Pen{g}sieve Vol 1. (III): Personal transformation through the power of inquiry

How do we think through big and abstract questions such as meaning, purpose, success, happiness? Actually, do big questions matter for builder types like us engineers?

The answer is Yes. Big questions do matter because personal transformation often starts with asking a good question. But not just any question, Frank Wilczek in the book “A beautiful question” captures it nicely:

A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change.

This blog is about how to use the method of inquiry to engineer self-transformation (as I somehow stumbled over in the past couple of months).

Big questions will find you

Like most engineers, I have lived a happy life and perhaps a somewhat successful career without getting bothered by any of those big questions listed above until last year.

Last summer, the company I worked for was thrust into a major event that made the future of my job and my team’s quite volatile. It was at that time I started to ask questions such as “what if I do not work?”, which leads to “why do I work?”, which somehow leads to

what is the meaning of life?

Questioning the meaning of life is perhaps a tell-tell sign of a mid-life crisis (or mid-life awakening, depending on how you frame it. So it’s my turn now :).

Then, when I finally made up the mind to be on the market, the practical question of “what am I looking for” turned into a more abstract one:

what does success look like to me?

This question made me re-examine what really matters. I know, for me, success is not status, title, or money, but what is it that I am aiming for?

More recently, just a month ago, another big question came my way, when I took an online course called Building the Second Brain. One of the assignments was a visualization exercise (to as specific as possible, down to a vivid picture) that asked us to visualize

what will your life be like in 10 years?

Initially, I had difficulty visualizing my 10-year older self to be much different from who I am now (except perhaps being more “successful” ?). That thought scared me: I cannot even imagine a different self, not to say become one. After much trying, I did come up w/ a new 10-year vision that I am somewhat comfortable with. And that vision led me to a very different place for my future self and indirectly contributed to the starting of this newsletter.

The Lightbulb effect: Using questioning as a tool

As if being hit by big questions is not enough, I somehow turned the situation on its head and started experimenting with questioning as a tool to piece through my belief system. I found that asking a good question is the only way that I can focus my mind on finding answers for things that are elusive and far-away. This quote from the book “A beautiful question” by Frank Wilczek captures it nicely:

Just asking or hearing a question phrased a certain way produces an almost palpable feeling of discovery and new understanding. Questions produce the lightbulb effect.

I also found that asking a good question has the effect of bringing clarity to my actions. For example, as I explained in Why do I start the blog, my hesitation to share my thoughts publicly was resolved by asking

what can I do to help someone like me?

And my decision to start this newsletter now was settled by asking

what will my future self want me to do right now?”

As I am writing this paragraph, I realized that the clarity came from the fact that those two questions gave a meaning/purpose for the actions I decided to take.

There aren’t many rules regarding how to ask questions that are thought-provoking. But one trick could be to formulate questions following some templates:

• "Why"-questions are designed to draw our attention to things that we are familiar with never given them much thought, such as “why do I work?”.

• "What if"-questions open up new possibilities that one may not have considered before, such as "what if I have no achievements?".

• "What is"/ "What does ... mean"-questions put familiar concepts under the spotlight so that we could truly understand them in our own context, such as "what does it mean to be authentic for me?".

• "How"-questions look deeper into the mechanism underlying a complex system (e.g., human, organization, society) such as “how do changes happen?”. Understanding how enables us to introduce design into our lives.

My List of Questions

In the post on My journaling system, I described a journal category called "A beautiful question" to help incorporate inquiry into my routine. I started the practice in May and already accumulated a list of beautiful questions. Here is a subset of the list that provokes my thoughts and perhaps yours too (Yes, it is totally ok to borrow from other’s questions). And I intend to cover some of them in subsequent blog posts.

Understanding for design

1. How does change happen, and how do we engineer change?

2. How are thoughts generated? How do I generate research ideas?

3. How to engineer flow?

4. How is my industry changing?

Self-examination

1. Why do I need to work?

2. What does success look like to me?

3. What fundamental beliefs of mine are severely limiting my potential?

4. What beliefs do I have that most other people do not?

5. What fundamental skills have I stopped improving for a long time?

Thought experiments

• What will I be doing 10 years from now (visualization)?

• What would my future self want me to work on right now?

• What is design, and how to apply design in my life?

Why questions

1. Why do most people not plan their careers or, for that matter, not planning for the most important aspects of their lives (e.g., finance, retirement, happiness)?

2. Why OKR feels like lip-service in practice but sounds so inspiring as a TED talk?

3. Why do the most valuable mental models often appear to be useless when dealing with practical concerns?

4. Why do most people not invest in improving their fundamental skills even though those may be the most cost-effect investment? 

Conceptual Clarity

• What does it mean to be authentic?

• What does it mean to lead?

• What is meaning, motivation, and purpose?

• What is problem-solving?

How do changes happen?

Anything concrete starts from a thought. Changes happen when a fundamental belief of yours is altered (often known as mind-shifts). One way to trigger mind-shifts is through questioning. In this newsletter, I will share some of my recent mind-shifts and dive deep into some of the questions on my question list, just so that people can grasp something abstract through more concrete examples.

You don’t have to use my question list and you don’t even care about my answers, but do build your own system of inquiry and find your own answers. As Frank Wilczek beautifully puts it:

To question well, it’s necessary to stop doing and stop knowing in order to start asking

Finally, I found this quote from Piccaso 50 years ago especially revealing (especially for us computer engineers):

"Computers are useless—they only give you answers".

We are human and intelligent because we know how to ask beautiful questions, don’t waste that rare gift.