When you think about what you'll leave behind, it's not just the money that matters.
Financial assets have their place, but the most lasting legacy often comes from something far more personal. Your wisdom, values, and love can live on through a heartfelt letter — something your family will hold onto for years to come.
This article covers how to write a letter that truly matters — and how Trustworthy's digital vault helps you protect it with features like Legacy Access, designed to preserve what’s personal for generations to come.
Why Words Can Matter as Much as Wealth
Financial inheritance can offer security and help your family handle challenges and reach their goals. But your words can be just as powerful — shaping values, character, and future decisions.
A legacy letter lets you share your values, stories, and support with loved ones. While money may fade, emotional and moral guidance can impact generations.
Writing a letter can also be a great source of comfort for your grieving family members.
“Losing a loved one can be an emotionally challenging experience for those left behind," says attorney John R. Merlino Jr. of Merlino & Gonzalez, a law firm based in New York and New Jersey. "Your words of encouragement, affection, and wisdom can provide them with the strength and reassurance they need to navigate life’s challenges without you.”
Leticia Mooney, an author and writing coach in Australia, puts it perfectly: “Letters are words from the soul, connecting one heart to another. Wealth, in comparison, is empty; money enables a person to buy things, but it doesn’t warm the soul in a way that a letter can.
"Wealth can’t be pulled out of a drawer time after time, read and re-read, or cause tears (happy or sad) in the same way every time.”
What to Include in a Letter to a Loved One
There are no rules dictating what you should include in a letter to a loved one. To decide what to include, consider the letter's purpose. This could include preserving your memory, connecting with loved ones, or providing comfort and closure.
Personal Stories and Life Lessons
This is a time to reflect on and share your personal stories and life lessons. These could include significant milestones like marriage and birth that had a lasting impact on your life or lessons you want to pass on to future generations.
Your loved ones can learn from your experiences and carry your wisdom to future generations.
Family Values and Traditions
Share the family values and traditions that mean the most to you. This could include religious beliefs that shaped your family values, like attending church or celebrating holidays.
Values like the importance of kindness or hard work can be passed down the family line.
Encouragement and Support
Remember, your letter can be a source of great comfort and encouragement. It can express your pride and love for family members and offer reassurance and motivation that they can navigate life with you gone.
You can highlight the strengths and passions of your loved ones that you admire and encourage them to continue pursuing those passions and dreams.
Apologies and Reconciliation
This letter is an opportunity to reflect on any regrets in your life and offer apologies to the relevant people. It will hopefully bring the recipient some peace during a stressful period.
This section of the letter is a time to encourage healing, honesty, and closure.
Expressions of Love and Gratitude
Your legacy letter is a love letter to your loved ones, an opportunity to tell them how much they mean to you. You can also emphasize the importance of relationships over material possessions and money.
How to Write a Meaningful Letter
Be Authentic
Write in your own voice and let your authenticity shine because this is how future generations will get to know you. Instead of focusing on what’s right or wrong, focus on being genuine.
Don’t be afraid to share your thoughts, emotions, and anecdotes. Share details and use vivid language.
As author and writing coach Mooney notes: "A person’s voice is unique and evokes so much about them, to the point where you can ‘hear’ them in your own inner ear."
Make It Personal and Specific
Tailor your letter to each recipient and make it personal by including shared memories you’re fond of, inside jokes, and specific advice or encouragement you know they will appreciate and benefit from.
Some people will also include personal artifacts like mementos and photos with their letters.
Keep It Simple and Heartfelt
There’s no need to write in complicated language. Just keep it simple. Your letter does not need to be long or elaborate as long as it is sincere and authentic.
Consider Digital vs. Handwritten
Handwritten letters require more effort but convey a personal touch. However, they can fade, get lost, or be damaged over time.
Digital letters are much easier to store and access for longevity. Trustworthy's Family Operating System® offers a secure way to store letters with the Legacy Access settings, regardless of which format you use.
Handwritten letters can be automatically uploaded to the Family Operating System® by scanning them with Trustworthy's mobile app. With the Legacy Access feature, you can ensure that specific people will be able to view your documents — including personal letters — after your death.
Overcoming Common Barriers
Getting started can be the hardest part of writing your letter. Here are a few ways to move past the most common barriers:
'I Don't Know What to Write'
Jumpstart your thoughts with these prompts:
What are the most valuable lessons you’ve learned?
What do you hope your letter will accomplish?
How do you want to be remembered?
What are your hopes for your loved ones?
Are there any traditions or memories you want to share?
What’s something you wish you’d known when you were younger?
'I Am Not a Good Writer'
You don’t need to be. The most meaningful letters are honest, heartfelt, and written in your own voice. Keep your language simple, your ideas clear, and your tone genuine.
'I Will Do It Later'
It’s easy to put this off, but there’s never a perfect time to begin — and the future is never guaranteed. Starting now ensures your words will be there when they’re needed most.
Need More Help? Try Using AI
Still feeling stuck? AI tools like ChatGPT can help you create a rough draft or generate ideas. Grammarly can polish your grammar and help with tone.
Other helpful AI tools include Google Gemini, Microsoft Copilot, and Claude.
Keep in mind: AI is a starting point, not a substitute. Your voice, your stories, and your emotions are what will make a letter truly meaningful.
Related: Planning Your Own Funeral
Frequently Asked Questions
How do I decide who to write letters to?
Consider those who have played a significant role in your life — people who matter the most to you and will appreciate your wisdom. To pass down your legacy, write letters to future generations.
Should I write letters for special occasions, even if I won’t be there?
Yes. Writing letters for future milestones, like weddings and graduations, can be a deeply meaningful gift, even if you can't be there in person.
Should I include practical advice in my letters?
While legacy letters are meant to share values and emotions, adding practical advice on life planning or finances can be incredibly valuable for your loved ones.
We’d love to hear from you! Feel free to email us with any questions, comments, or suggestions for future article topics.
Trustworthy is an online service providing legal forms and information. We are not a law firm and do not provide legal advice.
