Hi Reader,
We reach the end of the most tumultuous year in nonprofit history. We may earnestly hope that 2026 provides greater stability, but let's not presume that. Instead, let's make sure we focus on what we can do to innovate on behalf of those who count on us every day.
In this issue, you will find 5 items to improve your nonprofit right now (plus a sweet "What's Most Good" story about cookies):
- Do time-blocking the right way.
- Ask ChatGPT to ask you for more information.
- Use AI as a systems theorist to help you see the leverage points.
- Test your board about fundraising myths. And finally,
- A very brief video from Daniel Pink that explores how to fix your attention span, so that you can get the best work done.
First, my year in review.
Below is an essay I'm planning to publish early in 2026. I wanted to share it here first to get feedback from you, my most loyal and engaged readers:
For years, nonprofit leaders have been urged to plan better, govern more carefully, and manage risk more intentionally. Much of that advice is well meaning. Some of it is even correct. But this past year clarified something that often goes unstated: Most nonprofit failures are not the result of negligence, incompetence, or a single bad decision. They are the result of systems built for stability operating in an environment that no longer provides it.
I spent the year working with nonprofit executives, boards, foundations, and intermediaries on questions of risk, governance, and resilience. Across very different organizations, the patterns were strikingly consistent. Leaders were not asking, “What framework should we adopt next?” They were asking, “How do we carry this responsibility without burning out our people or breaking the organization?”
That question matters, because it reframes what effective risk management actually is.
At its best, risk management is not about checklists, insurance policies, or compliance artifacts. It is about clarity: clarity of roles between boards and executives, clarity about what can and cannot be controlled, and clarity about which risks are acceptable in service of mission. When that clarity is missing, even well-governed organizations accumulate blind spots that only become visible when conditions change.
Those conditions have changed.
Nonprofits are operating amid sustained workforce strain, board recruitment challenges, political volatility, and market shifts that directly affect their ability to function. None of these pressures is entirely new, but their persistence is. What used to be episodic disruption has become a standing feature of the landscape.
In that environment, resilience is less about perfect governance and more about shared responsibility. Boards cannot absorb every risk, executives cannot carry every burden, and funders cannot assume that individual organizations will always be able to adapt on their own. The work increasingly lies in the relationships between these actors, not just within them.
Foundations, in particular, are encountering this reality in new ways. When multiple nonprofits face the same external constraints, organizational failure is no longer an isolated event; it becomes a community problem. In some cases, that has led funders to explore capacity building, intermediary support, or system-level interventions that would have been outside their scope a decade ago. This is not uniform across philanthropy, but it is an emerging conversation. It needs to happen more—much more. Foundations need to recognize that they play a fundamental role in nonprofit sector risk management.
My most valuable work this year was not delivering more content or more tools, but helping leaders make sense of complexity, name tradeoffs honestly, and decide where focus would actually reduce risk rather than add to it. That kind of work is quieter and harder to scale, but it is often where the greatest leverage lies.
If there is one lesson I would carry forward, it is this: resilience is not something an organization installs. It is something an organization practices, collectively, under conditions of uncertainty. That practice depends as much on judgment, relationships, and restraint as it does on planning or policy.
The work ahead is not about making nonprofits invulnerable. It is about helping them remain governable, humane, mission-focused, and above all innovative in a world that is unlikely to become simpler anytime soon. It is about being relentlessly positive while also being relentlessly realistic. Or as I've written elsewhere, risk management is about striving to become radically aware in each moment, then taking the next reasonable response.
Please give me your feedback. I promise you it matters and will be incorporated into the version I publish. I value your thoughts.
Bakery Partnership Delivers 100,000 Cookies – and Joy – to Homebound Seniors
A creative partnership in Riverside, CA has delivered its 100,000th cookie to homebound seniors, proving that small gestures can have big impact. Since winter 2023, Riverside Meals on Wheels (RMOW) and the Riverside Cookie Shoppe have teamed up for “Sweet Fridays,” adding free cookies to weekly meal deliveries as a treat to combat senior isolation. Volunteers report that clients “absolutely light up” and sometimes even shed “tears of joy” on cookie-delivery days. The bakery donates day-old inventory (plus fresh batches when needed) that would otherwise go unsold, turning surplus sweets into meaningful connections at no extra cost.
The results go beyond smiles: RMOW now has no waiting list and its best client retention in years, and the nonprofit is “certain the cookies help immensely” with those outcomes. The Cookie Shoppe’s owner finds the program personally fulfilling and a win-win for the community, continuing a tradition of giving and exemplifying how nonprofits can innovate without major new funding to improve quality of life.
This is an easily replicable model. Let's get it going wherever there are nonprofits!
Do Time-Blocking Right
Time blocking works. But only if you do it right. Here's a prompt that helps.
Act in the role of a productivity coach who has mastery of time blocking. Start by explaining the core principles of time-blocking and why it improves focus and output. Then, help me design a personalized daily schedule using focused time blocks.
Show me how to:
Categorize my work into different types of tasks — for example: deep work (strategy, writing, coding), shallow work (emails, meetings), and personal tasks (breaks, exercise, learning).
Allocate specific time blocks for each category, with real-world examples of how a sample day could look.
Prioritize tasks inside these blocks so that the most important work gets done first.
Handle unexpected interruptions, meetings, or mental fatigue without breaking the flow of my day.
End the day with a short reflection or planning block to improve tomorrow’s schedule.
(Modified from Superhuman 11/13/25.)
Ask ChatGPT to Ask You
You can improve your AI results by asking the AI engine to ask you clarifying questions:
Before you start, ask me up to 7 targeted questions that would materially improve the answer. If, after asking your questions, any information is missing and you must proceed, state your assumptions clearly and provide ideas about how to research the ambiguous issue(s).
(Modified from The Neuron Dec. 21, 2025.)
Look for the Leverage Points...
Act in the role of a strategist who maps out how one move changes the entire system. I'm considering [describe your decision clearly].
Help me think beyond the obvious.
Identify the first-order effects (the immediate, direct outcomes).
Analyze the second-order effects (the indirect, follow-on consequences).
Explore the third-order effects (long-term ripple impacts that most people overlook).
Highlight any risks, unintended consequences, or hidden dependencies.
Suggest alternate choices or mitigants that could improve the outcome.
(Modified from Superhuman 12/2/2025.)
The Fundraising Mythbuster — (Fundraising/Education; 10 min)
Give your board members a quiz on the issue of fundraising. Use my draft list of top myths. This allows you to raise potentially sensitive issues without pointing fingers.
Setup & steps:
Present 5 statements, one at a time.
Members vote true/false.
Discuss one surprising fact (I have some quotes from fundraisers in the draft).
Then hand out the list of all ten myths.
Also, let me know if the list is valuable. I think it is, but I would love your feedback.
I found this video by Dan Pink to be very valuable on the issue of building your attention span in a world that works hard to distract you.
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Let me know what you are working on, and please forward this email to someone you know to spread the good news.
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I wish you all the best for 2026!
Ted
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Founder and CEO Risk Alternatives, LLC 202.758.7572 (cell) 608.709.0793 (office) Website
Author of Managing Your Nonprofit for Resilience
We help nonprofits thrive by providing practical tools and support to address uncertainty and improve risk management.
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P.S. Still working on the white space issue....
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