Let's Talk Fundraising

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

• Keith Greer, CFRE

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This Groundhog Day episode is a personal announcement and a fundraiser’s roadmap for change.

After fifteen years in nonprofit leadership, I’m stepping away from a role I loved—not because something was wrong, but because something bigger was calling. What began as one reluctant conference session turned into a growing invitation to speak, teach, and help nonprofits navigate the future of fundraising, AI, and trust.

In this episode, I share the full story behind my pivot, the fear and grief that came with leaving stability, and the practical framework that helped me choose expansion over comfort.

If you’ve ever felt stuck repeating the same fundraising year—holding tightly to events, grants, or strategies that no longer fit—this conversation is for you.

HERE ARE 3 KEY TAKEAWAYS FROM THIS EPISODE:

1️⃣ Growth Requires Space – The hardest part of evolution isn’t starting something new. It’s letting go of something good so the next chapter can flourish.

2️⃣ Not Letting Go Has Hidden Costs – Every strategy has a price: staff hours, burnout, turnover, and the opportunity cost of what you could be building instead.

3️⃣ Letting Go Can Be Strategic, Not Reckless – I walk through a simple nonprofit capacity audit to help leaders release sustainably, protect relationships, and grow without exhausting their teams.

This year, you don’t have to repeat the same fundraising loop.

If this resonates, subscribe at letstalkfundraising.com/subscribe, share with a colleague, and tell me: what will you let go of first?

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Keith Greer:

