Family Complexity
The Conversation Nobody Wants to Start: Long-Term Care Planning, and What to Know Before You Need It.

Robert Tilson, CFP®



There is a specific moment in our planning conversations that I have come to recognize. It usually happens after we have been through the retirement income picture, the Social Security timing, the tax projections. The client pauses. And then, quietly: “What happens if one of us needs care?”
It is the question that sits underneath almost every retirement plan we build. And it is the one that most households put off the longest.
This piece is about long-term care planning: what it actually involves, when to start thinking about it, and how to plan for long term care in a way that fits into the broader financial picture without overwhelming it. If you have been meaning to have this conversation and have not, this is a reasonable place to start.
Why long-term care planning is different from other retirement planning
Most of the financial planning work we do with clients is about things that will happen. You will retire. You will draw Social Security. You will take required minimum distributions. The amounts and timing may vary, but the events themselves are predictable.
Long-term care planning is different because it is about something that may or may not happen. According to the U.S. Department of Health and Human Services, someone turning 65 today has almost a seventy percent chance of needing some type of long-term care services and supports in their remaining years. But the range of what that care looks like is enormous. For some, it is a few months of home health assistance after a surgery. For others, it is years of memory care in a residential facility.
The cost range is just as wide. Home health aides, assisted living facilities, and memory care programs each carry annual costs that can reshape a retirement plan in a single year. The figures vary by region and level of care, but in our area the numbers are large enough that most families are surprised when they see them for the first time.
The challenge of care planning in long-term care is not that the costs are high, though they are. It is that the uncertainty makes it difficult to plan with the precision that most people are used to applying to the rest of their financial life. You cannot model a long-term care event the way you model a Social Security claiming decision. You can only prepare for the range of possibilities and make sure the plan is resilient enough to handle them.
The three ways families typically fund long-term care
When we help clients think through how to plan for long term care, we usually describe three broad approaches. Most families end up using some combination of the three.
The first is self-funding. This means setting aside enough in liquid assets, or designating a portion of the portfolio, to cover a potential long-term care event from savings. The advantage is flexibility. The disadvantage is that you are reserving a meaningful sum of money against an event that may never happen, which can make people feel like they are over-saving or under-spending in the years when they are healthy.
The second is long term care insurance. Traditional long-term care insurance policies, which pay a daily or monthly benefit when you need care, were once the standard recommendation. The market has changed significantly. Many carriers have left the market, and the premiums on remaining policies have risen substantially. For clients in their mid-fifties, the policies can still be reasonable. For clients approaching seventy, they are often prohibitively expensive or unavailable.
There is a newer category of hybrid policies that combine life insurance or annuity features with long-term care benefits. These long term care annuities and hybrid products have become more common because they address one of the main objections to traditional long-term care insurance: the feeling that you are paying premiums for decades and might never use the benefit. With a hybrid policy, if you never need care, the death benefit or annuity value still passes to your heirs. The trade-off is that the long-term care benefit is typically less generous than a standalone policy. Hybrid products can also be complex, often require a large upfront premium, and vary widely in their terms and costs.
The third is Medicaid, which can cover long-term care for individuals who meet strict income and asset limits, subject to a look-back period on prior transfers. For the clients we work with, Medicaid is generally not the primary plan, but it is worth understanding as part of the broader landscape, particularly for families with a parent who may not have had the resources to plan ahead.
When to start planning for long term care
The question of timing comes up often. When should you start thinking about this?
The honest answer is that the best time to address long-term care planning is in your mid-to-late fifties, when you are healthy enough to qualify for insurance if you choose that route, and far enough from retirement to integrate the planning into your broader financial picture. If that window has passed, it is still worth starting the conversation.
What we try to avoid is the situation where a client comes to us at 72 saying they just realized they have no long-term care plan. At that point, the insurance options are limited, and the self-funding math may require adjustments to the retirement spending plan that feel uncomfortable.
Senior financial planning that includes a long-term care component does not need to be elaborate. It needs to answer three questions. What is the most likely care scenario for this household, given family health history and current health? What would that scenario cost, roughly, in today’s dollars? And which of the three funding approaches, or which combination, best fits the client’s overall plan?
The family conversation that should come first
There is one aspect of senior care planning that is not financial at all, and it may be the most important.
Before you decide how to fund long-term care, it helps enormously to have a conversation about what kind of care you would want. Where would you prefer to receive care? At home? In a facility? Near which family members? What level of independence matters most to you? What would you want your spouse to do if you needed full-time care and they did not?
These are not comfortable questions. But they are easier to answer now, when they are abstract, than later, when they are urgent. And the answers shape the financial plan in meaningful ways. A client who is committed to aging in place at home needs a different funding strategy than a client who is open to assisted living.
In our experience, families who have this conversation before it is needed tend to approach the decision with more clarity when the time comes. The financial plan can absorb the cost of care more gracefully when everyone knows what they are planning for.
How long-term care planning fits into the rest of the plan
One thing we want to be clear about: planning for long term care is not a separate exercise from the rest of your financial plan. It is a layer within it. The decisions about insurance, self-funding, and care preferences interact with your retirement income plan, your estate plan, your tax strategy, and your legacy goals.
For example, a Roth conversion strategy in the years before retirement can increase the pool of tax-free money available to fund a future care event. An estate plan that includes a trust may need to be structured differently if long-term care is a realistic possibility. The spending guardrails we set for early retirement may need a wider corridor to accommodate the possibility of elevated expenses later.
This is why we raise the topic even when clients would rather not discuss it. It is not because we want to dwell on difficult possibilities. It is because addressing them early gives the plan more room to work.
Starting smaller than you think
The families who handle long-term care best are rarely the ones who built the most elaborate plan. They are the ones who started the conversation early enough that the plan had room to evolve. A thirty-minute discussion about preferences and a rough cost estimate is enough to begin with. The rest fills in over time.
This is one of the conversations we have most often with the families we work with, and it is one of the ones we are most glad to have had when it turns out to matter. When life gets complicated, we show up. Having this conversation early is part of how we do that.
This material is for informational and educational purposes only and is not personalized investment, tax, or legal advice. The strategies discussed may not be appropriate for everyone, and results depend on each person’s circumstances. Tax laws are subject to change. Consult your own tax and legal advisors regarding your situation. Tilson Financial Group, Inc. is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training.
Next Up

Tilson Financial Group brings clarity, confidence, and presence when it counts.
Clarity, once a month
Market perspective and planning reminders from the Tilson team. Short, practical, and no more than once a month.
The Tilson Financial Group, Inc. is a Registered Investment Adviser registered with the Securities and Exchange Commission. The material provided is for educational purposes.
© 2026 Tilson Financial Group. All rights reserved.









