At the end of every year, a disorderly pile of unfinished projects stalks me like a flock of perky Christmas carolers. They sing of a bright future, IF I were to only I were to FULLY COMMIT to the Spirit of Doing! And at the end of every year, I find myself IRRITATED, grouchily wondering when I will get my act together and get enough momentum to burst through the nebulous barriers that seem to drag my progress down. Sometimes these barriers are in the form of obligations I’ve made to other people or imagine that I should do to help out. Sometimes they are just the chores that make up the “incessant drip drip drip” of existence, to paraphrase Sherlock Holmes in Elementary. The projects seem to grow in number every year, each one of them with its own recognizeable smiling face, tormenting me.

I can’t really think why these projects never get done, other than it seems that deep in my heart I don’t really want to do them. This is despite knowing these projects would be wonderful for me, projects like “establish a thriving e-commerce business based on my original design work”, “write a compendium of productivity tips and tools based on the 15 years of work I’ve been writing about them”, “design software that is allows people to express complex interactions in viscerally compelling visual ways”, and so on. I’ve got a lot of idea and a lot of unique skills that give me an advantage in pursuing them. Still, I do not act, instead getting bogged-down by the “drip drip drip” of existence. I’m bored, but don’t want to act. I’m tired, but restless. It hasn’t all been terrible, as I’ve made progress in other areas and have increased my understanding across a variety of fields, but I still feel hapless despite all the freedom and choice I have.

Am I missing purpose or are otherwise lacking in character or will to become who I want to become? Maybe I need to just get a job. And by that, I mean giving myself one. This post is the first of (probably) several that explores my definition of my “job”.

MAKING UP A ROLE

I see the bestowing of a job as a way of giving myself some context for action. The ideal job would be one that gathers all the productive things I do under one umbrella. I’m not a typical worker seeking a career, so I have to write a pretty weird job description. I figure a good place to start is to just list what I’ve been doing outside of paid project work I’ve done as a freelancer.

WHAT I AM CURRENTLY DOING

In the time I spend not working on those unfinished projects, I seem to do quite a lot of other work:

• I run a coworking chat room on Discord, maintaining a culture of positive and authentic community.
• I do a daily YouTube livestream to “catch up with my friends on the Internet”.
• I do interactive development as a freelance digital media designer.
• I design productivity and workflow process forms that look cool.
• I research ways to improve my production systems or working environment.
• I try to find interesting and noteworthy people to follow.
• I write a lot to share my thinking with other people.
• I spend time socializing with like-minded people to help keep the positive energy moving around.

AND HERE IT THE MEGATASK

• I work on e-commerce, design, and writing projects to grant myself new capabilities and collect revenue.

It is that last item that’s the one that has me frustrated. I’m pretty sure I spend the least amount of time working on that one. Yet, it’s this task that I designated MOST IMPORTANT for the past three or four years in my Groundhog Day Resolutions-making. WTF!

SO AGGRAVATING! But let me put this aside for now, and consider a few things that I seem to be spending my time on:

• I’m always on the lookout for interesting people that are making interesting things, and am compelled to investigate their body of work.
• I’m also almost always willing to try connecting with someone who has the desire to make something that is new-to-them, and spend the time to do a little co-working.
• I’m compelled to think, categorize, collect, and package my thoughts into accessible chunks. I am obsessive about documenting. I have a strong desire to package and distribute my thoughts through blog posts and other finished forms (though this is where I also get stuck).
• I’m constantly thinking about my sense of self, my identity, and my role in society. I wonder how my personal desires relate to notions of truth and authenticity, and what my responsibility is with regards to standing up for these principles. My general desire is to be happy, to express what I love without fear of reprisal, and to be strong enough to make things happen to my satisfaction in an inclusive manner.
• I’m compelled to present a log of my personal truths and subjective observations as an example of how I face and solve problems. I don’t do this because I think I’m the best at it, but because I think it’s important that people know that it’s a messy process and it’s OK to fuck it up. Perfection of an original idea is attainable only through daring experimentation followed by error correction.

