In classic economics, when borrowing an amount of money that causes a debt to the issuer, it is not usual to have interest which can become larger than the principal. In the context of technical debt however, accumulated debt in the form of interest can in some cases quickly sum up to an amount that at some point, becomes larger than the effort required to repay the initial amount of technical debt. In this paper we propose an approach for estimating this breaking point. Anticipating how late the breaking point is expected to come can support decision making with respect to investments on improving quality. The approach is based on a search-based optimization tool that is capable of identifying the distance of an actual object-oriented design to the corresponding optimum one.