One of the most common disciplines in a business or economic project is timing and resource review. Despite the frequency of use, the level of sophistication is not high enough to maintain its level of importance. Exceeding deadlines and non-compliance with contractual costs is more than common. Moreover, there are projects where uncertainties are a naturally accompanying phenomenon. Research projects, implementation of solutions in a time-limited situation, or in an environment of limited knowledge creates risk. Any project proposal faces future realization risks when its planning management does not know with certainty where the current risks and uncertainties may come from. Decision-making, risk management dynamics, and simulations have developed in recent decades into an erudite and useful discipline. The aim is to indicate how much of the time–cost schedule proposal is stable, controllable, and economically feasible. The approach is based on the idea that modern resource scheduling requires nonlinear dynamic calculating models and simulations. The methodology presented is based on the dynamics of underlying physical and economic processes that form a spatial pattern of a time series. The article’s objective is devoted to the early indication of a dynamic project schedule’s instability and predisposition to bifurcation and chaos. In other words, the aim is to show not only what will happen but how diverse and damaging the project may become in the future.