The key challenges beyond the above noted issues (tax and political influence) are, once again, to refocus upon the impact that philanthropy has on the giver, not only on the benefactors. Many philanthropists refrain from discussing the impact of philanthropy on themselves, out of fear of being perceived as boastful. However, the new Thoughtful Funder is more hands-on when it comes to her philanthropic activities, exposing her to many of the challenges of giving, e.g., direction of funding: where and how much goes to the cause funded vs overall institutional infrastructure costs. The 'old' philanthropist used traditional infrastructures such as hospitals, universities, and NGOs to administrate her funding of projects. These projects usually came pre-packaged and combined with various incentives such as 'naming opportunities' and/or honorary titles. The Thoughtful Funders are of the DIY mindset, and as such, are most likely to be in direct conflict with the traditional infrastructures that are supposed to execute her giving wants and needs. The new Thoughtful Funders are mostly entrepreneurs focused on tangible and measurable results. Most traditional infrastructures are focused, not on meeting the donors' vision, but on meeting funding goals. This isn't to say that the traditional infrastructures have no vision but rather that their focus is at times in direct conflict with that of their funders.

The new Thoughtful Funders want to give more than just their money. Both individuals and families who engage in giving (funding) are doing so with much greater involvement than ever before (Andreoni, 2015). Organizations like 'The Giving Pledge' provide a forum for some of the world's most engaged philanthropists to discuss challenges, successes and failures, and how to be smarter about giving. The notion of just giving money to 'professional foundations' to execute their wishes is becoming a challenge to both sides of that transaction. The Thoughtful Funders are united by a shared commitment to learn about how best to leverage their philanthropy to address some of the world's biggest challenges. This kind of collaboration is almost impossible using the traditional infrastructures, since the latter's commitment is to fundraising goals not necessarily the vision of the funder/donor.