Michael Wong blogs here

The Examined Life

Socrates taught us that the unexamined life is not worth living. Presumably he meant that we should take some time to reflect on things. This is of course much easier said than done. For most of my life, I fluctuated between overthinking things and not thinking at all.

I’ll first admit that I still don’t really have a grasp on what I am doing with my life. But believe me it used to be even worse. I didn’t reflect much about my life mostly because I felt like there was just no time to think. When I was in high school, I needed to get good grades to go to a good college. In college there was always an exam and then a cool party. It was always hard to find time to reflect about what I was doing. I regret that. I ended up going down many mistaken paths.

And then for a period of time as college ended I found myself overthinking everything. Which was not productive either. I agonized over which career to pursue. I also agonized over whether or not to break up with my ex (and caused her much suffering). I spent months brooding. I felt emotionally drained, overwhelmed. Sometimes I was paralyzed in my decision-making. At other times I changed my mind incessantly. Many people told me I was overthinking things. And I could not stop.

It’s been said that ours is a generation full of doubt and indecision. I’d be a fool to claim that our generation is any different from other generations. J Alfred Prufrock famously agonized over whether he dared to eat a peach. Let’s not forget Hamlet either. But can we make some progress? Can we approach Socrates’ ideal of the examined life? What does it actually mean to lead an examined life?


Over the past year I’ve been trying out a different technique. Every day or two I come home and spend just a few minutes thinking about what made me feel rewarded and content and what made me unhappy and frustrated. Was I motivated and productive? Was my work meaningful? Am I getting better at it? Did I do something for my friends today? What can I do better?

I try to allow those thoughts to sink in and carefully listen to that inner voice. Sometimes I wrote them down and sometimes I wrote them on this blog. Sometimes I deviate a bit and try a new perspective, whether it’s because of a book I read or a person I talked to. And I try to be very honest with myself.

I was surprised to find out some quite unexpected facts about myself. For example, I don’t like startup culture. I was lonely more than I wanted to think I was. I realized that some of the harsh words my mom said to me in my childhood still bothered me. I found out that I was not motivated in my old job. Believe it or not, these facts didn’t fit with who I thought I was. So being honest helped me learn more.

In each case I’d then use what I learned from my reflection to rearrange my life. If I wasn’t satisfied with something that I did, I’d do one thing differently the next day. Call up with a friend. Start walking to a talk that interested me. Plan a holiday. Apply to a job. Write to my mom. Just one small thing. I did this iteratively, incrementally. Every day I learn something and I act on it the next day. So no day is wasted. I don’t wait for some unknown life-changing event. I “just do it.” I live, now.


Our culture asks us some big looming capitalized questions – like “Are you following your dreams?” or “Are you living up to your full potential?” I suspect many of them are less consequential than you’d think. I spent the last two years in three places. I can probably live anywhere happily so long as there are loving people I can have interesting conversations with. I’m also confident that there are other career paths out there that I’d be equally happy about. I just happened to stumble into this one. Does it really matter if this is my childhood dream?

In retrospect, many decisions were difficult for me because I cared too much about insignificant things. I saw the world as overwhelmingly complex. Too many potential complications could result from the actions I take. I worried not only about today and tomorrow, but every single day until I’m old and decrepit. I worried about how would I feel and what different people would think about me in every possible outcome. In the language of statistics, I had a dimensionality problem. There are too many variables in my model of the world. And when you have many dimensions to consider, you need a lot of data and a lot of computation to fit the model. Of course I would never have enough data or enough brainpower to figure it all out. To take this analogy a little too far: I ran out of RAM. Blue screen of death.

But I think only a few principal components actually matter. Just a few variables go a long way in explaining happiness and productivity. Think about it. Happiness and productivity probably just have to do with being surrounded by a community of people whom you love and who love you back, having meaningful and achievable goals to occupy yourself with, and realizing that you are incredibly lucky to be alive. What else?


Yes, there are still big, hard, painful life decisions to be made. But after I began to listen to myself, I slowly gained a better idea of what mattered to me. And with that knowledge, big decisions became a little less daunting. Once I came to be at peace with the fact I didn’t actually want to be a businessman, my decision to switch careers came pretty easily. Once I had a better sense of who I want my friends to be, putting myself out there to be judged became easier. Certitude came with self-knowledge.

Steve Jobs said, “Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything – all external expectations, all pride, all fear of or failure – these things just fall away in the face of death, leaving only what is truly important.” In the same spirit, I just try to focus on the things that actually matter to me – to love and to be a light unto the world as best as I can be. I trust, as Steve Jobs did, that the dots will connect, somehow, someday.

The examined life is hard work. I find that it is also meaningful work. Whether or not we are a more doubtful generation than ones before, I hope our generation is more vigilantly reflective than past ones. As our technologies provide us more options and more possibilities, it is all the more critical that we are able to keep our sight on the things that matter. Developing what we might call spiritual clarity or interior wellbeing can make us more effective people. I suspect a society that understands this will be a happier and more productive one too.

Read more here. Or send me feedback and comments.