(Outrage) If I Could Go Back and Do it Again — Retrospective

Kent Dahlgren
11 min readApr 27, 2019

Technology, all by itself, is never the solution.

If I could do it again, I’d stop looking for the solution in technology. It’s not there.

Marketing people will argue otherwise, but they’re talking self-serving bullshit.

The solution is in and among people.

Sometimes, technology might help people work more easily, more efficiently, or may afford a greater insight or whatever.

But people will be the ones who deliver the solution to any problem, and sometimes their efforts are encouraged or facilitated through the judicious use of technology.

I’m old. I was born 22 years after the end of WWII, and have been at this for a very long time.

Once upon a time, I began to ride my uncle’s skateboard, gifted to me when he returned from Vietnam, in the mid 1970's. It was fun. I dug it.

Later, I aspired to be a good skateboarder, and by then had fallen in love with the skateboarding community, but eventually learned that I could make a greater contribution to skateboarding if I focused my efforts on constructing a place for other people to skate.

After building a few skateboarding facilities, I soon realized that I could make an even greater contribution if I focused my efforts on advocating on behalf of skateboarders in the creation of even greater numbers of skateparks.

Later in life, I fancied myself a skateboarding advocate, but soon realized that I could make an even greater contribution if I helped create highly effective skateboard advocates.

And so it goes.

Concurrent to this evolutionary process, as I evolved through each level of the advocacy strata, I experimented with many tools, methodologies, and approaches as a product manager for publicly traded and privately held technology companies.

When it made sense, I would experiment with “crossing the streams,” so to speak, in the judicious use of technology which might augment my contribution to skateboarding.

I’ve had a chance to think about how I might do things differently, given what I’ve learned in the years since.

Technology has always been present, in one form or other.

In the 1970’s and 1980’s, we used telephony (technology) to augment our collaborations.

Of course there were message boards, in the 1980's, and as the Internet gained popularity, in the 1990’s, these Internet message boards and forums enabled small groups of ad hoc skateboarders to connect with one another and compare notes.

Technology continues to try and find a place within our lives, bumping up against problems we aspire to address, and at the present a great number of us hold the world in our pocket in the form of a smart phone.

The smart phone is not the solution.

Apps which run on a smart phone are also not the solution.

Decentralized architectures inclusive to blockchain are likewise not the solution.

If you change focus and watch the people surrounding the particular problem, you will see them clamoring to deliver a solution.

Some of these solutions might necessitate the use of technology, and it is at this particular intersection of experience, as it meets the current state and direction of decentralized technology, where I am invited to ruminate on how I might have done things differently if afforded the opportunity.

I launched a 501(c)(3) in the early 2000’s, and while it had its successes, by virtue of my philosophical orientation as a skateboarder, I have continued to obsess in the years since about how we might have done things differently to elevate the efficacy of our efforts.

The first lesson is the most important: technology needs to get the fuck out of the way.

The solution is right there; it’s in and among the people who are closest to the problem space.

The entirety of the solution is not on the Internet, or whatever.

Indeed, any organizational construct which necessitates or encourages almost all interaction to occur on the platform is falling short of the mark.

People should be encouraged to meet with one another, and if technology facilitates these meetings, so much the better — but almost all actual progress and change happens with feet on the ground.

However, within the context of volunteer efforts, which frequently feature high rates of attrition, there must be some basis of organizational continuity, or the effort itself devolves into chaos.

The basis of a collaborative relationship is built upon lightweight agreements between two or more parties.

These agreements are finite in scope, with terms that are transparent and easily comprehended by all parties.

The task itself associated with the agreement must occur within a limited timeline, or the parties lose interest. And ideally, these agreements need to include some quantitative measures of success, which would form the basis of productive retrospective analysis in pursuit of continuous improvement.

All of what I just said can be facilitated using paper.

Fun aside: the word paper is derived from the word papyrus, which comes from ancient Egypt, speaking of technology.

In fact, this is how I run software engineering teams. I get large rolls of butcher paper — a technology that’s literally 5,000 years old — and put them on the wall, and then the team designs a solution in support of a customer need.

The solution is broken into discrete activities which can be written on a single sticky note, and they are organized on the story wall.

