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Aunt Agatha Ponders Her Digital Legacy

I turned 50 earlier this month. To celebrate, I dyed my hair purple and wrote my 56th Take Control book, “Take Control of Your Digital Legacy.” This title was inspired by a number of conversations I’ve had with readers of TidBITS and Take Control in recent years, which have frequently turned to topics of data longevity. People have been asking me how they can be sure their photos, videos, email, documents, and other important data will outlive them, and this book contains the results of my research and thinking on the matter.

To introduce the book to you, I’ve framed a number of the questions that prompted the book, and their answers, as a conversation with my completely imaginary Aunt Agatha.

Aunt Agatha: Happy belated birthday, Joey!

Joe: Aunt Ag, I’d really appreciate it if, now that I’m 50, you’d stop calling me Joey.

AA: Sorry. Old habits. What brings you here today, other than my peach cobbler?

JK: Don’t be silly. I’m also here for the ice cream. And I wanted to chat with you about my new book.

AA: Not another one! What must I take control of this time?

JK: You’re going to like this one, because I wrote it with you in mind. The book is called “Take Control of Your Digital Legacy.” It’s sort of estate planning for your digital possessions.

AA: Are you’re saying I’m old?

JK: Not at all; 68 is the new 55. And anyway, people of any age can expire suddenly. But… (drumroll) your data can live on forever.

AA: And that’s a good thing?

JK: Absolutely! By deciding what data sticks around in the future, and in what form, you can shape the way people remember you. But if you do nothing, the stuff on your computer and iPad could suffer the same fate as that box of childhood souvenirs you found rotting in the basement. Not something you want to pass on, if you know what I mean.

AA: Ew. You may have a point.

JK: Cool. So now that I have your attention, what would you like to know about your digital legacy? Ask me anything.

AA: Well, for starters, what exactly do you mean when you say “digital legacy”?

JK: Your legacy is everything you leave for the future — not just your possessions, but also your stories, your accomplishments, and your contributions to the world. It’s the sum of how you’ll be remembered years from now. Your digital legacy is the part of that involving digital data: your digital photos, documents, email, and more. It’s stuff that Grandma and Grandpa didn’t have to think about, but that future generations will consider more important than scrapbooks and photo albums.

So, the starting point of the book is that you get to make decisions now about what will happen to your digital data after you’re dead — and far into the future.

AA: Shouldn’t all that be covered in my will?

JK: It could be, but conventional wills hardly ever address digital assets, at least not in sufficient detail. And because your files, photos, online accounts, passwords, and so on change so frequently, it would be a hassle to keep amending your will to make sure it’s always up to date. Furthermore, your executor may not have the technical expertise to deal with all your data properly.

AA: OK, if my will isn’t the best place, where do I record my wishes for this digital stuff?

JK: I suggest supplementing your will with a digital will that spells everything out, including a high-level list of your digital assets and your preferences for preserving and distributing data, dealing with all your accounts, and so on. And then you’ll select a digital executor who will carry out these instructions.

AA: OK, a picture is forming, but now it’s getting me worried. I have a zillion photos, files, and accounts. Some of it is important, but a lot isn’t. Realistically, how am I going to document all that stuff?

JK: Don’t worry. You start by filling in a downloadable template I made. It’s not complicated. Life is short, and you shouldn’t have to spend weeks or months pondering every last file and reorganizing your whole computer. Instead, I recommend thinking about your data in terms of broad categories, and creating a fairly short list that includes brief annotations about the kinds of stuff you have, where to find it, and what to do with it. Depending on how much detail you feel like providing, filling out the template could take a few hours or a weekend. That’s just part of planning your digital legacy, but it’s an essential component.

AA: Suppose I’m still feeling a little overwhelmed. Could you pick out just one piece of it to get me started? What do you think is the most important thing to deal with first?

JK: Without a doubt, it’s your passwords. If you got hit by a bus tomorrow, would Uncle Aubrey know how to unlock all your devices and get into all your accounts? As tedious as it might be, someone else could look through all your digital stuff and figure out what needs to be done, but if they don’t have the passwords, they’ll be stuck before they even get started. I mean, you’re not going to be passing on your passwords to your grandkids, but you will be passing on some of the stuff those passwords protect.

I should emphasize that working through even one topic from the book can make life way easier for you, Uncle Aubrey, Timothy and Felicia, and their kids. If you have the time and energy to do everything, that’s super, but picking and choosing the parts that are most important to you is also fine. Something is always better than nothing.

AA: I’ve got boxes of old family photos, and it would be nice to pass those on along with my digital photos. What should I do with them and other non-digital data?

JK: As you know, I’m a big fan of digitizing things that are analog. Not just photos, but audio recordings, home movies, and the like too. Someone gave me an MP3 file, digitized from an old reel-to-reel tape, of the audio from when Uncle Bill was on the TV show “To Tell the Truth” back in 1963. I think that’s cool, and if that tape had never been digitized, it wouldn’t have survived much longer.

