Grappling with the wickedest problem: insuring communities amid climate chaos
[Cross-posted from Greg Bloom’s Medium.]
With this announcement from the government of Plymouth, Massachusetts about their new “insurability planning” initiative, we see an exciting example of the kind of process that almost all communities will need to undertake in the coming decades.
In partnership with InnSure, a non-profit innovation hub that promotes climate-adaptive insurance, Plymouth will engage multiple stakeholders from the public and insurance sectors, together with community members and civic leaders, in participatory research that synthesizes intelligence about local climate risks, and informs coordinated efforts to mitigate these risks, while improving the affordability and coverage of insurance for their community.
This pilot project was conceived in part during the Insurability Planning workshop that we at CRISP, the Climate Resilient Insurance Strategy Project, co-designed and facilitated with InnSure in Boston last July. This event was held almost exactly one year after the initial Property Insurance Strategy Forum in Miami-Dade County.
Rather than sit everyone facing a speaker at the front of the room (which quickly results in most people zoning out and waiting for the coffee break) our workshops get participants right into small, focused group conversations that rotate through iterative, parallel cycles. The agenda for the second day is shaped by participants at the end of the first day, resulting in a dynamic flow of conversations that emerge across many perspectives and then converge together in a shared strategic framework.
In the course of these workshops, we helped public, private, and civic actors work together to develop a shared analysis of the property insurability crisis and then sketch out strategic opportunities to work through it together.
During our time together, we didn’t pretend that any of us could “solve” the problem. Instead, we were doing the next best thing.
There are no panaceas — neither for climate change, nor for insurance against its impacts.
Climate change is the ultimate “wicked problem,” in that it has many different causes which interact in nonlinear and unpredictable ways, yielding effects that are experienced differently by different people, who themselves might have different values and therefore different understandings of what the problem even is. And the megawicked problem of climate change is giving birth to more wicked problems, like the challenge of insurability in a changing climate: less predictable, more extreme weather is causing more losses from destructive events, which makes insurance more expensive, which makes it difficult to finance adaptation that can mitigate the risks of the changing climate.
We call these problems “wicked” because they can’t fully be solved, and not only that: they are hard to even think clearly about. Culturally, we tend to assume that, given any problem, there can be “an app for that” — just waiting to be designed by someone clever enough. But in these cases there’s no quick fix, and we might not even agree on what the problem really is.
That doesn’t mean the situation is hopeless. Societies have, over time, tamed some wicked problems. (For instance, we halted ozone depletion; we greatly reduced child labor. Notably, these problems are diminished but not fully resolved.) Taming wicked problems entails building capacities to cope with them. That process begins when different kinds of people get together to talk.
Plymouth’s project is what it looks like when a community moves from talk to action. Assuming the pilot successfully achieves its aims, it won’t solve the problem — but it will enable Plymouth to know which coping capacities they most urgently need to develop. (Of course, that will involve getting back together to talk. And repeating the cycle indefinitely.)
Start with low-hanging fruit, but think about the whole tree.
Though the insurability problem has no quick fixes, InnSure’s Plymouth pilot points to some relatively straightforward opportunities — ”no brainer” kinds of action — that can promote resilient adaptation in a community while simultaneously making it easier to insure. It won’t solve the whole problem, but it can buy time while building trust in our ability to make more progress in the future.
Another good example of such “no brainers” are initiatives like FORTIFIED grant programs — active in states like Alabama and North Carolina. These may be funded by some combination of government grants and insurance industry offerings, helping property owners get into compliance with industry standards for wind risk mitigation.
Similarly, InnSure is also working with municipal leaders in Salem, Massachusetts, leveraging funding from the QBE Foundation, to offer free flood risk audits to local property owners. These audits calculate the potential benefit (in future losses avoided) from various risk mitigation measures. InnSure then works with insurers to arrange for discounts on premiums paid by risk-mitigating property owners.
The expected result: fortified homes and lower premiums for homeowners; protected tax base and enhanced resilience for municipalities; confidence for insurers to keep serving the market. Win-win-win.
Of course, even if every one of these programs and others like it are totally successful, there’s only so much risk that coastal communities can actually mitigate. In the long run, many coastal communities will eventually become simply uninsurable.
To cope with this reality, it seems that we’ll need to entirely reimagine society’s relationship to insurance. We don’t have “no-brainers” for this. But we have to start somewhere. The easy-to-understand, immediately actionable, near-term solutions are exciting to people. They get important stakeholders to the table, ready to talk.
