Last time, I covered using non-judgmental observations to identify self-directing problems and then building sustainable plans of action. I also mentioned that as we proceed down these paths of action, we must accept that failure is a natural part of the process that allows us to reflect and build a feedback loop.

Today, I’d like to discuss my process of reflection: what it is (and what is not), how it works, and a tool I’ve found useful for doing it: writing.

Reflect: probe yourself

For me, reflecting is a methodical process where you probe your own past actions and related thoughts and feelings to arrive at a conclusion for the sake of improving yourself. This is different than ruminating, where we think about the same thing over and over again, spinning our wheels as if our mind is a car suspended in the air in a repair shop. Reflecting is also different than comparing, where we measure our standing in life by the yardstick of another person. Lastly, it is different from observing, which is a necessary but insufficient component of the process as it is too surface-level.

The word “reflect” is apt here because you are holding a mirror up to yourself to understand deeply what you see. This process involves asking some difficult questions: What happened and why? How does the result differ with my expectations? How can I adjust my behavior or expectations moving forward? This may seem like an easy way to overwhelm yourself, but I find that an easy way to transition into this mentality is to remember that this is grounded in the perspective of observing without judgment. The goal is not to flood yourself with scrutiny, which could easily lead to self-shaming. Instead, aim to probe yourself gently, one question at a time, giving it time and space for consideration at a pace that is comfortable for you. Over time this process can reveal low-level truths about ourselves or clarify problems that were previously amorphous or daunting.

It can be difficult to do this kind of reflection entirely in your mind. The amount of information and context you need to hold at once can grow large quickly, which makes it easy to spiral out into the modes of ruminating on a particular moment or comparing our experiences to that of others. Instead, I use writing as a tool for externalizing my reflections to maintain a neutral, productive focus on the series of probes from this style of reflection.

Write: externalize your reflections

To be clear: in this case, I am prioritizing writing as a private tool for self-reflection though it can have beneficial side effects for an audience. By putting pen to paper (or finger to keyboard), we cut through any haze or mental overhead that we have built up and emerge with a crisp idea of what is on our mind. This helps carve amorphous or daunting problems into self-directing problems, and it also helps maintain focus when reflecting on an outcome. Depending on the emotional quality of certain thoughts or outcomes, I use one of two methods of writing: stream of consciousness or recursive outlining.

I use stream of consciousness on a daily basis to empty my mind with no intent of revision. I like using full sentences and paragraphs to stimulate the feeling of conversation, but bullet journaling is a great way to start if you’re uncomfortable with exposing your emotions in a written format. By dumping all of my thoughts onto the page1, I can express myself in whatever depth I’m comfortable with and probe myself just a bit deeper as I go. In principle, this is similar to freewriting, but I find that my outputs are generally more structured, usually containing three sections:

  1. A daily reflection (How was the day? Did anything notable happen? What’s a fun story to remember later?)
  2. An exercise/meditation reflection (How was the process of sitting with the breath? How were my energy levels? Anything I can change to improve my experience next time?)
  3. A life reflection (Any trends from the past that explain the present? Any observations on the present that can inform the future?)

I’ve been doing this consistently for the last three weeks, and I’ve noticed a significant decrease in anxiety before I sleep as well as a dip in ruminating on “restless thoughts”. In this way, I view stream of consciousness writing as preventative maintenance: it flushes out the gunk that has accumulated in my mind throughout the day, leaving it clear.

On the other hand, I use recursive outlining to investigate a particular topic where I want to gain a productive insight that can be used. I also happen to use this process when writing things I share with others (e.g., these posts), but the technique itself is generic. We start by externalizing vague thoughts and then repeatedly probe them, editing them into clear observations with a narrative. This doesn’t need to be in a strict paragraph or sentence form. In fact, using bullets or phrases may be the best place to start. Once I have an observation out, I try to answer two questions:

  • How did I come to observe this?
  • Why do I think this?

This produces its own set of observations and insights, which I can fold back into my initial vague observation and clarify it. Additionally, it may produce some realizations that can branch off their own investigations. At this point, I repeat the process of examining the how and why of each thought I have so far. I do this until I am satisfied with the result or am able to produce a nugget of insight about my life that I can use for current or future actions. I find this particularly useful for examining difficult situations in life or distilling a personal philosophy on how I feel about certain values or actions and why. This process often produces a beneficial side effect that the finished product is something you can share with others to stimulate discussion and debate if you feel safe doing so.

Empathize: see others through your reflections

In a way, I find the two approaches of writing to be complementary. Stream of consciousness allows for an outlet for many thoughts in my head, leaving behind a focused mind. This helps me build empathy with myself by allowing me to handle my own mental overhead better. Recursive outlining brings forth clarity from vagueness, building confidence in my view and my ability to share it with the world. This helps me build empathy with others by deeply reasoning through a concept and understanding why someone would or would not arrive at the same conclusion as me.

I’d like to talk more about this concept of building empathy, which leads to another facet of improving mental health: listening. That’s for next time. Thanks for reading!


  1. The medium for doing this is not important; choose whatever works for you. I prefer to use pen and paper for a few reasons: (a) it gives me a known fixed amount to write (1 page); (b) it reduces the chance of getting distracted and physically cultivates focus by looking at the nib of the pen as the words come out; (c) in a world where everything can be electronic, I like improving my penmanship through a personal craft like journaling. If you’re looking for digital recommendations, my friends have used note-taking apps like Evernote, dedicated journaling apps like Day One, and freewriting platforms like 750 Words↩︎