GHDR Report 0505: Setting Sail!

⊕ show captionABOUT THE PHOTO // The Vasa was a Swedish warship that famously capsized on launch because it was an overbuilt project with no accountability. Which feels uncomfortably close to what I’m doing with my Groundhog Day Resolutions!
Licensed by Steven Lek via CC BY-SA 4.0

Previously on Groundhog Day Resolutions…

You know, the central idea in Groundhog Day Resolutions (GHDR) has been to find a way to be financially self-sustaining while doing things I actually like. The path itself has been surprisingly long and meandering, but a constant factor throughout all 19 years has been getting stuck on some boring part of the execution.

THE INSIGHT: A MISALIGNMENT OF ASSUMPTIONS

In the April 4 Report, I noted this stuckness again when doing simple marketing tasks like “making product listings on Shopify” was met by irrational resistance. Rather than continue to suffer, I instead took the time to question what I was doing. The key observations:

• Yes, there is an “Execution Gap” between what I want to do and actually doing it. I have used dozens of tricks to push through the gap in the past, but it is always expensive in terms of personal energy and the tricks lose their effectiveness once the novelty wears off. Perhaps a pivot was called for?
• I proposed a hypothesis: maybe my strengths aren’t actually what I think they are. After reflection, I conjectured that it was that I cared about how I did things for others, and that being prepared to act was part of that.
• I noted that this “caring and preparedness” inclination aligned strongly with my love for hospitality and operations. Could this be a new reframing device that I could use to change the context for doing marketing tasks?

THE PIVOTAL INSIGHT

Next, I workshopped these ideas in the April 30 followup Reframing Chores as Ship Operations. The key insight is that I had forgotten I was allergic to marketing, and that this had been the reason I had left my jobs and started freelancing in 2004. A few years later, I was starting to lay the foundation of “creative independence” and promptly fell into the trap of needing marketing for myself. Whoops! Apparently I’m allergic even to my own marketing?

THE REFRAME: MARKETING AS A SIDE EFFECT

Now, I’m trying to fulfill my marketing needs indirectly. Instead of making them the focus of my planning, I am hoping to harness my natural attraction to hospitality and ship operations as my focus because I simply like doing these things. In more crass terms, I’m defining a specialized form of marketing that is based on mapping the results of my hospitality/operations focus onto marketing needs.

Here’s roughly how I think the reframing works, based on the earlier writing from the Reframing Chores as Ship Operations post.

• Motivation, Reframed - I am not motivated sharing my own work to drive trade. I like telling the story of what I’m thinking and doing to anyone who might find it useful: myself, passengers, and maybe even a crew.
• Metrics, Reframed - Rather than counting “goods produced” per cycle, I would instead count how many acts of connection I experience. Such acts form the foundation of strong bonds.
• Skills, Reframed - Instead of leading with my technical and creative skills , I would instead lead with my practice of adaptive exploring, learning, building, and sharing. This shows skills applied in context, which is more like an interesting story than an unsupported claim.
• Personal Goals, Reframed - My goal is not simply to design goods that are “good enough to sell”. I would rather make products appear as I swirl and flow through living acts of care (hospitality) and operational preparation (ship operations).
• Mission, Reframed - Rather than use keywords and interests to find the demographic of people who “swirl and flow” like me, I will finally recognize that the very act of expressing those things that make me who I am. I am someone who is enthralled by stories of spaceships and hotels and organizations.

As an aside, all of the above could be said to define The Way of Sri. In my heart of hearts, it’s a childhood story in which “a variety of animals become friends”, working and playing together. They are explorers and storytellers, generous in sharing their experiences and supporting each other in their growth. They create a better place for themselves to thrive, and offer hope to others. This is a story that I very much want to be part of in real life. Hospitality and Operations happen to be key mechanisms that help make such a story work.

At this point, I have a stronger sense of how HOSPITALITY and SHIP OPERATIONS could reduce “stuckness” by leaning harder onto my natural sense of play. But how would it actually work?

To answer that question, I’ll use a hierarchical structure that starts with key assumptions and definitions. From that, I’ll develop the philosophical guidelines that govern their application. Lastly, I’ll outline procedures and mechanisms that I think would express the spirit of what I’m trying to do.

The Key Elements

I have identified three.

I’ve mentioned Hospitality and Ship Operations many times above. These are labels I’ve chosen that describe the two kinds of tasks I seem to enjoy, and can’t help doing when I’m procrastinating. These are two foundational ideas.

The third element is The Ship itself. Ships have autonomy and are by nature social constructs. The Ship takes care of crew, passengers, and guests. The Ship is the vessel that carries people and cargo to new destinations, providing opportunity for adventure and shared experiences.

The Ship is a metaphorical vessel that is mine to be shared. It is my responsibility to operate The ShipPractically speaking, The Ship is comprised of my blog, my online business activities, my in-person interactions, and projects.. When The Ship succeeds, that is my success. When The Ship struggles, those are my struggles. If I am very lucky, I’ll find people who want to share the challenge with me. But first, I need to have a ship that people want to belong to.

Establishing the Physics of Ship Movement

My first problem is figuring out how my ship moves. I’m not sailing the ocean or cruising through space. I’m not sailing through the Internet, either; it’s just a feature that I encounter in overall ship operations. So I’m defining movement in terms of hospitality:

Establishing a Charter

In my universe, a Charter establishes the philosophical guidelines for why The Ship even exists and how it operates. It answers these questions:

• What greater purpose does the ship serve? I am going with creating a sense of belonging.
• What roles will the ship play in achieving that purpose? I am going with the roles of creative exploration, expedition support, and trade.

