This Article uses comparative analysis of childcare deductions in the U.S., Canada and Israel in order to expose the non-technical nature of the distinction between business and personal deductions. The comparative analysis reveals significant differences in the ways courts in the three jurisdictions have interpreted the distinction in the context of childcare expenses. Courts in these countries have dealt with the question in different eras and faced different legislative environments. The differences in time and legislative background not only help explain some of the differences among the courts’ decisions in the three jurisdictions, but also expose the normative foundations of the seemingly technical distinction, demonstrating that the issue of childcare deductions in fact raises a question of baseline-setting. In allowing or disallowing the deduction of childcare, courts actually determine what counts — and more importantly what should count — for income tax purposes in general and deductions in particular. By exposing the baseline issues underlying questions of deduction, the Article demonstrates why it is preferable to explicitly use normative considerations in lieu of the so-called technical distinction between business and personal deductions. The comparative analysis further raises an institutional consideration; as shown, precisely because this is a baseline issue, legislatures, who enjoy a larger doctrinal tool box than courts, can offer greater flexibility as required when a variety of normative considerations should be taken into account.