Wishing you all the best in your battle! Stay strong but be prepared!

That's great news Mike! Wishing you a continued and long remission!

Helping Your Loved Ones Navigate Your Digital Life After You’re Gone

I’ve been battling cancer since 2021. First, Multiple Myeloma and then after beating that I developed Acute Lymphoblastic Leukemia caused by my Myeloma treatment. To say the last few years have been a challenge is an understatement. While my prognosis is very good, my mind can’t help but wander down the darkest path. With so much of our lives being online these days it’s surprising how we overlook equipping our less technical inheritors with a digital roadmap.

With that in mind, I’ve been putting together a strategy for making sure my loved ones have everything they need in the event of my untimely passing. Because it’s not something many people think about, I thought I’d share some of what I’ve been doing. This isn’t legal advice but merely what I’m cobbling together. Your mileage may vary.

Planning in 1Password

At the center of my digital estate planning strategy is 1Password, a password manager that my family uses already. We put all of our passwords in the tool and have a shared vault for things that both my wife and I might need access to. Think of things like brokerage account logins, streaming services, login for the kids and their various services, etc. 1Password has a family plan where up to five family members can share a single account. (Each family member gets their own personal vault and you can create shared vaults for the entire family)

The nice thing about 1Password though is it can store more than just passwords. It can also store documents and generate one-time passwords for use with two-factor authentication. The document storage is the key to my digital estate planning. In our shared vault, I’ve created a simple document (in RTF format) that has a list of instructions on what to do in the event of my death. Because the document is in a secure vault I can be candid with the information I put into it. I can also create links directly to the 1Password entries I’m discussing in the instructions. For example, if I’m explaining the details of our ETrade brokerage account, I can create a link to the ETrade 1Password entry so my wife can easily login and get the information she needs.

The instructions document isn’t where I put any flowery goodbyes. It’s a manual on what to do when I’m gone. First and foremost I start with a list of all accounts and services that should remain active and why. For example, I have a paragraph explaining not to cancel my cell phone plan until the estate is resolved. Why? Because a lot of services still use text based 2FA. Keeping the line active will make dealing with 2FA a lot easier. I also mention my debit card remaining active. Even though we have a joint account our credit card numbers tied to the account are different. Cancelling the account might cancel key services like 1Password. Again, not an insurmountable task if it happens but just a lot easier if you know and can avoid cancelling those key services until you know you’re ready.

Next I have instructions on how to recover my 2FA system, Authy. This will help to get setup for many of the other accounts that are protected with 2FA and Authy. An alternative would be to have 1Password be your OTP client, producing the codes right next to the passwords. The only concern there is if your 1Password account gets popped then the 2FA isn’t really helpful. But considering your Authy backup codes are probably in 1Password as well, this might be a distinction without a difference.

After that I enumerate all of the financial accounts that my wife doesn’t have her own specific login to. For us it’s things like our Treasury Bonds account, my personal brokerage account (where I experiment on the market with limited funds) and my company 401k information. All of these accounts are setup with the appropriate beneficiaries but listing them explicitly helps to remind my loved ones what exists. Worse case, the family trust is the beneficiary and they’ll eventually gain access to the assets. But for planning purposes it’s nice to be able to login quickly and have an idea of what the state of the accounts are.

Finally, I have instructions on where any digital versions of important documents are. We typically have physical copies but I note where the digital versions are stored in the event there was a fire or something and those documents perished with. me. This is also where I’ll put restore instructions for my laptop. A set of instructions on how to restore my document management system from our cloud backup solution. Again, I don’t want to have to rely on the idea that my wife will have direct access to my laptop.

Before I move on to a few other services there’s another thing I’d recommend specifically for 1Password. 1Password has the concept of family organizers. They’re basically account administrators and have elevated privileges in the account. If you created the account then you are a family organizer but it’s useful to have more than one. You can find more information about family organizers on 1Passwords website. Having your spouse be a family organizer will help to future proof with any additional functionality that the role may be granted. But most importantly, it will allow your loved one to update the billing information to ensure your 1Password account stays active even after your linked credit card information has been retired. For additional peace of mind you may want to store your 1Password emergency kit somewhere secure. It has all the information necessary to recover your 1Password account. Unfortunately at this time there is no mechanism for you to will or pass down the 1Password account so the emergency kit becomes your best option.

Legacy Contacts

A few of the larger services offer what’s known as a legacy contact. The legacy contact is (typically) a designated contact that you specify that will gain access to your data at the time of your death. Each service has a slightly different process for specifying a legacy contact and how that contact must engage to recover your data.

• Facebook Legacy Contact will allow you to specify a person that will manage and memorialize your main account after you’ve passed away. They also have a similar optionto memorialize an Instagram account.
• Apple Legacy Contact will allow you to specify a contact that will gain access to the data stored in your Apple account after your death. There are limits to what data you get but things like photos, messages, notes and device backups are just some of the things the legacy contact will gain access to.
• Google Inactive Account Manager is a little bit different. It acts more like a dead man’s switch, where if your account has been inactive for a specified period of time, Google will send an e-mail to your contact with a message of your choosing. When you set it up, you can also specify to share data with the contact. The e-mail will include links for the user to download the data.

Wrap up

This has been a bit of a learning experience for me. The tough part is that you don’t know if it worked the way you hoped because you’ll be gone! But hopefully I’ve sparked some ideas on how to pass down the digital bits of your life to your loved ones and make a difficult time just a little bit easier.

I’ve noticed that this is a spectrum in terms of how people want to be engaged. For folks I interact with regularly I’ve begun asking how they like to be engaged on chat and so far it’s a mixed bag. Sometimes it often depends on the message too. So “Hey, we need to talk” sounds way different from a manager and creates anxiety. Some people just want the full message at once. It’s kind of fascinating but also creates a mental burden for tracking the different preferences of people.

I really think that’s been the missing link in our strategy. The idea that if we do nothing, all of that emotional connectedness will bleed away. And what I’ve noticed is it’s different rates for different people. So managing that drainage has to be done at the direct manager level, meaning budgets will most likely need to come down to that level so managers can arrange events on their own with autonomy.