"Insurance spent centuries pricing the past. The future belongs to those who can price the present." — Futurist Jim Carroll
This is the Trends Scorecard series, where I go back into my own archive, dig up what I actually predicted years ago, and grade it honestly against the world of 2026. No cherry-picking, no quiet edits. This time the industry is Insurance. Here's the scorecard.
The setup: I've been talking about "the future of risk" since before it was fashionable
I have been keynoting the insurance industry for more than 20 years — property and casualty, life, group benefits, reinsurance. CEOs, CIOs, actuaries, brokers, the rooms full of people whose entire job is to price uncertainty. And from very early on, I kept hammering on one idea: that the very nature of risk was speeding up, that the old backward-looking actuarial model was about to be turned upside down, and that the industry was not moving fast enough to keep up. Here is how I framed it for a Property and Casualty Insurers Association audience — a framing I quoted again years later because it had aged so well:
The insurance industry today is immersed in a period of unprecedented, relentless change; impacted by hyper-innovation, fast-paced technological evolution, the rapid emergence of new forms of risk, and increasing business market turmoil. Permanence has been torn asunder, as customers and business organizations empower themselves with information, and as underwriting decisions become ever more complex.
That was the thesis. Below, the receipts.
And this isn't a sector I've watched from the sidelines. I had Claude dig through my blog and pull together the insurance and risk groups I've keynoted for over the years:
- Insurers & Carriers — Zurich, New York Life, MetLife, Chubb, Assurant, Lincoln Financial, Gore Mutual, Equitable Life Insurance Company, RBC Life Insurance, Sun Life, Great-West Life, Swiss Re
- Health, Benefits & Group Insurance — Cigna, Blue Cross Blue Shield, Highmark Health
- Brokers, Reinsurance, Actuarial & Industry Bodies — Brokers & Reinsurance Markets Association, Independent Insurance Agents & Brokers of America, LIMRA International, GAMA International, Certified Professional Chartered Underwriter Association, Insurance Institute of Canada, American Institute of Actuaries, Verisk
- Risk & Safety — National Safety Council, National Fire Protection Association, FM Global, American Automobile Association
And those are only the ones I've blogged about — there have been plenty more.
I've also led a private, closed-door future-of-insurance session for the C-suites of most of the world's largest carriers — Allianz, AIG, Travelers, AXA, Allstate, Liberty Mutual, The Hartford, State Farm, Progressive, GEICO, Nationwide, Farmers, CNA, Generali, Ping An, Lloyd's of London, XL Insurance, American Family, and RSA.
So how did the calls hold up? Let's pull the receipts.
Prediction #1 — "Underwriting complexity explodes" (2009) — Hit
Back in 2009, I sat in a room with the COOs and CIOs of some of the world's largest P&C insurers and told them that faster science and faster change were about to make risk assessment far harder, not easier. Specialized skills would become scarce. Here is exactly what I wrote:
Quite simply, faster change and faster science is leading to unique issues in assessing insurance risk, with the result that skills become far more specialized and unique.
The grade: Hit. The talent crunch in insurance is now one of the industry's defining structural problems — cyber underwriters, climate-risk modelers, AI-risk specialists, parametric designers. Whole categories of risk emerged that didn't exist when I wrote this, and the scramble for people who can actually price them is real. I was right that complexity, not simplicity, was the future.
Prediction #2 — "Performance-based, telematics-driven auto insurance" (2011) — Hit
In 2011 I told insurance audiences that the biggest wave coming for them was performance-based pricing — pay based on how you actually behave, not on a demographic average. And I was specific about where it would land first: the car.
One of the biggest trends which is going to hit the world of insurance like a tidal wave is performance based insurance policies. If you live up to or exceed some performance standard, you'll get a rebate or reduction on your insurance policy rate.
It's going to happen extremely quickly in the field of automotive insurance. A flood of GPS enabled performance measuring devices will soon come to inhabit most automobiles throughout the industrialized world. Insurance companies will set a policy price, and then give you a rebate if you exhibit better than average behavior.
The grade: Hit. This is usage-based insurance, and it is now mainstream — Progressive Snapshot, Root, Tesla's own embedded telematics policies, and a long list of others price drivers on real-time behavior. The "GPS enabled performance measuring device" I described turned out to be the smartphone in your pocket and the chip already built into the car. Called it.
