Insurance and protection

The right coverage, sized to your life

Insurance keeps a setback in health or life from turning into a financial one, for your family and for you. Getting the amount and the type right is a planning question, and that's exactly how I treat it.

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Jesse Plunkett seated on the office sofa in front of a deep green wall, hands clasped and smiling

Protection is planning, not a pitch

Insurance may be the least loved corner of financial planning, and some of that reputation was earned. Too often the analysis and the sales pitch come from the same person, and the recommendation drifts toward whatever pays best. I start from the other end: your plan decides what needs protecting, and the coverage gets sized to fit.

In practice, the households I meet are often under-covered and over-covered at the same time. There's the employer's life insurance, which stops at a number picked by a benefits committee and disappears with the job. And there's sometimes a permanent policy bought years ago that no longer fits anything in the plan. Sorting that out, keeping what serves your family and letting go of what doesn't, is the whole exercise.

One thing you should know up front, because it shapes trust: when coverage is called for, I can put it in place as part of your plan and may earn a commission on a policy. I'll always tell you when that's the case. The analysis comes first, in writing, so you can see exactly why a policy is or isn't recommended before any product enters the conversation.

Jesse Plunkett kissing his toddler daughter's head while holding his baby, his wife laughing beside them at an outdoor family photo session
The whole point of coverage: the people in the picture.

How I size and structure coverage

How much life insurance do you actually need?

Enough to replace what your income was going to do: pay off the mortgage, fund the years until the kids are independent, keep your spouse's retirement on track, cover final expenses. I add those up in dollars for your family, subtract what you already have in place, and the gap is the number we insure.

For a first pass on your own, the Life Insurance Needs Calculator walks through the same questions.

Term or permanent: which type fits?

Term insurance covers a defined stretch of years for a modest premium, and for the years when others depend on your income, it usually fits best. Permanent insurance costs far more and lasts a lifetime, which earns its keep in fewer situations: lifelong dependents, certain estate needs, some business cases.

If someone is presenting permanent coverage as an investment, slow down and get a second set of eyes on the numbers before you sign anything.

Why is disability coverage the gap I see most often?

Because through your working years, your ability to earn is the asset everything else depends on, and it's the one high earners most often insure last. Group coverage through work helps, but it typically caps the monthly benefit, may end when the job does, and benefits are often taxable when the employer pays the premium.

An individual policy can fill those gaps while you're healthy enough to qualify. Of everything in the protection review, this is the piece I'd least want you to skip.

Where does long-term care fit?

Late in life, the largest financial risk is often the cost of care itself, whether that's home aides, assisted living, or a nursing facility. It's worth planning for, though it isn't a risk everyone needs to insure. For those who do need care, it lasts about 3.7 years on average for women and 2.2 years for men, and you can approximate current costs in your area with the CareScout cost-of-care tool. The federal government's own estimates are a useful second reference for how much care a plan should anticipate.

From there, the decision usually comes down to three paths. Self-funding, paying for care straight from your own portfolio, is a sound choice for households with a few million in investable assets, where a few years of care won't derail the plan. Long-term care insurance is built for the middle ground, so an extended stay doesn't blow a large hole in the portfolio or push a family toward Medicaid. And Medicaid itself is always there as a backstop, even if most of the families I plan with won't need to lean on it. We map which of the three fits your numbers, rather than assuming a policy is the answer.

What about policies you already own?

Bring them, and I'll read them. We list what each policy covers, what it costs per year, and what job it was bought to do. Some earn their spot in the plan. Others were sold more than planned, and you may be better off redirecting that premium once we've confirmed replacement coverage is in force.

Term vs. whole life at a glance

This is the short version; the article linked below walks through the full comparison, branch by branch.

Term lifeWhole life
Cost Modest premiums buy large amounts of coverage during your working years. Premiums often run many times higher for the same death benefit.
Duration Covers a set period, often 10 to 30 years, then ends. Covers your entire life as long as premiums are paid.
Cash value None. It's pure insurance. Builds cash value slowly, on a schedule set by the insurer.
Complexity Simple to understand and compare across insurers. Harder to compare; riders, dividends, and surrender terms deserve careful reading.
Often the better fit when You need meaningful coverage for the years people depend on your income. There's a lifelong dependent, a specific estate need, or a business reason for permanent coverage.

A quick, useful starting point

7 Financial blind spots of high earners

1. Named beneficiaries override your will Beneficiary listings on investment accounts override your will entirely. Named an ex-spouse or a late parent? They still inherit, no matter what your will says…
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Let's find out what your plan needs protected.

A short, low-key call. We'll look at what you have in place, what's missing, and whether anything you're paying for has outlived its purpose.

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Common questions

How much life insurance do I need?

Enough to replace what your income was committed to: the mortgage, the years until your kids are independent, your spouse's retirement, final expenses. Add those up, subtract coverage and assets already in place, and insure the gap. The Life Insurance Needs Calculator gives you a first estimate in a few minutes.

Should I buy term or whole life insurance?

For the years when someone depends on your income, term usually fits: large coverage, modest cost, and it ends when the need does. Whole life costs far more and makes sense in narrower cases, like a lifelong dependent or a specific estate need. The honest starting question is what the coverage is for.

Do you earn a commission on insurance?

Sometimes, yes. I can put it in place as part of your plan and may earn a commission on a policy. I'll always tell you when that's the case. The analysis comes before any product, and if the numbers say you don't need coverage, that's exactly what I'll tell you.

Do I need disability insurance if I already have savings?

Usually, yes, unless your savings could replace decades of income. A long disability doesn't just pause your paycheck; it can stop retirement contributions, drain the accounts you meant for later, and add medical costs at the same time. Savings are built for months. Disability coverage exists for the years.

Do I need long-term care insurance?

Not always. Long-term care is a significant late-life cost, but insuring it is only one of three ways to handle it. Households with a few million in investable assets can often self-fund a few years of care without derailing the plan. Long-term care insurance suits the middle ground, keeping an extended stay from blowing a large hole in the portfolio and reducing the odds of relying on Medicaid, which remains a backstop for everyone. On average, care lasts about 3.7 years for women and 2.2 years for men, and you can approximate costs with the CareScout cost-of-care tool. We map which path fits your numbers.

Will you review policies I already own?

Yes, and it's often the most useful first step. We lay out what each policy covers, what it costs each year, and the job it was bought to do. Then we keep what fits, replace what doesn't, and cancel nothing until any new coverage is approved and in force.

Do you work with clients outside Florida?

Almost always. Everything is handled virtually, so where you live is rarely a barrier. The only exception is a handful of states where I'm not registered yet, and if that's you, I'll tell you on our first call.