While risk management gained popularity during the last decades even some of the basic risk types are still far out of focus. One of these is path dependency that refers to the uncertainty of how we reach a certain level of total performance over time. While decision makers are careful in accessing how their position will look like the end of certain periods, little attention is given how they will get there through the period. The uncertainty of how a process will develop across a shorter period of time is often 'eliminated' by simply choosing a longer planning time interval, what makes path dependency is one of the most often overlooked business risk types. After reviewing the origin of the problem we propose and compare seven risk measures to access path. Traditional risk measures like standard deviation of sub period cash flows fail to capture this risk type. We conclude that in most cases considering the distribution of the expected cash flow effect caused by the path dependency may offer the best method, but we may need to use several measures at the same time to include all the optimisation limits of the given firm.