How to Handle Discomfort in Fundraising: A Three-Step Practice for Fundraisers at Every Stage
"You can choose courage, or you can choose comfort. You cannot have both." — Brené Brown, researcher and author, Daring Greatly
We try hard to avoid it, but feeling uncomfortable is closely linked to fundraising growth. The more advanced the fundraising you pursue, the more likely uncomfortable feelings are to surface. Yet learning to work through those feelings may be one of the most valuable things a fundraiser can do — for themselves and for the organization they serve.
I want to write honestly about this because the fundraising literature tends to either ignore it or offer a quick fix. The literature says we should either push through it, or get used to it. It also says, remember you are asking on behalf of a cause larger than yourself. All of that is true, and yet none of it is quite enough — as a story from my own practice makes clear.
When Fundraising Discomfort Comes From Inside the Room
A few years ago, I was preparing for a $1 million donor ask meeting — part of a $5 million capital campaign — and the day before, the board chairperson who was also my asking partner called in a panic, emphatic that we were making a serious mistake requesting that amount and insisting we should ask for half. His doubt landed differently than doubt from a skeptic would have, because he was the person I was walking into that room with, and what arrived through his call was not the donor's resistance but my partner's anxiety — the kind of discomfort that fundraising guides rarely discuss, because it comes from inside the tent rather than across the table. If I had not found a way to stay grounded rather than cave to his fear, I am not sure what we would have asked for, but we held to the original figure and the gift came through.
Why Asking for Money Feels Uncomfortable — and What the Research Says
Fundraising involves asking for something — specifically, asking for money. For most people in most cultures, that is a double taboo. The ask itself can feel transgressive, and the money makes it more so. Taboos tend to be unconscious and are often the more forceful for being unexamined. The core message, absorbed somewhere in childhood in many families, is that it is impolite to ask others for money. There is a saying in Chinese culture that captures this plainly: "The mention of money severs human relations."
That message does not disappear when someone becomes a fundraiser. It tends to go quiet during training and then resurface at the least convenient moments — the night before a major gift meeting, during the silence after an ask, when a donor says they need more time.
Brené Brown's research at the University of Houston, conducted over more than two decades and described in her books Daring Greatly and Rising Strong, offers a framework that feels genuinely applicable here. Brown found that vulnerability — the willingness to show up in situations where the outcome cannot be controlled — is not a weakness but rather the condition under which courage becomes possible. A fundraiser sitting across from a donor and making a direct, specific, personal ask for a significant gift is doing something that requires real courage, because the outcome is genuinely uncertain and the relationship genuinely matters.
"Vulnerability is not winning or losing," Brown writes. "It's having the courage to show up when you can't control the outcome." That sentence describes the major gift ask with more precision than most fundraising training does.
Susan David, Ph.D., a psychologist at Harvard Medical School and author of Emotional Agility, adds a complementary dimension. David's research suggests that the ability to sit with uncomfortable emotions — rather than suppressing them or being hijacked by them — tends to predict professional resilience and effectiveness more reliably than many other factors. She describes this capacity as emotional agility: the ability to approach feelings with curiosity and openness rather than judgment or avoidance. It is a learnable skill, not a fixed temperament.
The Difference Between Productive Discomfort and Genuine Distress in Fundraising
Before going further, it is worth distinguishing between productive discomfort and genuine distress.
When something feels deeply wrong — not just uncertain or high-stakes, but actually wrong — that is a different signal and deserves a different response. If a donor or funder is pressing the organization toward something unethical, if personal boundaries are being crossed, if a situation feels unsafe in any meaningful sense, the right response is to step back, not to push through. Discomfort and danger are not the same, and conflating them does not serve anyone.
What this essay addresses is the discomfort that accompanies growth: the tightness before a significant ask, the uncertainty after a pause, the anxiety of doing something important where the outcome is not guaranteed. That kind of discomfort tends to be productive when it is engaged rather than avoided — not because suffering is good, but because the engagement itself builds something — and the people best positioned to support that engagement are the supervisors, coaches, and mentors a fundraiser works alongside.
How Supervisors and Coaches Can Help Fundraisers Handle Discomfort
Fundraisers who work with managers, coaches, or mentors who are willing to engage honestly with discomfort rather than dismiss it tend to develop more quickly. The most useful thing a supervisor can do when a fundraiser is anxious before a major ask is not to tell them the anxiety will go away or that they just need more confidence. It is to listen, to take the feeling seriously, and to draw the person out — asking what specifically feels uncertain, what they know and do not know, what they would need to feel more grounded.
That kind of conversation does not eliminate the discomfort. It does something more useful: it helps the fundraiser understand what the discomfort is actually about, which is frequently different from what it appears to be at first. The board chair in my story was not really uncertain about whether the donor had the capacity to give at the requested level. He was anxious about the relationship — afraid that the ask itself would damage a connection he valued. Once we talked about that specifically, the conversation shifted from the size of the ask to how to conduct it in a way that protected the relationship regardless of the outcome. That reframe made the meeting feel manageable in a way it had not an hour before.
How to Hear No in a Fundraising Conversation Without Losing the Relationship
One dimension of fundraising discomfort that does not get enough honest attention is what happens after a no — or more precisely, what a fundraiser tends to make a no mean.
