Are there career costs for family life? Are there social costs to career success? This chapter explores these two interrelated questions with an attention to gender issues. Women continue to find themselves before the unfair choice between family life and career success. In the first part of this chapter, there will be an emphasis on the prevalence of this problem. In the second part of the chapter, we discuss the roots of the problem, which we argue, rests in both the public and the private domains. Lastly, the chapter recommends a set of organizational, policy, and societal remedies to correct this imbalance between career and family, in hopes of improving the ability of US families to not “have-it-all”, but at least have the opportunity for more flexible choices.