean of 8% and standard deviation of 16%. Currently, financial planning software usually quantifies risk by forecasting the probability of an investment strategy succeeding, for example the probability of not running out of money over 20 years given an initial withdrawal of 4% of the portfolio, increased annually at the rate of inflation. This risk measure, like VaR, ignores the magnitude of the failure when the failure occurs. It treats running out of money in year 5 and year 19 as the same. An expected shortfall measure may be better.