This episode is coming out on Groundhog Day. That strange little holiday where we all pause for a moment to see if a groundhog sees its shadow and whether winter is going to stretch on just a little bit longer. But because I grew up in the 90s, Groundhog Day has always meant something deeper to me than just the weather. Because if you've ever seen the movie Groundhog Day, you know the real story isn't about seasons at all. 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. And I think that happens to a lot of us in fundraising. We run the same event because we've always run the same event. We write the same appeal, the same grant proposals, the same stewardship plans. Not because they're still the best path forward, but because they're familiar, because they're safe. Because letting go feels terrifying. And sometimes the hardest part of growth isn't starting something new. It's stopping something old. It's asking the uncomfortable question: what are we holding on to so tightly that it's keeping us stuck? And maybe even more importantly, what could be made possible if we made space? Space in our organizations, space in our calendars, space in our strategies, space in our lives. Because I've learned something over and over again. Advancement doesn't come from making a perfect one-for-one swap. It comes from having the courage to release what's comfortable before the next chapter is even fully visible. So today, on Groundhog Day, I want to talk about seasons of change, about the moments when you realize you've outgrown what used to fit, and about what it takes personally and professionally to step into what's next, even when it's scary. So let's talk fundraising. So I want to share something personal with you. When this episode comes out, I will have just stepped away from my most recent role. And I want to be really clear about something right from the beginning. This wasn't a decision I made because something was wrong. I wasn't unhappy. I wasn't pushed out. I wasn't running away from a bad environment or chasing some kind of dissatisfaction. In fact, it was one of the best positions I've ever had. It was the first time in my career that I got to truly be part of a large, well-resourced development team. And for the first time, I was able to focus on the part of fundraising that I love most, major gifts. I wasn't being pulled in a million directions. I wasn't trying to do annual giving and events and grants and marketing and donor stewardship and database management and everything else all at once. There were people on the team who were brilliant at the pieces that I didn't love. And for once I didn't have to carry everything alone. There was a budget. There was a structure. There was stability. And maybe most importantly, for the first time, I wasn't fundraising just to keep the lights on next month. I was fundraising so we could grow, so we could expand impact, so we could build something bigger than survival. It was really meaningful work. It was a great job. And that's what made this decision so difficult. Because the tension wasn't leaving something bad. The tension was leaving something good or something unknown. What started to feel misaligned was not the mission. It wasn't the people and it wasn't the work. It was capacity. Over the last couple of years, I started receiving more and more invitations to speak, to teach, to lead workshops, to share what I've learned about fundraising over the past 15 years, and what I was still learning about technology like AI and ethics and trust. And what I realized is that I was standing at a crossroads. I was being asked to grow into something new while still holding tightly to something I deeply cared about. And I knew in my gut that if I tried to hold both, they would both suffer. Because there are seasons in life where you can juggle a lot. And then there are seasons where you start to realize something has to give. Not because you're failing, but because you're expanding. And I'll be honest, one of the emotions that surprised me the most was grief. Not grief because I was leaving something harmful, 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. But I've learned that sometimes the next season of your life doesn't begin with a breakdown. Sometimes it begins with an invitation. A quiet sense that you're being called towards something bigger. And that's where I found myself. Not escaping, but expanding. And I think what's interesting is if you had told me even three years ago that I'd be doing this, speaking, teaching, hosting a podcast, I genuinely would not have believed you because I never set out to be visible. I was happy in the background. I was happy doing good work, being successful at it, and seeing the direct results of my impact inside the organizations that I serve. And if I'm being honest, part of that was because visibility felt risky. In the age of social media, it can feel like everyone is waiting for a reason to criticize. Everyone has an opinion. Everyone has a hot take that they want to unload on you. And I didn't want to invite that kind of attention or conflict into my life. I liked the size of my world. I liked that my work spoke for itself. I liked that my risk was contained to what I did in my role. And then a few years ago, someone I worked with, my dean, started encouraging me to share more. At first, it was just a small suggestion, a nudge here and there. You should submit a conference proposal. You should let people hear what you're learning. You have something valuable to offer. And I resisted it for a long time. I didn't see myself that way. I wasn't trying to be a keynote speaker. I wasn't trying to build a platform. I was just trying to do my job well. But he was patient. He didn't push in a way that felt forceful. He just kept believing in something I couldn't quite see yet. And eventually I said yes to one opportunity and just one. My first conference session. I still remember it so clearly. I think it was the last session on the last day of the conference, the kind of time slot where people are already halfway out the door. People were sitting in the audience with their bags packed, listening with one eye on the clock before heading to the airport. And I remember standing there thinking, okay, this is going to be a tough room. My heart was pounding. I was nervous in a way I hadn't felt in a long time. I felt exposed. But then something happened. People stayed. They didn't drift out early. They actually leaned in. And when it was time for questions, they asked brilliant ones, the kind of questions that didn't feel like judgment. They felt like curiosity. They felt like respect. They made me think deeper and harder and more expansively. And standing there looking out at a room full of fundraisers, I