The first thing that caught my eye in my latest Harvard Business Review magazine were the beautiful plate drawings of octopi. Surprising, right? What could possibly be the connection between an octopus and business—and for me, between an octopus and philanthropy?
I haven’t read Remarkably Bright Creatures yet, but when my kids were little, we loved the cartoon Oswald—an adventurous octopus who encouraged curiosity. I’ve been fascinated by this adaptable, intelligent creature for years.
“Become an Octopus Organization: How Your Company Can Adapt to a Complex World,” uses the octopus as a metaphor for organizations that thrive in complex environments –constantly sensing change and adjusting in real time. That idea of awareness—of ourselves and the impact of our actions—landed with me in a very personal way.
While the pictures drew me in, the content made me pause and reflect on my leadership as an entrepreneur, disruptor, fundraiser, grantmaker, and board member. This led me to thinking about the roles I play at every intersection of my life. Reading this on a snowy MLK weekend made me ask: How do I show up with my kids? With my friends and colleagues? With extended family? With grantees and community partners?
Am I an “Octopus” or a “Tin Man?”
The authors describe Tin Man organizations as “rigid, optimized for mass production, adherence to process, and top‑down planning.” That model worked in a simpler world but fails to fit today’s complex, interconnected nonprofit landscape. A Tin Man, like the character, struggles in complex environments, has trouble adapting, and avoids risks by limiting exposure and holding onto tight boundaries. As a leader and consultant, I often relied on strict processes and solo decision making to get my work done—but I now see how easily that approach slips into “Tin Man” mode.
My “customers”—the nonprofit and community partners I have supported through grantmaking and board leadership—depended on my curiosity, relationships, and openness to learning.
Avoiding risk often meant avoiding the very issues communities were facing. It was actually less risky to engage, support, and participate, because that allowed me to see the real impact of our funding.
Looking Back
Looking back, I see my “Tin Man” habits stemmed partly from the family foundation’s antiquated governance structure. At the beginning of my tenure, that was the guide that defined my success.
That structure suited a more top-down era focused on control and predictability, not today’s complex world where small actions and changes ripple unpredictably through communities. Even as I adapted the model, there were boundaries it was unacceptable to push.
I am not alone in this; many new family foundation executive directors struggle to move beyond outdated models and adapt.
Looking Ahead: Innovation, Adaptability, and Curiosity
In philanthropy, having the ability – and permission – to ask bold questions, innovate, and redefine risk is essential for genuine progress. The authors describe such habits as “antipatterns”—routines that hinder ownership, blur clarity, and stifle curiosity. I didn’t have that language at the time, but I certainly felt the effects.
Eventually, I realized that the processes built decades ago no longer serve the complex world in which we live. This is where the amazing octopus enters.
“Octopus Organizations”, as the article describes, tap the intelligence of the world around them, distribute decision-making, and learn and shift course at speed to navigate uncertainty. As a grantmaker, that translates directly into how we listen to communities, share power, and let the people closest to the work own the solutions.
Who are philanthropy’s customers?
This raises a vital question in family philanthropy: are our true customers our fellow family members–or the communities and nonprofits we serve? The article challenges leaders to obsess over whether their choices create more value for their “customers,” and, in philanthropy, that lens would push us outside of the boardroom and into the community.
Family involvement in foundations is important but ignoring better ways to serve communities means choosing Tin Man comfort over Octopus courage. The article urges organizations to “rewrite their DNA”—changing not only processes but the underlying rules and mental models, shifting from command-and-control to agency and trust.
We can keep focusing inward and granting transactionally, or choose to tackle root causes and system inequities for deeper impact. Foundations – and even individual funders- can absolutely do this work, but only if we are willing to look beyond our own reflection.
Remaking the Mindset: Evolving, Progressing and Learning because the System Needs Us
As an entrepreneur and a leader I choose to keep evolving and learning, until homelessness, poverty, illiteracy, youth mental health….etc. are truly addressed. And I hope to inspire other funders to do the same. As octopus leaders we can be “system architects” whose primary job is to work on the system, not in it, removing friction, clarifying purpose, and creating conditions where others can excel.
That vision defines my role in philanthropy designing adaptable blueprints that funders can use to guide their questions, funding decisions and, importantly, impact while evolving with community wisdom.
Holding Ourselves Accountable
Funders rarely have pressure to change, and in a complex world we seek is difficult to measure or see clearly. Years of nonprofit fundraising and grantmaking work have taught me this: flexible and consistent funding and advocacy create real impact. Once you see that impact, there’s no return to the alternative.
Like an octopus sensing its surroundings, the answers to the complex challenges in our communities are in reach should we choose to ask different questions, step out with courage, and do our part to act and problem solve differently. In short, take ownership of the impact of our philanthropy and consider our place within its community architecture.
Ultimately, we each must choose which direction we head, but I cannot promise that inaction, avoidance, or risk aversion to the problems will be solved that way. The more we can sense, and stretch like an octopus into the communities we claim to serve, the more likely we will change many of the paradigms that hold our communities back, ourselves included. I’ll hang with the octopus any day.
Allison Erdle is a Philanthropy Consultant and former Executive Director at a family foundation. She partners with foundations, individuals, and their advisors who want to be more intentional, strategic, and informed about the impact of their philanthropy, helping them rethink how their funding supports nonprofits and strengthens communities.
