Hi Penelopes,
I’m so honored to bring to you our first guest post. It’s from a fellow Penelope and commenter on this blog, Deren Monday from MeandYourHouse.com. Deren has some incredibly useful things to say about writing a Legacy Letter to his children. It’s a fantastic idea and I’m considering starting this habit myself.
What a wonderful gift to give to future generations. I hope you’ll let him know what you think.
-Meredith
Building a Legacy Letter
Like many things in my life, it started with agitation and festered into action.
I wanted to know where I came from. Not literally, because I understand biology pretty well, but contextually.
What were my parents thinking before I was born? Why did they try for a third child? What happened when I was young to make me who I am? What similarities do I share with my parents and grandparents when they were my age?
I wanted to go back in time and talk with them when they were in my stage of life. When they were raising kids, and dealing with social strife, and trying to build their future.
I just had to know. So I asked. And there was not much there. And I was disappointed.
Were they holding things back? No. That’s just how life is. It’s hard to remember. It’s impossible to remember. So I vowed my kids would never have to wonder.
And I started writing.
Two Years Later
My legacy letter to my kids is now 250 pages long. It’s filled with assorted snapshots of the life of my family. The depths of despair, the elation of success, the wonder of raising kids, the heartache of death, the fear of failure (a deep-down specialty of a Penelope), the resentment of hurt, the hope for a better future.
And each day, I add to it. One entry at a time.
My kids will never have to wonder what we were like. I write the letter as if I am talking to them as young adults. And when they are 18, they will receive a bound copy. They may just put it on a shelf somewhere, because at 18 we’re pretty stupid. But one day they will open it. And they will turn to their birth date. And they will read of a father’s love. And they will treasure it.
How To Build a Legacy Letter
Step 1 – Decide who to write to
Choose an audience. It could be your children, grandchildren, niece, nephew, heir to your business, young leader in your non-profit, children of your church/synagogue/mosque, future leaders in your city. Anyone who you think might benefit from your story.
After determining the recipient decide when you will give it to them. Pick a time in the next 5-20 years when you think they would most benefit from your words. Then picture this future person as you write. Write to them as if you are telling them a story on that future date. Become a storyteller to the future.
Step 2 – Decide when to write
As any Penelope knows, a task like this requires discipline. Choose a time each day (or week) to write. Make it consistent. Make it a time to focus. Make it short.
For me, I write in the morning before anyone else is up. A cup of coffee and a laptop and the stillness of the dawn. It takes me about 15 minutes to complete an entry. Sometimes more, sometimes less depending on current events.
Step 3 – Decide where to write
Pick a favorite spot where you can relax and be at peace. Try to remove yourself from temporal distractions. After all, it’s hard to think of the future when you are immersed in the present.
Step 4 – Decide how to write
Some of us are pencil-and-a-journal folks, others can type faster than we think. (Which leads to apologizing over hastily-authored emails…) No matter the medium, choose a writing method in which you think clearly and can tap into your deepest thoughts and feelings.
Step 5 – Decide what to write
Your audience will determine the depth and complexity of your legacy letter. Things we might write to our children surely differ from things we would write to acquaintances.
I suggest writing about whatever is on your mind at the time. After all, you are trying to convey who you are and what your life is like.
I write about an assortment of topics: family, politics, goals, news events, tough decisions, etc. I try to capture a mini-theme each entry depending on my mood.
Unexpected Benefits
Building my legacy letter has had unexpected benefits.
From time to time I peruse past entries. I’ve gotten great joy in looking back and remembering the good times. Goals met and dreams come true, relationships healed and lives changed.
It’s also become a form of accountability for me. My entries are sacred and I fear compromising them by not living up to my entries. If I write about a step I need to take in my life, I feel obligated to follow through. I can’t stand the thought of letting my children down. I know, they do not even understand the letter exists yet. But I still feel a sense of purpose in living my my words.
What about you? How are you passing on your knowledge and experiences to the next generation? Certainly there are many methods, and this is but one. I’d love to hear your story, as would the future…
Deren Monday is a professional remodeling coach helping homeowners improve both their homes and their lives. When not writing to the future, he does dwell in the present…

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{ 15 comments… read them below or add one }
this is so great. thank you for the inspiration. i wish i’d read this about a year ago for my first little one.
what a wonderful, invaluable idea!