felt something shift. It was a spark. And for the first time, I realized that what I had to share might actually matter beyond the walls of my office. That my impact didn't have to stay contained. It could grow. It could reach further. And once that door opened, it was like the universe kept offering small invitations to step through it. And believe me, I didn't suddenly become fearless. I didn't suddenly feel completely ready, but I did start taking small steps forward. And what surprised me is that those small steps started creating ripples much faster than I expected. I mean, it still took two years, which at the beginning feels like an eternity. But looking back on it, it all went so fast. At first it was just a few invitations. Conference session here, a workshop there. I spoke at a couple of AFP conferences in Texas to very full rooms. And each time I walked away thinking, all right, that went well. People are resonating with this. And then something even more unexpected happened. Organizations outside of fundraising started reaching out. Groups in marketing, college administrators, people who weren't in my industry at all. And I remember being genuinely confused. I thought, why do you want to hear what a fundraiser has to say about AI? But what they told me was simple. Fundraising is a trust-based profession. We have to think about ethics constantly. We have to think about relationships. We have to think about the long-term consequences of how we communicate, how we build credibility, how we serve people. And as AI started showing up everywhere, they didn't want the hype. They didn't want the shortcuts. They wanted a grounded perspective. They wanted somebody talking about technology through the lens of trust. And that was when I realized this wasn't just a speaking opportunity. It felt like a responsibility. And I kept moving slowly, still cautious, still getting used to being more visible than I ever thought I'd be. Because every step of the way, my nervous system was doing the most. And then we got to this past winter holiday season. And that's when things shifted. Because over the course of just a few weeks, I had several organizations reach out back to back, asking me to keynote their upcoming events. Not one, not two, several. And what was striking about it is that I wasn't doing anything to market myself. I didn't have some big speaker campaign, I wasn't running ads. I didn't even have a polished keynote website. It was all word of mouth. Someone saw me speak at an AFP conference. Someone heard me at an American Advertising Federation regional event. Someone listened to this podcast and told an event organizer, you should bring Keith in. It was entirely referral-based. And I'll be honest, my emotions were all over the place. Part of me was so excited, deeply excited, because it felt like this confirmation that this work mattered, that it was a landing, that it was helping. But another part of me was scared because every request came with a decision attached: a decision about my time, a decision about capacity, a decision about what I could actually hold. And I also felt something else, guilt, because I cared so much about the organization I was serving. I cared about the mission. I cared about the donors. I cared about the work we were doing. And I started to realize that I was being pulled in two directions. On one hand, I had this career that I'd built over 15 years, something stable, something I was good at, something I knew how to do. And on the other hand, I had this growing call to step into a different kind of impact, to teach, to speak, to share, to help fundraisers and nonprofit leaders navigate the changes happening in our sector. And the moment it really crystallized for me was when I looked at the number of requests coming in and I realized there is no version of this where I can do all of it. There is no version of this where I can keep saying yes to these opportunities while also staying fully present in my role without something breaking. And I tried for a while to rationalize staying put to tell myself maybe this is just a busy season. Maybe it will slow down. Maybe I can squeeze it in, but the signals kept coming. And eventually I had to face the truth. When people keep pulling value from you, when the world keeps inviting you into a larger room, it might be worth paying attention. Because sometimes the demand showing up isn't random. Sometimes it's direction. And that's where the crossroads showed up. Because it's one thing to feel a spark. It's one thing to get a few invitations, but it's another thing entirely to realize that what's opening in front of you might require let go of something stable behind you. And I want to be really honest about this part because I think sometimes we tell stories about change in a way that makes it sound cleaner than it is. Like you just wake up one morning, feel inspired, and leap into purpose without hesitation. That was not my experience. This was terrifying because what I was looking at was a very real trade-off. On one side was everything predictable, a steady salary, health insurance, benefits, structure, a clear role inside a respected institution, the kind of stability that most people work very hard to build. And on the other side was possibility, a bigger platform, a wider reach, a different kind of impact. But it also had uncertainty, no guaranteed paychecks, no clear roadmap, no safety net in the same way. Just the question of, can I make this work? And I think what made it so emotionally complicated is that I wasn't leaving something I hated. I wasn't escaping dysfunction. I was leaving something really good. And that's a different kind of fear. Because when you leave something bad, the decision feels obvious. But when you leave something good, you start questioning yourself. Am I being irresponsible? Am I being naive? Am I throwing away something people would be grateful to have? And the financial fear was real. Giving up a salary is not abstract. It's not poetic. It's rent. It's groceries. It's healthcare. It's the very practical reality of adulthood. And then there was the identity fear because for 15 years I had a title, I had an organization, I had a role that made sense immediately when people asked, What do you do? There's a certain prestige that comes with working for a major university, with being part of an established institution. And stepping away from that felt like stepping into a blink space. Like walking out onto a bridge that hadn't fully appeared yet. And I couldn't do that decision alone. The person I kept coming back to again and again was my boyfriend Christopher. We had so many conversations about this, practical ones, spreadsheets, timelines. What would it actually take for this to be sustainable? What would our first year look like? What would we do if it didn't work? But also emotional ones. The kind of conversations that aren't about numbers, but about meaning, about regret, about the kind of life that we want to build together. And what I'm so grateful for is that he didn't romanticize it either. He didn't just say follow your dreams in a way that ignored the risk. He treated it with the seriousness it deserved. And at the same time, he asked the kind of questions that changes everything. 