Jennifer Raess JD, CFP®, CLU®

Jun 22, 2026

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Why Every Client Needs to Look at This Conversation: Life Insurance Through a Personal Lens

Life insurance. Two words that make people either lean in, or tune out entirely.

After watching my mom navigate the financial aftermath of losing my dad unexpectedly, I’ve come to believe this is one of the most important conversations an advisor can have with a client. Not because it’s easy. Because it matters.

What Loss Taught Me About Planning

My parents were snowbirds. A condo in Wisconsin for the summers, a condo in Florida for the winters.

For a long time they owned a house in Wisconsin, but once both kids were out of the house and settled in homes of their own, my mom had a dream: a condo in a specific neighborhood, closer to me and my sister. One day a unit came on the market. They moved fast, got the house listed, made the move, and she had her dream condo.

About three years later, I was down in Florida visiting them. It was a good week, the kind that reminds you what life is all about. We had plans to go kayaking one morning, and my dad never made it out of bed. He seemed perfectly healthy, there was no warning. One day we were planning a kayaking trip; the next, we were planning a memorial service.

What followed was shock, grief, and then eventually the work of getting the finances in order.

My mom is very financially literate, and it was still a lot of work. Both condos had mortgages, modest, but real monthly outflow she’d now be managing alone. She eventually sold the dream condo in Wisconsin and moved to Florida full time.

My mom had always been a skeptic when it came to life insurance. But I hear it at least once a month, sometimes once a week: “Boy, I sure loved that condo in Wisconsin, but I just couldn’t afford to keep both.”

Had we had the life insurance conversation early on, a death benefit could have given her the financial flexibility to keep it.

The clients who don’t think they need it

Neither of my parents had an estate tax problem. But they had real planning needs, and life insurance was one piece of it. My mom’s situation is more common than most advisors realize, clients who are comfortable, who have built something, and who have never once thought about what happens to that picture if one person is suddenly gone.

Look at your own book. Who owns more than one home? Whose income would leave a meaningful gap if it disappeared tomorrow? These are often the clients who push back hardest on life insurance, and the ones who need it most.

Vanilla’s Life Insurance Calculator helps you make the case with specifics: what cash flow does the surviving spouse need to maintain their lifestyle, what debts would need to be paid off, and what liquid assets already exist. Run them through it and have the liquidity conversation before they need it.

The clients who are just getting started

My cousin and his wife are in their early thirties, married last year, and expecting their first child. Both are working and in the wealth-accumulation stage of their lives. They’re renting, with an emergency fund of around $7,000, and no family nearby to lean on if something goes wrong.

They don’t have an estate tax problem. But they have real exposure, and planning needs they may not even realize yet.

His wife has life insurance coverage through work, which is a reasonable starting point — but employer-provided coverage typically isn’t enough to replace a full income, cover outstanding debts, and fund years of childcare and education costs. It also doesn’t follow her if she changes jobs or leaves the workforce. For a family with a new baby and no nearby support system, the gap between what work provides and what they actually need can be significant.

If something happens to either one of them, that income disappears overnight. There’s no cushion, no nearby family to step in, and grief that makes even basic financial decisions feel impossible.

Social Security offers a widow’s benefit if the surviving spouse is caring for a child under age 16, but it doesn’t fully replace the salary of the person who died, and it stops when the child turns 16. The surviving spouse then waits until at least age 60 to claim again.

The death benefit from a life insurance policy pays out at the exact moment it’s needed. Your client doesn’t have to worry about lost income or what comes next. They get the time to simply grieve.

Term vs. whole life: the coverage question follows from the need

Both my mom and my cousin’s family could benefit from life insurance, but the right kind of coverage looks different depending on where someone is in life.

For clients in the wealth-accumulation stage, the conversation starts with how much coverage is needed. The type of policy follows from there.

Whole life is designed to last for your client’s entire life. It builds cash value that grows tax-deferred and can be accessed income-tax free through policy loans. Premiums are higher but remain level throughout the policy. For clients further along, that cash value functions as a flexible, tax-advantaged reserve in retirement, available when the unexpected happens.

Term life covers a defined period and is typically less expensive early on, making it accessible for clients who need meaningful coverage now but are watching their budget. The tradeoff: if your client outlives the term and needs new coverage, premiums will be significantly higher and insurability isn’t guaranteed.

A combination of both sometimes makes sense for clients in accumulation. For clients with taxable estates, Vanilla Scenarios allows you to model life insurance held inside an ILIT, so the death benefit is available to the family without adding to the taxable estate.

The conversation your clients aren’t asking for

My mom didn’t ask for the life insurance conversation. Most clients don’t. That’s exactly why it’s yours to lead.

The clients who need it most are rarely the ones raising their hands, and by the time the conversation feels urgent, it’s already too late to have it. Run the numbers on life insurance for your client and then Use the Life Insurance Calculator to make it concrete. Show them the number. Then have the conversation this week, not someday.

The information provided here does not constitute legal, financial, or tax advice. It is provided for general informational purposes only. This information may not be updated or reflect changes in law. Please consult with an estate attorney, financial advisor, or tax professional who can advise as to your particular situation.