The Hardest Conversation I’ve Ever Had With a Client

By Mike McCarthy, CPA/PFS, CFP®

In this business, you sit across from clients in some of life’s most difficult moments: job losses, market crashes, divorces, and deaths. But if someone asks me to name the hardest conversation I’ve ever had, I don’t hesitate. It involves a couple I’ll call Carol and Ray.

A Lifetime of Work, Built Into One Business

Carol and Ray had spent their lives building something. Decades of running a business together, long days, real sacrifice, and a level of commitment that most people never see up close. Like many business owners, almost all of their net worth was tied up in that business.

They had been listening to our radio show for years, and when they finally decided it was time to sell the business and start planning for retirement, they called us. They never made it to that first meeting.

When Everything Changes in an Instant

Before their first appointment, Ray suffered a head injury that quickly led to early-onset dementia. A man who had been sharp and capable his whole life was suddenly unable to care for himself.

The conversation shifted entirely. We were no longer talking about retirement income. Now we were talking about long-term care, which is one of the most financially and emotionally complex situations a family can face.

Long-term care costs are staggering. Depending on the level of care required, a family in Maryland can find themselves spending $12,000 to $15,000 per month, indefinitely. For a couple whose wealth was primarily tied up in a business they hadn’t yet sold, the financial exposure was severe.

We began working with Carol on long-term care planning. We reviewed her assets alongside a specialized elder care attorney and began mapping out her realistic options. The planning options in situations like this can work, but they are not simple. The financial decisions involved are time-sensitive and largely irreversible.

The Weight of an Unanswerable Question

Every month for about six months, I’d check in with Carol. 

How is Ray doing? What are the doctors saying? How are you holding up? 

Every month, the answer was the same: 

We don’t know. He’s stable, but unchanged. He may live for many more years. He may not.

Carol wanted guidance on when to move forward with a major financial decision, one that, once made, could not be undone. I couldn’t give her a timeline, and neither could her doctors. The decision had to come from her.

That weight is hard to describe from the outside. She was caring for a spouse who was present but unreachable. Month by month, savings were draining. The business she and Ray had built still needed managing, with no end date in sight.

After six months, Carol made the decision to move forward.

The planning required real sacrifice on her part. The financial steps involved were significant, carried immediate tax consequences, and could not be undone. Our team and the elder care attorney executed everything carefully, and it worked as intended.

A month later, Ray passed away.

Her Response Surprised Me

I’ll be honest. My first thought in the immediate aftermath was that Carol would never want to speak to me again. She had been through months of uncertainty, made irreversible financial decisions at considerable cost, and Ray was gone within a month of it all being completed. From the outside, it could easily have felt like she had gone through all of that for nothing.

Carol’s response has stayed with me. She said we had explained everything fully: the risks, the tradeoffs, the uncertainties. She had made the decision with clear eyes, and she knew it. She wasn’t angry, she had closure, and because of the planning we’d completed, her financial future was intact.

Had Ray lived another two or three years without a plan in place, the outcome would have looked very different. The business Carol and Ray had built over a lifetime would likely have had to be sold quickly, for whatever the market would bear, to keep pace with care costs. Everything they had worked for could have been gone.

Instead, Carol still has her financial stability. Today, she won’t make a major financial decision without calling us first.

When the Work Gets Hard

People who have built businesses know that the job description never captures everything the job actually requires. Financial advising is no different.

The credentials and the technical knowledge matter. And so does the willingness to sit with a client through months of difficult uncertainty and do the work precisely when the moment finally comes.

Long-term care is one of the conversations families most often postpone. The costs are real, the decisions involved are largely irreversible, and the timeline is almost never what anyone expects. Having this conversation before a health crisis changes what’s available to you.

If you’re approaching retirement and you and your spouse haven’t seriously thought through what a long-term care event would mean for your finances, we recommend starting that conversation. This is one of the things we walk through during our complimentary Financial Physical®. Call us at 410-823-7283 or visit financialconsulate.com to set up a time.

Frequently Asked Questions

What is long-term care planning, and why does it matter? 

Long-term care planning is the process of preparing financially for a time when you or a spouse may need ongoing assistance with daily living, whether at home, in an assisted living facility, or in a nursing home. Without a plan, costs can quickly deplete a lifetime of savings. Monthly expenses in Maryland commonly range from $12,000 to $15,000, and most families aren’t prepared for how fast those costs accumulate.

When is the right time to start thinking about long-term care? 

The right time to start thinking about long-term care is well before you need it. By the time a health crisis forces the conversation, your options narrow significantly. The planning process itself takes time, and some of the decisions involved are irreversible. For business owners whose wealth is tied up in a single asset, early planning preserves the most flexibility.

What happens to a business owner’s assets if a spouse needs long-term care? 

When a spouse needs long-term care, and there is no plan in place, a business owner can face a difficult choice: spend down personal savings to cover care costs or attempt to sell the business quickly and on unfavorable terms. Either path can undo decades of financial work. Proactive planning with a financial advisor and elder care attorney can help shield assets and keep options open.

What does a financial advisor do in a long-term care situation? 

In a long-term care situation, a financial advisor reviews your assets, models different scenarios based on potential care timelines and costs, and helps coordinate with specialists such as elder care attorneys. Because many of the financial decisions involved are time-sensitive and cannot be reversed, having experienced guidance through the process matters a great deal. And working with a fee-only financial advisor provides confidence that your best interests will be prioritized at all times.

About Mike

Michael McCarthy, CPA/PFS, CFP®, is the President and CEO of The Financial Consulate, a wealth advisor specializing in tax, estate, and retirement planning for small business owners and entrepreneurs.