Four Reasons to Dive into Philanthropic Failure


We are sharing what we and our partners have been learning through reflection in our Looking Back, Moving Forward blog series. This series is part of our Reflection, Analysis, and Planning (RAP) Process, which the Foundation is engaging in as our Moving the Needle (MTN) 2.0 strategic plan draws to a close and we prepare for what comes next.

For eight years–every year–my boss asked me to do something. Every year, I failed. It took her four years to convince me that failure was okay. It took another four years for me to figure out why.

Where I work is like much of philanthropy. We’ve got huge hopes, big dreams, and a vision for success. We regularly fall short of our hopes, are challenged by the viability of our dreams, and stymied by our vision. Yet, we continue to refine, expand, and extend our ideas every year.

One example is ForwARd Arkansas. ForwARd is our statewide initiative to totally change the way every child is educated in our state. The vision is that every child–no matter their income, ethnicity, or geography–will graduate from high school prepared for college and the workplace.


Today, ForwARd represents a bipartisan, ethnically, and strategically diverse group of organizations, communities, and philanthropic partners devoted to the same vision. It took us eight years of failing before we succeeded at crafting that partnership.

That work is just getting started, but here’s why I’m ready to DIVE into my next failure.

Failure is:

Desirable – To succeed at something the first time you try it probably means you haven’t set the bar high enough. We could have easily written our own strategic plan for education in the state of Arkansas eight years ago and avoided failing year after year. However, a strategic plan written just by WRF would have ONLY been WRF’s plan. We needed broad-based ownership if that plan was to have any chance of making the desirable impact we envisioned. We desired failure, for all the right reasons.

Inevitable – If you try something more than once and are pushing yourself to get will inevitably fail. It’s also inevitable that people who you think you know well will become suspicious of your motivations. It’s also inevitable that you will begin to doubt yourself. We accepted the inevitabilities of failure as part of the price for success.

Valuable – The return on investment for failure is not intangible. The last eight years of waiting for the right moment, struggling to build a coalition, and waiting for our primary philanthropic partner to emerge have been filled with valuable lessons learned. In terms of money, we were able to hold our major investments until we had failed enough to be surer of our potential for success. Failure is valuable in both tangible and intangible ways.

Exciting – Much of our philanthropic journey tends to be a series of investments in the safe stuff. We don’t want to rock the boat too much, and we try to stay away from the edges. If you are serious about realizing your vision despite your failures, you will be subject to commentary, criticism, and questions that bring a new level of excitement to how you operate in the field of philanthropy. Failure brings the excitement back to the work.

I’ve decided that next time I’m faced with a challenge, instead of sticking a toe in the pool or wading in from the shallow end, I’m going to DIVE in and reap the benefits of failing.

What will you DIVE into this year?


Created by
Rev. Cory Anderson
Chief Innovation Officer