As fundraisers, we all carry “rearview mirror” moments—the experiences we revisit in our minds, sometimes wishing we could replay them with more wisdom or courage. Reflection matters. It’s how we learn and grow. But if we stare too long at what’s behind us, we risk being paralyzed by regret. Our sector needs us to keep our eyes on the road ahead.
One of my earliest rearview mirror moments happened at a donor’s kitchen table. I was meeting with a long-time supporter, grateful for the chance to spend time in his home. Sitting right in front of me was a handwritten list of personal tasks. At the very top: “Update estate plans in my Will.”
I froze.
I wasn’t sure if this was an opening for me or simply a personal note, and I erred on the side of caution by saying nothing. Part of me knew this could have been the start of a meaningful conversation about legacy giving and the lasting impact the donor could have. But I was young and inexperienced, and I missed the chance to begin.
For a long time, I replayed that scene. What if I had said the right words at the right time? What opportunity might have grown from that conversation? But hindsight is not about regret—it’s about learning. That moment taught me that courage in fundraising is not only about asking for gifts, but about leaning into vulnerable conversations with authenticity and respect. Today, I approach similar opportunities knowing that thoughtful guidance and openness can help donors create a lasting impact.
Years later, I carried another rearview mirror moment, this time as a more seasoned fundraiser. At our fundraising gala, we designed a concept called “Lighting the Path to Hope”—an idea full of symbolism, with the potential to engage 750 attendees in a shared, meaningful experience. As donors arrived, they walked through twinkle lights representing those who had paved the way for our work. During the gala, as attendees made a donation they could illuminate LED light wands, creating a powerful visual display of how, together, we can bring light in times of darkness for mental health.
The concept was beautiful, and the intention was profound. Yet, on the night of the gala, the execution did not fully translate. The emotional impact we had envisioned—the collective awe, the moment of shared illumination—did not land as powerfully as we’d hoped. I felt the sting of disappointment.
But here is what the experience taught me: bold ideas come with risk. Even when something does not land perfectly, attempting it creates space to innovate, inspire, and learn. The gala reminded me that the work we do as fundraisers is not always about perfection—it’s about courage, creativity, and persistence. It also reinforced that donors value authenticity, passion and meaningful engagement, even when plans unfold differently than imagined.
From hesitant first conversations to orchestrating a gala, the lessons we carry evolve, but the principle remains the same: move forward with courage, humility, and an open heart. Both of these experiences—one at the very beginning of my career and one later—remind me that fundraising is about more than dollars raised. It is about persistence, connection, and hope. It’s about showing up even when the plan falters—carrying the lessons of the rearview mirror while keeping our gaze firmly on the road ahead.
Here is how we can forge ahead as fundraisers:
Fundraising is about people—imperfect, complex, wonderful people. And that includes us. We will all make mistakes. We will all carry rearview mirror moments that remind us of what we might have done differently. The true test is how we respond: with humility, resilience, and an unwavering commitment to keep moving forward.
Because, at the end of the day, our courage ensures that the communities we serve—the children, families, and individuals relying on mental health support—feel seen, supported, and hopeful. Our mission deserves our courage more than our perfection.
Marla Smith, CFRE, is the Director of Foundation & Communications at Pathstone Foundation, where she leads fundraising and communications efforts to advance mental health services in Niagara. With over 15 years of nonprofit leadership experience, she is passionate about fostering trust, transparency, and meaningful donor relationships through ethical and strategic fundraising practices. An active sector volunteer, Marla serves on the Board of the AFP Foundation for Canada and is a CFRE Ambassador. She also chairs National Philanthropy Day and Education for AFP Golden Horseshoe, championing professional development and philanthropy across the sector. msmith@pathstone.ca
