Imagine this: You’ve brewed a nice, hot cup of tea and settled into your favorite comfy chair. In your hands, you hold a brand-new notebook with that fancy cover you couldn’t resist, even though it cost more than you’d like to admit. You turn to the first crisp page, pen in hand, all the elements in place… and then pause. What now?
Everyone says journaling is a good idea. Socrates proclaimed, “Know thyself.” Jung said, “Who looks inside, awakes.” Aristotle added, “Knowing yourself is the beginning of all wisdom.” But none of them tell you how to do it!
So here you are, pen poised, ready to scribble your way to enlightenment. Annnndddd… crickets.
In my previous attempts at journaling, it typically took one of two forms. The first was a miserable rant about all my current struggles—hardly uplifting or helpful. The second? An incredibly tedious account of my daily life, chronicling how little changed from one hour to the next. In short, I was oscillating between two extremes: the overly dramatic and the mind-numbingly mundane. Neither approach was particularly inspiring or useful.
But in recent years, I’ve learned how to wield my pen in far more powerful ways. I’ve discovered it’s more than just a tool for recording thoughts—it’s a magnifying glass, a spade, and an antenna, all in one. The hardest-working multi-tool I own!
Journaling has helped me cultivate a deep, nourishing relationship with my innermost self. And let’s be honest—you have an innermost self too. If you ever find yourself in an internal conflict, ask yourself: Who’s fighting whom? We all have different parts of our psyche, but when I speak about the “innermost” part, I’m referring to the source of my intuition. Through journaling, I’ve made a surprising discovery: everything I’ve ever wanted or needed to know is already within me, waiting to be uncovered.
It’s no coincidence that “intuition” breaks down into “in-tuition”—an inner teacher. When we connect with this part of ourselves, it guides us, teaching us what we need to know.
The secret to tapping into this inner wisdom? Practice asking the right questions. That’s it. It doesn’t have to be complicated. To help you get started, I want to share a technique that has been very useful.
Instead of sitting down with no direction, start with something you’re currently struggling with. Is there a person, feeling, or situation that’s been taking up too much mental and emotional real estate? Maybe you’re grappling with anxiety, overwhelm, or fear. While you may have multiple things on your mind, I recommend focusing on just one feeling or situation for this exercise.
Once you’ve identified what you want to work on, we’ll use a technique I learned in business school: the Five Whys. Originally designed to find the root cause of business problems, this method works wonders in journaling too. You start with your issue, and then ask “why?”—and keep asking why until you’ve done it five times. Each “why” is like a spade digging deeper into the issue, peeling away the layers of confusion and chaos.
Write a problem statement that feels true for you at the top of your page. It might be something like, “I hate my job,” or “My relationship feels strained,” or “I’m not meeting my own expectations.” Then, start digging. Ask yourself, “Why do I feel this way?” and write down your answer. Then ask “why” again about that answer. Keep going—five times.
By the end, you’ll either feel like you’ve struck gold with an answer that resonates, or you won’t. And that’s okay. Not every line of questioning will lead to a breakthrough, much like not every hole dug leads to buried treasure. But when you hit on something that rings true, you’ll know—you’ll feel a sense of clarity, a recognition that you’ve uncovered something valuable.
Happy digging, friends! xx
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