This was our second time working with planner Debbie Gallant on our finances. It was more urgent now, as we were gliding into our full retirement and plotting the next 20 to 30 years. The subject was annuities.

"The thing that worries me most about annuities," I said, "is that when you die, the leftover money could go to the company that sold them, not your heirs." She told me that was easy to avoid, but I was brought up short when she went on, with a wry smile:

"You'll be dead, so it won't really matter to you."

This, and other aspects of our work together, got me thinking about our plans and values, just as Gallant — and any other planner worth her salt — would have intended. The question that leapt to mind: Do I want to die with my last dollar spent, or even, to quote one waggish adviser, "to bounce my last check"? Or is my priority to leave something behind: help for our daughter, the Steve Mencher Podcast Studio at the local high school, money for a beleaguered charity defending causes dear to our hearts?

Professional advisers weigh in

To consider these issues in ways that might be helpful to others, I decided to talk with a few financial planners, and some planning clients, about the money that may be "left over" when we die, and why that might still matter to us.

Bill Leeb, a Baltimore-area financial adviser, has a response ready for clients who walk in the door of his wealth management firm hoping to spend their assets down to zero on their deathbed. "'That's great,'" he says. "'You tell me when that's going to happen, and I'll land you right on the numbers.'

"And there's part of the problem," Leeb adds. "We don't know when that's going to be, [and] it's a big risk if you're wrong."

In my conversations with Leeb and other planners on this subject, two parallel thoughts emerge. Their work starts with trying to make sure you don't outlive your money, and an essential part of that is managing the risks of care needed in very old age or from unexpected serious illness.

Long-term care insurance debate

Mark McCallum, managing partner at Carson Wealth in Palatine, Ill., has this advice about handling the risk that the cost of care in our last years will rob us of that last dollar: "I would say for clients with a million dollars in this situation, or maybe even two, we would be talking about long-term care [LTC] insurance at retirement and saying, 'This is your chance to make this decision. It's not going to offset all of the cost of LTC. But if you're thinking about a legacy for your heirs, this will help to achieve that. You're just transferring the risk to the insurance company so that you can maintain a legacy.'"

Carol, who asked me to change her name in order to speak freely about her family's finances and planning decisions, says she's decided to take the LTC option off the table for her and her husband. "My mother paid into a LTC policy for at least 35 years," she says, "and when the time came for her to go into assisted living, we had an interview with the insurance company and they said she didn't need assistance at that point."

When her mother was 89 and very frail and unwell, Carol and her husband had another meeting with the LTC company, and they came and evaluated her. "And they said, 'Oh, OK, she's now meeting our standards,'" Carol recalls. "We got one check from them for $38 and another check for $150 and then she died. This is not a direction my husband and I are going to take."

My wife and I made a similar choice, mostly because we'd started thinking about LTC options late, when our premiums would have been prohibitively high. We've got serious money put aside that we can use when we can't take care of ourselves any more, so-called self-financing of LTC. Will it be enough? Who knows?

But I still wasn't quite answering my own question. Say the risk of outliving your money is mitigated with or without an LTC policy, should we — could we — develop a plan to spend down our dollars for maximum enjoyment and fulfillment during our lives? This could include travel, entertainment, a second home to escape the heat of summer or chill of Baltimore winters. I pressed this with Leeb, who was ready for the question.

Surprisingly little difference

"Say you have a million bucks that has been accumulated in 401(k), 403(b), and IRA [plans], all kinds of stuff," Leeb says, "and you invested those dollars averaging, say, 7 percent [return] a year. You could withdraw $5,800 a month, or [about] $70,000 a year, every single year for the rest of your life and never run out of money, because you're basically spending the return. You're making $70,000, you're spending $70,000.

"So, the question is, what if you knew that you were going to live 30 years? And the goal was to deplete it in those 30 years. The day you die, you spend your last dollar, right? To do that would allow you to spend $6,600 a month, $800 a month more than with the first scenario, and $800 times 12 is $9,600. So instead of $70,000 dollars a year, you'd be able to spend $79,000-plus a year. That's not a huge difference.

"The question becomes, is it worth the risk that you're going to live 31 years or 32 or that along the way you might have other needs that will require additional dollars? So again, even if people say, 'I want to spend my last dollars on taking my last breath,' people are often surprised to learn how little difference that would result in, in order to achieve the outcome where they run out of money."

Think about the next generation

For those whose resources allow them some flexibility to plan for something "left over," whose level of savings, good luck and good health combine to facilitate passing some money on to another generation, here's some wisdom from federal government retirees Jim and Janet Douglas of Takoma Park, Md.

"Our kids," says Jim, "face a less certain and optimistic future than we had when we were coming out of college and starting careers. I'll just say in my family, me and my siblings, we didn't really rely at all on our parents for our ability to get [launched].

"I think we had opportunities that our kids don't have for the types of jobs that are available, also just the cost of living [is higher]. Housing is a relatively greater expense for a growing household now than it was when we were young and [there's] child care and things like that. So, I think one of the things that affects our planning is what we can do to help them."

Assuming we've got another 20 to 20-plus years, there's going to be a lot of needs that they would have between now and then, and it would be nice for them to get some money when we're gone, but they probably need it more now than they do then. This thought is driving assistance they're offering today to their children.

Charities to help

For Carol and her husband, who don't have children or anyone in their families to whom they'd like to make a major gift, socially relevant contributions, both large and small, are top of mind as they consider financial "leftovers."

Years ago, Carol bought a rental property that has nicely appreciated, and they plan to give it to the longtime tenant. The local cat rescue and the nonprofit Doctors Without Borders are in their will. But closest to their hearts is a plan to donate their 7-acre property, along with a neighbor's 11 acres, to help create an addition to a national scenic trail that abuts the properties.

"We have deer and possums, and gazillions of squirrels, owls, hawks, lots of birds — about 150 different species according to my backyard count," Carol says. "I'd love to preserve that."

Carol has learned how that prospective donation will be welcome only if it comes with adequate funding for upkeep. Recently, she says, "we hired a crew to come in here and remove all of the invasive species: buckthorn and honeysuckle, invasive bittersweet and garlic mustard, Dame's rocket and all the nasty stuff that creeps into a woodland if you're not on it all the time." Money for this work in perpetuity will be attached to their donation.

So, where does that leave our own finances? I feel we're a little stuck, saving a big chunk of change for possible catastrophe at the end.

But I'll be taking a closer look at how we can help our daughter while my wife and I are both alive, and how we might ramp up our contributions to organizations we care about now, rather than leaving it all for that last moment.

Postscript

What we didn't know when we met with our planner Debbie Gallant last year was that she was dying, and would be gone within a few months. I wish we had discussed some of these big questions with her in more depth, but this dialog with other planners and clients, which I'll devote to her memory, will have to do.