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Why Writing Letters to Your Kids Is the Best Gift You Can Give Them as Adults

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 says “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.”

Here’s a letter he wrote to his children.

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 am a great believer in helping clients write down their thoughts and ideas.  If we have a meeting, to go away and write what you remember and share it with me.  It always helps clarify thinking.  In short, always write it down.

Here’s the blog in full.

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