This is a revisitation of my June 6 Groundhog Day Resolutions Review post, restructured to clarify why I need to shut down the blog as it currently exists while embracing a seemingly less-responsible model of conducting my business.

This post follows a number of insights I had on my recent trip to Taiwan. I start with the original goals and expectations I had for going on the trip in the first place, which didn’t quite go the way I imagined. By chance I happened to watch several television shows that put emphasis on “being weird” as a principled approach to life. After combining those new insights with past patterns of behavior, I come to the unexpected conclusion that I need to be less disciplined, less time aware, and less task oriented.

First, let’s start with the Taiwan trip assessment.

Taiwan Trip Objectives Assessment

My family is Taiwanese, and when I was a child our family moved to Taiwan from the United States for a number of years. I returned to the States for college, and have remained here ever since. My trips to Taiwan in subsequent years were related to serious family business such as the death of my grandparents. It was only in 2015 and 2016 that I decided to visit Taiwan because I wanted to. Dad just turned 88, and as I grow older it’s increasgly important to ensure my extended family relationships are strong. This requires me to be in Taiwan, though I am very much an American in my personal attitude and outlook on life.

The three main objectives of these trips were (1) spending time with Dad and our extended family, (2) overcoming negative childhood associations having lived there before, and (3) test my mettle as a “digital nomad” as preparation for trips to other countries.

(1) Spending time with Dad and family

The primary objective was to spend time with Dad and other family. There’s nothing like spending a lot of time together doing mundane things like eating together to help reaffirm the connection. I also got to know my uncle (Dad’s youngest brother) and his wife better as an adult.

I think this was really a good trip, setting the tone for future trips and reaffirming our love for each other. By the end of the trip, I was learning more about Dad’s most recent likes and dislikes, which will help develop stronger bonds across more interests. This of course extends to my uncle and aunt as well; we had some interesting conversations about life choices and personal belief.

(2) Overcoming negative childhood memories

A secondary objective was to overcome unpleasant childhood associations I have with being in Taiwan. This is important for me to feel comfortable when I am visiting Taiwan. I spent a number of years in Taiwan as a child in the 70s and 80s before returning to the USA, and I developed several anxieties from having lived there:

• feeling like an unwelcome outsider
• not belonging and not understanding the culture
• being functionally illiterate
• being misunderstood and misunderstanding people
• not having control of own destiny
• not having access to high quality information

Intellectually, I know that these childhood are no longer applicable to me as an adult, but they are very deeply imprinted on me and color my emotions. Combined with my October 2015 trip, I believe I’ve overcome these old feelings by replacing them with new knowledge and experiences. I feel that I can learn Chinese by building on my old memories and enjoy living in Taiwan, which is a pretty great place.

(3) Trying the “digital nomad” lifestyle

The last objective: testing my ability to work away from home for an extended period. I have a complete suite of software for running a digital media design and development business loaded on the MacBook, so there’s very little I can’t do. What I didn’t know is what the experience of being a digital nomad would be like, and whether I could be productive.

The verdict? I am not a digital nomad! I think I’m better described as a “digital homebody”, because I like my office environment. I also have need (or prefer) having multiple computers and monitors. The temporary office space I setup at my dad’s house was dimly lit with green-tinted flourescent overhead fixtures and was ergonomically terrible. I developed wrist strain almost immediately, with back pain and headaches soon to follow.

One of the primary draws of being a digital nomad is to travel and have adventures. I found that I was really not very interested in exploring or having adventures. I knew this to be true of me when visiting new cities in my home country, and I knew that I am not much of a sight-seeing wandering either, but I had thought that being in Taiwan would be a bigger adventure. NOPE. I can scratch “exploring and adventure” off of my list of “things I would like to do someday”.

Additional personal insights

As I discovered that I didn’t have the temperament of an adventurous traveller, I shifted to a self-analysis mode: if I wasn’t a world explorer, then what was I really looking for? Although I didn’t find nomadism in my blood, there nevertheless is the desire to seek something bubbling away somewhere within me.

The first major insight I had was that when traveling I still need lots of personal space and time to myself. Even within the familiar confines of my dad’s place, I still didn’t have a real place I could be fully alone to think. There are many small distractions and ad-hoc commitments that arise during the day, which disrupted my train of thought. When I spent a single night alone in Taipei, I was extremely happy to have an entire room to myself with no commitments at all. That sense of freedom is apparently very important to me; I hadn’t realized just how important it was until this trip.

