This dissertation includes two related chapters that investigate the value of multiple directorships. In the first chapter, I focus on potential tradeoffs between the costs and benefits of multiple directorships held by outside directors and attempt to determine how firm characteristics affect such tradeoffs. It is widely believed that outside directors of a firm play important functions of monitoring and advising. As a result, the basic hypothesis of the first essay is that multiple directorships by outside directors can have different implications for firms that have different levels of monitoring and advising needs. Consistent with this hypothesis, the evidence suggests that firm performance is positively associated with multiple directorships for firms with high growth opportunities and low agency conflicts. Such firms would benefit more from better advising while not suffering much from less monitoring. Likewise, firm performance is negatively associated with multiple directorships for firms with low growth opportunities and high agency conflicts. In the second essay, I examine how multiple directorships held by outside directors affect shareholder wealth during acquisitions. The evidence indicates that not all busy outside directors have the same effect and some types of busy outside directors may benefit the firms.