On September 2, 2021, the Tax Court issued a Memorandum Opinion in the case of Gaston v. Commissioner (T.C. Memo. 2021-107). The primary issue presented in Gaston v. Commissioner was whether the petitioner engaged in acting as a trade or business in the tax years at issue and, if so, whether the petitioner is entitled to deduct any reported expenses relating to that trade or business. Background to Gaston v. Commissioner: A Pink Cadillac The petitioner is a former national sales director for the Mary Kay, Inc. (Mary Kay). She began working for Mary Kay in 1967 and reached the position of national sales director (NSD) in 1974. As an NSD, the petitioner was entitled to participate in Mary Kay’s deferred compensation program known as the Family Security Program (FSP), which she joined in September 1991. The FSP imposed a mandatory retirement age of 65 and provided that, upon her retirement,…