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Designing a process for self exploration

Since a number of people have asked about my self exploration process and shared their desire to do some exploring themselves, I thought I’d write up my experience thus far. Not only is it helpful for me to document the process, but also reflect on it. I welcome any feedback and questions!

My initial intention was to stay and grow with my previous company for many years. As soon as I realized that it wouldn’t be possible last August, I decided to leave. This gave me the unexpected opportunity to reflect on what was missing both personally and professionally. First and foremost, I allowed my health to deteriorate while I was working there. That’s why I made sleep, eating healthy and physical exercise such a priority for the first 3 months of my break. Then I tried my best to reflect on the professional experience and decided that I should evaluate my next role based on skill fit, team fit, and mission fit. At a minimum, I had to feel confident that I’d add significant value to the organization, my working style and vision aligned with the management team, and the mission provided a net positive benefit to society. People often asked why I don’t start a company myself, to which I always answered “because I don’t have an idea I’m willing to die for”. The point wasn’t to be dramatic, but to acknowledge that there is nothing I am so passionate about that I’m willing to go all in. Almost everyone accepted that response as reasonable.

Of course, there’s something to be said for being unreasonable. When I returned from Nepal with a win under my smaller belt, I started to refocus my efforts on what’s next professionally. Again I was asked the question “why don’t you start a company?” to which I answered with my standard reply. Instead of acceptance, I was prodded, “Don’t you wish you knew? Don’t you think you’d operate at an entirely different level if you identified that passion?”. Touche. Convinced that building self awareness and accelerating my learnings would help me find this path, I decided to devote significant time to self exploration and mental fitness.

Developing a process for self exploration is a very interesting project in and of itself. Most of the online resources focus on transitioning between industries and encore careers. I decided to loosely break down my exploration into three categories:

  • Past – personal historical information, gathering data about a previous self
  • Present – putting a stake in the ground, understanding what is
  • Future – envisioning possible futures, exploration

In terms of tools, I’m using Google Drive and Lucidchart to gather information and organize my thoughts. Their diagram and mind map tools are very easy to use and integrate well with Google Drive. Since I wasn’t working at the time, I was able to accomplish all of these exercises within a 2 month period (hence the ‘present’ section). If these exercises were completed over a longer period of time, perhaps another structure would make more sense. It’s a life-long learning process after all!

Mentorship. My mentor has been instrumental in this process by asking pointed questions and “stirring the pot”. He has suggested articles, books, exercises and acted as a sounding board. He has also been my replacement for “dear diary”, since I can’t bring myself to write a journal (more on that later). Don’t underestimate the value of having an objective perspective (read not a family member or friend) to provide this type of motivation and support.

Here’s a summary of the activities I performed to gather information about my previous self. This is significantly easier if you keep a journal, but unfortunately I never have. Luckily, I write lots of emails and have been using Gmail for over 10 years. The fact that I live abroad also means that a number of my conversations with close friends and family happen online. Since I tend to be very forthcoming and transparent, they do provide accurate data points.

Data mining. Every year since 2010, I’ve thought back to my happiest memories of the past year and reached out via email to the people who shared them with me. Also, I’ve sent periodic email updates to my network since 2008. On top of that, I was able to search my email using significant life events as a starting point to find messages which were emotionally charged and/or included discussions about life changes. Luckily, I was also able to find a vision statement I wrote for myself back in 1999. If I searched my Skype history, I’m sure I would find additional gems. I gathered all of these references and put them in one folder, but I haven’t analyzed them completely yet. The search process alone helped me to recall many details about my past that I haven’t thought about in a long time.

Impacts brainstorm. Basically I took time to brainstorm two lists: most impactful life events and most impactful people in my life. I was surprised at how short the two lists were (roughly 10 items each). This helped me complete the next two activities.

Personal history timeline. For this exercise, I drew a line and labeled birth at one end and 35 at the other in Lucidchart. I marked major events in my life that I had no control over in one color (births, deaths, meeting key people, etc). Then I added firsts in another color (first international trip, first drawing class, etc). On top of that I layered opportunities (college, jobs, etc). Once there’s a baseline, you can start adding categories that seem relevant to you personally. The resulting visual helps to draw out trends and themes that you probably never realized existed (pictured above).