Beyond one-off events: envisioning a “laboratory of democracy”
When designing and facilitating InnSure’s Boston workshop, our main objective was to maximize people’s opportunities to talk — and listen — to each other. That means “no panels, no presentations.” Rather, we create spaces for different people to reflect on their different perspectives. There are no experts who can tell us everything we need to know to get where we need to go, but when we just listen to each other, a kind of magic happens.
Our workshops tend to get nearly-unanimously positive feedback, and at the end it’s typical to hear at least one or two people say something like “this is the best meeting I’ve ever attended!” I don’t think this reflects our extra special secret skills; rather, it reflects how poorly most meetings serve the purpose of grappling with complexity together.
That said, while I believe such spaces for multi-stakeholder dialogues are necessary for us to cope with these wicked problems, I will also be the first to acknowledge that they are not sufficient. Talking gets us started, but only doing can get us where we want to go.
By the end of two days, we generated a dizzying array of strategic objectives — and then invited participants to review them together and rank by priority. This helped shape the strategy for pilot projects that are underway this year.
By the end of two days, we generated a dizzying array of strategic objectives — and then invited participants to review them together and rank by priority. This helped shape the strategy for pilot projects that are underway this year.
In Boston, InnSure and their partners in Plymouth and collaborators in state government spent their time together conceiving a shared strategy that eventually bore fruit in this year’s pilot. This was understood to be just one step in a broader process of making Massachusetts what people described “a test-bed for innovation.” There was a lot of excitement about the idea of building “a platform” for insurability-oriented resilience initiatives — by which, fortunately, nobody meant an “app,” but rather institutional infrastructure for knowledge exchange and collaboration.
Since there is no one single actor who can take a single action to solve this problem, we need many different actors in many different arenas to chart their own course in coordination with each other. This kind of “polycentricity” is difficult — so we need to invest in it, and even better, make it enticing. So: no panels! No keynotes! Let people talk to each other. Since we’re never going to fully solve the problem, we’ve got to make it gratifying — even fun — for people to come together and cope with it.
If you’re interested in learning more about InnSure’s pilot programs, reach out to Steve Brandt at steve@innnsure.org. And if you’re interested in organizing a fun, participatory event about climate adaptation and the insurance crisis in your community, reach out to us at insurancestrategy@aspirationtech.org. And stay tuned for more reflections on what we’re learning.
Insurability planning amid climate chaos
Massachusetts has more time than Miami. Leaders there are thinking ahead.
Massachusetts has more time than Miami to address climate & insurability issues. Leaders there are thinking ahead.
Charlie Sidoti, executive director of the nonprofit InnSure, discusses his vision for “insurability planning” with a group of participants at our July 2025 workshop in Boston.
Even in places where the cost of insurance isn't already rising precipitously out of reach every single year, the writing is on the wall: our situation is untenable. Civic leaders want to get out ahead of the predicament already unfolding in Florida and California.
So we (Greg Bloom, Kate Stein, Wallis Greenslade) initiated the Climate-Resilient Insurance Strategy Project with a convening in Miami-Dade County in July 2024. We were thrilled to continue this work by supporting the Boston Green Ribbon Commission with a property insurance workshop in October 2024, where among other successes, we deepened our connections with InnSure, a nonprofit insurance innovation lab based in Cambridge.
This past July, the CRISP team helped InnSure co-design and facilitate an "insurability planning" workshop that brought together insurance industry leaders and innovators with leaders from local and state government, as well as civic planners from across Massachusetts and the broader region. Together, we discussed opportunities to keep insurance affordable through risk mitigation measures and climate-smart economic development. We also identified options to harness new sources of finance for resilience and expand available insurance capacity. And, we mapped out strategies for operationalizing pilot projects.
Here are some of our key takeaways for communities in Massachusetts – and beyond.
Why Massachusetts, why now
Communities in California and Florida have been making headlines as harbingers of a climate change-driven property insurance crisis. Coverage highlights how climate risks drive unaffordable (or unavailable) premiums. But there’s less discussion of what communities can do to decelerate these price increases and ensure that insurance remains an affordable tool to support communities in disaster preparedness and recovery, and longer-term climate change adaptation.
