Philosophical Meditation: 3 Journaling Questions That Untangle Stuck Thoughts

Philosopher in Meditation, Rembrandt van Rijn, Paris – Source

Philosophical Meditation is a practice that assumes that a good chunk of the troubles in our minds comes from thoughts and feelings that have not been untangled, examined, and confronted with sufficient attention.

Journaling about these unexamined thoughts and feelings allows us to better grasp our minds by becoming aware. The goal is not to fix the mind but to experience the relief that comes from being aware and feeling in control of our minds. We attempt to move from vagueness to clarity.

The three questions or journaling prompts for philosophical meditation are:
– What am I presently anxious about?
– What am I presently upset about?
– What am I presently excited about?

A few principles when answering the above questions:
– Write as if you are talking to a kind, considerate friend.
– Constrain yourself to a time limit and think fast instead of deeply. This enables us to not get lost or fearful of introspection.

What am I presently anxious about?

The first question of the philosophical meditation is to understand anxiety.

For 15 minutes:
– Write down what you are anxious about until you cannot think of anything else. Aim for 8 things – and consider all areas of your life.
– Each entry is a single word or a few words.
– Don’t judge them, whether they are small or large.

For each one of those entries, unpack them further by writing about:
– Why is this a source of anxiety? Describe it to a friend.
– What steps do you need to take?
– What do others need to do?
– What needs to happen?

What am I presently upset about?

The second question of the philosophical meditation is to unpack being upset.

For 15 minutes:
– Write a list of current upsets. How have others hurt you? What are you sad, distressed, nostalgic, wounded about?
– Ask yourself: If this had happened to a friend, how would you advise them?

What am I presently excited about?

The third and last question we attempt to get clarity on focuses on excitement. It helps us understand what we aspire to be.

For 15 minutes:
– Write a list of things that have caught your attention and sparked your interest.
– Think through a time when you were envious, your daydreams, or how nice something felt.

When I studied the journals of Bruce Lee, I found entries on willpower, emotion, and reason that are essentially this practice — he just hadn’t given it a name.

Thinking on paper allows us to articulate the scattered thoughts in our minds. We all have the capacity for growth, change, and adaptation, but lack the opportunity for expression – journaling does that for us. If you want ready-made questions to begin with, these 100 journal prompts for self-discovery are a good entry point.

If you want a one-page version of these three questions to keep beside your notebook, that is the kind of practical follow-up my newsletter sends. Subscribe here if useful.