Several years ago, I attended a 2-day conference put on by the dynamic group, the Philadelphia College Prep Roundtable. During those two days, jammed packed with great sessions, information and conversations, many ideas about how to best prepare high school students, and even some older adults students, for the rigors of post-secondary education were presented and discussed. One of the things that really struck me – both then and now – was the passion of the nearly 200 people in attendance to help students to be successful beyond high school or community training programs. However, from my participation in the conference – along with my own nearly 30 years of helping to prepare students for post-secondary education or the workforce – what has become increasingly challenging is the ability to persevere in spite of the landscape in front of us. Getting students to understand the importance of sharpening their foundational skills in English, science and mathematics is really hard work. Getting school administrators and state departments of education to understand what truly engages students, in a high school classroom or an out-of-school-time program, can be even harder. And let’s not even talk about the lack of adequate funding that school districts and community programs have to face! Yet while those of us with the “fire in the belly” keep trying to make legislators and others understand what is really needed to make our educational system work properly, we still have students to educate in the meantime. There is still so much work to be done “in the trenches” to provide a viable, adequately educated workforce that will keep our country competitive in the global marketplace. To keep going, in spite of the lack of understanding of so many with the power – and the purse strings – to help, is a tough job. To instill hope in our students, in spite of their own attitudes about what obstacles or opportunities lie ahead, is what we have to work so hard to do. This is the underlying, ongoing challenge for those of us working to help our students successfully move forward.