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  • Margaret Gerety

(UPDATED!) Checklist Review: Online tools for end-of-life planning

See the end of this blog for a few new options I found and reviewed this summer!


When the idea of Sprinkle Trust first came to me, I surveyed my friends and family to learn about their experiences with estate planning, as well as downsizing and retirement. I asked about the resources they’d used, how often they’d discussed their plans with their family, and how far along in the process they were. I also wanted to test some ideas for products and services, so I asked if they would consider purchasing any of the following: retirement coaching; personal legacy projects; move and downsizing management; and life planning checklists. The last item was by far the most popular, with 62% of respondents saying they would pay for “interactive checklists to help work through the tough conversations, challenging processes, and critical to-dos of retirement and estate planning.” In the comments sections, people also described wanting a “step-by-step guide,” “one-stop-shop,” and “central guide” that would “walk them through the entire process.”


So it got me thinking, what’s out there for end-of-life planning and is it any good?


Below are some of my findings, from Google searches and recommendations by friends. While there are a lot of articles and books on end-of-life and estate planning, I tried to stick to true checklists, worksheets, and toolkits - resources that force you to work through questions and to-dos and write down or actively process your answers. I have organized them under the following categories:


  • Storing & Sharing Important Stuff 

  • Pre- & Post-Death Planning

  • Aging & Future Wellbeing

  • For the Executor


Nothing I found was particularly exciting, and nothing was as comprehensive as I would like. A lot of what I saw was clickbait to get you to purchase more expensive, bespoke services. Another large category I found were those color-tabbed, three-ring binders you pay to have mailed to you (see “Storing & Sharing Important Stuff”); these gave me flashbacks to high school, and not in a good way. Even the most interactive and personalized apps didn’t use the right motivating tactics for me. For whatever reason, I just didn’t want to work through someone else's checklists. It made me think a lot about what Atul Gawande says in his Checklist Manifesto, how you need for buy-in from users for checklists to work (and he still had difficulty convincing doctors to use his checklists in operating rooms, despite data showing how they saved lives!).


Storing & Sharing Important Stuff. 


The most interactive, online life-planning tools, like Tomorrow, Everplans, and Fabric, tap into a growing anxiety of millennials (and Gen Xers) about getting their life organized. These apps help you securely upload your important information, including insurance information, will, bank accounts, and the like, and share them with trusted, designated individuals. The apps begin by asking you some questions to help (marginally) curate the information you need to create and/or upload, which are bundled into basic categories (e.g., Family, Digital, Health & Medical, Legal) on your landing page. Some use OCR (optical character recognition) technology so you don’t have to manually enter any data - just take a picture and the app will populate the form with your account numbers, name, etc. Seems great, right? I was impressed, but none of the apps gave me a real checklist or status update on my progress toward completing this unpleasant and daunting project. And their end of life to-dos remain pretty cursory (the app is more about organizing your life not planning for your death, although Everplans does have some helpful executor checklists). Note: For those of you who like those aforementioned three-ring binders, check out: My Life Packet (Clearly in Place); My Final Checklist; and End-of-life Planning Workbook (Life in Motion).


Pre- & Post-Death Planning. 


Someone recently pointed me to Lantern, which was founded by two women left shocked by the decisions they had to make following the death of a loved one (and how little guidance they found online). Lantern is about as close as you can get to a comprehensive, pre- and post-death planning checklist, without too much of the formal stuff you find in an executor’s to-do list (see below). You work through a quick questionnaire to edit the list according to your needs and circumstances. You are then given access to your own online checklist that you can annotate, check off (yes, it's kind of satisfying!), sort, and print. While clean and user-friendly, with helpful articles and links, the legacy parts of Lantern can feel a little forced. For example, there’s something weird about a to-do box next to the question “what do you remember most about your teenage years?” Moreover they could beef-up their email reminders; being told "I'll feel instant relief by getting it done" doesn't make me any more likely to tackle the to-dos.


Aging & Future Wellbeing. 


This is an important, but much narrower, category of toolkits because it focuses solely on your health and wellbeing. These guides help you preserve your autonomy and ensure sound decision-making and good communication as you age, fall ill, and/or become unable to advocate for yourself. Most of what I found are PDF booklets to download, print, and work through (agh, such a turn-off for me!). Some, like the one by The 40/70 Rule, are more focused on conversations around aging as compared to dying, while others, like Compassion and Choices’s guide, help document your preferences for specific therapies and medical interventions at end of life (they do a nice job reviewing your values too). If you haven't worked through the latter type of checklist, or have an advance directive, it is particularly important to do so now, as COVID-19 can quickly leave you isolated and gravely ill. Other aging and health-related toolkits to check out: Toolkit for Health Care Advance Planning (ABA); Starter-Kits (The Conversation Project); and A Planning Guide for Families (AARP).


For the Executor.


I was very surprised by how many free, online checklists for executors I found. Most are marketing materials published by small to medium-sized law firms who want you to retain their lawyers. This makes sense since many first-time executors need more guidance than a simple checklist can offer. In fact, my advice for overwhelmed executors with more than the simplest of estates is have a good attorney on speed dial who is already familiar with the estate documents. If you think you can do it yourself, you may want to check out some more professional products (which I haven’t tried!) to help you tackle the subtleties in state law and keep on top of the various deadlines. While I haven't tried any of these, the New York Times recommends the books by Nolo (see, for example, their Executor's Guide and Executor’s Checklist and Notices Kit) and the software offered by EstateWorks and EstateExec.


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Update August 2019!  I recently learned about a few more end-of-life planning checklists that are worth checking out (sorry for the pun). Here’s the update!


Peacefully was started by another set of women founders, who saw a critical need for a comprehensive, post-death planning system. While you can use Peacefully to start documenting your end-of-life preferences, Peacefully’s competitive advantage is helping folks who have lost loved ones manage the chaos. Not only will Peacefully help you document choices, it will give you real live quotes (e.g., from funeral homes) and referrals (e.g. to estate attorneys). You can also purchase their estate closing software, which will close accounts on your (as executor) behalf, fill out forms, even create a personalized obituary (this software reminded me a lot of the program I used when I changed my name, Miss Now Mrs.). 


I loved the clean interface, which was very task and deadline focus, although there are certainly improvements that can be made, including consistency in how you save and view your information, and the ability to set your own timeline. I had the privilege of talking with co-Founder, Kiley Zeiler, and was amazed that it’s only been around since December 2019. They are ambitious have a lot of amazing upgrades cooking. 


Cake has been in the news, featured with the likes of Lantern and other end-of-life apps that have been gaining visibility in the (bleak) time of Covid. Their interface gives you a list very similar to Lantern’s, with helpful prompts and examples of how you might state your preferences, skewed millennial in my Gen X opinion. You can download a PDF of your decisions, which is a nice feature, and you’re given the option of uploading key documents which is a bonus. This platform felt approachable, so important for folks wary to start this process. I’m all for helping folks kick off their thinking on these difficult topics, but having seen the dark side of it all, Cake felt a little glossy.


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Note: I made no purchases, nor was asked to review, any of the above apps, websites, and workbooks. Please always be careful in sharing your information online!

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