Jargogled Impressions.

Milestones are a good way to keep yourself on track.  Building tangible, discrete milestones into your plan helps you celebrate step-victories and stay energized about the long road ahead.  

At work, what this means is to draft some checkpoints that lets you track, measure, assess and also celebrate the mini victories and keep your stakeholders involved and informed. It’s typical of multi-year product roadmaps to follow a program-like model with built-in proxy checkpoints and milestones that keeps steerage aligned and distractions at bay. 

With your personal projects – like this million word writing project of mine – using interim milestones effectively can clarify the core objective of the project. For me, that is to learn to write well, and implicitly to think well. Ancillary benefits include giving me a space to be creative, to think big, and to think outside the narrow confines of my immediate world. Also, the intent for me with this project is to chug along with writing lest it gets rusty for when I would want to go head-first into it as an aspirational second innings career. I don’t know how far or close I am to that goal of mine but knowing I am better off now, 100 posts in, than when I started on this journey is a comfort in itself. 

If you want to be a better writer, write.  I have come across variants of this advice from multiple quarters – from established authors to writing sages to newsletter creators.  Starting small, a sort of low pressure outlet, to streamline thoughts and get better at the basics of writing.  With this writing ‘program’, I was hoping to write for 15-20 minutes and pour out a 1000 word stream of consciousness.  But I ended up with a slightly more refined version of 1000 word posts that required more than a few hours to draft.  

The post themselves mostly focused on the below themes per an agentic scan courtesy Perplexity’s comet: 

• Personal Growth & Self-Reflection: Many posts (e.g., “The Myth Of New Beginnings,” “Editing Our System Prompts”) explore the complexity of starting over, the importance of habits, agency, and building resilience. The author often discusses how we can only control our actions (inputs), not outcomes, and how new beginnings reveal deep truths about ourselves.
  
• Mindsets & Habits: Topics such as how habits scaffold us during difficult times, the importance of routines, and the ability to “edit our system prompts” (psychological defaults) recur throughout the series.
  
• Meaning, Motivation & Agency: Posts like “The Pathless Path” delve into life’s meaning outside of prescribed social or professional scripts, critiquing hustle culture, and emphasizing intrinsic goals and intentional living.
  
• Emotional Intelligence & Relationships: Several posts reference the importance of understanding and articulating emotions, building deep relationships, and the transformation of friendships and connections through adulthood.
  
• Creativity, Writing & Identity: The introductory post frames writing itself as an act of self-discovery. Many pieces reflect on writing as a tool to understand internal chaos and clarify personal identity, with discussions of the craft and purpose of communication.
  
• Philosophy & Modern Life Critique: There are regular references to philosophical concepts, classic literature, and a questioning of contemporary productivity culture, all used to probe deeper questions about work, value, and purpose.
  

The themes aren’t much of a surprise.  I am interested in exploring anthropological domains, in technology’s impact on modern society, in the inner machinations of the human brain, in writing as a sort of meta topic, and others. And lately, in guiding myself through the journey of parenting two little girls. These areas will likely stay as I continue my journey with writing. 

What I am interested in now though, is if there’s a better medium than essays to do that.  Video logs aren’t my thing and it isn’t writing anyways. Nor does the idea of writing LinkedIn or Twitter posts interest me – even though the reach could be higher on these platforms versus a humble WordPress blog. I try to maintain a work-related Substack but am intermittent there due to a lack of real interest in chasing the constructs of the organization man. 

Fiction is a fish bait for me – that is, the mystique around the stories and the world it introduces is a natural attraction for my restless soul. I have dabbled in short stories, and have been at work on my novel since awhile now.  But, outside of the novel, where I have made some progress, the stories aren’t much to make a dent.  And so, I am wondering if I could explore these same themes that I have done via essays so far, but through world building – that is, through fiction and science fiction. 

What that would mean is 1000 word short stories that explore themes through human (and sometimes machine and non-human) interactions.  Basically stuff our life is made of – stories.  Maybe the next 100 posts will be those? What do you all think? I am thinking something like Borges, Joyce, Kafka, or Saunders, Munro, Saki, O’Connor, and others.  🙂 

I kind of like the idea.  But I am guessing it’s going to only add the time I need to spend on a single post.  I don’t mind that necessarily if I am growing in the process. But what that may come at the cost of, is my attention wavering from all the other places that it is needed.  And that’s going to be a challenge.  It already is. 

The previous 99 posts helped with making writing a tool I can easily call, with decent results and more substance than words just barely put together.  Moving away from monkeys on a type writer to maybe hominids on a computer.  I need to get to a human on a notepad – slow, ruminating, reflective.  Still exploring the personal gripes, modern paradoxes, yearn for slowness, but with a make believe bent. It does allow for more creative and experimental milieu so I am kind of excited about it.  

Do sign up if you are in for the ride! The stories will go nowhere maybe. And then they will find a natural home. Same as me.