Of all the things I encourage people to do when preparing their affairs, this is the one that provokes the most emotion — and the most resistance. Writing a letter. A real, personal, hand-from-the-heart letter to someone you love.
Most people find a reason to put it off. 'I'll do it when I feel more ready.' 'I don't know what to say.' 'It feels too final.' But I've never met anyone who regretted writing one. And I've met many people who deeply regretted not receiving one.
Why a Letter Matters More Than You Think
There is something irreplaceable about words written in your own hand — or typed in your own voice — that no legal document can replicate. A Will tells your family what you want them to have. A letter tells them who you are, what they meant to you, and what you want them to carry forward.
I've heard stories of people clutching a letter from a lost parent on their wedding day — reading words of love and pride from someone who couldn't be there in person. I've heard of children, decades on, turning to a letter their mother wrote when they face a difficult decision, hearing her voice in their head as they read.
That is a legacy. That is presence beyond presence.
You Don't Need the Perfect Words
This is the most common barrier — the fear of not knowing what to say. But the truth is, the words don't need to be perfect. They just need to be yours.
Start with what you feel. What do you want this person to know? What are you proud of in them? What has your relationship meant to you? What do you hope for their future? What would you say if you knew you only had one more chance to say it?
Write that. Even imperfectly. Even messily. The imperfections are part of what makes it precious.
Different Letters for Different People
You might write one letter for all your family. Or you might write individual letters — one for each child, one for your partner, one for a close friend. Letters for milestones: a wedding, a difficult time, a graduation.
Some people leave instructions with their executor about when letters should be shared. Others leave them openly in a folder with their other important documents.
Where to Keep Your Letters
In our Honouring My Wishes workbooks, there is space to record that you have written letters and where they are stored. This is important — a letter tucked away and never found helps no one.
Make sure someone knows the letters exist. And make sure they can find them when the time comes.
Write the letter. Write it this week. It doesn't need to be long. It doesn't need to be perfect. It just needs to be real.
— The Evelyn48 Team 💜