Boomer RealitiesOct 28, 2025As we explore the themes around The Greatest Wealth Transfer in Human History, a few folks have asked me how our parents and grandparents might respond to helping the next generation. Nervous? Excited? Possessive? Overly generous? Yes. Prepared? Maybe…This is their life. This is their legacy. This is their decision. And one we have to respect. “Financial longevity—the ability to maintain financial well-being throughout an extended lifespan – is fundamental to preserving dignity and ensuring quality of life as we age. It encompasses not just having enough money to cover basic needs, but also the resources to engage fully in society, pursue personal interests, and maintain independence.” (Again, from our friends at The Milken Institute https://milkeninstitute.org/content-hub/insights/financial-longevity-key-dignity-aging)Of course we all agree with this sentiment. But the Boomers can also help their families for the inevitable. According to caring.com, “only 24% of Americans have a will in 2025, down from 33% in 2022.” That’s wild. Without the proper wills and trusts and other critical familial documents in place, a life’s work can be sent to probate courts and negotiated by lawyers.I’m reminded of The Talk I had with my father, who reminded me that he didn’t like facing his own mortality. I get it. I don’t like this conversation either. But me not liking gravity doesn’t stop the cup of coffee from falling off the table.One of the grand lessons of life that we all must confront daily is easier now, harder later versus harder now, easier later. With some thoughtful planning and courageous conversations, we can protect our families, preserve our parents’ and grandparents’ legacies, and move our families forward…
Boomer RealitiesOct 28, 2025As we explore the themes around The Greatest Wealth Transfer in Human History, a few folks have asked me how our parents and grandparents might respond to helping the next generation. Nervous? Excited? Possessive? Overly generous? Yes. Prepared? Maybe…This is their life. This is their legacy. This is their decision. And one we have to respect. “Financial longevity—the ability to maintain financial well-being throughout an extended lifespan – is fundamental to preserving dignity and ensuring quality of life as we age. It encompasses not just having enough money to cover basic needs, but also the resources to engage fully in society, pursue personal interests, and maintain independence.” (Again, from our friends at The Milken Institute https://milkeninstitute.org/content-hub/insights/financial-longevity-key-dignity-aging)Of course we all agree with this sentiment. But the Boomers can also help their families for the inevitable. According to caring.com, “only 24% of Americans have a will in 2025, down from 33% in 2022.” That’s wild. Without the proper wills and trusts and other critical familial documents in place, a life’s work can be sent to probate courts and negotiated by lawyers.I’m reminded of The Talk I had with my father, who reminded me that he didn’t like facing his own mortality. I get it. I don’t like this conversation either. But me not liking gravity doesn’t stop the cup of coffee from falling off the table.One of the grand lessons of life that we all must confront daily is easier now, harder later versus harder now, easier later. With some thoughtful planning and courageous conversations, we can protect our families, preserve our parents’ and grandparents’ legacies, and move our families forward…
As we explore the themes around The Greatest Wealth Transfer in Human History, a few folks have asked me how our parents and grandparents might respond to helping the next generation. Nervous? Excited? Possessive? Overly generous? Yes. Prepared? Maybe…This is their life. This is their legacy. This is their decision. And one we have to respect. “Financial longevity—the ability to maintain financial well-being throughout an extended lifespan – is fundamental to preserving dignity and ensuring quality of life as we age. It encompasses not just having enough money to cover basic needs, but also the resources to engage fully in society, pursue personal interests, and maintain independence.” (Again, from our friends at The Milken Institute https://milkeninstitute.org/content-hub/insights/financial-longevity-key-dignity-aging)Of course we all agree with this sentiment. But the Boomers can also help their families for the inevitable. According to caring.com, “only 24% of Americans have a will in 2025, down from 33% in 2022.” That’s wild. Without the proper wills and trusts and other critical familial documents in place, a life’s work can be sent to probate courts and negotiated by lawyers.I’m reminded of The Talk I had with my father, who reminded me that he didn’t like facing his own mortality. I get it. I don’t like this conversation either. But me not liking gravity doesn’t stop the cup of coffee from falling off the table.One of the grand lessons of life that we all must confront daily is easier now, harder later versus harder now, easier later. With some thoughtful planning and courageous conversations, we can protect our families, preserve our parents’ and grandparents’ legacies, and move our families forward…
As we explore the themes around The Greatest Wealth Transfer in Human History, a few folks have asked me how our parents and grandparents might respond to helping the next generation. Nervous? Excited? Possessive? Overly generous? Yes. Prepared? Maybe…
This is their life. This is their legacy. This is their decision. And one we have to respect.
“Financial longevity—the ability to maintain financial well-being throughout an extended lifespan – is fundamental to preserving dignity and ensuring quality of life as we age. It encompasses not just having enough money to cover basic needs, but also the resources to engage fully in society, pursue personal interests, and maintain independence.” (Again, from our friends at The Milken Institute https://milkeninstitute.org/content-hub/insights/financial-longevity-key-dignity-aging)
Of course we all agree with this sentiment. But the Boomers can also help their families for the inevitable. According to caring.com, “only 24% of Americans have a will in 2025, down from 33% in 2022.” That’s wild. Without the proper wills and trusts and other critical familial documents in place, a life’s work can be sent to probate courts and negotiated by lawyers.
I’m reminded of The Talk I had with my father, who reminded me that he didn’t like facing his own mortality. I get it. I don’t like this conversation either. But me not liking gravity doesn’t stop the cup of coffee from falling off the table.
One of the grand lessons of life that we all must confront daily is easier now, harder later versus harder now, easier later. With some thoughtful planning and courageous conversations, we can protect our families, preserve our parents’ and grandparents’ legacies, and move our families forward…