The Power of Journaling for Wisdom and Connection

Source: Milan Popovic / Unsplash

I’m a very in-my-head kind of person. I mentally replay scenarios all the time, not to scare or beat myself up. But to try and understand them better, wringing every element out of them until they have nothing left to offer.

I’ve been like this all my life. As a kid, I remember my English teacher telling me I was an old soul and my mom constantly alluding to my happy-go-lucky cousin. Or reminding me that my thinking face looked like a scowl, and it would become wrinkled before its time.

And so I began to wish I weren’t so in my head. I would see people move from one moment to the next as though they never lived the previous moment at all. And I would dream of that lightness of being, of that carefree feeling of having said or done something and left it at that.

As I’ve become older, I’ve started to own this part of myself for two reasons. One, with age, you come to care less and less about what other people think. You’re done hating, rejecting, and apologizing for parts of yourself others don’t like, and twisting yourself like a pretzel to fit into norms and expectations that never considered your joy.

It’s also because I find that in this world of incessant external noise, my musings and reflections are the one thing that keeps me guided and true to myself. I become aware of not just what worked or didn’t work, I also get to connect to the feelings I had in those situations and experiences.

I get to ask myself what those feelings were trying to tell me. I get to question the lessons I learned growing up and the stories that I believe to be true in all circumstances. Because stories are meant to be challenged and rules are meant to be broken. But I find that many of us who do so are simply rebelling against the old stories because they don’t sit well with us any longer.

The opposite of a false story doesn’t make a true story. The truth is always far more nuanced, and my truth can only come from me, just like your truth can only come from you.

Just a couple of hours ago, two men came from Ikea for a pickup on an item that I wanted to return. The delivery and pickup people I often see are young, with the energy and hunger of big dreams and expectations of life. These two men were different. They were older, yes. But their faces had a different look. The eagerness wasn’t for more advancement, but more connection.

I’ve seen that look before and often thought about it. I believe it comes from the whiplash of life and the innate desire to be seen by another. I wanted to invite them in, offer them a warm drink, and talk to them about their lives. But I knew it wasn’t wise or practical to do so. They had work to do and pickups and deliveries to fulfill. Besides, didn’t we all learn to be wary of strangers growing up?

There’s certainly truth in that lesson. But it’s not the whole truth. We can always make people feel seen. It is incumbent on us to do so and perhaps the most important and fulfilling work we’ve been given.

I did what I could. I looked them in the eye, asked them about the weather outside, and joked about the package being heavy. Laughter is such an instant connector. I then gave them a nice tip to “get something small for your family” and hearing their happy voices recede in the building corridor as they left, I couldn’t help but smile to myself.

I’ll tell my daughter about this moment when she comes home from school, just as I’m telling you about it because our reflections and lessons are the wisdom we offer others. In his book Learning to Love Midlife, author Chip Conley says that in a world being taken over by AI, this wisdom may be the greatest and most irreplaceable value we bring to our homes and workplaces.

He suggests keeping a wisdom journal for this reflection where once a week, you reflect on the experiences you had that week and what you learned from them. Journaling is a wonderful practice, and research has long shown that journaling about our emotions helps us make sense of them and let go of negative rumination.

I believe that journaling about our experiences moves us from the realm of emotions to that of the soul. It helps us make sense of our lives, and stay true to ourselves by connecting to our voice and what we have to say and contribute.

You can also begin a journaling practice of a daily, weekly, or quarterly review of your experiences. There is no right or wrong way of doing this. But there are a few questions that can guide you:

Wisdom Essential Reads

Do We Get Wiser as We Age?

A World Without Grandmothers: What Would We Lose?

• How did that situation make me / others feel?
• What does that point to / remind me of / teach me about life?
• Are there changes I can make to how I show up or what I pursue?
• Can this be of value to someone I know?

Keep listening to your soul with curiosity, and courageously tweaking how you show up, so your life is a gift to the world and a legacy you’re proud to leave behind.