Conquering the Fear of Asking

In my mid-twenties, I developed a motto for my life that was “face your fear.” Over the years, after much self-reflection and many conversations with my wife, I changed this motto to “identify your fears and break through them.” This motto seems more appropriate, for facing your fear is great, but moving past your fear is even better.

Last year, I decided to tackle a fear of mine, the fear of asking for charitable donations. After three decades of supporting charities, I felt it was time to break through this fear. For me, this irrational fear was based on the following:

1) Being rejected.
2) Annoying the potential donor.
3) Sounding like a stereotypical used car salesman with high pressure tactics. I do apologize to great used car sales people.
4) Asking someone who could not afford a donation and embarrassing them.
5) Friends avoiding me because I am always asking for donations.
6) Setting up a quid pro quo expectation to give to their meaningful charity.

In full disclosure, I have read books and attended seminars on sales for both for profit and non-profit companies. I have worked with and even mentored great salespeople in both sectors. With all of this experience, my fear still prevented me from actually doing the work to become a successful fundraiser. Even stranger, I have a few friends who are excellent at asking for donations for their favorite charities. I have a ton of respect for them and would be proud to be like them. Yet, my fear still ruled me.

The Tariq Khamisa Foundation (TKF) is one of my favorite non-profit organizations. I have proudly worked with TKF for over ten years. Their vision is to create “a world free of youth violence.” The founder’s 20-year-old son was murdered by a 14-year-old boy. The founder realized that “there were victims at both ends of the gun” and created TKF as a solution to end youth violence. This organization does important and impactful work, so I was motivated to conquer my fear and help TKF and the kids we serve at the same time.

TKF created an email campaign that was based on a request for one dollar. The idea was to inspire one million people to each donate one dollar to TKF. However, a few months after the campaign started, TKF had less than one hundred donations, though one donation was for $25,000. That donation said a lot about what could happen when you ask someone for a dollar.

On the day I started my campaign, I had 1,117 contacts in my email list. I crafted a generic email with the help of a TKF board member who was the best at marketing. She and I drafted an email containing both a logical and emotional reason to give. I decided to personalize each email with a few sentences that made it clear to the recipient that I was speaking directly to them. The thought of personalization made my fear grow because the fear of reject would be more real for me. However, I believe that the path that produces the most fear is often the best path to take, so I continued with my effort.

I started with the A’s in my contact list and disaster struck immediately. My first contact was a fellow partner in San Diego Social Venture Partners (SDSVP) and there is an unwritten rule that partners are not supposed to ask each other for donations to their specific causes. I labored over this dilemma for literally days. I began rationalizing that fundraising was not for me and this was a sign from God that I was not supposed to do this work. As I looked through my contact list, there were hundreds of contacts that I had some rationale as to why I would not ask them for money. Clearly, this task was too difficult for me.

However, the quiet and persistent voice in the back of my head told me to press on. So, I looked at my contact list with a different perspective. I looked for contacts who I would feel comfortable asking for a donation. Much to my surprise, the majority of the people on the list were perfect for my ask. I was only asking for a dollar and that would probably not anger them. I skipped the second name on my list as I was courting her for SDSVP and did not want to court her for two charities. I went for the brass ring on the third name. I wrote her a nice couple of personal connection sentences, pasted in the generic ask and sent the email off. I was exhausted by the process, so I quit for the day.

Miracle of all miracles, this absolutely wonderful lady responded five days later with a $25 donation! I was beyond excited. I sent off a grateful thank you note and a few more requests for the one dollar donation. More money came in and, lo and behold, not a single person sent me a nasty email as my unrealistic fear had predicted. In fact, I received some incredibly nice responses about TKF and my efforts. I was actually getting energized by my work. Honestly, I was still mentally exhausted from my fear, but I was really excited every time I checked my email for donation notifications.

Over the course of a year, I asked 671 out of my 1,117 original contacts for a dollar. I decided to not ask 446 contacts for a few reasons. As I said before, anyone associated with SDSVP was a no ask. Some contacts I did not know well enough to personalize an email, and others I felt would be inappropriate due to my close relationship with them. On my best days, I made ten asks. At times, I went weeks in between asks and even took a break from November to January in order to not compete with year-end asks from other charities.

There were many highlights from my involvement in this campaign effort. I reconnected with old friends and they were as grateful as I was. One man gave me money even though I had only seen him twice a few years back. A few donations came in from friends who were unemployed. They were grateful to contribute even though money was tight. One person donated five months after receiving my email. He was a salesperson in a slump, but he donated when things brightened up for him. One donation came from a former coach of mine who I had not had contact with for eight years.

All in all, a third of the emails I sent resulted in a donation. Twenty-two donations came from friends of my contacts and the average gift size was $71.52. I raised just over $16,000 for TKF. Twelve donations were for a dollar and five donations were for $500. One of the $500 donations came from someone I did not even know. All of the donations were exciting to receive and they inspired me to send out more requests.

Interestingly after getting through 80% of my contact list, my views of asking changed from feeling bad to feeling obliged. I started to realize that the recipient is an adult and has the right to choose. Without my ask, I would have denied people the opportunity to decide for themselves due to my fearful assumptions. I was always kind and sincere in my ask, so why should I feel bad? When I get asked and the ask is sincere and not too frequent, I appreciate it. I am capable of saying yes or no to an ask, so I now assume the people I ask are also capable.

Overall, I am grateful for all of the donations that were generated for TKF and opportunity to break through my fear. The fear is not gone, but it no longer rules me. TKF’s email campaign was a great first step and there are more steps for me to take, specifically with asking for donations face-to-face and over the phone. TKF needs my help and there are other great charities out there that need your help. Are you ready to take a step to break through your fears?


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