Introduction

I turned 50 on January 9, 2017—a little over 21 years after I started writing books about technology. For whatever reason, much of my audience over these years has been a generation or so older than me. I constantly get email from readers in their 80s and 90s, and when I speak to user groups, I’m often the youngest person in the room by a considerable margin.

For a long time, this phenomenon was a mere curiosity, and I didn’t consciously tailor my writing to an older reader. But then I started noticing that lots of the questions and comments I received had to do with topics I hadn’t thought very deeply about myself: namely, how to deal with files, photos, email, online accounts, and other digital items when their owner died or became unable to handle them personally. People would come up to me after a talk about passwords or backups and say something like, “Well, I’m 89 so I won’t be around much long­er, and I want to make sure my son can get into my accounts when I’m gone,” or “I’m trying to figure out how my great-grandchildren will be able to read my documents 50 years from now.”

Those questions deserve answers, and that’s what I aim to provide in this book. Your digital legacy—whether, how, and in what ways your data will carry on without you—is a hugely important topic in the 21st century. No matter your age or health, something could happen to you at any time, and having a plan in place to deal with your accounts, files, and other digital data is a great kindness to your family and friends—to say nothing of future generations who may want to know all about you. (And, lest this all sound terribly morbid, the very same steps can be equally useful to someone who needs to take care of business for you temporarily if you’re sick, injured, or even just on vacation.)

We have tools such as wills and trusts to spell out what should happen to our physical and financial assets, but more often than not, those instruments say nothing about our incredibly valuable digital assets. Maybe you have tens of thousands of beautiful family photos, but what if they’re on an encrypted computer and no one else knows the password? What will become of your Web site, Facebook account, or email if you alone know how to access it, and leave no instructions? And what will happen to all the data you’ve trusted to various cloud services when your credit card expires and no one else is paying the bills?

These are just a few of the many questions I help you answer in this book. I walk you through the process of inventorying your digital assets, figuring out what to do with each of them, drafting a digital will, choosing a digital executor, and much more. I also talk about information that isn’t currently digital, but maybe should be if you want to preserve it for a long time—things like paper photos, analog video and audio tapes, and important family documents. And I discuss at length the nuts and bolts of decisions you’ll have to consider like which file formats and physical media you should use to preserve data for posterity, whether you should entrust any of this data to a cloud service, and how to be sure all your preferences are clearly spelled out.

In short, this book is about digital estate planning. It’s not going to teach you new tech skills or get you excited about the latest apps and gadgets, but I’ve done my best to make this essential topic interesting and engaging. By the time you’ve finished the steps in this book, you should be confident that your data will be in good hands when you’re no longer able to manage it. In the process, you may just find yourself becoming more organized and better prepared for random, fleeting emergencies too.

In much the same way that a book could walk you through the mechanics of writing a will but not tell you which assets to leave to whom, I can’t give you precise step-by-step instructions for everything, because each person’s situation is unique. My goal, instead, is to provide a thorough framework that will help you identify what you need to do and make smart decisions about how to carry out your plans.

Whether you’re 25 or 95, and regardless of which devices or operating systems you use, I hope you’ll find the resources here to put your digital affairs in order—and, with any luck, have some fun doing so.

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