What Affluent Families Get Wrong About Healthcare—and Who Fixes It

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By Lindsay Loomis, SVP, Emry Health

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You’d never manage your assets without expert guidance. But when it comes to health insurance and medical decision-making—areas just as complex and consequential—many high-net-worth and ultra-high-net-worth families are effectively winging it.

As someone who’s spent a career inside this system, I can tell you: what surprises me most isn’t the complexity of healthcare. It’s how few people—even sophisticated, successful ones—truly understand how their health coverage works.

Clients often tell me they “know enough to be dangerous.” I promise you—if that’s your stance on insurance, you’re not just dangerous. You’re exposed.

Sophisticated Families, Costly Healthcare Blind Spots

In wealth planning, complexity often signals importance. The same is true in healthcare. What’s different is that the system was never built with your lifestyle in mind.

You may live across multiple states, travel often, or support a range of family healthcare needs—yet still find yourself on a one-size-fits-all insurance plan that doesn't account for your lifestyle.

One recent client was. They lacked any out-of-network coverage. That meant if they saw a top-tier physician outside their home state, they’d be paying the full bill—thousands out of pocket for each visit.

In that case, we performed a detailed review of the family’s insurance coverage, mapped it against their healthcare usage across multiple states, and identified better-aligned options that supported their mobility, care preferences, and long-term needs.

It’s often labeled an insurance consultation—but at its core, it’s a form of risk management: protecting health and preserving wealth through smarter coverage decisions.

Out-of-Network Costs and Insurance Gaps for UHNW Families

We’ve seen it all:

Missed Medicare enrollment deadlines, leading to lifetime financial penalties.

Out-of-network surprises—especially from boutique physicians or hospitals.

Years of overpayment due to incorrectly coded claims that no one ever reviewed.

High-deductible plans that offered zero protection for second-opinion visits or cross-state care.

One of the most shocking realities for clients: many medical claims contain errors. That lab bill you got after your executive physical? It might have been miscoded—and if no one scrutinizes it, you’ll quietly overpay again and again.

What a Private Healthcare Advocate Actually Does

When people hear the term “healthcare advocate,” they often picture someone helpful on the phone—navigating paperwork or resolving billing issues. But for families with more complex needs, the role is far more comprehensive and strategic.

A true healthcare advocate serves as a behind-the-scenes steward—someone who ensures that coverage, access, and logistics are all working in sync.

That often includes:

Reviewing insurance options across multiple states and carriers

Assessing network adequacy for preferred physicians and facilities

Clarifying out-of-network rules and reimbursement potential

Managing claims, appeals, and ongoing billing follow-up

Handling the routine but time-consuming tasks that burden busy families

This work often takes place in close collaboration with family offices, estate attorneys, executive assistants, and other trusted advisors—because healthcare doesn’t operate in a vacuum. It intersects with travel, legal planning, privacy, and even emergency preparedness.

When one family member became ill overseas, it wasn’t the toll-free insurance hotline that made a difference. It was an advocate that was able to secure and coordinate medical transport home.

That’s the kind of planning no one thinks about—until it becomes urgent.

The Case for Expert Healthcare Navigation Services

If you're unsure what your current insurance covers—or if it’s keeping pace with your family’s lifestyle—it’s time to bring in a healthcare strategist.

Because in this system, ignorance isn’t bliss. It’s expensive. It’s time-consuming. And it’s avoidable.