Editors’ note: This article, first published in print during Sep/Oct 2012, has been republished for Nonprofit Quarterly with minor updates.

When I look back over the 35 years I have been in fundraising, I have to admit that I have made almost every mistake a person can make. Any mistakes I haven’t made are only because I was saved by someone else helping me. I have also seen others make many mistakes, and over the years I have come to believe we often learn more from our mistakes than from our successes. In training people to be consultants, coaches or trainers, I always encourage them to share their mistakes and shortcomings with groups, along with their triumphs. In addition to all we can learn from sharing our mistakes with each other, it is also a good reminder that you don’t have to be flawless to be good at your job.

Making the same mistake a second or third time is what really gets to me though. I believe that I should at least be pioneering new mistakes, creating new mistake stories to tell. But again, if I look over my career, I see I have sometimes made the same mistake over and over, and those are the most embarrassing ones.

In this article, I want to look at three mistakes I have made way too many times, in hopes of steering some of you away from them. But first, I want to look at when a mistake actually happens. My failure to recognize the actual moment when I was making a mistake has been the main reason I have made the same mistakes again and again.

Take a simple example: Driving to a meeting in a rush, I turn right when I should have turned left Now I am lost. My mistake, however, is not the wrong turn. The cause of the wrong turn is that I forgot the directions because I was in too much of a hurry when I left my office. But that isn’t the mistake either. I was trying to finish a number of projects before I left, making me late to leave the office, and then causing me to race out the door without thinking about what I needed to get to my meeting. So the mistake was made much earlier: the day was planned badly. Everything after that was just the result of the real mistake. Ironically, I am now losing way more time being lost than if I had only taken the time to focus on what was required to prepare for the meeting.

If we are to truly learn from our mistakes, we must know where they begin and change them at that point, or else we will only address their symptoms. The most transformative social justice organizing is focused on addressing root causes. We know that figuring out the root cause is not always easy, but it is necessary. Real and lasting change requires identifying the “choice point”— the moment you made a decision which led to a series of bad decisions. When I know I need to plan better, I will choose to take the time to plan. If I think it is just a matter of leaving the office earlier, I may cease to be late for appointments, but still will not really have solved the problem.

IF WE ARE TO TRULY LEARN FROM OUR MISTAKES, WE MUST KNOW WHERE THEY BEGIN AND CHANGE THEM AT THAT POINT, OR ELSE WE WILL ONLY ADDRESS THEIR SYMPTOMS.

First Mistake: Not Listening to My Instincts

The mistake I have made the most often in fundraising is not listening to my instincts and acting accordingly. This mistake has come up in many ways, but I will share just two examples here.

Last year, I was consulting with a fairly large organization that wanted to raise $50,000 in six weeks for a specific project. I have written widely about these kinds of campaigns, which I love, so I looked forward to running one for this organization. They had three people in their development department, good donor records, and a seemingly enthusiastic board, making it a situation that seemed easier than most. We made the plan, created excellent materials, and launched. All things said and done, the campaign raised maybe $1,000. It was the worst campaign I had ever managed.

My mistake: I didn’t listen to my instincts. The first clue I overlooked was the way the development director talked about the board members. “Entitled dimwits” was a favorite catchall phrase he used in addition to the derogatory nicknames he had for most individuals on the board. The second clue was that during the three months I worked with them, they went through three development assistants. I met each of them but could never learn why they quit. Another clue: I was tasked with training the board at a board retreat. I was supposed to have two hours, but the meeting ran late, so my training was shortened to one hour, and then finally to 15 minutes. The chair said, “Just give us the cliff notes.” (Later several board members complained that they were not well-briefed by me.) The development director said afterwards, “I knew they wouldn’t do anything—we just pretend something is going to happen.”

A second example is a direct mail program I supervised at a large organization determined to send 20,000 pieces as a test to see if direct mail would work with their constituents. They were a sophisticated and well-respected group. They were in charge of pulling together the list, while I focused on creating an effective package. I overlooked several big problems: they had a donor database that no one knew how to use; they did not have a mail house; and they had never done a mailing through bulk mail before. They did not have a bulk mail permit and were not

registered in any state. They reassured me that this would be a good way to learn all that they needed to know. It certainly was an expensive way: the list they created was terrible, the printer made some mistakes with the package, the mailing was very late, and the overall response rate was about .025% (one-fourth of one percent!). I kicked myself several times about this one: I should have insisted that we not send this size of mailing. I should have insisted they not send anything until all the permits were in place. I should have really examined how they were building their list. Shoulda, woulda, coulda.

