One of these days we’ve got to get organized.

When we try we often try harder

Geting there is half the battle

Sound familiar? You bet it does – and for good reason.

We’re drowning in the sea of papers, snapshots, receipts, recipes, legal agreements, contracts, and other documents we’ve inherited and accumulated, but have rarely organized and prioritized. Despite our best intentions, we dread the prospect of organizing and filing your papers, snapshots, receipts, recipes, legal records contracts, and the myriad of other documents that we’ve amassed during the course of living our lives.

Some of these documents are invaluable and irreplaceable – as I learned the hard way when my grandmother suddenly fell ill and we couldn’t find her medical records. By the time we did, days later, valuable time had been lost. That one experience taught me that the consequences of document disorder could be very serious.

It also got me thinking. I’ve always loved history, but felt that much was missing about actual historical figures. For example, we know a great deal about the Roman Empire’s politics, military conquests and social structure, but surprisingly little about Julius Caesar’s personal life. I realized that this same loss of personal history impacts all of us if we don’t take control of which documents we keep and how we protect them.

Having worked in the IT industry my entire life, I realized that the only way to keep these vital records safe, secure and accessible was to make digital copies impervious to fire, flood or other catastrophe. I also learned that today’s cheap (even free) digital and online storage didn’t do the job – and that the situation was getting worse.

But that’s not the most critical problem we’re facing.


You heard me. The entire point of going through all of that stuff is to find the really important items – wills, trusts, deeds, mortgages, insurance policies, priceless photographs, and the like – and to make sure that they’re safe, secure and accessible. Not just by us, but by others (especially future generations) of our choosing. (Ask anyone who’s been through a life-changing fire, flood or other disaster.)

No problem, you say! After all, there’s cheap (even free), unlimited, password-protected digital and online storage. Sounds great…until you start digging deeper.


Organization, not Accumulation

It turns out that there are several fundamental, irreversible flaws with the “file now – find later” approach typically used to handle digital records – and things are only getting worse.

How many USB drives and tiny memory cards can you keep track of? What happens when (not if) they’re lost or stolen?

Not a single expert believes that today’s technology will be viable tomorrow. (Remember the floppy disk? Even the USB cable connector will be changing soon!)

Videotapes are unlikely to more than 20 years, even under ideal storage conditions, and can become unreliable after five years

CD-ROMs are only reliable for 10 years or less

The hardware and software needed to use CD-ROMs will be obsolete within 5 years

Online storage sites may not accept original, high-resolution images of photos or other documents where visual detail is critical.

The more you store – locally or online – the harder it is to quickly find what you need.

When your “free” online storage services goes belly-up, so do your files.

If your online storage fee doesn’t get paid – now or later, by you or your descendents – your data disappears.

Online services must store huge amounts of such quickly-accessible files indefinitely into the future – and with total storage costs rising in step with rapidly-increasing volume and competitive pressures to lower fees, your service may be forced to close its doors.

In their user contracts, many online backup companies do not accept any actual responsibility for keeping your records safe.


The kicker: How will your descendents find a specific document exactly when it’s needed if it’s stored somewhere in those USB drives, portable hard disks, online storage bins, and other digital dumping grounds?

In college I was asked what I’d write on my epitaph. At that time, I couldn’t have imagined that my life today would be captured as digital records – or that these digital records would be a complete mess. Backups, security, floppy disks, USB keys…all have contributed to a disorganized digital garage. But if you’d asked me to write my digital epitaph before figuring out what a digital legacy was, here’s what you would’ve gotten:

Here lies Stephen’s Digital Identity. If you can even open these files, good luck in finding the important stuff – Sarbanes-Oxley documents from the many successful companies I founded, notes of my ideas, and the many love letters I wrote to my wife. Somewhere in the 600 hours of video is footage of my kids walking for the first time. My will and medical directive are on a USB key (the silver one, not the blue). So to my future generations, please find the important info and write a nice book.

