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  • Ben Chambers

My “first dollar,” and what it taught me about resilience in fundraising

Updated: Sep 1

I started my first Development Director role the same way many of us did - after a chaotic series of jobs guided by a passion for helping my community. I earned my stripes working in various program roles all around the nonprofit and public advocacy space and then spent years doing frontline fundraising work with a big, experienced team at a large nonprofit. It was time to take the plunge into leadership.



I was ready. And I was terrified.


It’s one thing to do this work when you have people to fall back on and experience in the room to defer to. It’s another when a big question pops up and everyone looks to you for an answer. I had those answers (most of the time), but I can’t deny that there were times that it took a toll on my mental health.


The voice in the back of your head second-guessing you is a real force to contend with, especially when you’re dealing with an aspect of fundraising that isn’t your biggest strength (or as we like to say, what you’re “very best at”). We believe in training fundraisers to find their biggest strength while having a working knowledge of all aspects of the work, which is exactly what you have to do when running a small fundraising shop.


My strengths are grant writing, strategy development, and donor communications. I LOVE telling the story of a nonprofit, researching to demonstrate the value of the mission, and getting in front of people to talk about it. I’m both a writer and a consummate people person, so I’m a natural at all of these things.


My weak points? Events, which I’ve also talked about at length, and soliciting major gifts from individuals. Events make sense - frankly, I get overwhelmed with everything that goes into them. I love connecting with people at events, but the little details of planning aren’t something I have a natural affinity for. Major gifts have always been trickier though. I love people, so why wouldn’t I love asking individuals for major gifts?


I really struggled with this question for a while and had to come to terms with an uncomfortable truth: major gift fundraising intimidates me. I’m a lot younger and a LOT less wealthy than the people I work with, and that second-guessing always kicks into overdrive. Am I saying the right thing? Am I the right person to have this conversation with this donor? Am I going to say the wrong thing and put an important gift in jeopardy? It was especially odd considering the fact that I never had trouble asking for corporate or foundation gifts.


Underneath my discomfort with these solicitations was the fact that I was clearly experiencing imposter syndrome. Those feelings of inadequacy and self-doubt are hallmarks of imposter syndrome, and it’s not uncommon for fundraisers to experience it. I felt like there were others who were more experienced and more qualified, and that there wasn’t a place for me in that type of work.


I was still feeling this a year into the job when I was approached by a donor I found particularly intimidating at our annual gala. He was one of the nicest people to interact with, but his standing in the community - and what he meant to the organization - was considerable. When he approached me, he shook my hand and gave me a $2 dollar bill with his signature.


I was a little confused at first, but he told me as he goes through his philanthropic work, this is something he does for young people (okay, this was before my hair really turned gray) who impress him. He had seen a TV interview I did and wanted to make this gesture to show me that my work stood out to him.


It’s honestly one of the most gratifying moments of my fundraising career.


I didn’t close a gift or do something that would make waves in the organization. What I got was validation. Hearing someone I respected so much say they were impressed by something I did was a tremendous confidence boost, and came at a time of great self-doubt.


I framed that $2 bill - which I call my “first dollar” - and keep it in my office as a reminder of that little victory. I share the story because all fundraisers, regardless of how long they’ve been in the profession, need to stop and appreciate those victories. It’s not always closing the gift or hitting the goal; sometimes it’s the reminder that every day we do the job makes a difference, and we’re connecting with people in ways we don’t always appreciate.


If you’re like I was before I got my “first dollar,” here are some tips to help build and maintain your confidence:


Find a mentor: We all need someone in our corner when we face a crisis of confidence. Find that person who can talk you through the ups and downs while also helping you find solutions to your biggest problems. Whether they light a fire under you to do something different or reassure you that you’re on the right path, having that person is vital.

Find your community: One of the best parts of the fundraising profession is that it’s a tight-knit community, and there are plenty of groups around where you can connect with others. Most cities have an AFP chapter, as well as other organizations that will let you connect and share your experiences with others who will understand them.

Take time off: If the work is getting overwhelming and you’re losing confidence in yourself, step away for a while. Without self-care, burnout is inevitable. Recharge, connect with what’s most important in life, and come back to work reinvigorated.


If you’re feeling like there’s an aspect of the work you’re struggling with, you’re not alone. Look for the little victories and do everything you can to remind yourself of the impact you’re having.


Need some encouragement to keep growing your career and fundraising expertise? Our team of Fundraising Consultants are here to help you! Drop us a line for a free consultation


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