Between family-related activities and trips, I found myself spending more time to myself watching NetFlix in my room. I watched signicant portions of RuPaul’s Drag Race and Elementary, which provided additional resonating insights:

• A recurring theme in RuPaul’s Drag Race is the acceptance of one’s self, which I gather is a common mantra in the LGBT community. I hadn’t realized before that drag queens create highly-developed characters that draw on their personal interests; I could identify with this from the online character roleplaying community in MMORPGs. It’s a fringe subculture that has increasingly been brought into the mainstream by the popularity of celebrities like Mr. Charles, but it is still pretty “weird”. Within this subculture are further distinctions made by the drag queens themselves, from “pageant queens” to “comedy queens” to every shade in between. My takeaway from the show is that it takes incredible strength and perseverance to be a drag queen in the face of judgement not only from the mainstream, but also from the catty members of the subculture itself. Secondly, I recognized that it was important for me to embrace MY OWN weirdness as a game-playing nerd that likes designing productivity forms and experimenting with media. What I do is very weird, and for a long time I felt have felt pressure to conform to mainstream expectations of being a “valuable contributing member of society”. In marketing terms, I have also felt pressure to make my “product offerings”, which includes both the writing I do and the products I make, more understandable to a demanding audience.

• The television program Elementary is the American retelling of Sherlock Holmes (Jonny Lee Miller) and Joan Watson (Lucy Liu) in contemporary NYC. There’s an episode where Joan’s mother, who doesn’t approve of Joan’s current work as a “sober companion/babysitter” for addict Holmes when she was once a surgeon, is having dinner with them at a restaurant. Holmes regales Watson’s family with tales of their mystery-solving adventures, thoroughly charming and causing them to see Joan’s decision as a selfless act of immense social value. In the taxi ride back to their abode, Joan thanks Sherlock for what he did, and he comments that he merely framed their activities in terms her family could understand as mainstream people who were uncomfortable with the strange and unusual. He identified Joan as one of those people who were drawn to such things, which made her different and therefore a suitable partner. This struck a resonant chord in me as well…I am drawn to the weird and unusual in my own unique way, and am constantly feeling that I’m somehow not meshing with the rest of the world. Perhaps, as Holmes had pointed out to Watson, I am just not that kind of person and need to embrace my own reality instead of trying to fit it into someone else’s comfortable understanding. Holmes himself lived by that rule, and I found the show’s depiction of his “consulting detective” practice to be comparable to what I was doing, “writing about what catches my eye and sharing what I learn”. I’ve tried to convert that proclivity into a business plan that made fiscal sense, but perhaps I don’t need to follow the standard template. If I can make it work for myself, why not just accept it?

Spinning new insights into new directions

Having largely overcome my childhood negativity and filled with new insights about embracing and living one’s own weirdness without concern for what other people may say, I contemplate what was really bothering me. By the last week of the trip, I was quite anxious to get back to working on my own projects, but recognized that I was likely going to continue the cycle of frustration that I’ve had for many years. Perhaps more extreme measures are called for…time to reconsider my approach.

It occurred to me that I was frustrated because my many projects were stalled for any variety of reasons. I had previously thought that the solution was to become “more dedicated” to spending time on them by revisiting them every day; this had been the entire premise for my 300 Days of Groundhog Day Resolutions push started this year. If I finished more of what I needed to do, even slowly, I would be a little bit closer to achieving these long term goals. All I need to do is force myself to work on a tiny bit at a time every day, and results will follow!

Sherlock Holmes again comes to mind; he didn’t seem to do anything that he didn’t feel like doing. In that respect, I’m quite a bit similar, but the Sherlock character (as portrayed in S1 of Elementary at least) is very aware of his needs and is quite selfish about it. As he’s brilliant at solving cases he can get away with it. I would hesitate to claim that I’m brilliant and deserve a free pass, but at the same time there’s no reason not to recognize my own proclivities and challenge the assumptions that I need to be MORE disciplined to get my work done and achieve goal-related greatness by following the common wisdom. Perhaps I am sabotaging my own version of brilliance by trying to impose a mainstream set of expectations on how a responsible adult achieves their goals.

Contemplating irresponsibility

Let me assume for a moment that I’m an IRRESPONSIBLE adult, selfish and not given to meeting other peoples’ needs over my own. If I was that way, I wouldn’t make commitments that I didn’t want to have. I would not help other people if there was no way that it helped myself. I would not care about what other people thought of me, and I would not care that I let people know how little their own responsibilities mattered compared to my own desires. My goal in life would be to pursue what was interesting to me with the greatest attention I was capable of. In Sherlock’s case it’s solving interesting murder cases so he’s not bored. In my case, it would be “investigating what catches my eye, writing and sharing what I learned”.

If I continue to hold this template as a comparison point, I can make the following observations:

• Maintaining my current website and blogging schedule is not so much for me as it is for maintaining some kind of content freshness. As it is now, I write blog posts when I can find a connection between thinking things through (this post, for example). This is not a great reason to have a blog, as it is a disservice to readers and is not the kind of attitude that leads to a great content experience.

• Much of my frustration comes from “having” to do a lot of pre-requisite work to actually get to the “interesting” part. I’ve been thinking of it like an engineering project manager, forcing myself to be disciplined and dilligent in my work. Because I’m not experiencing the “interesting” parts of the work and forcing myself to do the “foundational but boring” parts instead, I am singularly unmotivated.

