Envision Your Digital Legacy

I know almost nothing about my paternal grandfather, who died a few months before I was born. I’ve seen photographs of him, examined census records in which his name appears, and heard a few stories, but that’s about it. And of his parents I know even less. There are complicated reasons why so little information about these family members survived, but the fact remains that whatever documents or genealogical data I might dig up, I’ll never be able to know what they were like. What were their interests, hopes, beliefs, and fears? Did they have a sense of humor? How did they interact with other people? Were they kind or cruel, interesting or dull? The answers to all such questions are beyond my reach.

By contrast, my descendants should have a bountiful supply of information about me. During my lifetime I’ve written many thousands of pages of books and articles, recorded hundreds of hours of audio and video, bared my soul in innumerable email messages, and posed for countless photos. I don’t fancy myself a person of particular historical significance, but I would at the very least like family members in future generations to be able to find out what sort of person I was—what made me tick. And as long as I preserve all that data carefully, they’ll be able to do just that. They won’t have to rely on faded photos in a shoebox and half-forgotten, second-hand stories. And whether they consider me a hero, a villain, a champion, or a loser, at least their feelings about me will have a pretty strong basis in reality.

That’s a big part of how I envision my own digital legacy. In this chapter, I want to help you get a sense of what yours might entail. Crucially, that includes not just the things you’ll preserve for future generations, or even the stuff you’ll want your next of kin to know about in the days leading up to your funeral. It also entails information and concrete steps that can improve your life today (see How Digital Legacy Planning Can Improve Your Life Now). At the same time, the complexities of preserving your digital legacy may be more involved than you imagine, and I hope to give you a realistic overview of the challenges you’ll face (see Understand the Challenges). I also offer a few quick reminders about conventional, non-digital estate planning that you’ll want to take action on if you haven’t already done so (see Review: Estate Planning Basics).

What Your Digital Legacy Means

I’ve given some examples of what I mean by a digital legacy, and al­though the details of your vision may differ from mine, the underlying concept is this:

You get to make decisions now about what will happen to your digital data after you’re dead—and far into the future.

If you’re a public figure, or if you’ve done things that people are likely to write about in history books a century from now, you’ve probably al­ready begun to take steps to insure that future generations look back on your life in a complimentary way. But even those of us who consider ourselves ordinary folk usually care about how we’ll be remembered by our friends, family members, and descendants. My great-grandchildren, should I have any, probably won’t see a statue of me in the park or sing songs commemorating my mighty deeds. But they might like to know what Grandpa Joe was like way back in the olden days of the early twenty-first century, because their lives will have been shaped, in part, by my choices.

Your actions, and the chains of events they cause, are part of your legacy. Your possessions, and indeed your family members them­selves, are part of your legacy too. But in this day and age in which nearly everything is digital, when most people carry supercomputers (with built-in cameras, microphones, and video recorders) wherever they go, and when your every thought and emotion can be instantly transmitted around the world via social media, the data you create and accumulate over a lifetime is likely a larger part of your legacy than your money and house. It will almost certainly last much longer, too!

So, when I speak of your digital legacy, I’m thinking of the following:

• Digitizing aspects of your life (such as old photos) that are still analog
• Making crucial digital information about yourself accessible to the right people, in the right ways, at the right times (and, as a corollary, destroying information that you don’t want to persist)
• Caring for your loved ones immediately after your death by providing them all the information they need to handle your affairs and your digital assets
• Enabling future generations to have as much information about you as you like

Whether your fondest desire is to be remembered forever or to be for­gotten immediately, you can craft the digital legacy you prefer. But if you do nothing, your legacy will be entirely in the hands of other people, with lives and preferences of their own, and however much care they devote to preserving your data, it may not turn out the way you would have liked.

How Digital Legacy Planning Can Improve Your Life Now

Apart from giving you greater peace of mind, a regular will won’t do much to improve your life right now. But planning for your digital legacy can serve lots of purposes while you’re still alive. For example:

• Better organization: If your digital documents, photos, and other files are stored in a careless or haphazard way, you may decide that it’s time to organize them in order to help anyone who may need to find things after you’re gone. But guess what? Better organization will also make it easier for you to find things, reducing clutter and enabling you to work faster and waste less time searching.
• Improved sharing: Your friends and family members may enjoy seeing photos, old documents, and other artifacts that are currently stashed in a box, but that you’ll scan as part of your digital legacy preparations. And (per the previous point) even items that are already digital, such as videos and music, are easier to share if they’re well organized.
• A backup plan: When my wife and I go out for the evening, we write instructions for the babysitter. When I had a conventional job and took time off for a vacation, I’d leave instructions for my colleagues on how to handle my tasks in my absence. One of the things you’ll be creating as part of your digital legacy is a similar—but more detailed—set of instructions that a friend, loved one, or other trusted person can follow to take care of any crucial business or personal tasks that, at this moment, only you know how to do (see How to Be Me).

  Those same instructions can enable someone to take over for you temporarily if you go on vacation, or become sick or injured. Plus, they can help you remember how to do tasks you perform infrequently, so you don’t have to figure them out from scratch each time.