In both of these cases, I listened to “reason.” Both organizations were large and well-funded. They were confident in their own abilities, and I was caught up in their confidence. Several times I thought to myself, “I should put my foot down and stop this right now.” In the first case, I did try to talk to the Development Director about how he talked about the board. I told him that his constant belittling of them made me wonder if he really could work with them effectively. But the choice point was when I decided not to confront him with the fact that you can’t really have a great working relationship with people you think are stupid and ignorant. I should have known that things are not going to work well when a leader in an organization regularly makes fun of others behind their backs. When I saw this was part of the organizational culture, I should have left right away.

In the second instance, the choice point was when I overlooked the bleak reality of having a database no one knew how to use. My failure to listen to my instincts cost a lot of money, time, and opportunity, and the group is now quite demoralized about their ability to raise money from individuals. My real mistake here was not just not listening to my instincts, but also not talking with a colleague about what was happening, which would have likely reinforced my instincts. It is hard to listen to yourself when you only talk to yourself.

Second Mistake: Taking On Too Much

My second big mistake is one shared by millions of Americans: I take on too much. This problem is not evidence that I am a poor time manager. In fact, I am an excellent time manager. I estimate quite accurately how long things will take, but my mistake is that I don’t build in any time for all the things that happen in a day that I have no control over. A day with four tasks that will take one to two hours each seems reasonable. I will be able to keep up with e-mail as it comes in, and I’ll have time for lunch, maybe even a short walk. I will get home at a reasonable hour and have time for more exercise or calling a friend. So, three tasks later, why is it already 5 pm? And I have already triaged my walk?

The simple Fact Is that a 40-hour Work Week can only include 20 Planned hours.

The root of my mistake is not realizing that any eight-hour work day is likely to have about four hours of unplanned activities come up. Some of these will be major and recognizable: The financial report I need for the foundation report I have to write includes a serious miscalculation and has to be redone. A friend calls telling me that her mother died, and I take the time to talk to her. But a lot of time is spent in much smaller ways: The computer freezes and has to be rebooted. A colleague emails me asking for the address for a meeting, which reminds me that we haven’t ordered food for that meeting. I take care of that, only to find out that someone else has already taken care of it, so I have to cancel the order I just made. I feel irritated by this person until I look at the minutes and see that she took it on, so then I feel irritated with myself. This causes me to eat a donut which makes me tired and less productive.

The simple fact is that a 40-hour work week can only include 20 planned hours. This seriously inhibits the amount of work that can get done in a week, or, if you are like me, means that you often work evenings and weekends. This is the true mistake. I love and enjoy my work, but my work is not my life, and I cease to enjoy it when I can never get away from it.

Third Mistake: Rushing the Process

By far and away, my biggest mistake and the one I have made most frequently is when I have tried to get staff board or volunteers to make important decisions too quickly. Part of the context here is the fact that feminism—the theory, the movement, the questions, the people asking the questions—is what has most shaped my political and personal life. When it comes to decision-making, feminists believe that decisions should be made by the person or people most affected by an issue (i.e., whether or not to have an abortion should be made by the pregnant woman, not the church or the state). If a group of people need to make a decision together, they should take whatever time it takes to talk the issue through and come to consensus.

Because feminism is such a basic principle to me, you might assume that I am in favor of this type of process. I am, in theory. But in practice, I am very impatient, and I especially cannot stand spending a lot of time discussing an idea that is obviously (to me) a good one. I have developed several strategies for moving decisions along. These include, but are not limited to:

  • Making fun of and gradually silencing people who are raising questions
  • Figuring out ahead of time who is most likely to be opposed and scheduling the meeting when that person cannot come
  • Raising my voice slightly and allowing a note of irritation to slip in, giving the impression that we have been over this material several times and people just need to pay better attention
  • Challenging the questioners to come up with a better idea To be sure, I am not in favor of this behavior, and I do not like it in others. The only reason I know I do this is because good friends have taken me aside and pointed it out. This kind of behavior is wrong for two reasons: one, it can border on bullying; and two, if you don’t get clear agreement on the front end for an important decision, the decision will not work anyway.

