There is both gain and loss in early male formation: men gain a certain clarity, power, and even vision in their separateness, yet may pay the cost in mutuality, responsiveness, and connectedness. Mentors can help men heal their connectivity deficit while retaining the strengths of their distinctiveness by reminding them that they have within themselves what they need for the journey and that some men are already underway. This article offers insights into mentoring men toward wisdom and is based on the notion that growth into a more grounded and connected wisdom entails transformation of the pillars of traditional masculinity: (1) procreating; (2) providing; and (3) protecting.