The Pivot: What I’m Stepping Away From—and What I’m Stepping Into

If you grew up watching movies in the 90s, Groundhog Day probably means more to you than a weather forecast. Because the real story of that film isn't about a groundhog. It's about repetition. It's about waking up and realizing you're living the same day again. The same routines, the same expectations, the same patterns you didn't consciously choose but somehow ended up inside.

I think about that movie a lot when I look at nonprofit fundraising. Not to be uncharitable about it, because the work is genuinely hard and the people doing it are genuinely committed. But there is a version of Groundhog Day that plays out in development offices all over the country. We run the same event because we've always run the same event. We write the same appeal, the same grant proposal, the same stewardship plan. Not because they're still the best path forward, but because they're familiar. Because letting go feels terrifying. Because the next chapter isn't fully visible yet, and stepping into uncertainty feels irresponsible when the mortgage on the mission is already overdue.

I want to talk about that today, because I recently went through my own version of this. I made a significant career transition, stepping away from the best position I'd ever held to pursue something larger and less certain. And what I kept learning through that process, painfully and repeatedly, is the same thing I've watched nonprofits struggle with for years.

Advancement doesn't come from a perfect one-for-one swap. It comes from having the courage to release what's comfortable before the next chapter is fully visible.

The Lesson I Keep Learning

The position I left was, by almost every measure, the best job of my career. For the first time, I was part of a large, well-resourced development team. I wasn't being pulled in fifteen directions at once. There were people on the team who were brilliant at the pieces I didn't love. There was a budget, a structure, stability. And maybe most importantly, I wasn't fundraising just to keep the lights on next month. I was fundraising to grow, to expand impact, to build something bigger than survival.

It was meaningful work. And that's what made the decision so difficult.

What started to shift wasn't my satisfaction with the role. It was capacity. Over a couple of years, speaking invitations started arriving. Then workshop requests. Then organizations outside of fundraising, marketing teams, college administrators, groups with no connection to the sector, asking me to speak about technology, ethics, and trust. And what I realized, slowly and then all at once, was that I was being asked to grow into something new while holding tightly to something I deeply cared about. And I knew, in the way you know things you don't want to face, that if I tried to hold both, they would both suffer.

The moment it crystallized was when I looked at the number of requests coming in and understood: there is no version of this where I say yes to what's opening in front of me while staying fully present in my role. Something would have to give. And the question was whether I'd make that choice deliberately or whether I'd wait until the choice was made for me.

What surprised me most about the process was grief. Not grief because I was leaving something broken, but grief because I was leaving something meaningful. A chapter that was good. A chapter that helped shape me. A chapter I hadn't expected to outgrow. There's a different kind of fear that comes with leaving something good. When you leave something bad, the decision feels obvious. When you leave something good, you start questioning yourself. Am I being irresponsible? Am I throwing away something people would be grateful to have?

And through all of that, the person who mattered most helped me ask a different question. Not what if it fails,but what if you don't try? What if you stay in what's comfortable and always wonder what could have been?That question changed everything. Because courage isn't the absence of fear. It's looking at the fear honestly and still deciding to move forward with your eyes open.

I share this not because my story is the point, but because I've watched this same dynamic play out in nearly every nonprofit I've ever worked with or worked for. The particulars differ. But the pattern is the same.

How This Shows Up in Nonprofit Fundraising

Nonprofits do this constantly. We hold on to what's familiar even when it's draining us. We keep the gala. We keep the golf tournament. We keep repeating the same annual appeal formula. Not because it's the best approach, but because it's known. Because it's predictable. Because it produces some revenue, and the thought of losing it feels like stepping off a ledge.

So we tell ourselves we'll let go once something else fully replaces it. Once annual giving grows enough, then we can reduce the events. Once major gifts are bringing in more, then we can shift away from the grants. Once we have the next thing built, then we'll let go of the old thing.

But what often happens is we never let go. We just stack it. We add more and more and more. And then we wonder why our teams are exhausted. Why our fundraisers burn out. Why innovation feels impossible. The answer is usually the same: we haven't created capacity for it. We're too busy maintaining what we've always done to build what we actually need.

What we're reaching for in a growing fundraising program isn't a substitution. It's an expansion. And expansion requires space. You can't receive what's next if your hands are already full.

The cost isn't just financial. It's human. Fundraisers are not infinite resources. The data on this is clear: continuity matters enormously in major gift work. The longer a gift officer stays in a role, the deeper the relationships, the more successful the outcomes. Burnout isn't just a staffing issue. It's a revenue issue. And when we pile every old strategy on top of every new initiative and hire no one to absorb the added load, we don't actually do either of them well. We dilute our focus, we stretch our people thin, we stay busy without moving forward.

