Documenting Your Past for a Better Future

By Laura A. Roser


“We’ve been doing some organizing,” my mother announced. She pointed to cardboard boxes resting on their basement floor. “That’s your stuff. Figure out what you want to keep.”

I sighed. This is not how I wanted to spend my family visit.

I begrudgingly opened one of the boxes. It was high school: year books, dance photos, art projects, research papers, debate trophies. I gazed at my prom photo from junior year. There I am – red dress, corsage on my wrist, stately up-do – with David – gray suit, black hair poking out from the sides of his head. Oh David, whatever happened to you? We’d spend hours talking about random topics in art class – his year traveling abroad on a boat with his mother’s rich lover, our aspirations to leave Utah, rumors about the crazy gym teacher. I pulled out the larger picture of us. Damn it, I’m half closing my eyes. So embarrassing!

I flip through a yearbook, reading comments from friends. At least five people wrote, “Never change.” For a brief moment, I wonder why anyone would ever want to stay the same. And then I come upon a journal. It’s one of those cheesy ones with pastel flowers printed all over the front framing an inspirational quote. I open it and read a passage I wrote on July 14, 1997. There’s a sticker of a cartoon giraffe in the corner. It starts out, “Tomorrow’s the big day. Jenny is going in for surgery at about 6:00 am.”

The journal entry goes on to explain how strong my parents had been through my sister’s health issues, which led to my sister having open heart surgery at 2 years old. The entry was short. One page. Five paragraphs. But, it made me proud to read those words and remember that time. It made me proud to see the kind of teenager I was and the kind of character my parents showed.

Learning From Your Wiser Self

I hate to admit this because, as a legacy planning expert, you’d think I’d have stacks of journals. But the truth is, I didn’t begin serious journaling until a few years ago, which is why it’s rather amazing I actually had a journal that captured the day before my sister went into surgery when I was seventeen. Mostly, I just let life happen and didn’t document any of it.

There is, however, a great power in documenting your life. Even experiences I’ve had as little as a week ago teach me great things when I look back and read what I wrote. It’s easy to get distracted or forget how far you have come. Without a tangible record, your memories fade and that learning is lost.

Last night I read something I had written four years ago when the world was falling apart around me and it gave me strength to realize how much I had learned and how far I had come. Happy times can also be a great inspiration. When times are dark or I need to switch my brain out of a negative mode, it helps to look at photos of loved ones or read what I have written about fun experiences.

In a world of ongoing distraction, getting clarity is difficult. I have moments where everything is clear and then, like a vivid dream that disintegrates upon waking, the clarity is wiped away by fear, daily stresses or input from others. If I can look back at my journal or personal mission statement, it brings the clarity back. “Oh yeah,” I think to myself, “that’s my goal. That’s my purpose. That’s what I learned.” And it gets me back on track.

Marcus Aurelius’s Notes to Himself

One of my favorite texts is Meditations, written by the Roman Emperor Marcus Aurelius from 161 to 180 AD. The reason I think it’s so powerful is that Aurelius did not write these notes with an agenda. There was no outside audience to appeal to. No reason to write other than for the purpose of improving himself and documenting wisdom he had learned throughout his life.

Meditations is not a recounting of events, but a mental exercise of self-analysis and an exploration of stoic philosophies.

Like Aurelius, I believe we should journal with the intent to extract deeper meaning from events in our lives, books we are reading, lessons we are learning and so on. Although, it’s better if we go back and read what we’ve written at some point, the process of writing something down (even if we never look at it again) dramatically increases the likelihood that it will be remembered.

5 Ways To Enhance  Your Journaling Experience

1. Keep It Truthful. Be vulnerable. Tell the whole truth. Admit to your dark side. Don’t hold back. (Sometimes telling yourself the truth can be hard.) Here’s the exception: if you are writing for an audience – like your children or future generations – then you may want to keep some things a mystery. So, determine the purpose of your journal before you start. Because self-analysis is so powerful, I’d suggest having a journal that is only for that purpose (your eyes only) and then one that is for your family to read.

2. Keep It Private. In order to be truly vulnerable, you need to be sure no one is reading your words. Whether this means you hide your journal or have an insanely secure password for a digital journal, is up to you.

3. Date Each Entry. I have notebooks where I’ve written things that I wish I had dated.

4. Write In Your Own Voice. Don’t try to sound distinguished or literary. Write how you would talk with a friend at a coffee shop.

5. Review Your Writing. Every once in a while, go back and read what you wrote. This will give you insights and deeper appreciation. Sometimes your interpretation of an experience can be completely different when looking back.

Avoid That Hole

Below is one of my favorite poems:

There’s a Hole in My Sidewalk

“I walk down the street. There is a deep hole in the sidewalk. I fall in. I am lost… I am helpless. It isn’t my fault. It takes forever to find a way out. 

I walk down the same street. There is a deep hole in the sidewalk. I pretend I don’t see it. I fall in again. I can’t believe I am in the same place. But, it isn’t my fault. It still takes me a long time to get out. 

I walk down the same street. There is a deep hole in the sidewalk. I see it is there. I still fall in. It’s a habit. My eyes are open. I know where I am. It is my fault. I get out immediately.

I walk down the same street. There is a deep hole in the sidewalk. I walk around it.  

I walk down another street.” 

Portia Nelson, There’s a Hole in My Sidewalk:  The Romance of Self-Discovery

When we record our thoughts, self analyze and look back at what we have learned, it gives us the emotional resources to walk around that hole, avoid it the next time or, at the very least, have empathy for people who keep falling into the same hole (because so do we).


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by Laura A. Roser
CEO and Founder of Paragon Road
#1 Expert in Meaning Legacy Planning