The Charter is intended to provide general guidance for how purpose and role are fulfilled.I’m drawing inspiration heavily from Star Trek stories, particularly the idea of Starfleet Doctrine but scaled way down to my own needs. The scale is more like Firefly or Farscape which have informal doctrines that developed over their episodic arcs..

This provisional charter captures a good chunk of what I’m thinking. It’s a work-in-progress. I think it’s worth noting that this charter is about how people should feel when they belong. It is not a business document or marketing strategy.

• Inclusivity is mere table stakes. Belonging is something that is actively practiced and expressed consistently with authenticity and transparency, with genuine curiosity and caring. It is an invitation offered, accepted, and strengthened over time.
• As an autonomous owner/operator of this “ship” that I call my website, it’s my job to ensure that a culture of belonging and operational excellence develops. I enjoy this challenge because I can imagine other people enjoying the experience with me.
• All my previous skills, designs, writings, and project experience are available to meet the needs of this charter. They are offered gladly to anyone aboard the ship as an act of camaraderie and shared purpose, never out of servitude or social obligation.
• Ultimately, the goal is to create a ship with its own legendary culture that uplifts the people that encounter it.

I expect these principles to change as I try putting them into action.

Establishing Mission

Now that Purpose, Roles, and Ship’s Charter is roughly defined, I can now define what Mission is. In my universe, a Mission is a set of strategic goals for a ship, the stars toward which the Ship sails.

Missions are set for a period of time, after which they are assessed and a new mission may be applied. A ship can have multiple overlapping missions.

Missions are very similar in structure to Groundhog Day Resolutions, and it makes sense to me to repackage it for The Ship. I defined a long list of starting directives in Groundhog Day Resolutions 2026 Kickoff Part III: The Plan (see sidebar) but these are my current focii:

Those are two separate missions running simultaneously.

There is also a de-facto mission: See how The Ship works in a shakedown cruise to test operational effectiveness. After all, this is an entirely new class of vessel, and there’s a good chance that there are operational issues I have missed.

I am optimistic that The Ship won’t immediately capsize and sink before I get anything done, but that is a statistically significant risk given my track record with stuckness and marketing resistance. Eeep!

Creating Operational Structure for Belonging

The Charter and the Mission define the aspirational philosophy of The Ship.That’s great! The next step is to establish operations that I think will actually fulfill those aspirations in the real world. This section will be more of an outline, defining the concepts that I think will provide structured tasks that fulfill the Ship’s main purpose. That purpose is creating belonging.

As it happens, I already have a system based on the concept of Expeditions, Campaigns, and Sorties.A sortie is conceptually similar to a sprint in Agile Software Development, which is a scope-limited period of time during which a particular objective is worked toward. I liked the idea of a more romantic framing.. This maps well onto the idea of a Ship, I feel.

Expeditions - Organizing for Exploration

Expeditions are essentially projects. They are planned activities that fulfill some need of the ship’s charter or yearly mission. They have a starting date and an ending date, with a starting directive to investigate. At the end of the expedition, whatever is found or created is logged.

Campaigns - Targeted Strategic Objectives

Campaigns are like subprojects. They are also planned activities that are designed to fulfill a strategic goal related to an expedition. Campaigns are more tactical, though, in that they arise based on what is encountered in the field as conditions change.

Sorties - Daily Tactical Actions

Sorties are like the subtasks in a project. These are short, running from a few hours to a day or so, and have limited scope.

A sortie is a known type of activity that is well understood, like making an omelet or delivering a package. By comparison, expeditions and campaigns have a lot of unknowns that need to be discovered, which requires a different kind of thinking. Sorties help convert that uncertainty into certainty by providing real world data.

Examples of Sortie Types

Creating Opportunities for Invitation

Expeditions, Campaigns, and Sorties are all ways describing different levels of project scope, which I think of in terms of these main parametersDerived from my conversational scoping approach with clients, who tend to lead with what they want done rather than why. It’s my job to pull the details out before I can write a brief.:

• Motivation — the reason to do the thing
• Intention — the immediate action to get the thing
• Expectation — the expected/desired result of thing
• Urgency - why this thing now instead of another thing

I think Expeditions/Campaigns/Sorties plus the scoping parameters turn into a quest card that can function as an invitation to join as a participant.

I imagine that people might peruse the list of expeditions awaiting volunteers—similar to quests in a roleplaying game’s adventure guild—and decide if they can commit to it. Or perhaps if they have less time, they can join a campaign or even just participate in a sortie. I think it’s a nice way to structure the invitation beyond simply saying, “we’re looking for volunteers”. And providing this structure in a clear and accessible way is certainly part of hospitality and operations!

The Month Ahead

While I have a lot more notes, I think I have enough to get started. I’m not entirely sure how it will work, or if I will instantly capsize like the old Swedish Warship Vasa and sink under the weight of my own hubris. I suppose in either case, it will be a spectacle worth watching!

As a quick aside, last month was quite busy with doing my federal income taxes, handling family internal issues, and trying to keep my head above water. While I set the groundwork for some stuff like finding some business information for Shopify, I didn’t actually make any new listings on Shopify. That was what triggered this entire giant reframe of what I was doing!

To keep myself honest, I will document the starting mission as I put this ship into the metaphorical water to see what she’s got. I am tempted to write the log in-character as if I were a character in a story, which might be a lot more fun!

I’ll update this post as events warrant.

INDEX of GHDR 2026 POSTS