Why knowing when to transfer wealth is only one part of preparing the next generation to receive it.
This article builds on a recent argument by wealth advisor and Forbes contributor Jonathan Shenkman about the importance of timing in meaningful inheritance. Read Shenkman’s original Forbes article.
Jonathan Shenkman recently made a compelling argument in Forbes: inheritance can have radically different meaning depending on when it reaches the next generation.
In his article, How To Shape A Meaningful Inheritance While You’re Still Here To See It, he contrasts wealth arriving late in life with a smaller gift arriving decades earlier – perhaps when someone is buying a first home, funding an education, raising a family, or building something of their own.
The insight is simple but important: the value of an inheritance is not measured only by its size. Timing can change its impact.
Shenkman also makes a broader point about the traditional approach to inheritance planning. In his words:
“That approach is not wrong, but it is incomplete.”
Jonathan Shenkman
AIF®, Forbes
That distinction matters. A will or trust can establish intent and legal authority. It can define who should receive what, under which conditions, and through which structure.
Intentional lifetime giving adds another dimension: when should some of that wealth move so that it can make the greatest difference?
But there is still another question.
Will the people who eventually inherit know what actually exists?
Quick answer
Meaningful inheritance has at least two separate dimensions.
Meaningful inheritance combines timing and visibility: wealth should reach people when it can matter, while beneficiaries also need enough visibility to understand what assets exist and where to begin.
- Timing determines whether wealth arrives when it can make a meaningful difference.
- Visibility determines whether the wealth that remains can actually be found when the time comes.
The gap timing alone doesn’t close
Imagine a family that gets intentional giving exactly right.
Parents help their children when they are buying their first home. They contribute to education. They explain why they are giving and what they hope the money will make possible. They use those moments to build financial responsibility rather than simply transferring wealth.
That part of the plan works exactly as intended.
Years later, however, the estate still contains an old brokerage account, an insurance policy, several investment accounts, and perhaps digital assets or a crypto wallet that no one else knows about.
The legal documents may be perfectly valid. The beneficiaries may be clearly designated. The family may understand the values and intentions behind the estate.
But they cannot act on assets they do not know exist.
Key InsightThe giving strategy worked. The visibility strategy did not.
That is a different inheritance problem.
Estate planning can establish rights without creating visibility
Traditional estate planning and inheritance visibility solve different problems.
A will or trust can establish legal rights, responsibilities, and authority. It can document who should inherit and who has the authority to administer an estate.
What it does not necessarily provide is a continually updated picture of everything a person owns.
Financial lives have become increasingly fragmented. A person may have bank and brokerage accounts, insurance policies, employee benefits, investment platforms, digital wallets, online businesses, domain names, and other assets spread across multiple institutions and jurisdictions.
Some may have been opened decades apart. Some may never have been discussed with family members. Some may not even be known to the lawyer who prepared the estate documents.
The gap between having a legal right to inherit an asset and having enough awareness and information to locate, claim and access it in practice.
This creates what we at DGLegacy call the Invisible Asset Problem: an existing asset can become difficult for loved ones to identify or handle because they do not know it exists, where to find it, or where to begin.
Digital assets make discoverability even more important
Historically, physical records often created clues. A bank statement might arrive in the mail. An insurance policy could be found in a filing cabinet. Correspondence from a financial institution might eventually point a family toward an asset.
Digital financial lives can leave far fewer obvious physical prompts.
An investment account may exist only inside an app. A crypto wallet may be known only to its owner. A digital asset may require specific information before a beneficiary can even begin the process of locating or claiming it.
This does not mean digital assets are inherently inaccessible. It means awareness has to be planned for deliberately.
As more of our financial lives become digital, the question is no longer simply whether appropriate legal documents exist. It is also whether somebody besides the owner has enough visibility to know where the search should begin.
That is one reason digital asset inheritance is becoming a distinct part of modern inheritance planning.
Two questions, not one
Timing and visibility address two different failure modes. A complete plan needs to consider both.
Timing
When should wealth move?
“Will it arrive at a moment when it can materially change someone’s opportunities, choices, or trajectory?”
Visibility
Will the family know what exists?
“When the time comes, will beneficiaries know what has been left, where it is held, and where to begin?”
Shenkman’s argument raises an important question: when should wealth move?
For many families, the answer may indeed be earlier than traditional inheritance planning assumes. A well-structured gift made while the giver is alive can provide opportunity at precisely the moment it matters and allow the giver to offer context, guidance, and experience alongside the money.
But every inheritance also contains a second question: will the people who inherit know what there is to inherit?
These questions should not be collapsed into one.
A family can have excellent visibility into an estate but transfer wealth only after the moments when it could have had the greatest impact. Or a family can execute lifetime giving thoughtfully and still lose awareness of assets that remain behind.
Neither problem is solved simply by getting the other one right.
What complete preparation looks like
The strongest inheritance planning combines these ideas rather than choosing between them.
Give with intention when it can matter.
Consider which resources may be more meaningful when transferred during life, with context and guidance.
Maintain a current picture of what remains.
Keep an accurate inventory of important financial, digital, business, and other assets instead of relying on memory alone.
Separate legal authority from practical discoverability.
Use wills, trusts, and beneficiary designations for legal intent while making sure the appropriate people have enough visibility to know what exists and where to begin.
Plan deliberately for digital assets.
Where financial lives include investment apps, digital accounts, crypto, or other digital assets, digital legacy planning can help preserve transparency and awareness.
None of this competes with intentional lifetime giving.
A thoughtfully structured gift made at 28 instead of decades later may still be the gift that changes someone’s life.
A meaningful inheritance needs to arrive when it can matter
And whatever remains needs to be findable.
The families who plan for both are not expecting the worst. They are simply making sure the people they love are not left with an unnecessary puzzle.
About DGLegacy®
Inheritance visibility for modern financial lives
DGLegacy® is a secure digital legacy planning and inheritance app designed to help people catalogue their financial and digital assets, designate beneficiaries and trustees, and keep that information current. This way DGLegacy gives transparency and awareness for loved ones, so they can easily locate, claim and access what’s been designated for them.
