When (and How) to Take Big Risks

Designing Tomorrow: Creative Strategies for Social Impact

The social impact sector isn’t known for being very risky. In fact, it’s often quite the opposite. Too many orgs play it safe, afraid of over-scrutinization (the double standard is real here) and hoping to protect their mission and resources.

But here’s the thing — sometimes the most dangerous thing is playing it too safe.

In this episode, Jonathan and Eric dive into the topic of risk: when to take it, how to de-risk it, and what to expect if it doesn’t pay off.

We cover actionable tips for when (and how) to take risks, like:

→ Be bold, but calculated: Every impactful org will face a time when they need to try something big — even if it’s daunting. Develop a framework to know which risks align with your mission and will benefit your team.

→ Build resilience for the outcomes: Not every risk will pay off, but treating failure as a teacher rather than an enemy is essential for growth.

→ Communicate your “why”: Take your team and stakeholders on the journey with you. Being clear about the purpose of the risk and the goal it serves builds trust and sets everyone up for success.

Whether it’s experimenting with a new program, trying fresh approaches in fundraising, or tackling a major pivot, we believe risk-taking can — and should — have a place in social impact.

Listen to the full episode for deeper insights and personal stories from Jonathan and Eric.

Episode Highlights:

• [02:15]: The cautious nature of the social impact sector, vs. the high-risk, high-reward environment of startups
• [03:05]: Developing a framework for taking calculated risks in organizational settings
• [03:32]: How to navigate risk daily - seeking opportunities for high leverage while mitigating potential losses
• [05:18]: Eric recounts his early career and a pivotal risk he took to secure workspace, which transformed his business
• [08:09]: Importance of having a support system in place when undertaking major risks, ensuring buy-in from those affected
• [10:45]: Jonathan emphasizes the value of running ideas by trusted colleagues and advisors to de-risk risky decisions
• [13:08]: Dangers of hesitating mid-risk and the parallels between sports and business risk-taking
• [16:09]: Clear communication with teams when embarking on risky initiatives

Resources:

• In Defense of Moonshots: True Social Innovation Requires Taking Risks
• Dare to Be Bold: Making a Case for Better Social Impact Branding
• Jeff Bezos is A/B Testing Philanthropy. Here's What He'll Find.
• To Solve the World's Problems, Start by Building Consensus
• The World is in Crisis—Now is the Time for Your Nonprofit to Act

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1. When and How to Take Risks (00:00:00)

2. Navigating Risk Through Intuition and Commitment (00:09:36)

3. Calculating Risks for Success (00:13:59)