Crypto, Passwords, and Photo Libraries, Oh My! The Estate Planning Conversation Most Advisors Haven't Had Yet

Think about everything you've accumulated online in the last ten years. The investment accounts. The social profiles. Maybe a crypto wallet. The cloud storage that’s packed with photos (even the embarrassing ones). 

Now think about how much of that is in your estate plan.

For most people, the honest answer is: none of it.

That's the conversation I brought to the Trust & Will Financial Advisor Contributor Panel this month. From crypto to digital photo libraries, the digital side of someone's estate is growing fast and it’s often completely unplanned for. What do advisors need to know, and how are they helping clients get their digital house in order?

The estate plan as most families know it was built for a different world. The financial assets, the legal documents, the filing cabinet; that infrastructure wasn't designed with two decades of digital accumulation in mind. And for most clients, that accumulation has never made it into the plan.

The List That Doesn't Exist (Yes, I Know That Rhymes)

Bob Chitrathorn, CFP®, CPFA®, Co-Founder & CFO of Simplified Wealth Management, starts here: most clients have no inventory of what they own online.

"It's spread across platforms, devices, and accounts that no one else knows how to access," he said. "And unlike traditional assets, there's no paper trail sitting in a file cabinet."

What surfaces in conversations instead are phrases like "I have some crypto somewhere" or "my passwords are saved on my phone." Bob is direct about what those phrases actually mean: "That's not a plan. That's just a future problem."

And it's a problem with real estate planning consequences. A will or trust can only transfer what it accounts for. If an asset isn't in the inventory, it's effectively not in the plan; regardless of its value. Bob's framework for closing the gap is as follows: build a list of what accounts exist and where, document access in a way someone else could actually use, and name a person who knows what they're stepping into. "It doesn't have to be perfect," he said. "But it does have to exist."

Accumulated But Unaccounted For

Ryan Goldschmitt, founder and managing director of Geminus Wealth Partners, has a longer view on how we got here. Earlier in his career, he sold digital cameras and camera phones. He remembers telling customers they'd be amazed at how much more they'd capture with those devices.

"I had no idea how right that would turn out to be," he said. "We have created a monster of data that nobody fully anticipated, and almost none of it has ever been printed. It lives behind passwords that loved ones will never find."

His message to clients is direct: "This is not optional anymore. I tell my clients that directly." His starting point is a password manager—a single organized place where access information can be shared with someone trusted. He also points clients toward tools that platforms have quietly built for exactly this purpose. Apple's Legacy Contact feature and Google's Inactive Account Manager let users designate someone who can access their account when the time comes.

For clients who create their estate plan through Trust & Will, there's a parallel feature worth knowing about. Trust & Will's Legacy Contact allows account holders to designate a trusted person who can access their estate inventory, plan documents, and Digital Safe after they're gone—subject to proof of death and identity. It takes only a name and email address to set up.

Al Faber, CFP®, Founder of DIWY Financial Planning, adds a layer that tends to catch people off guard: the terms and conditions they agreed to and never read. Many platforms explicitly prohibit password sharing. Some—Apple being the clearest example—have provisions for account access in cases of death or incapacity. Knowing that and acting on it while there's still time is exactly the kind of thing advisors are positioned to surface.

The Photos Are An Asset Too

Charles Thomas III, CFP®, Founder of Intrepid Eagle Finance, thinks about the digital estate in two distinct halves. The financial side—crypto, online investment accounts, anything on a balance sheet—is one conversation. The sentimental layer is another. And in his experience, the sentimental layer is what actually moves clients to act.

"Less and less of that lives in a family photo album," he said. "More often it exists in a data center somewhere."

To make the stakes real, Charles tells a story from his own family. His wife's grandfather was a pilot and amateur photographer stationed at Pearl Harbor before World War II. In the weeks before the attack, he took unauthorized aerial photographs from his plane—images he had no business taking. He kept them. He survived the war. Years later, sharp and tech-savvy well into old age, he had every photograph scanned at high resolution and stored on his computer.

When he passed, a family member settling his affairs didn't know the files existed. The computer was donated to Goodwill. Everything was gone.
"A museum would have liked to have had that stuff," Charles said. He tells this story to clients roughly fifty times a year—not as a technology lesson, but as a reminder that irreplaceable things need more than one home. His rule of thumb: at least three copies of anything important, across at least two different storage mediums, never all in the same physical location. He sends clients a backup reminder twice a year because most people need the nudge more than once.

Matthew Ricks, CFP, founder of Haystack Financial Planning, keeps it practical. He asks clients to store copies of their estate planning documents in an encrypted vault through his planning software—so there's a path to them beyond whatever's filed at home. He also points out that platforms like Apple and Google already let users share photo libraries directly with family members through their account settings. It takes minutes. It requires no emergency thinking to activate.

When Crypto Is In The Picture

Cryptocurrency is its own conversation, and a different one depending on how it's held.

There's a meaningful difference between crypto held with an established custodian and crypto held in self-custody on a hardware wallet or a thumb drive in a drawer. Self-custodied crypto is a bearer asset in the most literal sense. Whoever controls the private key controls the funds. If the key is lost…or if no one else knows it exists, those funds don't pass to heirs. They don't appear in probate. They're simply gone.

Charles draws the parallel to an early-career client who walked into his office carrying a briefcase full of physical stock certificates. Getting that client to move the holdings somewhere protected (where fire, theft, or simple misplacement couldn't erase them) was its own project. This lesson transfers. "There are actual reasons why you want to hold this with an investment company," he told clients who prefer to stay off-platform. "It's much harder for it to get lost, stolen, etcetera."

Al is equally direct: clients with crypto need to make sure their beneficiaries know those assets exist and have what they need to access them. He also flags that crypto holders are disproportionately targeted by scams and phishing attempts, which makes security education as important as access planning.

Getting It Into The Plan

The digital estate touches every part of a traditional estate plan. Beneficiary designations don't cover platform accounts. A will can name an heir to a crypto wallet but can't transfer the private key. A trust can hold digital assets—but only if someone thought to put them there first.

That's why Al's recommendation is to raise it proactively, as part of the planning process itself. The platforms won't prompt anyone to act. The accounts won't organize themselves. And the families left sorting through it later rarely have what they need.

Bob puts the advisor's role plainly: "We don't need to be tech experts. But we do need to be guides." The opening question is simple enough. If something happened to you tomorrow, could someone you trust find everything that matters—and actually get to it? For most clients, the honest answer is no. That's where the conversation begins. And that's where the plan has a gap worth closing.

"Data that is inaccessible does not wait," Ryan said. "It is simply gone forever."

An estate plan that doesn't account for the digital life of a client isn't protecting everything a family stands to lose. The financial assets, the photographs, the accounts…all of it is part of the estate. The plan for them should be too.

Conversation Starters for Advisors

• "If I asked you to list every account you have online—financial, social, cloud storage—could you do it? Has anyone else ever seen that list?"

• "Where are your passwords stored right now, and could someone you trust use that information to access your accounts if they needed to?"

• "Do you hold any cryptocurrency? Is it with a custodian, or is it self-custodied? Does your family know it exists and how to access it?"

• "Have you set up a legacy contact or trusted person through your Trust & Will Account?

• "Is there any account or digital presence that generates income? Do you know what happens to that revenue if something happens to you?"

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