Here is an example: I was the executive director of a nonprofit that covered a very specific geographic area. A donor approached me and said he would pay the costs for our organization to expand into two more counties. He would cover the full costs for one year and half the costs for the second two years, as well as help raise the money to keep the project going. He was well-respected and reliable. Our organization had hoped to expand eventually, and these two counties were in the mix of places we were considering for expansion. I brought it to the board and staff, who, to my great surprise, were lukewarm to the proposition. They felt we had more work than we could do already, and even if we brought on more staff, they would need to be supervised. Some board members thought we should find out if there were other agencies in these two counties who would want to take this on or perhaps partner with us. There were several other objections and doubts put forward that I don’t remember because I stopped listening. I could not believe that we might turn down this offer. Where were people’s values? Why wouldn’t they take a risk? Couldn’t they see that, in addition to being mission fulfilling, this would bring in a lot of new donors?

Using a variety of the tactics described above, I wore everyone down until the board and staff agreed to the expansion. The expansion did not go well. The person in charge of hiring staff did so without checking references, and the staff members that were hired had to be fired. The costs were much higher than we had expected, so we had to dip into our reserves. While the donor put in a lot of effort to raise more money, he could not find very many people that shared his enthusiasm and were willing to donate. We had to scale back services to these counties, which made our work there ineffective overall. The staff and board, bless their hearts, never blamed anyone. If they were asked about the mistake, they would cite a number of causes, from bad hires to lack of accurate information about costs.

But those were just symptoms of the mistake. The choice point of the mistake was my disregard of process. When we disregard process, we often set up an either/or scenario. Then we have to argue in favor or against the proposal in question. But most decisions are not that clear cut. When we allow the time for deliberation, a whole new idea may emerge that is even better. If I was to do it all over again, I would bring the idea to the board and staff as just that: an idea. I would even invite the donor into the discussions. We could all then discuss prioritizing these counties over others, timing (we could have waited another year to expand), calculating costs, and so on. The board and staff were not opposed to the idea—they simply wanted to discuss it. We needed to form a small committee, which may have included the donor, to look at all the variables and decide when and how to expand. With all that in place, we could only then really consider the donor’s offer in a meaningful way.

I BELIEVE IN PROCESS AND KNOW FROM YEARS OF EXPERIENCE THAT A GROUP OF PEOPLE DISCUSSING SOMETHING WILL ALMOST ALWAYS COME UP WITH A BETTER IDEA THAN I CAN ON MY OWN.

Conclusion: Avoiding and Learning from Mistakes

How do you avoid these mistakes? How do I avoid them (on the days that I do)? First, I make it a habit to discuss my work with colleagues and friends. I have to be clear about confidentiality, as discussion should not be confused with gossip, but listening to my instinct is much easier when my instinct is given a voice. Second, I am more and more disciplined about my time. Having built my life around my work for many years, I now pursue a life that includes not only work, but also exercise, gardening, friends, arts and culture, pets, eating, reading, and sometimes just looking around and doing nothing. And of course, when I have more time, I am much less impatient. I believe in process and know from years of experience that a group of people discussing something will almost always come up with a better idea than I can on my own. With these mistakes and all the others that I make, I try to look for the moment when I made a decision that began the mistake. Real and lasting corrections of mistakes require accurate identification of that choice point.

When we learn from our mistakes, they become a form of information—we can transform them into opportunities for growth. In the unpredictability of grassroots fundraising, we must welcome our fist mistakes on the job so we can reveal the lessons within. When I make a mistake and actually learn from it, I often learn much more than if I had done it right the first time. I am not afraid of mistakes. I am only afraid of not recognizing them, which, in the end, is far more harmful than the mistakes themselves.

Kim Klein is the founder and publisher emerita of the Grassroots Fundraising Journal. Her classic book, Fundraising for Social Change, has recently been updated in a sixth edition, available from josseybass.com. Kim can be reached at kleinandroth.com.