Expatriate preparation is an ever growing area of interest in a globalized economy sharing a globalized workforce. For decades, scholars have sought methods for best preparing expatriates for host culture experiences. Research has revealed an array of factors leading to intercultural readiness success which has led to the creation of various assessments and training programs. Many of these programs offer strong returns on investment for governmental, private, and missions organizations that regularly send people abroad. However, even in the presence of research-based expatriate preparation programs, the expatriate failure rate still reaches nearly 65 percent. There seems to be a disconnect between even a high quality expatriate preparation program and the corresponding experience, revealing that even the best programs can fail to adequately prepare expatriates for an abroad experience. After a decade of studying and teaching intercultural communication, plus years of training pre-departure expatriates, the author offers a culmination of insight into potential issues that can arise in providing effective intercultural readiness training. Following examinations into the areas of trainee accountability, time required for growth, and trust between trainer and trainee, suggestions are provided for the implementation of an international travel preparation program that produces expatriates ready to face the challenges of life abroad.