This chapter explores the challenges that “career-oriented” and “high-achieving” men may encounter when their financial and career aspirations result in an opportunity cost in overall relational and emotional well-being, i.e., loneliness. High-status careers, such as those in the medical, legal, finance, and technology fields, require significant external and internal resources, which can impact critical developmental tasks, thereby delaying and/or hindering deep and meaningful connectedness in social and romantic relationships. By focusing on the developmental tasks/crises and the barriers that delay social development, this chapter offers insights and practical supports to men who are trying to or have achieved careers at the top of their field.