What We Learned - Legacy Letters: What Will You Leave Behind?

Emily Trask
16 hours ago
6 min read

Transformation Tuesday | November 25, 2025, Hosted by Gray Panthers NYC

Speaker: Amy Paul, Founder of Heirloom Words

As we closed out our 2025 Transformation Tuesday season, Amy Paul invited us to think not just about what we leave behind, but how we want to be remembered—and how our words can carry love, wisdom, and comfort long after we’re gone.

This session reframed “legacy” from dollars and documents to something more human: the stories, values, and hard-won lessons that shape who we are.

What Is a Legacy Letter?

Amy explained that legacy letters and ethical wills are really the same thing:

They are not legal documents, but personal ones.
They’re meant to share life wisdom, values, experiences, and love with the people who matter to us.
They are often kept, reread, and passed down—becoming a thread that connects generations.

Unlike a legal will, which divides property, a legacy letter answers a different set of questions:

What did I learn in this life?
What do I want you to know, remember, and carry forward?
How can I comfort and encourage you when I am no longer here to do it in person?

Amy emphasized that many of us instinctively want to leave something meaningful behind; research even suggests we’re hardwired to pass on more than genes or money. A legacy letter gives that instinct a voice.

Beyond Money: The Legacy of Values

Amy shared a striking insight: most people, when asked, say their greatest hope is not that heirs inherit their money, but that they inherit their values—their sense of humor, compassion, resilience, and beliefs about what matters in life.

A legacy letter can include things like:

The values that guide you (kindness, integrity, curiosity, faith, justice, humor, etc.)
Stories that taught you those values—small moments, not just big events
Sayings, poems, songs, or proverbs that have carried you through hardship
Blessings, hopes, and encouragement for the recipient’s future
Words of forgiveness and requests for forgiveness that never made it into conversation

Amy’s own journey began when she helped her father write his memoir. After he died, family members told her that rereading parts of his story helped them through loneliness, grief, and tough days. That experience convinced her that not everyone will write a whole book—but almost anyone can write a letter.

How Legacy Letters Help the Writer

For the author, the process can be:

Clarifying – It forces you to ask: What really mattered? What do I stand for?
Healing – It offers a chance to give and receive forgiveness, to explain difficult choices, and to put lingering regrets into perspective.
Grounding – Writing down values and stories can bring a sense of coherence and meaning to a life that may have felt chaotic.
Empowering – It’s one way to reclaim your own narrative, instead of leaving your “last word” to legal boilerplate or silence.

“Don’t lie,” Amy advised. If something is too painful or private, you can leave it out, but this is not the place to invent a different life. Truthfulness, expressed with compassion, is part of the gift.

How Legacy Letters Help the Recipient

For the recipient, a legacy letter can be:

A compass in hard times, returning to again and again
A reminder: You are loved. You belong. You come from somewhere.
A way to feel less alone in grief, doubt, or transition
A bridge back to family, culture, and history that might otherwise be lost
A tool for resolving old questions: Why were things the way they were? What was my parent or grandparent going through?

Amy noted that this is especially powerful for younger people who may feel isolated or overwhelmed by social media. A letter that says, in effect, “Here’s what helped me survive tough times—and here’s how much you matter to me” can become an anchor.

A Quiet Act of Resistance to Ageism

One of the most powerful themes of the session was how legacy letters push back against ageism.

In some cultures, elders are seen as living libraries—people whose wisdom is actively sought out. In ours, older adults are too often sidelined, dismissed, or treated as burdens instead of resources.

By reviving the ancient practice of legacy letters, Amy believes we:

Reclaim older people as teachers, guides, and culture-bearers
Make it visible that a lifetime of experience has value
Give elders a clear, honored role: to gather and pass down wisdom
Help younger generations see aging not as decline, but as depth

In that sense, each letter is not just a personal gift; it’s a quiet, tangible challenge to the idea that older lives are less important or less meaningful.

How Do I Start Writing One?

Amy stressed that there is no “perfect” format and no required length. But she offered practical guidance:

1. Take Your Time

Think of it as a process over several days or weeks.
Jot down notes first—memories, lessons, values, sayings—before shaping them into a letter.
Make at least two drafts; don’t hand over your very first attempt.

2. Decide Who You’re Writing To

One letter for everyone?
Individual letters for children, grandchildren, or chosen family?
A mix: one general letter plus specific notes to certain people?

3. Use Prompts to Jog Your Memory

Early school memories: What did they teach you about fairness, courage, or kindness?
Moments when you changed your mind about something important
Songs, poems, or sayings that stuck with you (like “this too shall pass,” or the Chinese proverb Amy quoted: “The gem cannot be polished without friction, nor man perfected without trials.”)
Photos, family stories, and even difficult chapters that taught you something.

4. Focus on Love and the Recipient’s Future

Ask yourself: Will this help the person I’m writing to live better, with more strength and understanding?
Be honest, but not harsh. This is not the place to scold or settle scores.
Write with the assumption that your words may be reread many times, over many years.

5. Consider How You Present It

Handwriting can feel incredibly intimate and personal—like holding a piece of the author.
At the same time, technology and fading ink are real concerns, so Amy suggested doing both:
- A handwritten copy, and
- A typed or digital version, possibly stored in an archival folder or keepsake envelope.
Some people also record video or audio, but Amy cautioned that technology changes fast—so pairing media with something on paper is wise.

Questions We Explored Together

In the Q&A, participants raised thoughtful questions, including:

Is there a “right” length? No! It can be a page or many pages. Amy’s only caution: think about what your recipient will actually read and find helpful.
What about secrets or painful material? Some people do reveal long-held secrets or hard truths. Amy’s rule of thumb: always ask, “Will this help my recipient?” If disclosure brings understanding, healing, or safety, it may belong. If it only relieves the writer’s burden and harms others, it may not.
Can I continue a legacy letter for someone who has died?Yes. One participant asked about writing to better understand a parent’s life and legal battles after their death. Amy suggested this can help future generations understand the family story and mend old rifts.
Is handwriting necessary? Handwriting adds warmth, but not everyone can read cursive anymore. The group agreed: a combination—handwritten and typed—is often ideal.
Can we get help? Yes! Amy is open to reviewing letters and encouraged people to work with trusted friends or in small writing groups to gain feedback and support.

An Invitation to Begin

As we head into the holidays and toward a new year, this session left us with a simple, profound invitation:

Start a letter to a child, grandchild, partner, friend, or chosen family member.
Capture one story that changed you.
Write down one value you hope they’ll carry forward.
Tell them, plainly, that they are loved.

One participant shared that she’s beginning her legacy letter to her brand-new grandson. It’s hard to imagine a more hopeful way to step into 2026.

Amy closed with a line from Dr. Andrew Weil:

Writing a legacy letter lets us hug family and friends forever.

May we all find ways to extend that kind of embrace—across time, across generations, and across the barriers of ageism we’re working together to dismantle.