The tasks are executed upon within a finite period of time, and at the end of each cycle there is a review, and changes are made to the process as needed

The process I just described might well have supported efforts to construct a bridge 10,000 years ago, if you think about it.

It doesn’t really require technology, it’s just that technology can make the job a little easier, provided it knows its place and stays out of the way.

Participants within the collaboration should not be able to change the terms of the agreements without consent of the other team members.

If everybody knows one another, that’s great. But sometimes participants are not well known to one another, or are geographically distant.

If I can go back to the 1980’s, when I was spending a lot of time finding and draining backyard swimming pools, I would’ve liked to have had something that would fit in my pocket, and enable me to enter into lightweight agreements with two or more fellow contributors, within agreements whose terms are not easily modified by somebody who might have joined the collaboration recently.

Participants come and go. Attrition happens.

It would’ve been nice to have the ability to perform retrospective analyses so changes might be made to how we do our particular collaboration.

Within a for-profit company, what I just described are called standard operating procedures, (or SOP), but and another more common term for this is governance.

Typically when you use the word governance there are some that assume you’re talking about creating a replication of the European Union, which is false and ridiculous.

I’m not suggesting that there is no such thing as a person who wants to do that.

I’m just saying that the people who aspire to create an entirely novel replication of existing centralized governments are already members of the model UN, and, well… there’s just not very many of them.

In the real world, governance is really just lightweight agreements regarding roles and responsibilities, processes and procedures, just enough structure to keep the chaos at bay, without encumbering the collaboration with expensive unnecessary bullshit.

Interesting aside: I used to work at Xerox. When I started we had 80,000 employees and when I left we had shed 20,000 of them. We emerged more efficient and more capable, and do so by eliminating unnecessary, non-vital operations perpetuated by outdated governance.

Formal definition and codification of standard operating procedure (governance) tends to become entropic in nature.

Everybody has an anecdote about working at a company or within an agency where there are people who still pursue policies or regulations that are completely ridiculous.

This sort of entropic tendency will completely drown a lightweight collaboration, and so while a certain limited amount of governance is necessary to keep the chaos at bay, there should be certain protections to ensure that governance is kept in its place.

One such protective measure is simply quantitative and qualitative analysis regarding the efficacy of these procedures, coupled with a ruthless discipline in the streamlining and elimination of that which is no longer necessary.


Any policy which must be executed upon in a ruthless, disciplined manner will require a certain personality type.

Ruthless doesn’t mean cruel. Look it up. It means doing it because it needs to get done, even if it’s unpopular.

The collaborations that I’m describing are frequently embraced as examples of anarchy, which irritates me to no end.

To 99.999% of the world, the word anarchy is synonymous with the word chaos.

Chaos sucks. I’m not encouraging chaos. The world does not need more chaos.

For this reason, you will never hear me say that I’m a fan of anarchy.

I’m not going to try to re-educate such a vast majority of the population regarding the secondary or tertiary definition of the word anarchy.

I don’t actually desire to be drawn into any black hole of ridiculous divisive political discussion, because it’s all nonsense to me.

I’m not talking about politics. As I am fond of saying: Cowboys versus the Steelers, it’s still fucking football to me, and I’m just not a fan.

I’m not a spectator; I’m a participant.

I have spent the bulk of my life in pursuit of small, single-issue collaborations, and sometimes these collaborations necessitate an orderly way to address inevitable conflict.

I was executive director of that 501(c)(3) and I realized that one of my most frequent jobs was firing people because they just weren’t a fit.

I had structured the nonprofit in pursuit of a single goal (safe legal skateboarding for kids, average age: 9–17) with three quantitative / qualitative measures in support: a greater number of high-quality skateboard parks, delivered more frequently than current baseline.

This attracted a lot of participation, and at one point we had nearly 2,000 members, but eventually they introduced fringe, but tangentially-related, interests.

There was a woman whose son was not actually a skateboarder, but he was interested in graffiti, and some of his friends were skateboarders, so she demanded that we add graffiti walls to our charter.

I could fill volumes of examples of how people tried to expand our charter, and every time I would politely ask them to pursue their interests elsewhere.

Evidence of the divisiveness was easy to identify, because it would manifest as contention and disagreements within our communication medium.

