The PhilanthropyChallengeA strategy simulation game
People Systems Planet

Can your
philanthropy save
your world?

Every day, philanthropy works to close the gap between the world we have and the world we imagine. Where to direct limited resources. What to prioritize. What to let go. The tensions are real — and the trade-offs are never simple.

The Philanthropy Challenge is a crisis-driven strategy game that puts you in the seat of a philanthropic leader. Choose a focused four-crisis run or the full six-crisis simulation. Three dimensions of world health. Hard choices with real consequences.

1

Play Solo

Experience the simulation on your own. Make every choice yourself.

15+

Host a Workshop

Run the Challenge with your team or conference. Facilitated & competitive.

Have a join code? Tap to join a workshop in progress.→
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Part of the Impermanence series · Gary Community VenturesPlay time · ~25 min
four pillars · four moves
A game of strategic choices.
season 01 · MMXXVI
From Gary Community Ventures
Volume I · Essay
The PowerofImpermanence
“What becomes possible when you have a deadline?”

The Philanthropy Challenge was born from this question. The same urgency that drives the game — limited resources, compounding crises, a world that won't wait — is the lived experience of philanthropic organizations choosing to embrace impermanence.

Gary Community Ventures is spending down its endowment by 2035 — not because the work is finished, but because the future is too uncertain to defer it. Watch the film. Read the report. See what we are choosing to leave behind.

How It Works

Three moves · Six years

The game mirrors the real choices philanthropic organizations face every day — where to direct resources, what to prioritize, and what to let go.

Step 01

Build Your Foundation

Name your world, create your foundation, and set your strategy. How much will you spend each year? Will you invest for returns or for impact?

Step 02

Face Crises

Every round brings a new crisis. Allocate resources across Direct Service, Systems Change, Civic Infrastructure, and Environment. Every choice has a trade-off.

Step 03

See the Consequences

After 6 rounds, your decisions play out over 10 more years. Did you build something lasting, or just put out fires? The answer reveals itself.

The Real Question

Three tensions.
One world.

Philanthropy exists in a world of tensions. Speed versus sustainability. Direct service versus systems change. Financial returns versus mission alignment. These trade-offs are hard to see in spreadsheets and strategy documents. The Challenge makes them felt.

P
People

Do you help people now?

Direct service helps people today, but the need keeps coming back.

S
Systems

Do you fix the system?

Systems change is slow and uncertain, but can shift the conditions that create crises.

P
Planet

Do you protect the future?

Environmental investment takes years — but without it, there is no world left to save.