Designing Tomorrow: Creative Strategies for Social Impact

There's a push right now to democratize strategic planning. Survey the community, poll the staff, put the big calls to a vote.  I get the instinct, but it goes too far. Influence is not the same as decision-making power, and collapsing the two is how good orgs freeze.  In this episode, Eric and Jonathan draft their ideal strategic planning teams fantasy-sports style from a pool of ten possibl...

There's a number treated like gospel in philanthropy: the 5% annual payout private foundations are required to hit. It was written into law as a floor.  Kristin Todd has watched it become a ceiling instead. After nearly two decades at the Daniels Fund, a $1.5 billion private foundation, she now leads the NoCo Foundation in Northern Colorado, where she's more than doubled annual grant-mak...

Everyone keeps predicting the death of the website. First it was social, now it is AI. But it is still the one channel you actually own and control, which is exactly what makes it your most durable asset. So when a site has gone untouched for five years and a redo runs six figures, the real question is whether it is worth it, and when. Episode Highlights: [00:03:00] The identity impact gap, and wh...

For the last 50 years, we've operated under a single dominant idea: the purpose of business is to maximize shareholder value. But what if this whole era of extraction and short-termism isn't the natural order at all? What if it's just a blip? Sarah Gillard, CEO of Blueprint for Better Business, has spent 25 years inside major corporations watching what happens when companies forget...

Jonathan recently learned that the Seymour Center is about to absorb a permanent new expense in the $150,000 to $200,000 range. On a $2.2 million operating budget, that's roughly 10% of the whole thing, and it's not a one-time hit.  The instinct for most leaders is to pull back: tighten the budget, pause the big swings, and try again in a few years. But contraction changes the story you...

Most social impact campaigns are built on two ingredients: information and emotion. The data makes the case. The storytelling makes people care. But caring, on its own, has a shelf life. Saralynn Finn, founder of Sett & Sley Consulting, joins Eric in the studio to argue that the third ingredient, what she calls "the hands", is where campaigns succeed or quietly die. Not more awarenes...

Most social impact leaders got into this work because they care deeply about the mission, not because they wanted to be public figures with opinions. But that instinct to stay quiet and let the work speak for itself may be doing more harm than good. Developing and sharing a strong point of view isn't a nice-to-have; it's a moral obligation for leaders in this space. Episode Highlights: ...

There's an unspoken rule in the social impact sector: we tell the truth, we follow the science, we play fair. But those rules are increasingly a losing strategy, because the industries we're up against don't have to win the argument. They just have to muddy it. Joelle Lester, Executive Director of the Public Health Law Center, has spent 25 years studying how Big Tobacco manufactured...

There's a trend called looksmaxxing that says appearance is everything, and optimizing it is just pragmatism. Apply that same logic to nonprofits and you get an interesting thought experiment: what happens when an organization goes all in on brand? And what happens when one deliberately strips brand away entirely? This episode explores the spectrum between "brandmaxxing" and "d...

Every major technological paradigm shift has broken society before it fixed it. The printing press, radio, television. Each one reshaped how we communicate and what we believe. Now the internet, social media, and AI are repeating the pattern at unprecedented speed. Joel Breakstone, co-founder and executive director of the Digital Inquiry Group, has spent over a decade studying how people evaluate...

There's a quiet belief running through the social impact space that being too visible somehow cheapens the work. That good organizations should let their impact speak for itself. But the orgs that get the funding, the talent, and the momentum aren't always the ones doing the best work; they're the ones who've made their work visible. This episode makes the case that visibility...

The social impact sector has made community co-creation almost sacred. Design with people, not for them. Give everyone a voice. But what happens when the loudest voices aren't the most informed, and the planning process stalls because nobody can make a call? Taylor Stuckert, CEO of Lead for America, has lived this tension from every angle. Eric and Taylor dig into the question nobody in socia...