These division were ruthlessly identified and eliminated, but we’d direct them to pursue their advocacy in a separate endeavor, and we’d actually offer to help them get started.

I’d say we have no monopoly on advocating for these people, and we’re finding it hard just to do this single thing as it is. We encourage you to pursue your perspective, and we’d be happy to work with you, as it pertains to our single charter.

Indeed, it was in this manner that our aggregate contributions actually grew in strength and effectiveness. We cleaved these separate interests into independent efforts, which enabled us to remain true to our charter, while expanding the scope of our influence.

If I could go back in time? I’d make it a lot easier to package up what we have and help bootstrap these spawned efforts.

They should be able to hit the ground running, with minimal disruption. I’d make it turn-key simple for rivals to spawn and contribute/compete, which only benefits the meritocracy, anyway.

If I could do it all over again, I would have a far more formally-structured conflict resolution process, within clearly-defined parameters which would help support perception that people were asked to leave on terms consistent with the organization’s charter, versus claims that they had lost a popularity contest or whatever.

If you think about it, this arbitration process is just another example of governance, which in an ideal form is almost entirely invisible.

Just enough governance to keep chaos at bay, and absolutely no more.

Which means: a well-functioning arbitration process is one that doesn’t really expose any of the underlying governance.

Metaphor: the tool should never get in the way of the artist.

Remember that I’m talking about people who have made it their hobby to pursue a certain vision, and they’re probably doing so on a voluntary basis.

They are artists. They don’t want to be encumbered with a lot of bullshit. Get out of their fucking way and help make them heroes.

Their identities are wrapped up in the quality of their contributions and the evidence that they have helped effect change, which brings up another thing I wish I had: a reputation metric.

And I’m not talking about some fucked up Black Mirror, 1984-Orwelian bullshit like they’re doing in China.

These imagined reputation metrics would reflect quantitative and qualitative measures of a person’s contribution within a meritocracy, with built-in passageways to redemption.

Redemption is really fucking important.

Success is an illusion. Failure is likewise an illusion.

The best we can muster is a smooth reversal of an imaginary sine wave which varies between the two imaginary extremes.

Strangers will meet within this collaboration, and of course they want to demonstrate the quality of their contributions in a way that others can easily evaluate, but it also needs to be fair, honest, and pragmatically resistant to peoples’ inevitable propensity to engage in fraud.

I should mention something about fraud and trust. Quick anecdote:

I used to be responsible for algorithms that could evaluate and identify the difference between fraud behaviors on a platform which actively monitored almost 4,000,000,000 devices every day.

Traditional anti-fraud and security infrastructure has been constructed under the baseline assumption that everybody is a potential thief.

The manifestation of architecture in alignment with such an untrusting philosophical orientation flags trustworthy people as suspicious on a seemingly random basis.

One day we started evaluating the data from a different perspective, and the results were shocking.

Rather than construct the data analytics in support of a supposition that everybody is a potential thief, the data scientists tried a different approach.

Why not assume that everybody is trustworthy, and then handle each deviation as an exception, with a path to redemption?

We’re talking about machine-learning algorithms, so we’re really talking about our data analytics which can predict likely behavior, and the rates of efficacy increased by orders of magnitude.

This means that the AI’s are completely fucking wrong.

They need to be calibrated to how humans actually are, which is inherently trustworthy, with rare deviations.

A reputation system should be constructed in alignment with how humans actually work, not through the perverted lens of an inherently untrusting institution.

Finally, if I had a magic wand and could go back to the 1980’s, when I had begun my advocacy journey in earnest, I would to do this utilizing technology which is so lightweight that it is nearly invisible to contributor interactions.

And, I would expect that same infrastructure to provide the option for our effort to generate revenue in support of our goals, but do so in a manner which is transparent, and easily audited.

Not everybody is trying to get rich or even make money as an advocate, but man, it sure would be nice if that option were available, even if it were in pursuit of financial self-sufficiency which would remove the often demeaning exercise of begging for donations.

We’ve created a light-weight platform for small communities which seek to secure self-sufficient economies, with built-in tools for collaboration, and if you’d like to learn more, contact us at www.214alpha.com.



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”