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? What if this is your next season and you ignore it out of fear? And slowly through hours of talking, we came to the decision together that we could make a plan, that we could set a timeline, that we could build a runway, that this wasn't about recklessness, it was about intentional growth, about choosing something uncertain because it was aligned. And that's what courage actually is. It's not the absence of fear. It's looking at the fear honestly and still deciding to move forward with your eyes open. And then came the day. The day where the decision stopped being theoretical and became real. The morning I was going to give my notice. I woke up with a mission, and my stomach was in knots from the moment I became conscious. You know that feeling where your body wakes up already bracing? That was me. My heart was racing before my feet even hit the floor because no matter how much planning you do, the moment you walk into the conversation that makes it real is something else entirely. And that morning I needed courage badly. And then something happened. Before I even had the first conversation, I got a phone call. Another organization wanting me to keynote, another invitation, another unexpected confirmation. It was like the universe reached out at the exact moment I needed it and said, keep going. And thank goodness it did, because I had more than one conversation ahead of me. I invited my dean to coffee, the person who had been encouraging me for years, the person who first planted the seed that I had something to share beyond my role. And sitting across from him, I told him. I told him I was stepping into something new. And I'll never forget that moment because he did what great leaders do. He listened, he cared. And then he tried to keep me. He offered possibilities. He explored options. He reminded me of what I meant to the organization. And for a moment I felt myself wobble. Because when someone believes in you, when someone wants you to stay, it makes leaving even harder. Not because you doubt the next chapter, but because you realize how meaningful the current one has been. But that call that morning, that signal, it gave me something to hold on to, a reminder that this wasn't impulsive, that this wasn't coming out of nowhere, that something real was waiting on the other side of this decision. And after that, I went and had the second conversation I needed to have. And I kept it simple. I shared the news and I moved through it. And when it was finally done, I remember walking back to my office feeling like I could breathe again, like I had just done the hardest part. And then almost immediately another message came through, another organization reaching out, another request, another speaking opportunity, right on the heels of that scary moment. And I just stood there almost in disbelief. It felt like confirmation, stacked on top of confirmation, like the path was rising up to meet me. And I remember looking up quietly in my own way and saying, thank you. Thank you for the support. And also, I'm gonna need more of it because this is scary. This is new. This is unfamiliar. I'm giving up stability, a salary, benefits, a title, and stepping into something I've never done before. But that day, that day felt aligned. It felt held. It felt like courage met confirmation. And I think the reason this moment has felt so significant to me is because it connects to a pattern I've noticed in my life over and over again. A through line, something I keep learning whether I want to or not. And it's this I have rarely been able to move into something better while holding tightly to what came before. I keep wanting life to work like a perfect trade, a one-for-one swap. I want to line everything up neatly, have the next job fully secured before leaving the current one, have the next chapter completely mapped out before closing the last one, have the replacement in hand before I let go. And maybe you can relate to that because it feels responsible, it feels safe, it feels like risk management, but what I've learned is that growth almost never works that way. Because what we're reaching for isn't usually a substitution, it's an expansion. And expansion requires space. I can look back and see how many times I tried to do this in my own life, times where I held on longer than I should have because I wanted certainty first, because I wanted guarantees, because I wanted to avoid discomfort. And every time the lesson has been the same. You can't receive what's next if your hands are already full. There's an illusion of safety in holding on. We tell ourselves, I'll let go once I know exactly what's coming. But the truth is sometimes the very act of holding on is what keeps the next thing from arriving. Not because it isn't possible, but because there's no room for it. And I've seen this not just personally but professionally, all throughout 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 doing the same grant strategy, 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's revenue producing. And the thought of letting go feels like stepping off a ledge. So instead, we say, we'll stop doing this once something else fully replaces it. We tell ourselves, once annual giving grows enough, then we can reduce our events. Once major gifts are bringing in more, then we can shift away from 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, because we haven't created capacity for it. And I think that's the hardest part of change, especially in the sector. Fundraising is built on relationships, it's built on trust, and that trust takes time. So when we keep clinging to the old model while trying to build the new one, we don't actually do either of them well. We dilute our focus, we stretch our people too thin. We stay busy, but we don't always move forward. And I think that's the invitation here. For me, this wasn't about abandoning something good. It was about making space for what's next. And I think for nonprofits, the question is the same. What are you holding on to because it feels safe, even if it's costing you? What are you afraid to release because you want certainty first, even though certainty might never come that way? Because advancement