Elisabeth Kübler-Ross, the Swiss-American psychiatrist whose work on grief and human response to difficult moments remains among the most widely read in the field, observed something that translates directly to the fundraising context: "No is a complete sentence." It requires no apology, no negotiation, and no immediate response. In a solicitation conversation, a no deserves the same quiet respect — a pause, an acknowledgment, and then genuine curiosity about what lies behind it — rather than an instinctive rush to soften it or argue past it.
A no in a major gift conversation is almost never the end of a relationship but is usually a statement about timing, or capacity, or the particular gift vehicle being proposed, or a competing priority in the donor's life at that moment — and it is rarely a statement about the organization's worth or the fundraiser's competence, though it is understandable that it can feel that way.
Developing the ability to hear a no without interpreting it as a relationship failure is one of the more significant skills a fundraiser can build — and it is built the same way the broader capacity for discomfort is built: through practice, through reflection, and through the willingness to go back to the same donor and continue the conversation. Some of the most significant gifts I have been involved in came after an initial no, sometimes more than one. The practice that supports this capacity is worth describing specifically.
Three Steps for Managing Fundraising Discomfort: Observe, Smile, Inquire
Here is the three-step practice I have used with my own discomfort in fundraising situations for many years. It is not a technique for eliminating the feeling. It is a practice for staying in relationship with it rather than letting it run the room.
Observe the feeling carefully — where it is in the body, what it feels like, how intense it is — without trying to deny it or push it away. This often takes me a few days to do honestly after a difficult moment. There is a temptation to move quickly past the feeling and on to the next thing, but the observation step is where the learning tends to live.
Smile at the feeling. This may sound odd, but there is something in the gesture — a deep breath, a deliberate softening of the face — that shifts the relationship to the feeling from adversarial to curious. It is a form of self-care that does not require pretending the feeling is not there. It is simply a way of being gentle with yourself in a moment that is genuinely hard.
Inquire. Ask questions of the discomfort — what it is about, what it might be pointing toward, what it wants you to notice. Questions that start with What, How, When, and Where tend to be more useful than Why. Why questions tend to produce defensiveness and self-criticism, while What questions tend to produce information. "What specifically made this moment feel high-stakes?" is more productive than "Why am I always so anxious before these meetings?"
When I follow this practice with some consistency, I tend to have more range in subsequent fundraising situations. Not because the discomfort disappears — it does not — but because I have a relationship with it that is based on curiosity rather than avoidance. That seems to make a difference.
How Internal Emotional Work Produces Better Fundraising Results
The natural question after any internal practice is: then what? If observing, smiling, and inquiring help me understand my discomfort, how does that understanding translate into what actually happens in the room with a donor?
The connection is more direct than it might appear. When discomfort is suppressed rather than examined, it tends to leak into behavior in ways that are difficult to control — the slightly rushed pace of a solicitation visit, the over-explanation that follows an ask, the instinct to soften a number in the final moment, the difficulty sitting with silence after the ask is made. These behavioral signals are readable to a sophisticated donor, and they tend to reduce the donor's confidence rather than strengthen it.
When discomfort has been examined and is understood — when I know, before I walk into the room, that what I am feeling is specifically anxiety about damaging the relationship rather than doubt about the gift level, for example — I can address that specific thing rather than let it run as background noise throughout the meeting. In the board chair story, once we talked through what was actually driving his anxiety, the pre-meeting conversation shifted from the amount of the ask to how to conduct it in a way that honored the relationship regardless of the outcome. That reframe changed the meeting completely — not by eliminating the uncertainty but by giving us both something useful to do with it.
The three steps, practiced over time, tend to produce a specific capacity: the ability to be present in a high-stakes conversation without being controlled by what you are feeling about it. That presence is what donors experience as confidence, though it is something different underneath — it is closer to settled awareness than to certainty. A fundraiser who is settled is genuinely listening, genuinely curious about the donor's response, genuinely open to what the conversation produces. That quality is rarer than technique, and donors tend to respond to it.
There is no shortcut to building it. It develops through the kind of honest internal work the three steps describe, repeated across many situations over time, and supported by relationships — with supervisors, mentors, and peers — in which the emotional dimensions of fundraising can be discussed openly rather than pushed through alone. That last point matters especially for those who are newest to this work.
A Note for Fundraisers Early in Their Careers
If you are new to fundraising and reading this, I want to say something directly: the discomfort you feel before a significant ask is not a sign that you are not suited for this work. It is a sign that you understand what is at stake and that the relationship and the mission matter to you. Those are assets, not liabilities.
The sector loses too many good fundraisers too early — the average tenure in a single position is now around 16 to 18 months — and anxiety before difficult conversations is one of the factors that contributes to that. Not because anxiety is disqualifying, but because it can be isolating when it is not named and not talked about. If your organization's culture treats fundraising discomfort as something to overcome alone rather than something to discuss openly, that is worth noticing — and worth raising with a supervisor, a mentor, or a peer.
The fundraisers who stay long enough to build careers of genuine impact tend to be the ones who found a way to develop a working relationship with their own discomfort rather than a running battle with it. That relationship takes time to build. It tends to be worth the effort.
How do you handle discomfort in fundraising — and has a difficult moment ever turned into something unexpected? Share your experience in the comments section of the website.
A Note on Use
This post is offered freely for educational purposes. Please share it with fundraising colleagues, development directors, and mentors who may find it useful — provided the author's byline remains intact: By Laurence A. Pagnoni, MPA. Reproduction in publications, training programs, or institutional materials requires attribution.
