GHDR Report 0505: Setting Sail on a Metaphorical Ship

⊕ 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 beyond Groundhog Day Resolutions (aka GHDR) has been to find a way to be financially self-sustaining while doing things I actually liked to do. The path itself has been surprising and educational, but in all 19 years so far, I’ve always gotten stuck on some boring part of the execution.

In the April 4 Report, I noted the stuckness yet again doing simple marketing tasks like “making product listings on Shopify”, and took the time to question my assumptions about what I was working. Paraphrasing my April 4 thoughts:

• Yes, there is an “Execution Gap” between what I want to do and doing it. And I have used dozens of ways to push through but it is always expensive in terms of personal energy.
• To pivot, I proposed a hypothesis: maybe my strengths aren’t actually what I think they are. After reflection, I conjectured that it was that I enjoyed caring about how I did things for others, and being prepared to do so was therefore also enjoyable.
• I noted that this “caring and preparedness” inclination seemed to align with my love for hospitality and operations, particularly in cool hotels and in stories about spaceships (e.g. Star Trek). Could this be a new reframing device that I could use to change the context for doing marketing tasks?

I ended the report pondering how that might work, which I workshopped 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 started freelancing in the first place all the way back in 2004. My push to develop “creative independence” —the desire to be my own boss and support myself through creative projects I picked—started nine years later in 2013, and promptly fell into the trap of needing marketing for myself. Apparently I’m allergic even to my own marketing? Whoops!

The rest of the Reframing Chores as Ship Operations reframes my marketing needs as a byproduct of “hospitality” and “ship operations” as I defined them. You can look at the post itself for the details, but briefly I outlined the following:

• Motivation, Reframed - not motivated sharing my own work for trade, instead telling the story of running my own ship for myself, passengers, and maybe even a crew.
• Metrics, Reframed - not measuring “goods produced”, instead counting acts of caring connection. The payoff is “trust earned over time”, which is what I like!
• Skills, Reframed - not based on a list of technical/creative skills, but instead through practice of adaptive exploring, learning, building, and sharing which utilize those skills.
• Personal Goals, Reframed - Not simply designing goods that I can sell as an independent creative, but instead to swirl and flow, which are living acts expressed in the moment of living care (hospitality) and operational preparedness (ship operations)
• Mission, Reframed - In the past, I tried to find people who wanted to “swirl and flow” the way I did. But I am already doing that through blogging and running coworking communities. I had justified the immense amount of time this took because it technically could be called a form of marketing, but now simply doing it as something I enjoy is now a form of expressing my kind of hospitality. I just have to make the invention more obvious to people who themselves like to swirl and flow.

All of the above ties into The Way of Sri, a childlike story where “all the animals become friends”, working and playing together. They grow and explore together, sharing their stories and experiences in mutual support. They create a better place for themselves to thrive.

So that is where I am today on May 5, 2026. I have a strong sense of how I want to think about my work in the context of HOSPITALITY and SHIP OPERATIONS, but I need some operating principles to structure it. Otherwise, I won’t know if I’m staying on-course or am just doing busywork that goes in circles.

To avoid getting stuck in a perfectionist cycle, I decided to declare this starting list of principles and directives that incorporate my notion of ship operations and hospitality in that context.

Starting with a Charter

For my purposes, a charter sets the philosophical guidelines for operating my “ship”, which is comprised of my blog, my online business activities, my in-person interactions, and projects.

So how is this like a ship?

And what of the philosophical guidelines that affect this ship?

The Charter is sort of similar in intent to Starfleet Doctrine in Star Trek. Below I declare my working set of principles:

• Creating a sense of belonging is my business. The Charter is a statement 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 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.

This is a provisional charter, so I expect these principles to change based on experience as I try putting them into action.

Declaring a Mission

A Mission, as I’m defining it, is a set of strategic goals for a ship. 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.

As I am just getting started on this elaborate reframing of my business operations, my starting mission is simply to see how it works in a shakeout cruise. This is an entirely new class of vessel, and there are likely all kinds of problems that need resolution.

The most accessible context is simply my own Groundhog Day Resolutions practice, which can be described as a yearly mission I’ve given myself. In Groundhog Day Resolutions 2026 Kickoff Part III: The Plan I defined a list of starting directives (see sidebar) but these are the ones that I have been focusing on recently:

Those are two separate missions running simultaneously. A third mission is simply:

Structuring Action

With Charter and Mission defined well-enough to start, I want to think about an invitation structure that is compatible with the way I already work. I’m resurrecting the concept of Expeditions, Campaigns, and Sorties as a way to structure operationsA 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..

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 decided 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 Shopiy, 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