It may come as no surprise that, right now, as I shepherd a college senior through the final stretch of the college process (yes, it is May 6 of his senior year), we are spending a lot of time talking about the “big picture,” the “end game,” and even “vision.”
As we held onto spots on two waitlists, other ideas surfaced in our conversations: being comfortable with the uncomfortable, and the story of Jesus in the wilderness—a story, and a symbol, of waiting, patience, planning, and thinking intentionally about where you ultimately want to end up, who you want to be, the sum of all of your resources, your efforts, your choices.
In my role as an advisor to individuals and foundations making significant decisions about their hard-earned and carefully invested money—what I call philanthropic capital—I am continually struck by how often the big picture disappears in the moment of the transaction.
Giving becomes compressed into deadlines and logistics: before June 30 or December 31, during a day of giving, in response to a request from a colleague or friend, or within a quarterly meeting where a list is handed off to a banker, assistant, or foundation staff member. The act is completed, but the intention behind it is often left underexamined.
Where did the notion come from that this money is somehow less purposeful, less worthy of our time, less precious, or less economically important than any other capital we manage?
And from a more human perspective: does the good we feel when we make a donation exist only in that brief moment? Or could we change how we give so that the relationship, the interaction, and the impact endure far beyond the transaction itself?
Lessons from Intentional Choices
Right now, I am talking about the big picture of philanthropy, but the conversation could easily be about education, our marriages, our families, our work.
Each of us directs certain resources to efforts and outcomes in our lives, and then, more often than not, we step aside and move on. If we take the college process, for example, or let’s say the fundraising process between donors and nonprofits, are they that dissimilar?
The end game is succesful acceptance to your college of choice. Years of academic work, review of what your goals are, what your field of study is, what you can afford, what activities you will take on, and planning for that investment involve students, parents, schools, teachers, coaches, and advisors. What about the fundraising process? Are we clear what we want our “investment” to achieve? How do we want to change the world and what outcome are we seeking in partnership with nonprofits and communities?
To be clear, I am not advocating for donor micromanagement. That would be not only counterproductive, but unethical; nonprofits should—and must—retain control over how funds are used once a gift is made.
But what if we approached giving differently? What if each of us—regardless of whether we give a little or a lot—considered the broader vision and long-term impact of our philanthropy?
The Accountability Factor: Seeking Vision and Impact
Nonprofits and communities are navigating increasingly complex challenges across housing, mental health, education, and more. These organizations are the experts in their fields. Yet many spend close to 40% of their time and resources managing donor expectations, fundraising repeatedly, reshaping budgets to meet artificial overhead constraints, and producing reports and messaging designed to reassure donors that their money is being used “correctly.”
We hold nonprofits to extraordinarily high standards. But do we hold ourselves, as donors, to any standard at all?
Historically, the answer is no. While some donor networks and philanthropic institutions have developed principles, guidelines, and even urgent calls to action around donor behavior, these efforts are difficult to enforce. Often, they are constrained by the very audiences they seek to influence or are perceived as too prescriptive for donors to fully embrace.
Real change in donor behavior requires stepping back and resurfacing the big picture. What do we want the philanthropic ecosystem to look like? Why does that matter? And what must change—in our behaviors, our expectations, and our decisions—to make that vision possible?
The past several years in America have been challenging, eye-opening, and, at times, deeply divisive. Regardless of perspective, there is broad agreement on that reality. What is often missing is a sustained focus on the big picture—on how individual actions, small shifts in behavior, and deeper engagement with our communities can collectively shape a different future.
America, and our individual lives, are long games. Democracy, capitalism, and the pursuit of opportunity depend on sustained participation and shared responsibility. While government at all levels plays a critical role, the private sector—and individuals within it—has always been a powerful force in shaping the country’s trajectory.
Recommitting to Shared Vision, Outcomes and Impact
And sometimes, the clearest reminder of the power of the long game and the big picture shows up close to home.
Our son applied to eight universities and was accepted to seven. His first choice, the University of Virginia Engineering School, did not come easily—he was waitlisted. What followed was not a single defining moment, but a series of intentional ones: writing letters, improving his grades, continuing to show up, and, just last Friday, sending a video of himself welding a spatula (notice I did not say wielding, he was actually using tools to make a metal spatula– engineering school remember?) On Tuesday, May 5, he was one of 260 students admitted from the waitlist.
That outcome was not the result of one application or one decision. It was the culmination of years of academic effort, character development, curiosity, and engagement with the world around him. He saw what he wanted, stayed with it, and achieved it. I am extremely proud.
It is a reminder that the most meaningful outcomes in life are rarely transactional. They are built over time—with vision, persistence, and a willingness to stay engaged even when the path is uncertain.
Philanthropy should be no different.
Like any meaningful decision, the power lies with the individual. Vision matters. Understanding the end game matters. The big picture is where lasting impact—and our most meaningful contributions—take shape.
So the question becomes: what kind of world do we want to help build? How intentional are we willing to be? And who do we choose to stand alongside in that effort?
Philanthropy cannot be reduced to one-off transactions or check-the-box moments. We are part of a broader community, and we are all invested in what comes next.
How will you engage with the big picture? And what will your contribution be?
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