I love this idea!! I have journaled for years, but never “to someone”. What a great idea!! My husband and I are trying to get pregnant, and this would be a great way to document that journey to pass on to our child someday!
As someone else who’s (hopefully) about to start a family, I am definitely stealing this idea. It makes complete sense that you’re more likely to follow through with what you say if you think your kids will someday read it. You want others (and especially offspring!) to see you as the best version of yourself. Thanks for the idea, Deren!
WOW!!! What an amazing gift to pass on to my children.
I’ve never heard of this (and as usual) you’re introducing me to something new:)
I don’t have children–yet, and will definitely be storing this idea in the vault for later.
I love this idea.
What an incredible post. When I was two years old all the women in my family wrote me letters to be opened on my 18th birthday. I treasure those letters as so many of them had passed away prior to my 18th birtday. I love to read how they felt about me and what their hopes and dreams for me were. This idea takes it a huge step forward. Thank you so much for sharing.
i have been writing letters to my children on each of their birthdays since they have been born. when they are finally married, or maybe when i pass away, i will gift them to them. they are all sealed and it makes me so happy to know that those little special thoughts about them and how i felt so blessed to be their mommy over that particular year will someday be theirs to read. i am sure that my children know that i love them now in their little years, but i think it will be a great thing for them to read these things as adults with their own children as well.
i do love the idea of really writing down the history of family. i know that it really makes me sad when i ask my parents things about their parents or their parents parents, and they don’t know what to say in response to my questions. so much lost that didn’t have to be.
Thank you so much for this post! I just read the great article on the late John Hughes in this month’s Vanity Fair, and he left tons of letters for his family and grandkids that are labeled with ages of when to read them. I was so impressed by the idea, but didn’t know where to start (maybe start by having kids?!) and then here is your post. You are such a mindreading Penelope! Thank you!
Thank you for sharing such an inspirational idea. What a touching gift to give your children. It will truly give them a taste of who you were at the ages they will become. Fantastic!
The questions I’ve come to in adulthood, i must admit, are a bit more selfish. Instead of wondering what my parents were like at my age, I wonder what I was like at my children’s ages. I want my kids to know the fears I had, the mistakes I made, the feelings of anticipation, the thrill of that first crush, the joy in achievement. I want them to know those things so that when they are having their own moments, they can know that they are not alone in them. Their mom felt exactly that way, too. And it will be okay. But it is hard to remember all of those things. It will be hard for them to remember. So a few years ago, on the last day of school, I began a tradition of writing a letter to each of them to share what the previous year held. I too sit down with a cup of coffee and some moments of silence and share with them all about their feelings, friends, teachers, successes, difficulties, family changes and dreams for the years to come. Then I add in a few pictures from the year and put it in an art binder that I have for each of them, filled with their writings and projects from the previous year. Even though my 1 year old does not yet have a binder, he has a letter. And that’s a start.
Deren, you have definitely inspired me to write to my children more in terms of who I am today. Strange, it hadn’t occurred to me before that they would be that interested. But they will. I’m sure of it. And perhaps it will make them feel that much closer to the one who loves them more than words can say.
What an incredible idea!! I really need to start jotting down everything the dude does since it seems like he’s learning a new thing every day now!
I really, really love this. I’m a touch-and-go journal writer, going in strong spurts that taper of into nothingness for a few months until guilt motivates me to pick up the pen again with a resolution to do better. But it’s a never-ending cycle. Your guidelines are so helpful in keeping oneself going! Because it really is so important. It’s how people will remember you and glean strength for their own life’s trials. Thanks for sharing!
I love the way you put that, Meredith: through the Legacy Letter, our loved ones can “glean strength for their own life’s trials.”
That really brought this home for me.
I’ve wanted to do this for maybe 20 years now. My son is 23, my daughter 16 and I’m so terrified that I won’t remember important events, or feelings or just a special kind of day that stands out. I’ve bought blank books with the intention of starting, but never have. It’s about time and your post has made a monumental task seem possible. Thank you.