Mind maps. After reviewing the impact brainstorms and the personal history timeline, I prioritized a few topics to build mind maps around. Usually you place the event or idea in the center and then allow your thoughts about this event radiate on spokes outward. For example, I often point to my father’s death as the most significant life event that many of my beliefs and traits stem from. In this case, I placed “Impact of father’s death” in the center and surrounded it with points like “taught impermanence” and “no strong male figure growing up”. Then I thought about what each of those points lead to and allowed the mind map to grow from there. If you’re interested, I’m happy to share.

In addition to digging into the past, I think it’s equally valuable to understand what is. Below are a handful of exercises I have done so far to gather this kind of information.

Personality tests. Myers BriggsEnneagram and DiSC are the three personality tests I took to get a better understanding of my preferences, strengths and working style. These were recommended by people in my network. I am sure there are other useful measures, but this is certainly a good starting point.

In the flow exercise. Over Chinese New Year I started reading “15 Commitments of Conscious Leadership“, which offers a more holistic perspective on leading and some interesting frameworks to understand thoughts/feelings/actions and how they impact your leadership. One of the commitments challenges readers to discover when they are most “in the flow” by asking 50 people in their network. The questions are:

  1. What am I doing when you experience me most energized and happy?
  2. When you experience me at my best, the exact thing I am doing is ___________.
  3. What do you see as a special skill of mine?
  4. What are your 3 favorite qualities that you see in me (one word each)?

The reason you ask 50 people is because only a portion of them respond. I received 21 responses from a mix of people that I’ve known for less than 1 year to over 25 years. They also spanned different contexts and locations (high school, university, shoe industry, start-ups, HK friends, etc). Some of the results were very expected (almost 50% chose the word “optimistic”), while some were unexpected (creativity was less than 20%). There are many other ways I could process the data and incorporate it into my findings.

Informational interviews. While all the activities have been interesting and informative, this one was probably the most fun! I identified people in my network who I believed had it “figured out” and were pursuing their passion in a role that matched their skills and with ideal teammates. Then I reached out to them, explained my goals and asked to interview them about how they arrived at this point in their life. Most did not go through an accelerated learning process and stumbled into their current situation as a result of trial and error. It was also surprising to hear some of them speak strongly of passions that did not directly relate to their current mission. It certainly makes it feel like a moving target.

Meditation. While meditation doesn’t directly relate to self exploration, I think it is a form of mental fitness that helps you build awareness. When you are more present, you begin to notice how you act and react in certain situations. This skill can then be applied to identifying activities and environments that are the most blissful and bring you the most joy. It also makes you more cognisant of when you are lacking motivation so you can more easily figure out the cause. I took a free 10 day silent Vipassana meditation course to kickstart this effort and have been meditating regularly ever since.

This folder literally sits empty on my Google Drive because I haven’t touched it yet. When I do, I’ll happily share the experience.

While I’ve gathered a lot of information about my past and present, I haven’t done nearly as much processing as I’d like. In a design research process, you usually analyze the collected data with a small group of people to see what trends and patterns emerge. It would be really interesting to perform that kind of exercise with this data set.

Accepting the offer at Insight Robotics has slowed me down, but it’s great to have an environment to test theories so I’m not operating in a vacuum. Also, I want to incorporate meditation and reflection into my routine so they become habitual like eating well and exercising regularly. That’s easier to do when you have no conflicting priorities, but harder when you are working for a start-up that is constantly demanding your attention.

Sadly, I’m still not keeping a journal. It seems like the easiest thing in the world, but for some reason I have a mental block around it. Somehow writing to myself is much harder than writing to another person, regardless of the information I share. When someone else is “counting on me” to provide information and there’s an external deadline (even if artificial), it is easier to motivate myself to complete the task. This explanation is a perfect example. In fact, this blog is a direct response to the issue and that I hope to use as an outlet to organize my thoughts.


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