Let’s grandfather all these things into my job description. I think these activities are all useful. If I were to take a stab at defining them as line items on a job offering, maybe they’d be:

• analyst / epistemologist / archivist
• process coach / mentor

EVALUATING THE WORK ITSELF

Having described some of the qualitative aspects of my “job”, let’s look now at what I find difficult. The following statements are all relative to the “hard” MEGATASK I defined earlier.

• I find it difficult to build the infrastructure and distributable packages by myself. I think these are things that have to come from me, because they’re EXPRESSIONS of me. It’s important for me to express as myself, and therefore what I express/share has to be of myself.
• I find it hard to stay motivated in the face of entropy/uncertainty/existentialist thoughts.
• I find it difficult to maintain regular progress because the steps are so small, and no one really cares except for me.
• I find it easy to share what I’m working on in my YouTube livestreams.
• I like hanging out in the chat room and seeing what people are working on in the space.
• I like talking to people to find out what they’re doing and why they’re doing it.
• I like talking about what I’m doing with other people; this often leads to new insights that motivate me to work more.

These are all thoughts I have had before. I was unable to extract a useful pattern from this until Susan posted this in our chatroom; the last paragraph really resonated with me (emphasis mine):

SUSAN: I’ve always felt pulled in so many directions… my quasi-social work […] However, I’ve always had a strong sense of self-as-problem-solver which meant that I had a drive to increase my tools in various areas, and to use them, so I tend to say “yes” to more things than most other people, some fraction of which turn out to be real opportunities.

SUSAN: Also, that constant gathering of skills/processes/relationships/experience means that when I have an opportunty I can make something of it. It’s less of a “steps to a goal” model and more “investment in a set of strategies, the application of which is highly environment-dependent”

SUSAN: That reactivity can have its down sides: for example, it is VERY hard for me to progress on large, complex problems in isolation. I need the input of interacting with others or seeing the work impact something real, or the work isn’t real and I lose direction.

I very much dislike working on projects by myself, but I also have felt that I NEEDED to do them solo. The historical reason I have for this is that (1) other people aren’t interested in what I’m doing therefore (2) I was the only person who could be expected to do them. However, there is also the unspoken belief that doing these projects solo was a sign of competence and good character. Because I was not able to push myself to complete these projects, I think part of me believed I was flawed in my process and therefore functionally (if not mentally) incompetent. My automatic reaction to feeling incompetent is to improve my process and/or redefine the problem in a way where my other competencies might bring more firepower to bear on the target. If those approaches don’t work, then I start doing more radical experiments…however, Susan’s remarks have given me pause and I am rewriting my original line of reasoning into the following hypothesis:

1. I have big projects (aka MEGATASKS) that would be hugely beneficial to me, but I am unmotivated to do them. This is irrational but I can not break out of the cycle.
2. I have tried to develop more discipline and better starting habits. This has had some positive results, but they have not produced a persistent increase in productivity levels.
3. My new hypothesis is that I just don’t like working by myself on projects. It is not an issue of technical competence or even character at all. I am just inclined to work with people to solve challenging problems together, and this is what motivates me.
4. Therefore, my “solo projects” need to be converted to group projects if I am going to make any progress on them. This means I have to rethink the structure of the projects so they can be of interest/utility to other people. This also means I have to be willing to invest time into making my project work more accessible, which happily is something that I already like doing.

This is a HUGE insight, and I am going to end this blog post here to give me a day or so to mull it over.

As far as the “job description”, for today let’s try to write a temporary one:

My job is to collect actionable bits of data and compile them into high quality packages that empower people to create their own version of excellence.

I’ll work more on the description in the next blog post. Oh, I guess I’m writing in the blog again! I figure that until I get the new blog system working, I might as well keep posting now that I know WHY I hate using WordPress these days, and can now avoid those aspects of it.