Prediction #3 — "Underwriting becomes one question: can I look you up?" (2011) — Live / partly too early
In that same 2011 piece, I went further and made a sharper, riskier call about life underwriting — that the old battery of blood tests and forms would give way to data. I quoted an industry source approvingly:
"Assuming privacy regulations require it, by 2020 underwriting will consist of one question: 'Can I look up everything about you?'"
The grade: Live, but honestly early on the specifics. Accelerated and data-driven underwriting absolutely arrived — many life policies now skip the needle entirely and price off external data and digital records. But "look up everything about you" ran straight into privacy regulation, and the social-media-profile version of underwriting got reined in rather than unleashed. The direction was right; the 2020 date and the "everything" were too bold. I'll own that.
Prediction #4 — "Performance-oriented insurance: rewarded for measurable health" (2014) — Hit
By 2014 I was being quoted in the American Academy of Actuaries' own magazine, where I gave the trend a name — "performance-oriented insurance" — and extended it from cars to your body:
"And if your measurable activities reduce or eliminate any risk, you will be rewarded through a rebate or reduction in insurance cost."
The grade: Hit. This is now the explicit model behind John Hancock's Vitality program and a whole wave of wellness-linked life and health products: share your wearable data, hit your activity targets, lower your premium. The wrist-to-policy feedback loop I described is shipping product. Solid hit.
Prediction #5 — "Just-in-time insurance and the death of backward-looking actuarial pricing" (2016) — Hit
This is the one I'm proudest of, because it's the whole thesis in two sentences. In 2016, in front of a room of senior P&C and life executives, I laid out the structural shift:
Predictive analytics will shift the industry away from actuarial based historical assessment to real-time coverage. Policy niches, micro-insurance and just-in-time insurance will drive an increasing number of revenue models.
The grade: Hit. "Just-in-time insurance" is no longer a futurist's phrase — it's a product category. On-demand and episodic coverage you switch on for a single trip, a single rental, a single drone flight, a single gig shift, is here and growing, and embedded micro-insurance is sold at the point of need by the thousands. The move from historical actuarial tables toward real-time, instance-oriented coverage is exactly the path the industry took.
Prediction #6 — "From looking back to looking forward, accelerated by AI" (2023) — Hit
By 2023, with AI accelerating everything, I distilled the entire decade-plus of these predictions into a single line about the deepest shift in the business:
we're moving from a world in which insurance risk is assessed by actuaries looking back in time, to one that involves real-time or forward-oriented predictive risk analysis. That's a substantial, significant change, and AI helps to take us there.
The grade: Hit, and accelerating in real time. AI-driven risk assessment, drone-and-digital-twin property inspection, real-time claims triage, and forward-looking predictive models are now everywhere in the underwriting stack. The orientation of the industry genuinely flipped from rear-view mirror to windshield. This is the trend I planted in 2009 and watched mature for fifteen years.
The one I want to flag
Here's where I keep myself honest. For all the talk of real-time, forward-looking, instance-oriented insurance, the uncomfortable truth in 2026 is that the bedrock of the business is still the annual, backward-priced policy — and meanwhile the thing I warned about earliest, the changing nature of risk itself, has outrun the industry's ability to price it. I said it plainly in 2025:
The fact is, the insurance industry finds itself at a pivotal moment where traditional models are colliding with accelerating risk. The very foundations of insurability are being challenged by climate, technology, and societal shifts.
I was right that risk would accelerate. What I underestimated was that acceleration would, in places, win. Insurers are pulling out of Florida and California. Whole categories are sliding toward uninsurable. The transformation I predicted is real, but it has not yet arrived fast enough or broadly enough to keep pace with the risk it was supposed to absorb. New risk demands new thinking; uninsurable risk demands bold thinking — and the industry is still catching up to its own future. Verdict on the transformation: real and underway, but incomplete.
What the scorecard tells us about what's next
The method behind all of this is the same one I've used for 30 years: I don't guess at gadgets, I watch the direction of structural trends — where connectivity, data, and falling costs are pointing — and I follow that arrow to its logical conclusion, often years before the industry is ready to act on it. On insurance, the arrow has pointed in one direction the entire time: away from pricing the past, toward pricing the present and the future.
So where does insurance go from here? That's a separate conversation, and a longer one than a scorecard can hold. I've mapped it out sector by sector in my current series, The Way Forward — the trends, the barriers, and the playbook for acting on them. If these receipts convinced you the method works, that's where you'll find where it's pointing next.
Next in the Trends Scorecard series: Financial Services & Banking — where I made some equally bold calls, and where the grading is going to be just as honest.