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I went into this conversation expecting to talk about claims the way most people imagine them: paperwork, delays, frustration, maybe a denial that needs to be appealed. What I didn’t expect was how quickly the discussion shifted to something more unsettling—the realization that many people buy disability insurance believing they’re protected, only to discover years later that the policy language quietly gives the insurer a way out.

In this episode of The Income Protection Journal Podcast, I talk to Mark DeBofsky, an ERISA litigation attorney with more than four decades of experience challenging insurer and plan-administrator benefit denials, is the principal of DeBofsky Law Ltd. and a frequent author, congressional witness, and adjunct law professor on disability and insurance law who has litigated disability claims in federal courts, including cases that helped shape how insurers define disability in the first place. His vantage point is different from brokers, carriers, or consultants. He sees policies only after they’re tested—when income has already stopped, work has already changed, and assumptions collide with contract language.

The perspective changed everything.

When disability policies get tested

There’s a point in many careers when insurance decisions fade into the background. Policies are purchased early, premiums get paid automatically, and life moves on. What came through clearly in this conversation is how dangerous that quiet period can be.

Mark Debofsky kept returning to the same idea: disability insurance rarely fails in dramatic fashion. It fails through definitions—through terms that sound reassuring when a policy is sold and become restrictive only when a claim is filed.

One case he described has stayed with me. A dentist believed he had own-occupation coverage. When a medical condition limited his ability to practice dentistry full time, he adapted. He taught part time. He earned less than half of what he once made. And then the insurer denied his claim anyway.

The denial wasn’t based on medicine. It was based on a single word.

The policy said “own occupation,” but it also said benefits wouldn’t be paid if the insured was engaged in another “gainful occupation,” according to DeBofsky. The policy never defined what “gainful” meant. The insurer did—after the fact—by deciding that any work paying more than the median wage in the state disqualified the claim.

Hearing that logic explained out loud, in real time, lands differently than reading a summary, DeBofsky said. There’s a moment in the audio where you can hear how routine this kind of reasoning has become inside claims disputes—and how jarring it still sounds when you step back and listen to it.

Why true own-occupation isn’t just a checkbox

We spent a lot of time talking about own-occupation coverage, not as a feature list, but as something that behaves very differently once a claim is underway.

Mark made a distinction that often gets lost in sales conversations. A true own-occupation policy pays benefits if you can’t perform your occupation, even if you go on to work elsewhere and even if you earn significant income doing so. Many policies marketed as own occupation quietly reduce benefits once the insured earns income in another role, reclassifying the disability as partial.

That distinction matters most for specialists—surgeons, interventional physicians, dentists, litigators—whose skills don’t transfer cleanly. A minor hand tremor can end a surgical career. A cognitive impairment can derail a trial attorney. In those situations, the ability to pivot shouldn’t come at the cost of losing benefits, but in many policies, it does.

What’s striking in the conversation is not just the rule itself, but how often professionals don’t realize which version they bought. Mark talks about this without exaggeration. You can hear how frequently he encounters policies that look protective on paper and behave very differently in practice.

Group coverage and the illusion of security

Another assumption we challenged in the episode is the idea that employer-provided disability coverage is “good enough.” I hear this constantly from high-income professionals: I have a solid group plan through work. I’ll be fine.

What Mark DeBofsky describes is a different reality. Group disability policies are designed to protect salary at a moment in time, not long-term earning power. They usually replace a percentage of income up to a cap, integrate with Social Security Disability, and often switch to an any-occupation definition after a limited period.

For high earners, that structure creates gaps that aren’t obvious until work stops. There’s a moment in the conversation where we talk through how insurers decide what “any occupation” means—using vocational assessments and transferable skills analyses that often rely more on internal guidelines than on treating physicians’ opinions.

Listening to that process explained, step by step, changes how you think about relying on group coverage alone. It also reframes why individual disability coverage behaves so differently when it’s written well—and why it can fail just as quietly when it isn’t.

The claims that break expectations

One of the most revealing parts of the conversation comes when we talk about which claims are hardest to get paid. It isn’t always the catastrophic injuries people imagine.

DeBofsky describes slow-progressing conditions—Parkinson’s disease, multiple sclerosis, rheumatoid arthritis—where professionals keep working as long as they can. There’s a counterintuitive point he makes that stuck with me: there is no logical incompatibility between being totally disabled and working full time. People adapt. They push through. They hang on.

Paradoxically, that persistence would later be used against them.

He references court decisions that recognize this reality, but you can hear how often insurers still argue the opposite. That tension—between how people actually behave and how insurance logic evaluates them—is one of the quiet fault lines in disability claims.

Mental health claims reveal a similar gap. We talked about benefit limitations that cap payments at 24 months for behavioral health conditions, even when those conditions are just as disabling as physical ones. The way Mark frames this isn’t ideological. It’s practical. No one knows what will disable them. Accepting a discount in exchange for a limitation feels harmless—until it isn’t.

Why listening changes how this lands

I could outline the technical takeaways from this episode, but that wouldn’t capture why the conversation matters. What makes it worth hearing is the way these issues surface in real time—the pauses, the emphasis, the moments where decades of experience show up not as advice, but as concern.

There’s a point late in the episode where Mark reflects on clients who once resented paying premiums, only to later realize those policies were the difference between stability and chaos. That shift—from annoyance to gratitude—is something you feel more than you read.

If you’re a physician, attorney, dentist, executive, or business owner who assumes disability insurance is a solved problem, this conversation is likely to unsettle you in a productive way. The article gives you the outline. The audio gives you the weight of it.