isn't a perfect swap. Growth requires room. And sometimes the most courageous thing you can do is open your hands. So what does this look like inside a nonprofit? Because I know the moment we start talking about letting go, the fear shows up immediately. Boards worry about revenue gaps, executive directors worry about donor expectations, development teams worry about workloads, and fundraisers especially worry about being asked to do more and more while being told that somehow it's all gonna work out. And I want to say clearly, those Fears aren't irrational. This sector operates on shoestring budgets. The stakes are real. You can't just casually walk away from revenue. So letting go isn't about being reckless. It's about being intentional. It's about strategy. And I think one of the most helpful questions a nonprofit can ask is not just how much money does this bring in, but also, what does it cost? Because every fundraising strategy has a cost. Not just financially, but emotionally, operationally, relationally. So here's a simple audit I want you to consider. If your organization is holding onto something tightly, an event, a grant strategy, a program model, ask three questions. First, what does this cost us financially? Not just gross revenue, but net, staff, labor hours, vendor expenses, and opportunity cost. If your gala nets your organization$100,000 but costs 2,000 cumulative staff hours, what else could those hours do for your organization? Second, what does this cost us emotionally? What does it cost our team in stress, in burnout, in constantly operating at the edge of capacity? Because fundraisers are not infinite resources. And the data is clear. Continuity matters. The longer a fundraiser stays in their role, the more successful they tend to be. Because relationships deepen over time. Burnout is not just a staffing issue, it's a revenue issue. And third, what does this prevent? What is this keeping us from building? What new strategy can't take root because all of our energy is going toward maintaining what we've always done? That last question is the one nonprofits often skip. And I've lived this firsthand. I worked with an organization once that hired me because they wanted to grow their philanthropic revenue. They wanted to become less reliant on grants and events. They wanted to build annual giving, major gifts, planned giving, the whole thing. And I was excited, because that's exactly the work I love. But only two months after I started, they let their grant writer go, and then their communications staff. And instead of pivoting thoughtfully, what happened was that everything just piled onto one plate. Grants, two huge events, a CRM overhaul, annual giving, major gifts, planned giving. All at once, it wasn't just a candle burning at both ends. It was a candle being hit with a flamethrower and melting fast. And then the pandemic came. Events disappeared overnight. Grant funding dried up as funders shifted priorities toward emergency response. The revenue sources the organization had been holding on to, they were suddenly gone. We were forced to let go, not because we were ready, but because we had to. And you know what happened? We raised more money than we had the year before. Because the crisis created space. We focused differently. We leaned into relationships. We adapted. And I think about that often because I see nonprofits doing this all the time. Leadership says they want to pivot, they want to grow major gifts, they want to strengthen stewardship, they want to modernize, but they don't want to release the old model. They don't want to let go of the grant revenue until major gifts replace it. They don't want to let go of the gala until annual giving fully supplements it. And when annual giving grows, they usually keep the gala anyway, because now it's extra. But what they don't always do is hire extra staff to support the added workload. So instead the fundraisers carry both. And what happens? They burn out, they leave, and the organization loses that continuity. And in a profession built on trust, that setback is enormous. This is also where technology, including AI, can play a role, but only if we use it ethically. AI isn't here to replace trust, it's here to help create space, to reduce the manual burdens that keep fundraisers stuck in those repetitive tasks, to help teams spend more time on what actually drives philanthropy. The relationships, listening, stewardship, care. Letting go is not failure. Letting go is strategy. It's making room for the future instead of endlessly repeating the past. So as we come to the end of this episode, I want to leave you with a couple of questions. One personal and one organizational. So first, personally, what is something in your life or career that you might have outgrown, but you're still holding on to because it feels familiar? Not because it's bad, not because it's broken, but because it's comfortable, because it's known. And letting go feels uncertain. And the second question is organizationally. What is your nonprofit holding on to so tightly that it's preventing the next season of growth? Is it an event? Is it a funding model? A strategy that once worked beautifully, but now takes more than it gives? What would it look like to make space, not recklessly, not impulsively, but intentionally? Because here's what I hope you take away from my story today. You don't have to repeat the same year over and over again. Groundhog Day is a funny tradition when it's about the weather, but it's a much heavier thing when it becomes a metaphor for our lives, for our organizations, for our work. Waking up to the same patterns, the same exhaustion, the same, this is how we've always done it. This year doesn't have to be that. This year can be a new chapter. And if you're listening to this and thinking about what change could look like for you or your organization, I'd love to connect. I'm available for keynote presentations, workshops, and this year I'll also be launching an ongoing webinar series to help fundraisers navigate technology, methods, major gifts, and the future of our work in a really grounded way. If you want to stay up to date with everything that's coming, you can subscribe on my website at letstalkfundraising.com forward slash subscribe. And whether you're stepping into something new or just beginning to ask the question, I hope you give yourself permission to reflect honestly on where you want to go and what you might need to release to get there. Because growth requires space, and you're allowed to choose it, even when it's uncomfortable. Thank you, my friend. I'll see you again real soon.

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Keith Greer, CFRE

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