Eddie Thompson

Estate planning can feel overwhelming for many donors, often leading to delayed decisions or even giving up entirely. With so many options—charitable trusts, wills, beneficiary forms—and the added complexity of tax laws like IRS §170, it’s no wonder people experience “choice overload.” This article dives into the very real struggles donors face when navigating these decisions, sharing relatable examples of how too much complexity can stall the process. It also offers practical advice on how simplifying choices and having thoughtful, sincere conversations can help donors move past indecision and confidently align their giving with their values.

Luckily, the most important lessons I’ve learned in my 40+ years of fundraising and charitable estate planning came near the beginning. Many of those experiences were painful, and it’s still somewhat embarrassing to shine a spotlight on my greatest mistakes. Nonetheless, things I learned from my stumblings have become essential elements of my fundraising career. Here are my top ten greatest mistakes (so far).