• Over the years, the frustration of having so many unfinished projects has created a huge mental burden. A major subproject has been the working space itself. While my Living Room Cafe project is an attempt to fix it, the greater challenge is to catch up with all the unfinished projects, or dump them and start again.

• My “brilliance”, if I possess anything resembling it, is that I’ve still managed to learn how to do a lot of things. I like exploring stuff on my own time when it is driven by my interest of the moment, but I lock up as soon as it becomes a “mandatory” action. If I am honest with myself, I find the very premise of “having to do something” beyond the needs of my own interests distasteful. I had thought of this as a character flaw that I needed to correct through redirecting my thoughts in a more positive (or at least non-negative) manner. If I am following the Sherlock template, however, the solution is merely to ignore such demands. This has some similarity to “structured procrastination”. Everything of note I’ve made that I like has been made on a whim. There are a few things I’ve made that are impressive because I’ve had to do them, but it’s only when I allowed myself to pursue my own angle on them rather than anticipate other people’s expectations that I have been able to soar.

I am now thinking that I should start from scratch, and drop the notion of discipline being a foundational pursuit. I am not wired that way. I am, however, wired for extreme pursuit of my own interests and function very highly when I am motivated. Taking a page from structured procrastination and the lessons gleaned from RuPaul’s Drag Race and Sherlock Holmes, I can perhaps drop all pretension of becoming a methodical and conscientious practioner of fine productivity-boosting habits. I would be much happier if I didn’t have to plan anything, and just did what I wanted because it was interesting to me in that very moment.

I’m sure that a lot of people would say that this approach is foolish and doomed to failure, but I have two hypothetical counters:

1. I have already been working like this for years, but have assumed that to improve greater productivity I would need to learn ways to become more discplined. Perhaps the true secret to unlocking my productivity is to entirely discard discipline instead and allow my impulses to run as unchecked as possible. I have nudged myself toward this way of life here and there (my free-exploration mandatory “happy bubble time” is a past attempt to formalize it within a more structured system of working). I wonder now what would happen if I just dropped it all.

2. It stands to reason that if someone is left to pursue whatever catches their interest in the moment, they are never going to get anything productive done. Their learning will be haphazard and ineffective, producing low-quality work and limiting advancement toward loftier goals. I entirely agree with the logic, but I also know this about myself: I am constantly learning and developing skills based on my interests. I also am obsessive-compulsive about organizing information so I can find the patterns and principles hidden within it. I can’t help it; all the writing on this website, well over a million words, is the result of thousands of hours of reflection and analysis that no one told me to do.

So, I think it’s possible that moving away from discipline to spastic pursuit of interest might work for me. The kind of discipline I have is dogged determination to ferret out the truths and principles in the world around me until I own it, and it is an extremely powerful force. I have been holding it back for years because people don’t get it. Perhaps I owe it to myself to really wield this power in a manner that people would find irresponsible and anti-social, and find out what happens.

To put this into practice, I am considering the following courses of action:

• Dropping the blog, at least for now. It does not serve my current needs or highlight my interests in a way that helps me conduct my investigations in a way I regard as useful.

• Stop doing things I ‘have’ to do. There are several ways I will interpret this. While I do have contractual project commitments, I am no longer going to use traditional project management techniques as the means to an end. Really, such techniques are a lie anyway due to the number of unknowns in any creative endeavor. The discoveries will be made as I investigate the challenge, and I can trust myself to adapt and deliver the solutions that have the most integrity. Answering interesting questions is the way I like to work already, and I have already tried this approach before in other guises. For example, I’ve used “tech journaling” and “live coworking” as a way to get myself unstuck so I could start working on the “scheduled work for the day”.

• Stop paying attention to time. Time awareness is a curse. I have developed time awareness and estimation to a fairly high level over the years, as it is the currency of traditional project management. As I have noted in the past, however, time awareness is the LAST thing that contributes to creativity and dealing with the uncertainty of making something new. Ignoring time was a directive I made for myself a couple years ago for my Groundhog Day Resolutions, but now I see it more clearly for its lack of usefulness in what I’m doing: creative product development of works that have never existed before. There is a place for time awareness when the situation is well-quantified with known procedures and recipes. I am not in that situation at all. So, smell ya later, time! Instead, I shall focus on questions of particular relevance of the moment.

I think can trust that my daily drive to learn, make, or perfect something every day will maintain forward momentum. Even when I’m playing video games I’m quantifying and testing ideas that arise from the design patterns I perceive.

I suspect that a lot of people won’t understand what I’m trying to do here, but that’s fine. If I fall flat on my face I’ll be the first to admit it, but this is the real adventure that I want to go on. I don’t care a lot about being a digital nomad in the physical traveling sense, but I do crave intellectual nomadism, which I define as the freedom to pursue what catches my eye to see where it goes.

Today is the first step of a new journey!