Stephen Pieraldi – Loving Husband, Father and digital hog


Thankfully, there’s good (really good) news: I’ve devised a simple, straightforward way out of this skyrocketing digital mess. I solved my own document dilemma by creating a framework for building and preserving what I call a Digital Legacy. In essence, a digital legacy is the collection of vital documents that are scanned into digital form and stored in a special, permanent digital vault that only you, your descendents and your carefully chosen delegates can access. This digital vault has to have certain unique properties to qualify as a digital legacy repository:

Simple document deposit process

Permanent file preservation

Secure storage technology

Easy-to-use document retrieval software

One-time payment – no recurring fees

In the end, I realized that everyone could experience the peace of mind that I now enjoy – so I started a digital legacy set of posts.  Diamonds in the Rough is the set of posts for anyone who needs to assemble, prioritize, preserve and maintain any number and type of personal, family or home business documents.

In other words, for everyone.

Diamonds in the Rough posts alerts you to the critical importance of selecting only key documents for protected digital storage, debunks the widespread belief that technology alone will solve the problem, and provides step-by-step tools to immediately put this new awareness into action. It’s the first book of its kind and the only one you’ll ever need.

Now that I can build and preserve my digital legacy, I can write this digital epitaph instead:

Here lies Stephen’s Digital Legacy Safe Deposit. In it are his most important memories and journals filed and kept for posterity. His loving wife and children have access to the files, so if you’re interested ask them for a copy. Stephen’s publishers have been given access to those directories containing his many patents and poems. Soon this Vault will be added to the Smithsonian digital vault library.

Stephen Pieraldi –Service Beneficiary


Lao Tzu, a famous Chinese philosopher and poet, wrote that “a journey of 10,000 miles begins with a single step”. The first step in building your digital legacy is to think differently about how you organize and store your files. While it’s a simple philosophy, selecting your most important documents means reviewing them all – and that takes time and discipline.

You need to have two main sets of documents when you’re done: a relatively small number of vital records (your A-List), and everything else (your B-List). Some of what you have will be obviously slated for your digital legacy; the challenge may come when you review items with emotional significance, but which, if truth be told, are not essential.


Source: InfoTrends

You know the ones I mean. Like so many families in the digital camera age, you may have hundreds – even thousands – of family photos[1], scores of CDs and DVDs, receipts from bygone tax returns, lists of things to do, and much more. If you want to hold on to these, fine – but they’re not really suited for your digital legacy.


Divide and Conquer

I know that you might be overwhelmed by the prospect of going through all of these documents. The first thing you need to do, without exception, is to create a simple, manageable way to organize your A-List and B-List documents.

What worked for me? File boxes!

Create two sets of file boxes matching the categories covered in the following chapters – personal, financial, medical, legal, and (if you have one) home business. One set will hold you’re A-List digital legacy documents, while the other is for your B-List documents. (For documents that are already in digital form, create a corresponding set of folders and subfolders on your computer.)

Although this requires more up-front effort, it’s infinitely better than (1) separating your files into A- and B-Lists, (2) taking a second pass to categorize your A-List documents (those you’ve selected for digital preservation), and (3) taking a third pass (yikes!) through your B-List files. I wouldn’t even want to imagine going through that again!

Once you have your files boxes (and, if needed, computer file folders) in place, you’re ready to begin creating your digital legacy. The following chapters provide simple step-by-step advice that makes the process much more approachable:


Ö    The specific types of personal, financial, medical, and legal documents you need to find, set apart, and digitally preserve


Ö    A chapter written specifically for those of you who run a home business


Ö    Tear-out checklists and document retention timetables to help you select the right files for your digital legacy


Once you’ve completed your A-List selections, you’re three steps away from protecting your future.


  1. Since you’re preparing to build a digital legacy, your A-List documents have to be scanned into digital form. The various ways to do this are covered in Chapter 8.
  2. Once all of your A-List documents are in digital form, rent a safe deposit box (at your bank, for example) and deposit them there for safekeeping.
  3. You’re now ready to select a digital vault, deposit your digital A-List files, and enjoy the perpetual peace of mind that comes from having a digital legacy!


You may also want to see how others use my system, seek additional information, or request further assistance. Read my Digital Legacy blog posts here, review case studies, and utilize additional resources.


The rest is up to you. And if you get frustrated, take a break – and remember: Organization, not Accumulation!

[1] InfoTrends, a research company, estimates that 67 percent of U.S. households had digital cameras last year – up from 42 percent in 2004.

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