Slaying the Dragon, one Pin-Prick at a Time

Kent Dahlgren
4 min readJan 6, 2023


The other day I shared something about how a “one bag at a time” execution methodology helps accomplish a large endeavor through a dogged, bite-size commitment to execution.

In the world people longed for sustained rain, and we brought forth three holons of three

The example of “one bag at a time” referred to 90-pound bags of cement, used one at a time to build a huge concrete skateboard park, over the course of years, and right in the heart of Portland, Oregon, without formal endorsement, (and therefore illegally).

Built without permission in the center of Portland, Oregon, Burnside skatepark is attributed with triggering “the second coming of the skatepark” in the manner by which the example of citizens “doing it themselves” broke the spell of inaction and institutional opposition

Here’s something else that’s related: humans (as animals) are endurance hunters, and not frequently hunters that are good at performance-based attacks.

We think of ourselves as cheetahs, but we are more like a relentlessly slow-moving pack of relay runners.

This means that although a gazelle can outrun us, they can’t persist as sprinters, and we tend to catch up with them before they have an opportunity to recover.

Lather rinse repeat, and the gazelle is soon saying “ugh y’all are wearing me down, just kill me already” and in the ancient tradition the hunters would pause, thank the gazelle for its gift, and would use everything, to honor the gazelle’s sacrifice.

There’s a complementary strategy for targeting prey that’s significantly larger than ourselves, and that’s by pestering them repeatedly.

The larger prey can lash out, but they can’t do it many times before they wear themselves out, which places them in an extremely dangerous, defensive posture, kind of like a cornered dragon.

As I like to put it: “good news for me is that I have more patience than you motherfuckers have (authorized) resources.”

Going back to the story of the large concrete skateboard park: I am fond of reminding people that our successful endeavor was built upon a foundation of “five years of failure.”

Which means that henceforth, we had learned the hard way that structures built out of wood are too easily vandalized, stolen, destroyed, etc.

But concrete?

We learned that building at a persistent slow pace bought us the time necessary to earn warm collaborative relationships with local stakeholders, inclusive to the business community, the neighborhood association, and neighbors.

And the more we built, the more expensive it would be for the city to requisition resources necessary for the concrete’s destruction and removal.

All wars are based upon logistics, and are therefore all wars are ultimately wars of attrition.

And so 18 months later, and just about at the time when the city of Portland had built sufficient momentum necessary to remove the park, they ran face-first into the multi-stakeholder alliance upon which the park’s viability continues, 32 years later.

I don’t have many good things to say about politicians, but I will observe that ultimately: they are pragmatic, and the politicians of Portland were able to read the tea leaves, so to speak, so they brokered an agreement that to this day enables the park to serve as a self-stewarding community, in collaboration with neighbors and other partners.

To win that trust, we not only broke the rules, but we persistently worked to earn the goodwill necessary to ask our neighbors and partners for a favor, which meant that we picked up trash, we cleaned up graffiti, we literally faced down gunfire and gang activity and drug dealers.

We did the work necessary to earn our place by improving the conditions of the surrounding area, while constantly poking at the dragon.

This is why I have a bone to pick with many modern day communists, libertarians, and other persons of bizarre and mostly theoretical ideological utopian affiliations.

Their heart is in the right place, but very few have experience with what’s called praxis, otherwise known as getting out into the world and doing the work.

So: they limit their contribution to the posting of memes, which seems edgy, “based,” and cool, except that there are real people that are in need of assistance, and at some point limiting your contribution to posting memes starts to make that individual look pretty decadent and detached from reality.

If it’s your contention that you and your people are going to vanquish the dragon, then you better get off your ass and start pestering it with your spears until it’s exhausted.

Concurrently, you better get into the world and start negotiating goodwill among partners, because that’s how the real world works.

That’s what the Black Panthers did; by protecting their people and providing social services, and they were murdered as a result.

Like I said: the cornered dragon is very dangerous, and that’s probably why most people just limit their contributions to buying crypto and posting memes.



Kent Dahlgren

Product management fix-it guy. World-famous people skills. Extremely small hands. (edit) marketing lady says I’m also supposed to say “CEO of software company”