At a time when the higher education as a whole is experiencing an incredible leadership turnover and a narrowing pipeline of prepared or willing leaders to step into these important roles, the industry is also experiencing more scrutiny than ever before, creating a challenging time for the leaders of these institutions. Small private colleges in New England, in particular, have their own unique set of complications, which makes finding the right kind of future leaders particularly important. This phenomenological study explored the lived experiences of 14 small private college presidents amidst an incredibly unique set of factors which substantially complicate the roles for leaders of small, private institutions in New England with modest endowments. The study found two primary roles that the presidents must fulfill: a Leadership Paradox of communication strategies and a Leader/Follower responsibility to its Board. Finally, the emotional consequence of fulfilling these two roles is explained in the Treading Water in a Changing Tide theme. This study fills a gap in the literature related to this specific niche of the industry, at a time when leadership succession and the future of small private colleges is an important conversation for the future of higher education.