Why Writing Letters to Your Kids Is the Best Gift You Can Give Them as Adults
Writing clarifies. It illuminates.
Jim O’Shaughnessy is a Wall Street legend and the founder, chairman, and chief investment officer of O’Shaughnessy Asset Management, which has $6.2 billion in assets under management.
He is also my friend, so I asked him to write a guest column that has nothing to do with his role as an investor. In this post, O'Shaughnessy reflects on his most important role: a father.
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Why Writing Letters to Your Kids Is the Best Gift You Can Give Them as Adults
“Letters are among the most significant memorial a person can leave behind them.” ~Johann Wolfgang von Goethe
I’ve always believed in the written word. Having to put your thoughts in writing helps you understand if you clearly understand what—and how—you want to say something. And if you keep written journals, there is simply no way to let hindsight bias take over, for there, in your own hand, is what you thought about something at the time, with revisions through selective memory impossible.
Writing clarifies. It illuminates. It helps you follow your own growth (or decay) in the way you look at the world and how your ideas have changed—or remained the same—over the course of your life. As someone with boxes and boxes of old journals, if I want to know what 21-year-old me thought about something, all I must do is pull out that journal and read. Sometimes I’m amazed by how much my views have changed—often dramatically—as I have made my way through life.
Yet equally telling is how little some of my foundational beliefs have changed. For the most part, I find that that, if anything, they have become stronger, better articulated, and better supported.
I’m a big believer in reading as much as you can that takes the other side of what you think. We’re all subject to confirmation bias, and a great habit to build is to always search out beliefs that counter your own. If they make you change your mind, as has happened with me, then your original belief really wasn’t that sound to begin with, so, by always challenging yourself, you make your thinking stronger and more truly reasoned.
You should also try to seek out the best arguments for things you don’t agree with—called creating a “Steelman” as opposed to the far more common “Strawman.” You’ll often see nothing but Strawman arguments in popular media and I’ve sadly concluded that, for the most part, popular media stopped presenting serious, well-articulated essays that might help sway you to a different point of view. But there are more great, serious essays available today to all of us than ever before—it’s part of what I call “The Great Reshuffle” which is the ongoing transformation of almost every aspect of our lives that technologies and inventions are ramping up for society at an exponential rate.
We could be living through one of the most interesting periods of human history, and you have a chance to narrate it for yourself and your children. I’ve long advocated writing continuous letters to your kids, but given all the changes we’re living through, it might give you an extra special opportunity to let your kids see it all unfold.
Related: Jim O'Shaughnessy on Bitcoin, Investing Psychology, and the Secret to a Long-Lasting Marriage
This compels me to again urge every parent reading this to get in the habit of writing your children a series of letters so that they too can understand you, and, with luck, themselves better. Having to articulate thoughts in a letter allows you and your children time to reflect on things in a way that is often difficult in the day-to-day events of your lives together.
It’s something that I always wish my dad had done, as we had a rather difficult time understanding each other and I think a series of letters from him would have helped me understand him much better than I ultimately did.
Ideally, you should start as soon as you can and continue to write over the years. I started when my son, Patrick, was 7 days old and continued until my last child turned 21. As each child hit 21, my wife—the true marvel in the parenting hall of fame–would select photos and publish the letters in book form for each of my kids. The last letter of each book was written specifically to the child the book was for, but otherwise, all the letters were for all my kids.
Below is the first letter I wrote, which I hope spurs you on to do this for your kids. Rarely are things 100 percent win/win, but in the case of letters for your kids, that’s the reward for taking the time as your kids grow to have a conversation with the adult they will become.
April 22, 1985
Dear kids,
Firsts are exciting and somewhat perplexing. This is the first entry in a book I’m going to keep for you; its direction not yet known to me. Thus, the thought of giving you something created over the years excites me, but I am also perplexed about what I really want to write here.
I know that I don’t want this to be a diary, detailing the days, for although we already love you we know that a diary of when you eat and sleep wouldn’t be exciting reading. In some ways, I hope to be able to say all the things fathers want their children to know, yet so many times forget, or neglect to tell them.
If nothing else, you will see how I changed, from a 24-year-old brand new father, to one who has watched you grow up, and, with luck, grown up myself.
Most of all, you may be able to know both me and yourself better through this collection of “letters” and we must all strive to understand ourselves and those we love, for through our understanding and experience comes the wisdom that no one person can teach another, no school can transmit it. It must come from within, from learning, from logic and experience. If I could, I would describe it for you; I can’t. Perhaps you will agree when you are older.
I also want to tell you about me, my life, my thoughts, perhaps you can gain some understanding of yourself through understanding me. If I was going to describe my own impulses in a paragraph, it would be advice to you as well, so here, in Lao Tzu’s words, it is:
“He who knows much about others may be learned, but he who understands himself is more intelligent. He who controls others may be powerful, but he who controls and has mastered himself is mightier still. He who receives his happiness from others may be rich, but he whose contentment is self-willed has inexhaustible wealth. He who occupies a place provided for him by others may live a long life, but he who dwells in his own self-constituted place, even though he decays, is eternal.”
That bit of wisdom really embodies many of my goals, and many of my beliefs.
You will always be only as good, only as happy, only as successful as you perceive yourself to be. Happiness springs from within, never from without. Virtue too; honor; and love. All the things that make a life worth living. Thus, if you are unhappy, don’t look outside yourself for causes, the reside within; likewise, if, like me, you are happy, understand the source within your soul.
Love,
Dad
I created email addresses for both of my kids and send them emails occasionally. It is hard to look back on those experiences with the same emotions, so it's good to capture them while they are fresh. Great article!
Wonderful suggestion. I am a father of 1.5 months old baby-girl and I am starting this practise now.