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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.


  1. Adler says

    Inspiring, Happy and Creative, that’s how would I describe you. It was always a pleasure to meet up for lunch and leave inspired and happy. Your excitement and energy in the way you chatted or taught were contagious. Your way of dressing and photos from your airbnb home made me always curious to learn about how you create beautiful looks 🙂 Thanks for the wonderful moment you created. Miss you

  2. squorch says

    • Love love love the timeline (Leadershape! I didn’t know you played volleyball! Forgot about your time at New Balance!)
    • So great that you talk about your mentor and give them credit where credit is due.
    • Jealous of your data mining efforts and the results they’ve brought. My life is online as well, but due to running my own email server from 2000-2004, I lost a lot of emails from the GT timeframe.
    • I really really want to use Lucidchart right now.
    • Thoroughly intrigued about your “impact” mind map. Like want to sit by a fire with an adult beverage or two and just talk about that.
    • Were there any correlations between length of time that someone has known you and what they tended to tell you in the flow exercise?
    • Why is the future folder empty and untouched?
    • Slowing down is good. Goooood. Being passionate about work can lead to phenomenal results, but they’re all moot if burnout leads to a negatively charged personal life.

    • Glad that you found the ideas inspiring! There was surprisingly little correlation between how long I knew someone and what they said. The future folder is just waiting to be filled I guess! I think once I process more of the “past” and “present” data, how to envision the future will fall naturally into place. Once I’m further along in this part of the process I will definitely share my learnings.

  3. Dirk says

    Thanks for sharing Erica! A really interesting blog post!

    Funny enough I also left my previous job behind last August and have embarked on my own journey of self-exploration, which was then followed by my personal makeover project. Let me share a little of my journey with you:

    For me two things came together: 1) a professional environment that was slow and afraid to change making me feel limited in what could be achieved and 2) the diagnosis of a medical condition that required me to dramatically change my lifestyle.

    Travelling through Australia and New Zealand I gave my body some desperately needed time to recover, enjoyed the freedom, did what I love – taking photos, and invested a lot of time to figure out what to do next.
    I did not use a similar structured approach as described by yourself above but the result can be nicely summarised in what I call my three pillars

    1. Surround yourself with the right people
    2. Live an active and healthy life
    3. Work hard on the right tasks within borders

    For each of the pillars I have developed a set of guidelines, rules and recommendations for myself to follow and I try to focus on those that act across them as – being an efficiency freak – I consider them the strongest e.g. I want to do team sports (being active & surrounded with the right people) or simple things like switching off the phone while eating (living healthy & working within borders).

    Every weekend I sit down and look at the past week and reflect on what happened and if the week supported my three pillars or if I have to think about changes for the future. In the same way I look at the week (and further) ahead and make sure that what I am going to do is in line with the framework I want it to be within.

    For me that works quiet well so far, with a slight lack of discipline at times, but I am happy with the way I changed over the past months and will continue the journey on the road chosen. The biggest challenge at the moment is finding a new job that offers a dynamic environment with an enthusiastic team but given the experience from my last job, I will invest the time and effort that is necessary to surround myself with the right people.

    To be continued…

    • Wow – thanks so much for sharing your experience! Your process for reflection reminds me of the “Win Learn Change model”, which I haven’t implemented rigidly myself, but hear very positive comments from the people who have.

      As for the “right” people and “right” tasks – how do you define right in this context? Are they consistent or a moving target? Would love to talk more about it!

  4. Dirk says

    I on purpose did not specify the “right” parts of my three pillars and if we are going to be very precise it is actually not the “right” people or the “right” task but the ” right mix of” people and tasks. I basically had a look at the people surrounding me and their influence on me and the tasks and actions I was performing (current state) then comparing the mix with what kind of people I want to be surrounded and what kind of tasks I want to perform (target system).

    Talking e.g. about people I think we all need our very individual share of people that love us, people that give us comfort, people that stop us, people that mentor us, people that make us laugh, people that are crazy, people that encourage us, people that kick our rear when required and more.

    What I had to realise, especially in my professional environment, was that I was surrounded by too many people that were frustrated, lacked creativity, excitement and the willingness to change, so I decided to devote more of my time and efforts to those friendships and relationships (private and professional) where I do not encounter the same slowness as I used to call it.
    As it was clear to me that the problem was and is a problem with the company culture of my previous employer or at least a problem of me not being a comfortable fit, I had to leave and did so.

    I also do not believe that the mix is stable. As we grow and develop as a person we develop new interests, new habits and desires and with it changes our target mix, while in the same way people and tasks around as are evolving as well.

  5. All makes sense to me. One of the things I notice is that this constant evolving target mix means that you grow closer to and away from people who do/don’t share those interests, habits and desires. Managing those changes has been interesting for me personally.

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