For several years, a case study based on an Indiana farming family was used in Purdue´s Annual Farming Together Workshop to teach alternative approaches to planning for the transfer of family farm business ownership and management interests. Lessons learned from the experiences of this farm family with planning for just one intergenerational transfer of the farm´s management were presented for consideration by workshop participants. The case illustrates how one family farm responded to changing expectations regarding their opportunities for management succession over a multi-year period. It provides an example of the need to remain flexible in the planning process. It also provides a fine example of the benefits of planning with successors rather than planning for them. In this sense, the case provides a cautionary tale for farm families. The PowerPoint presentation summarizes ten lessons evidenced by the case study of this family´s experience. These lessons are confirmed by the author-instructor´s many years of experience with helping farm families with intergenerational family business transfer planning.