I love to read people’s reflections. Michel de Montaigne and Marcus Aurelius are giants of the introspection genre. Warren Buffet’s annual shareholders letters and Howard Marks’s investment memos are must-reads for investors and reflection-aficionados alike. In the Chinese world, technology writer Dan Wang writes eloquent annual reviews, as does my friend Meng Yan. Scriptures and classics push me to be better day after day.

 

Many people also love to reflect. They write year-end summaries, project reports, and introspective journals. Tech firms even redefined the word “post-mortem” to mean project analysis, instead of autopsy report. 

 

Ray Dalio says “Pain + Reflection = Progress.” I wholeheartedly agree, but it’s not completely true. There are many subtleties behind this truism, things that can easily change the outcomes of reflections. 

 

Reflections work. They just don’t work as often and as well as we’d like.

 

Despite my repeated attempts at introspective journaling, the results have been disappointing. My blogging attempts keep failing until recently. I’ve always had setbacks, so something must have changed this time with the way I reflect. Oral and verbal reflections are comforting, but reality sometimes makes me doubt such reflection’s true effect. What if reflections are just placebos or ways for us to cope with the cognitive dissonance between reality and expectations? 

 

There must be something fundamental to why we reflect.  

 

I think the answer is simple. We want to be better. The attitude, also known as modest or spirit, matters. This definition raises another question. If people are reflective because they want to be better, then how come one person’s reflection can yield progress, while another’s reflection may result in nothing? 

 

Based on my past experience, three components seem to influence the outcomes. If the change gets my actual buy-in and stays realistic, then my behaviors can match my thoughts and things go well. There is my takeaway: change one’s identity and be more than willing to pay the real price, or the hopeful message stays as a message. 

 

I’ve always wanted to be a writer, but that’s exactly the problem. My writing role model Michael Lewis says, “make sure what you want is not to be a writer, but to write. You see this a lot in colleges and creative writing programs, all these people who love the idea of being a writer who actually don’t particularly want to write. And so they moan and groan and kind of preen as writers, but they don’t actually write.” 

I was that groaning person for years! 

 

I was too idealistic with the shift in identity and had no realistic plan, so failure was guaranteed. My recent “success” was different, largely because of three people: Paul Graham, who taught me how to realistically approach writing; my dear friend Samuel, who bettered my thinking and style by an order of magnitude; and my friend Andrew, who made sure my words remain easy-to-understand yet authentic. I had the buy-in, the pragmatism, and people who made sure my actions matched my goal. Of course, I also worked pretty hard!

Now I sort of understand the “why” in reflection, it’s time to examine some additional aspects to how we reflect and what we reflect. 

We often don't record our reflections. They come up during conversations and later disappear. The lack of posterity and proof breeds inaccuracy. We often forget the details of our reflective moments. Sometimes our brains can alter the memories altogether. Thus, we need to record our reflections to avoid distorting reality. Good memories can't win against ballpoint pens and sticky notes.  

Our reflections are by definition subjective. Like any action and decision, not considering contexts and additional perspectives come with consequences. We are fish that cannot recognize water most of the times. What was the weather like? Did anything pleasant happen that day? What about unpleasant events? Questions like these aren't always answered during reflective moments, yet neglecting them is lethal. It helps to be more open minded when reflecting.

 

We also need to be more accepting of our limits and our reflections’ limits. Lessons don’t always exist. In fact, sometimes tangible lessons do not exist at all. Most if not all failures are due to multiple factors, but reflections often address only a limited number of them. The rest are either neglected or bundled together as “bad luck”. If we have no ability to discern the nitty gritty, how will we truly learn from the past?

 

Hence there lies the danger to incomplete reflections. We often guess why things fail, because finding out the exact mix of factors is next to impossible. Yet we still come up with takeaway lessons, because such process is largely unconscious and natural. Humans run on narratives. Reflections are narratives. As a result, we may dupe ourselves and invent fake lessons, simply because we need some kind of explanation when things don’t go our way. This may be the most difficult urge to control during reflective moments. Sometimes we just need to be firm and finish with zero takeaways, because life is simply too complicated.

 

These reflections on reflection may seem too abstract, but they reveal certain practicalities as well. In my case, an effective feedback system must be easy to use, so I can record as many time-specific contexts as I can. Such system also needs to address the potential effects of emotional and cognitive biases. To that end, a checklist approach will perhaps help me consider more angles during the reflection. Templates over small iterations also seem very helpful. Indexing is extremely important post-writing, so a clear index is a must. In the end, a system needs to be low-stakes, yet work well in the long-run. If someone unfortunately decides to write my biography, I want to at least make this dreadful job as easy as possible.

 

With all this being said, I still don’t know how to reflect. It takes many baby steps to get things right, but baby steps are all I want to do anyways - being okay with reality’s constraints, yet take one step and another after that. After all, I don’t want to reflect for reflection’s sake. I want to reflect because I want to be better.