Most nonprofit leaders have been through some version of the brand strategy process. Eric calls it process theater: brand strategy work that sounds great in proposals but leaves everyone wondering what they're actually building toward. This episode puts ten common elements of brand strategy on trial. Eric and Jonathan each rank them as essential, important, or overrated, and the results surfa...

Technology promised to close the digital divide, but too often the people building it don't reflect the communities affected by it. Tina-Marie Gulley, former CEO of Ada Developers Academy, sits down with Eric to talk about what it takes to build a more intentional, equitable tech industry, from embedding AI into nonprofit curriculum to running hackathons that solve real problems for community...

There's a post going around LinkedIn right now where a fundraiser is calling out a foundation for not structuring a grant as multi-year support. The tone is essentially: our work matters, so funders should give us what we need. That sparked the thorniest disagreement Eric and Jonathan have had on the show. Jonathan's take is blunt: nonprofits need to stop treating funders as fuel for the...

The nonprofit sector has a marketing philosophy problem. We adopted a playbook built almost entirely around conversion: get the click, get the gift, optimize the funnel. But all of that activation depends on something most organizations never intentionally build: a brand people actually know, remember, and feel something about. Brady Josephson, Head of Growth & Innovation at charity:water, spe...

A single phrase from a previous episode sent Eric into an existential tailspin, and reshaped how he thinks about organizational identity. In this episode, Eric and Jonathan unpack why "Who are we becoming?" hits harder than any strategic planning question, how it works as a daily filter for every decision you make, and why the social impact sector needs to be asking it right now. Episode...

The social impact sector has gotten very good at describing problems: white papers, statistics, annual reports filled with data on gaps and needs. But it hasn't built a system for telling stories that actually move people. Heather Mason spent 20 years producing the biggest convenings in the sector before building The Impact Lounge, a traveling hub that brings together funders, filmmakers, and...

Everyone claims to be strategic. But what does that word even mean anymore? In this episode, Eric and Jonathan dig into a question that comes up constantly: what actually separates strategy from tactics, and why do so many strategic plans end up collecting dust? Eric makes a bold claim — that strategy, at its core, comes down to one word: conviction. Not frameworks. Not 200-page documents. Convict...

There's $1.5 trillion sitting in American foundations right now. Add in donor-advised funds and the total climbs past $1.7 trillion. Most of it isn't moving. Meanwhile, the organizations on the front lines of housing, health, democracy, and climate are being told to do more with less. In this episode, three leaders behind the Level Up campaign make the case that the 5% minimum payout rat...

AI slop is flooding every channel. Here's what changes, what doesn't, and how to cut through the noise. In this episode, Eric and Jonathan dig into the great content reset — the collision of AI, shifting media formats, and a growing hunger for real human connection. They unpack where AI actually helps (and where it creates "AI slop"), why Derek Thompson argues everything is bec...

If solving the world's hardest problems requires the world's best people, why do we pay social impact professionals like they should be grateful just to have a job? The sector still treats its workforce as a cost to be minimized rather than the most important element to its success. So what would it look like to invest in people with the same urgency we bring to our missions? Rusty Stahl...

Every organization has a “someday” list. The rebrand that never quite gets prioritized. The content strategy that’s been “in the works” for three years. The bold idea that came up in a board meeting, got tabled for further discussion — and was never discussed again. But what if the right time already came and went? In this episode, Eric and Jonathan go behind the scenes on a project that almost di...

In the social impact sector, we talk a lot about systems. Structural barriers. Root causes. Power structures. But I've watched systems-focused thinking become its own kind of trap: top-down, abstract, and alienating the very people it aims to serve. Because systems aren't just structures and policies. They're people. And you can't change a system by imposing solutions from abov...

After months away, Jonathan Hicken returns to Designing Tomorrow — and this time, we're recording from the brand new Seymour Studios at the Seymour Center in Santa Cruz. In this episode, Eric and Jonathan take a real look back at 2025: a year that felt like a grind but delivered surprising wins across the sector. They dig into what the data actually says about giving (spoiler: it's not a...