Weekly Love Letter 10/10/25 - Secret #6: America’s most expensive secret is about to wreak havoc on families everywhere
There’s an unseen, silent epidemic that’s about to have a tidal wave of impact. And, I don’t see many people talking about it.
In fact, that’s the problem.
It’s called the “Silver Tsunami” or “the Great Wealth Transfer” … perhaps you’ve heard of it?
Whether you have or not, you’re likely part of it. Or will be impacted by it.
Over the next twenty years, the remaining living members of the Silent Generation and the early Baby Boomers will die and pass more than $100 trillion to their heirs — the largest transfer of wealth in human history.
Once you read today’s love letter, please hit reply and let me know which part of this massive wave is going to impact you and how you are preparing.
Are you a Boomer passing on wealth, or receiving it from a parent of the Silent Generation?
Or are you Gen X caring for aging parents and kids?
Or a solo ager wondering who will care for you, and what you’ll do with your wealth?
Or, are you a Millenial/Gen Z who will be on the receiving end of this Great Wealth Transfer?
Wherever you are, it’s time to prepare, now. And, today’s Life & Legacy Secret is here to get you prepared.
Life & Legacy Secret #6:
Talk About Money, Early & Often
While it’s not the case that “the financially wealthiest families” talk about money early and often because I certainly know plenty who don’t, what I have found is that the holistically wealthiest families do.
So let’s first of all talk about what I mean by “holistically wealthiest” families.
Holistically wealthy families aren’t just financially rich. They are rich in relationship, emotionally rich, and connected with each other. They are rich in their spiritual lives. They are rich in their creative abilities, and in their know of their creativity and their resourcefulness.
Their relationship with money is an outward expression of their wealth, and holistically wealthy families who have created financial wealth and maintained it over time -- and not succumbed to the common tale of “shirtsleeves to shirtsleeves in 3 generations” - talk about money, early and often.
Yet, only 70% of families will talk about money before a loved one dies (or becomes incapacitated), and the ability to have conversations about money is over.
What happens then?
Oftentimes, chaos. Relationships destroyed due to conflict that could have been avoided.
Families stuck in a public, crowded court system, when well-timed conversations and action ahead of time could have resulted in a private, easeful process.
Instead of a legacy of love, anger, hurt and resentment will pass from one generation to the next.
And here’s the thing …
It’s not themoneythat will break families apart.
It’s thesilence.
Study after study shows that when inheritances turn into conflict, it’s almost never about the numbers. It’s about what wasnever said— the conversations about money, meaning, and intent that were postponed until it was too late.
Wealth advisors call it“communication breakdown.”
I call itthe silence that destroys families.
The Secret No One Talks About
Parents often think they’re protecting their children by not talking about money.
They worry it will make them entitled, or anxious, or fight.
Or, maybe, they just don’t know what to say.
How to say it.
When to say it.
So they say nothing.
And the kids don’t know how to ask.
What to ask.
When to ask.
They don’t want to seem greedy, entitled, needy.
So they say nothing.
The parents.
The kids.
But silence doesn’t protect.
Silence confuses.
Silence creates chaos.
Silence stunts growth.
Because when people don’t have information, they fill in the blanks with stories —
stories about who was loved more,
who was trusted less,
and what mom and dadmust have meantbut never said.
By the time the will is read, those stories are cemented.
And the cost of that silence isn’t measured in dollars —
it’s measured in distance.
What Wealthy Families Do Differently
The wealthiest, most enduring families know this truth:
Love that’s never spoken becomes resentment that can’t be undone.
That’s why wealthy families normalize talking about money early — not as transactions, but as values. They gather their children around the same table where they used to share holiday meals, and they start the conversation with something like:
“We have financial resources that you’re going to receive when I die, and you’ll need to manage for me, if I mentally decline before I die. I’m ready to talk about that, so we all know what matters about that.”
It’s simple. It’s human.
It replaces silence with story.
Your Action Step
If you haven’t yet talked with your loved ones about your intentions — start small.
Write a single paragraph that begins with:
“Here’s what I want you to know about what the money I have means to me … ”
Don’t focus on numbers. Focus onmeaning.
This one act can begin the process that will prevent decades of confusion, mistrust, and heartbreak.
Because money without context creates chaos.
But money wrapped in love creates legacy.
The Great Wealth Transfer is already underway.
You can’t control the markets, the tax code, or how your heirs will use every dollar.
But youcancontrol the message that travels with your wealth —
the part that says,
“I trust you. I believe in you. And here’s why this matters.”
That’s how families stay connected, generation to generation.
To your eyes wide open life,
Ali
P.S. Did you sign up for the Financial Liberation Challenge yet? It officially starts on 10/20 with the Liberate Masterclass - a 90-minute+ session that will open your eyes to a new relationship with money - and there’s some pre-game goodness you won’t want to miss, like the 9 ways to save money on your taxes report coming out next week.