Three Questions Worth Asking Before You Hold On Any Longer

I want to be clear that letting go isn't about being reckless. The boards and executive directors who push back on this aren't wrong to worry. This sector operates on shoestring budgets. The stakes are real. You can't casually walk away from revenue. So this isn't a call for impulsiveness. It's a call for honesty.

If your organization is holding on tightly to something, an event, a grant strategy, a program model, start by asking three questions. Not just once, but with real rigor.

The first question is financial, but it's more specific than it sounds. What does this actually cost us? Not gross revenue, but net. When you account for staff labor hours, vendor expenses, volunteer coordination, follow-up stewardship, and the opportunity cost of what those hours could have produced otherwise, what is the real return? A gala that nets $100,000 but consumes 2,000 cumulative staff hours looks very different when you ask what else those hours could have done for your organization.

The second question is emotional. What does this cost our team? Stress, burnout, operating perpetually at the edge of capacity: these aren't soft concerns. They're organizational risks. And the fundraisers who leave because they're burned out take their donor relationships with them, or at minimum interrupt them, at precisely the moment when continuity is most valuable.

The third question is the one most nonprofits skip. What does this prevent? What new strategy can't take root because all of your energy is going toward maintaining what you've always done? What relationship can't be deepened? What donor can't receive your best attention? That last question is often where the real answer lives.

What Happens When You're Forced to Let Go

I worked with an organization once that hired me to build their philanthropic revenue. They wanted to become less reliant on grants and events. They wanted to grow annual giving, major gifts, planned giving. I was excited, because that's the work I love. But two months after I started, the grant writer left, then the communications staff, and rather than pivoting thoughtfully, everything collapsed onto one plate. Grants. Two major events. A CRM overhaul. Annual giving. Major gifts. Planned giving. All at once.

Then the pandemic arrived. Events disappeared overnight. Grant funding dried up as foundations shifted priorities toward emergency response. Every revenue source the organization had been clinging to was suddenly gone. They were forced to let go, not because they were ready, but because they had no choice.

And they raised more money than the year before.

Because the crisis created space. The team focused differently. They leaned into relationships. They adapted to what the moment actually required. And the work that had been crowded out by maintenance suddenly had room to happen.

I think about that often, because I see nonprofits doing this all the time. Leadership says they want to pivot, want to grow major gifts, want to modernize. But they don't want to release the old model. They want the new thing to fully replace the old thing before they let go. And as a result, the fundraisers carry both. The team burns out. The continuity breaks. And the organization loses the very thing, the relationships, that were supposed to justify the strategy in the first place.

Where AI Fits in the Space You Create

This is also where technology, including AI, can play a role, but only if we use it with intention rather than just piling it on top of everything else.

AI isn't here to replace the relationships that drive philanthropy. It's here to reduce the manual burdens that keep fundraisers stuck in repetitive administrative work, so they can spend more time on what actually matters: listening, stewardship, and the kind of sustained attention that turns a prospect into a major donor. Used well, it's one more way to create space. To help your team get out of the repetitive cycle and into the relational work that moves the mission forward.

Letting go is not failure. In fundraising, letting go is strategy. It's making room for the future instead of endlessly repeating the past.

The Questions I'll Leave You With

I want to close with two questions, one personal and one organizational, because I think they're worth sitting with honestly.

First, personally: is there something in your career that you might have outgrown, but you're still holding on to because it's familiar? Not because it's bad. Not because it's broken. Just because it's known, and letting go feels uncertain?

And organizationally: what is your nonprofit holding on to so tightly that it's preventing the next season of growth? An event that costs more than it returns? A funding model your team has long outgrown? A strategy that once worked beautifully but now takes more than it gives? What would it look like to make space, not recklessly or impulsively, but intentionally?

You don't have to repeat the same year again. Waking up to the same patterns, the same exhaustion, the same this is how we've always done it, is a choice, even when it doesn't feel like one. Growth requires space. And you're allowed to choose it, even when it's uncomfortable.

If this conversation opened something for you, I'd love to stay connected as the work continues to develop. You can subscribe to my weekly newsletter at letstalkfundraising.com/subscribe, where I share practical tools, reflections, and ideas you can put to work in your organization. New subscribers get access to all the free resources I've developed, and will be the first to hear about upcoming learning opportunities. I hope to see you there.