In addition, you may well undertake improvements in the ways you back up your data and handle passwords; eliminate unneeded accounts, files, and apps; learn more about your family history; and even get to know yourself a bit better.

Understand the Challenges

Leaving your house or your car to someone is relatively simple. I mean, it’s not truly simple, as in merely handing over a key—there’s all sorts of paperwork, and there are legal and tax considerations, and so on. But there are also well-worn procedures in place for facilitating such handovers, and if your will states that your son gets the house, then there’s little else you, while still alive, need to do to make that happen; your son (along with your executor, lawyer, spouse, and other relatives) will deal with all the irritating details when the time comes.

At first blush, it may seem as though your digital data is far easier to pass on. If your data is on a computer, why, someone can just take your computer and have all your data, right? Well…kinda sorta maybe but not really. Preserving your digital data for the future is in fact considerably more challenging. Here are just a few of the reasons:

• Encryption and passwords: I’m a big proponent of using encryption and strong passwords, but the very tools that keep your data safe now can make life difficult for your heirs. If your computer’s data is encrypted—for example, using FileVault on a Mac, or Device Encryption, BitLocker, or TrueCrypt on a PC—no one will even be able to boot the machine, let alone read your files, without your password. Similarly, the passwords for your online accounts protect them from snooping and identity theft, but someone else may need to access those accounts when you’re gone. I talk about account access issues in Deal with Passwords.

• File formats: I know a lot of people who, years ago, created tons of documents using software called AppleWorks. But that software was discontinued, and nowadays, even apps that convert AppleWorks documents to more modern formats are getting hard to find. The same is true for many file formats—what’s easily readable today might be completely opaque a decade or two in the future. Even if you have a current app that opens your files readily, who knows if that app—or something comparable—will run on the devices and platforms that will exist years from now. I discuss these problem in Decide on File Formats.
• Hardware and media degradation: Nearly all kinds of digital media, from floppy disks and hard drives to CDs and DVD—and even flash drives—suffer random data loss over time. Whether the media itself physically degrades, a magnetic charge dissipates, or a cosmic ray flips a value from a zero to a one (or vice versa)—and yes, that really happens!—data can, over time, develop errors or even become completely unusable. Hard drives can also suffer mechanical failures that render them worthless, regardless of whether the data itself is intact.

  And who knows what interfaces will exist on tomorrow’s devices? In the 1990s, computers and peripherals often had SCSI ports, for example, but I have no idea how I’d go about reading data from a SCSI drive today. I cover issues like these in Preserve Your Data for Posterity.

• Organization: Even if someone in the future can read all your data on some storage device, how will they find anything of value? My computer has well over a million files, including more than 200,000 email messages. Sure, someone can search all that data for a word or phrase, but no one will know, unless I spell it out, that an oddly named file deep in a forgotten folder hierarchy is actually a fragment of brilliant writing that was part of a novel I never finished.

  In other words: you can’t search for something if you don’t know what you’re looking for, and I don’t think anyone is going to take the time to examine a million files individually just to see if I might have used a clever turn of phrase in one of them. I discuss organizational issues in Inventory Other Personal Data.

For these and many other reasons, the task of ensuring that all (and only) the right people can access your crucial data in the future is more complicated than it initially appears—and that’s exactly what this book aims to help you with. Every issue can be overcome with careful thought and planning.

Review: Estate Planning Basics

Your digital legacy is intended to be a part of your overall estate plan—not a substitute for it. If you haven’t already dealt with the other steps, I urge you to do so—perhaps even before following the instructions in this book. Life is too uncertain to leave these important things to chance.

I am not by any means an expert in conventional estate planning, but as a quick reminder, a typical person will want to include (at least) the following elements:

• A will: This legal document spells out what will happen to your possessions when you die. It will name your beneficiaries (who will receive items you now own) and the executor (who will manage your estate and carry out the distribution of assets).
• Guardianship: If you have minor children, adults for whom you have legal responsibility, or pets, your will (or a separate document) should specify who will care for them after your death.
• A living will (or advance directive): A living will spells out what you want to happen (particularly in terms of medical treatment) if you are still alive but unable to make decisions for yourself.
• Power of attorney: A power of attorney gives another person the right to make certain legal decisions on your behalf while you’re still alive. (Often, a living will and power of attorney go hand in hand.)
• Trusts: A trust is a legal agreement to transfer property to someone else (a trustee) who will hold it for the benefit of one or more other people (beneficiaries). Some trusts take effect while you’re still alive, while others kick in only after you die. A lawyer can advise you as to the situations in which a trust is helpful.
• Life insurance: Whether just to pay for your funeral or to provide living expenses for your family after you die, life insurance is a wise investment for most people.

All these elements come in many varieties and are governed by rules that vary by jurisdiction. If you’re just getting started with estate plan­ning, a site like GYST can help you find the resources to work through each of these items. Some of them you can do yourself (possibly even for free), while others will require the paid services of a lawyer or other professional.