The Living Legacy Plan
Your voice, your notes, and your videos will mean more to your children than your crypto — plan both.
A will is a financial and legal document. It distributes assets, names executors, establishes trusts, and provides guidance for burial wishes. What it does not do — and what Sam Grice argues most people completely overlook — is address the emotional inheritance: the voice, the messages, the stories, the explanations of why decisions were made. This is the layer of legacy that survivors grieve most acutely.
Grice's own loss of his mother at 27 made this concrete for him. He has recordings of her voice only as fragments in odd videos, never a sitting conversation. He has since sat his father down for an hour on camera — not a will-writing exercise, not a death-focused conversation, just a recording of his father talking about his childhood, his memories, his life. That recording becomes invaluable if his father dies tomorrow and remains a gift regardless.
The Living Legacy Plan extends this to a practical model: alongside the financial will, prepare a set of personal documents, recordings, or messages. Grice's company offers a 'legacy box' with prompts and a dictaphone. But the actual instruments are irrelevant — a phone voice memo, a letter, a video recorded over a coffee. The substance is the message to a child at a future milestone: their wedding, their first job, their 18th birthday. These can be written to be delivered by someone else if needed.
- Financial inheritance handles the practical future; emotional inheritance handles the relational future — both require deliberate design.
- Your voice, recorded for five minutes, will mean more to your child at their wedding than most financial gifts.
- The emotional side of a will — messages explaining decisions, notes for milestone moments — is almost always an afterthought.
- Writing messages to be read if you are gone is not morbid; versions for if you are alive are equally valuable and can be shared now.
- Death eliminates conversations you meant to have — legacy planning is the practice of having them in advance.
- Record or write a message for each major milestoneIdentify the milestone moments in a child's or loved one's life where your presence would be most meaningful: their 18th birthday, first job, university departure, wedding, birth of their first child. Write a letter or record a video for each. These can be held by a trusted person and delivered when the moment arrives.Pro tipMake a version for if you are alive too — it can be shared now and becomes something you can refer to together. The death version and the life version can coexist.WarningDon't make it a goodbye message — make it a presence message. Speak to who they are now and who you hope they'll become.
- Record a life history conversationSit down with a parent, grandparent, or yourself and record an hour of life story: childhood memories, formative events, how you met key people, what you believe. This requires no special equipment — a phone and a comfortable chair. The recording becomes an irreplaceable artifact.Pro tipUse an interview format — ask questions rather than monologue. 'What was your first job? What did you learn from your parents?' produces richer material than an unstructured recording.WarningDon't wait for a diagnosis or a health scare — record when the person is well, articulate, and not associating the conversation with death.
- Write a letter of reasons in the willAlongside the legal provisions of the will, include a letter (not legally binding, but held with the will) that explains the reasoning behind each major decision — why one child received more than another, why a charity was named, why the trust is structured as it is. This context prevents conflict and allows beneficiaries to understand rather than only receive.Pro tipThis letter can be updated separately from the will itself — you can amend your reasoning without redrafting the legal document.WarningIf a beneficiary is excluded or receives less than expected, this letter is essential — absence of explanation is the most common catalyst for post-death disputes.
- Tell the people who matter what they mean to you nowGrice's most direct point: the conversations people wish they had had after a death are often conversations they could have had before it. Legacy planning surfaces the things you want to say — which you can say now, without waiting for death to make them meaningful.Pro tipStart with one conversation. Pick the person whose loss would leave the most unsaid, and say one of those things today.
After losing his mother with no proper recordings of her voice, Grice sat his father down for an hour on camera to talk about his life — childhood in New Zealand, formative memories, how he met people, what he believes. No special occasion, no morbid framing.
Octopus Legacy provides a physical 'legacy box' containing prompts, a dictaphone, and instructions designed to make the process of capturing a personal legacy tactile and accessible rather than abstract.
The host jokes that his son can watch his podcast episodes and think 'that was actually all right' after he is gone. Sam Grice reframes this: the hosts have a significant advantage over most people — thousands of hours of themselves on record — but it is incidental, not intentional.
Sam Grice developed this framework partly through his mother's death and partly through Octopus Legacy's evolution beyond pure will-writing into broader estate and legacy planning. The legacy box product emerged from watching families in bereavement wish for exactly this kind of pre-prepared emotional material. He observed that video content creators — like the podcast hosts — have an accidental advantage: thousands of hours of themselves recorded and accessible. Most people have almost none.