Telecommuting has been regarded as an alternative work arrangement that provides higher levels of resilience and flexibility for the workforce. To provide a robust estimation of telecommuting activity, it is important to understand the extent of telecommuting and the underlying factors that contribute to telecommuters’ decisions. One line of discussion in behavioral decisions (including telecommuting) is the endogeneity issue, also referred to as simultaneity in cause and effect. The question is whether certain activity travel behaviors are the causes of telecommuting adoption or telecommuters are manifesting such behaviors because they telecommute. For instance, are people traveling more or farther because of the higher spatial–temporal freedom brought by telecommuting, or are they choosing to or having to telecommute because they already have those activity arrangements (e.g., take care of kids) in place. Exploring such interrelationships between the choice to telecommute, activity travel plans, and other personal and household decisions is the major motivation for this research. Structural equation models were developed. Results showed that adding feedback effects to the full model improved the goodness of fit of the model, and this improvement is statistically significant ( P-value = .032). Furthermore, it could be inferred that a decision to participate in nonmandatory activities has significant positive impact on propensity to telecommute, and it is more in favor of a full-day telecommuting arrangement (versus a part-day arrangement). This study used the 2010–2011 regional household travel survey data from the New York metropolitan region.