Anyway, about the photos: Yes. Get a scanner, make a nice cup of tea, and start scanning. Keep notes as you go about who’s in each photo, and anything else you know. You’ll gradually build up an annotated index of sorts. Maybe you do this for a few hours every Saturday afternoon, one small batch of photos at a time. It’ll take a while, but don’t think of it as work, think of it as a relaxing stroll down memory lane. Even if you never get through all of them, each photo you scan is another piece of history you can easily share online with the rest of the family, and a useful addition to your digital legacy.

AA: Do I need to worry about what file format I use? I’m thinking mainly of photos, but the same question could apply to all the files on my computer.

JK: Worry is a strong word. But yeah, you should think about it. Remember all those documents you created years ago in AppleWorks? And how hard it has been to find any app today that will open them? That may be an extreme example, but file formats become obsolete all the time. It’s a complicated topic, so in the book, I explain what formats experts recommend for various kinds of files, and you can decide whether, or to what extent, it makes sense to convert your existing files.

AA: You mentioned email earlier. Should that really be part of my digital legacy? It feels kind of weird to let other people read it.

JK: You don’t want anyone to see how many messages you get every day from Publishers Clearing House?

AA: Hey… I may already be a winner!

JK: You’re always a winner in my book, Aunt Ag. But let’s think about this. If someone were to read through all the hundreds of thousands of email messages on my computer… well, first of all, that person would need to be committed, in either sense of the word! Most of that email would be excruciatingly boring. On the other hand, by reading my email, someone could produce a detailed biography of me — they’d know exactly where I was, what I was doing, and what I was thinking on virtually every day of my life. I can imagine that being interesting to my distant descendants, or to historians once I become famous. (That’s on my to-do list for the next decade.) I
know I’d be thrilled to have that sort of information about Grandma and Grandpa.

Of course, your email could also include messages that are embarrassing or that contain secrets you really don’t want to add to the family record. Not that I’m judging. If you want to pass on your email but exclude certain things, you’ll have to go in and weed out those messages manually, I’m afraid. Better to do it now than have Tim and Felicia stumble across them later.

AA: Food for thought. Speaking of potentially embarrassing material, what will become of my Facebook page when I die?

JK: Facebook lets you set someone up as a legacy contact (your digital executor would be the perfect choice) so that when you die, that person can decide what to do with your account. That might mean memorializing it online, with one final message to your friends, or deleting the account altogether. Some other social media services offer something similar, some don’t. But as long as you spell out your wishes in your digital will and give your digital executor access to the accounts, that person can ensure that your posts are handled in whatever way you think is best.

AA: I see a theme developing here. All right, besides passwords, photos, email, and social media, what else I should be thinking about?

JK: Well, it’s a long list, frankly. I know you have lots of online accounts. Some of those, like Dropbox, iCloud, and CrashPlan, could contain tons of important data. Plus there are all those miscellaneous files on your computer, like letters you’ve written, artwork and music you’ve created, calendars, contacts, apps, and all the rest. All the major categories are included in the template I made. Not everything needs a long-term legacy plan, but it’s important to at least think it through.

AA: OK, here’s a puzzler. What about all the music, movies, and TV shows I’ve purchased from iTunes? Can I leave those to your cousins?

JK: Purchased media is, as they say, a bag of hurt. Most purchased media uses copy protection to prevent anyone other than the licensed purchaser from using it. That’s because you don’t actually own this stuff, you’ve only purchased a license to consume it, and that license is exclusive to you. So it gets tricky, sometimes in a technical sense and other times in a legal sense, but I talk through the issues in the book.

AA: Assuming I organize and document everything the way you describe, do I just leave my computer to my digital executor in my will? Is that how the data gets passed on?

JK: It’s definitely helpful for your digital executor to have access to your computer when you’re gone. But your computer won’t keep working forever. I mean, your descendants 100 years from now aren’t going to be gathering around great-great-grandma Agatha’s antique iMac to look at photos. The same is true of most storage media — hard drives and SSDs don’t last forever, and CDs and DVDs deteriorate over time. You can buy so-called “archival” media, but there’s no telling whether someone in the distant future will be able to find a device that can still read it. Imagine if someone handed you a floppy disk that was recorded 30 years ago. Even if the
data’s still intact, it’s basically useless to you.

There are many ways to approach this problem, and although there aren’t any perfect solutions, using more than one kind of storage media, storing copies separately, and asking your heirs to occasionally copy your data onto new media are steps in the right direction. If you can get Tim and Felicia to integrate your data into their own, which is then backed up regularly and passed on to their kids, that will increase the longevity of your files significantly.

AA: So now you’re going to tell me that if I want all the details about how to plan for my digital legacy, I have to buy your book?

JK: You? Nah, you get the family discount of 100 percent off. But definitely tell all your friends to buy it!

Thanks to my imaginary Aunt Agatha for cleverly asking all the right questions about “Take Control of Your Digital Legacy.” The book, which costs $15, goes into complete detail about all the topics mentioned here and much more. It shows you how to inventory your digital assets, prepare a digital will (with the included template file), share passwords securely, scan old photos, make decisions about social media accounts, and much more. I hope you’ll find it helpful in planning your own digital legacy.

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