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General “Dotson,” 81, had been my client for more than 20 years. He has always been a model for me when thinking about intentional best outcomes for my clients and their families. He’s also a model for who I want to be like.
He’d been widowed for two years and was taking a hard, honest look at what was coming next when I heard him say to his adult children:
“I’m going to try, and I’m probably going to fail, but I promise I’ll try to accept more help. I won’t like it. I don’t like being treated like I can’t do something. Actually I hate it. I’ve always been the captain of my own ship. Unless you outrank me, which you don’t, I’m usually the one giving the orders, not taking them. Your mom outranked me, of course.
“But here’s the thing. I love you more than I love being the captain. I promise I’ll try. I guess I’ll need some practice.”
He turned his eyes from his two adult kids and towards me – “Any suggestions, Tom?”
What is the measure of a man?
In the years following this conversation, he didn’t just try, but absolutely succeeded in asking for and accepting help from others.
He and his wife, “Sarah,” hired me right after the Dotcom crisis. He was a few years into his retirement, and with the Nasdaq going bananas, he growled that he had no idea what to make of the markets and needed to call in reinforcements. So I got to work.
“Yes, sir,” was how I typically started my responses to his questions and requests. It just seemed to fit the situation. Our first few years working together were formal and pretty regimented.
During a meeting at their house, that dynamic changed. After an odd pause, the General asked me an unexpected question. Across the kitchen table Sarah opened her palms with a baffled look when he asked, “Tom, what is the measure of a man?”
Sarah looked at me as if to say, ‘I have no idea what he is talking about.’
Almost involuntarily I blurted out a lyric from a song I’d heard recently. No consideration at all in my head, “Sir, the measure of a man is a measure of love and respect. Hard to earn, easily burned.” It felt a bit like cheating.
But after a few moments, he responded, “Good answer. It’s time we got to the hard work then. The first thing you are going to do is to start calling me ‘Dave’ and knock off the ‘sir’ shit.”
And from that point forward, “Dave” and Sarah showed me some of the most effective ways families can communicate their priorities to me as their advisor, so I could translate their motivations into actionable advice for over 25 years.
Because they were so thoughtful, thorough, and transparent about what was important to them, I learned that even the most heartfelt priorities change over time. Life happens. That lesson influences me to this day.
The most important things
The sequence of Dave’s most important things—things that involved money but were always about something else—was as follows:
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Secure Dave and Sarah’s lifestyle under all circumstances
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Help their children establish their own new households and careers
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Underwrite the education of their grandchildren
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Support veterans charities with Dave and Sarah’s “time, talent, and treasure”
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Participate financially in social efforts of their faith community
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Spoil their grandchildren, occasionally with the permission of their parents
Then, Dave’s priorities changed, and kept changing, as Sarah’s dementia progressed:
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At first, he wanted to be Sarah’s primary caregiver. He felt that no one else could or should do it. But of course he burned out.
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Then, the priority became staying in their home, so he accepted caregiving help for Sarah and support for himself.
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When in-home care wasn’t enough, staying together became more important than staying in their home, and they moved to assisted living together.
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Ultimately, his priority was to ensure a comfortable and dignified dying process for Sarah when her health failed, while keeping the kids supported and close as they lost their mom.
Practicing asking for help
After Sarah died, we found ourselves at my conference table, brainstorming ways that Dave could practice asking for help. Maybe start using Uber before he couldn’t drive. Get his groceries delivered. Automate some of his bill payments. Thin out the rest of his inventory that he didn’t need. Get his kids onto accounts. Lock down passwords.
All the while, Dave reminded me that he could still do all of these things. He just didn’t want his kids to have to deal with “the bullshit that’s coming.” He wanted his last years to be as burden-free on his kids as possible.
Receiving help, he told me, was the hardest thing he ever attempted. Harder than a decorated tour in Vietnam, harder than caregiving for a memory-impaired wife. I told him that was hard to believe.
But Dave insisted.
“All the other stuff was about other people. Bigger things. I could always fight, endure when duty called. But getting all of this help is really about me. Just me. And I feel like I’m giving up on myself somehow.
“It’s not though. I’m not giving up. It’s about giving something to my kids. I’ve been a hard-ass my whole life. They know. They are terrified that I’m going to fight, well, everything when things start slipping.
“But I won’t, that’s why I’m practicing, because this is hard. If I don’t practice receiving help, God knows it won’t come naturally. But I promised that they are going to see a Dad who is at peace with whatever comes. I want that for them.”
And here it is, years after Dave died, I still wonder: Could I do the same?
The not-golden age of generosity
Since our views of accepting can be shaped by our understanding of generosity, I can’t help but consider the current lack of generosity. I wonder, if we’re all getting used to not giving, how does that affect our ability to receive? How can we get ourselves ready to receive assistance as we age if it looks like no one wants to do any giving?
If I end up not volunteering or participating in my community as I get older, what does that do to my mindset when I might become more dependent myself?
Of course, the reality of the so-called giving crisis is more complex than it often appears in the headlines. While monetary giving has declined, many other forms, including mutual aid, have been increasing.
As a Vox article put it, “Measuring generosity is a bit like measuring ‘happiness’ or ‘loneliness’ — weird. Trying to nail down a feeling with statistics requires quantifying something that can’t really be quantified.”
I consider the generous lessons Dave left me with and how I can try to be more like him as I age. His way of modeling interdependence is unquestionably a type of generosity that slips through the traditional measures.
WWDD: 7 principles for our future selves
As I got to know him, I learned Dave was a devout Catholic. His faith in the church and his country was unwavering. He didn’t expect those institutions to be perfect. Institutions inevitably break, he said, and then people inevitably repair them. If he were around to provide input on this post, I'm sure he’d offer a variant of WWJD—What would Jesus do?
I’ll take that inspiration and share my best attempt at What would Dave do?
The WWDD principles for the key inflection points in the last third of our lives:
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Always know your SITREP (situation report).
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Current status
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Recent developments that matter
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Immediate issues or concerns
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Planned action or next steps
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Discipline and practice strengthen performance and character.
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You are accountable for you.
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Facing and overcoming fear and change is necessary for growth.
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You can’t do everything by yourself.
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Commitment to mission (aka your most important priorities) inspires others, and communication of mission enables others.
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And finally, preparation and planning can reduce uncertainty, enhance confidence, and support the things you care the most about.
Aye aye sir, here we go.