In the present study, we compared the professional culture, mentoring, and work-life expectations of six female emerging professionals in the field of learning in retirement to what they actually have experienced. To date, we have not encountered prior published studies related to emerging professionals in this field and only one study, Peterson (2006), conducted research regarding learning in retirement professionals. In the present exploratory multiple case study, we described and interpreted the professional culture, mentoring functions received, and work-life experiences (e.g., successes and challenges) of emerging professionals in lifelong learning and measured the professional expectations of the participants against their actual described experiences. We identified five themes that describe the situational positioning of emerging professionals in learning in retirement within their institutes, universities, profession, network for professional growth, and overall professional network. The impact of the present study may help to provide targeted professional development, succession planning, and greater opportunities for networking to personnel in this field.