Though Massachusetts has faced fewer losses than front-line states, flooding impacts are already being felt. Local communities and the state have been trying to cope – with decidedly mixed results. As InnSure explains, the current state of the private insurance market may be failing to drive the adaptation we need, but communities can work to leverage property insurance as a tool in their economic development and resilience plans. Through the development of multi-sector partnerships, communities can enable their planning processes to unlock opportunities that ensure insurance remains available and affordable – while also accelerating efforts to adapt to rising climate risks.
What is insurability planning?
InnSure defines “insurability planning” as “a strategic process to improve a community’s access to affordable insurance.” In essence, when communities plan for insurability, they proactively identify and address risks that could increase premiums or lead to exclusions or restrictions on coverage. They might model risks, conduct insurability assessments, or work with partners on pilot projects for more accessible and affordable risk financing solutions. Communities can integrate these considerations into their existing planning processes – aligning economic development and resilience planning with accounting for insurability in the future.
Insurability planning helps communities gain leverage over rising insurance costs, shifting from being price-takers to price-makers. To be successful, it requires collaboration among partners across the insurance “ecosystem,” including communities, the insurance industry, NGOs and regulators.
What we achieved – ideas & recommendations
Though Massachusetts faces different challenges than Florida, we still observed themes that echoed our 2024 Miami-Dade County Insurance Strategy Forum. Participants in both events enthusiastically discussed prerogatives to:
Build insurance literacy among communities and policyholders, and climate literacy among insurers, agents and brokers.
Promote risk mitigation actions by ensuring that they result in premium reductions – through coordination across organizations and sectors, including improvements to data supply, modelling processes, and insurance product portfolios.
Foster a regulatory environment that promotes innovation and risk mitigation, without compromising on consumer protection.
Unlock new sources of funding and finance for risk mitigation, resilience and adaptation – in part by highlighting how insurers and lenders can mitigate risk in their portfolios by building communities’ capacity to address climate risks and housing affordability challenges.
Our discussion in Boston generated a range of additional recommendations specific to the Massachusetts context, and relevant to ongoing national and international efforts. These include:
Promoting Massachusetts as a “test-bed” for innovation: The state’s track record of supporting innovative local resilience initiatives means it’s primed to incorporate insurability planning into its strategy. Participants discussed the criteria for local “insurability planning” pilot projects – and opportunities to take action – which might involve replicating the success of already-existing programs like Mass Save’s property audit and retrofit initiative, or designing innovative new strategies. Participants also identified opportunities to galvanize such action through legislative vehicles such as an Environmental Bond Bill.
Developing strategies to translate risk mitigation into insurance discounts: Participants considered opportunities such as insurance discounts for developers of affordable housing that are working with local governments to reduce risks at both a property and district level. They also considered the role of large employers – like community anchor institutions such as universities and hospitals – in development of new insurance products and financing of district-level resilience engineering. A longer-term vision also emerged for community-based risk pooling institutions that could help with financing and insuring of resilient developments – taking inspiration from community development financial institutions (CDFIs), and GreenieRE, which provides reinsurance for insurers underwriting new and emerging clean energy technologies.
Exploring the potential to establish flood insurance coverage for all policyholders statewide. Because of relatively low flood insurance uptake rates, Massachusetts residents and communities could be left with little funding flowing in for post-disaster recovery. To address problems caused by low levels of flood insurance coverage, participants in our workshop considered an ambitious scenario in which the state might mandate flood coverage through various means – such as requiring all FAIR plan policy holders to purchase flood insurance as well (a strategy that’s been adopted in Florida) and establishing a statewide fund to subsidize flood insurance costs for low-income homeowners. They also proposed exploring opportunities to scale up the availability of private flood insurance, for instance by working with insurers to include it as part of broader homeowners coverage; and they proposed intermediate steps such as requiring flood risk disclosures, subsidizing vulnerability assessments and promoting consumer education on flood risks.
Establishing coordinating capacity that can drive complex strategies forward. Systemic climate risks and insurability challenges can’t be solved in siloes. They require collaboration across sectors and scales. To that end, participants proposed developing a “platform” for capacity building, implementation support, research and knowledge dissemination that can help facilitate coordinated action. InnSure is one of just a few organizations doing this kind of work, and we’re excited to continue partnering with them to amplify their impact.
What’s next?
The CRISP team is in discussions across the U.S. and globally about convenings where frontline communities, governments, NGOs, and insurers co-develop strategies to reduce risk and leverage insurance for resilience. Interested? Reach out to us.
You also can connect with InnSure to learn more about their work.
The Boston crew celebrates two successful days of collaboration & insight.