As a financial adviser, I have managed hundreds of millions of dollars for clients. But my own father, a retired railroad foreman, never discussed his finances with me. He didn’t want to burden me—and I never pressed the issue.

Then my 74-year-old dad was found by the police wandering the streets at 4:30 in the morning, confused. He was diagnosed with Alzheimer’s disease, went directly into a care facility and never returned to his old life.

I had to make wrenching choices about his living situation, his money and his possessions for which I was totally unprepared—because he and I had never spoken about such things.

Based on my personal and professional experience, here are the most common roadblocks put up by parents and other elderly loved ones when you try to discuss their futures—and the strategies to deal with them…


Roadblock: Your parents refuse to discuss the details of their financial lives. If you press them, they say, “Don’t worry about us. We’re fine.”

Your immediate goal: To know whether they really are financially safe and secure.

What to do…

  • Break the ice by asking for help with your own financial affairs. Say, “Dad, I’m planning to withdraw 5% a year from my portfolio when I retire. Is that realistic? How do you do it?” Asking for your parents’ advice makes it easier for them to drop their guard and open up. It often leads naturally to discussions about their finances.
  • Acknowledge that they are in control. Say to your parents, “I appreciate the fact that you’ve done well financially and that you can—and should—handle your affairs now. But if there comes a time in the future when you can’t take care of your investments or other finances by yourselves, who would you like to handle them?”
  • Frame the conversation in terms of accountability. If your parents expect you to bear any responsibility for their finances in the future, then you need to have enough information to be faithful to their wishes. Say, “Mom and Dad, if you suddenly become sick and can’t handle your finances, do you expect me to step into a crisis situation blindly? If you can’t open up to me, then don’t make me responsible.”
  • Ask your parents to go for a second opinion. If they do open up to you and you’re concerned about their financial situation, reserve direct criticism, which may make them feel inadequate. Instead, say, “I appreciate all the work you’ve done on this. Would you be open to talking to a professional to verify that your thinking is correct here?” I find most parents will reject a son’s or daughter’s financial advice, even if it is sound—but they will accept and implement an identical proposal from a qualified third party, such as a financial planner.

You even might offer to pay for their visit to the planner. Don’t attach conditions, such as requiring them to see a planner of your choosing or letting you sit in on the session.


Roadblock: Your parents complain about, or don’t seem to be keeping up with, the clutter in their home. But they refuse to pare down their possessions or even talk about how they would want their possessions dealt with in a crisis.

Your immediate goal: Make life more manageable for them—and for you—as they age.

After my father was hospitalized for Alzheimer’s, it took me the equivalent of two full workweeks to deal with his property. Example: He had hundreds of high-quality tools. I had no idea which ones he wanted to sell or give to family members or friends.

What to do…

  • Initiate a conversation about belongings as soon as you get clues that your parents may be open to it. Typically, the signal is a comment such as, “I can never find anything in this mess,” or “I would like you to have my ring someday.”

Your response: “Mom and Dad, why don’t you tell me what crosses your mind when you think about what to do with all your stuff in the future?” To start the winnowing-down process, say, “If you had to move next month, what would you keep with you forever? What would you put in storage? What would you give away or sell?”

  • Address faulty solutions. Elderly people generally offer two rationalizations to avoid dealing in a constructive way with being overloaded with belongings…

“We’ll have a big tag sale one of these days.” Your response: “Sorting through a lifetime of possessions, including cherished keepsakes, is going to take a lot of energy and emotion. You’ll need plenty of time to do it right.”

“If the time comes to move, we’ll have the Salvation Army take what we don’t want.” Your response: “Charities no longer act as haul-away services. They’ve become very picky about what they will transport from your home.”

  • Ask them to help take a huge weight off your shoulders. Say, “Mom and Dad, it will be so much harder if I have to go through all your belongings in the future myself.”

Rule of thumb: It’s natural that your parents will want to keep everything. However, I’ve found that elders who are downsizing decades of clutter generally need to get rid of one-half to two-thirds of their possessions to make a serious difference in the quality of their lives.


Roadblock: Your parents insist that they plan to remain in their home forever. You know that this may take some real planning—if it’s possible at all.

Your immediate goal: To make sure that they can handle the responsibility of staying in place as they age and that their living environment is safe.

What to do…

  • Acknowledge that you really want what they want. Say, “I’d hate to have to give up my home and move to a smaller place or a care facility. In order to stay here, what changes would you be open to? For example, what would you do if it became difficult to go up and down the stairs?”

Helpful: Your local Area Agency on Aging. This organization helps older adults remain in their homes, aided by services if necessary. Contact: National Association of Area Agencies on Aging, 202-872-0888,

  • Point out realities. It is common for parents to say, “We’ve got family and friends who could stop by and check on us if we ever needed it.” Your response: “Yes, you will be checked on some of the time, but there won’t be visitors dropping by all the time, and visitors may not want that responsibility.”
  • Accentuate the positive. Instead of focusing on limitations, focus on new possibilities. Say, “You don’t have to ever move to a smaller place, but consider how freeing an apartment would be. You wouldn’t have to worry about constant upkeep.” Or, “The extra money you would have after selling your house and buying an apartment would provide you with more security.”

Estate planning

Roadblock: Parents usually can be convinced to write a will, but getting them to update their estate plan as the years go by is surprisingly difficult. They say, “Our attorney is taking care of it,” or “Why are you so eager to make sure our will is up-to-date?”

Your immediate goal: Making sure their estate plan is current, especially if there is a major tax-law change or a death or change in marital status of a family member. My long experience with estate attorneys is that they tend to be short on follow-up unless the client initiates contact.

What to do…

  • Phrase the task of updating their plans in terms of making your job
    easier. Say, “Dad, I know you’ve done a good job planning your estate. In your view, is there anything that needs to be changed that would make my job (or insert the name of the appropriate party) as the executor easier?”

Important: If your parents are threatened or offended by your interest in their will and other estate documents, say, “I’m sorry that you’ve interpreted what I said as eagerness to get your money. My eagerness is to make sure that your affairs are the way you want them, regardless of the money.”

Helpful: The National Academy of Elder Law Attorneys offers the latest news on legal issues affecting the elderly and can assist in finding an elder-law attorney in your area. 703-942-5711,