Technology

Never Tell Me The Odds

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(This column is posted at www.StevenSavage.com, Steve’s Tumblr, and Pillowfort.  Find out more at my newsletter, and all my social media at my linktr.ee)

Han Solo’s famous quote (and Harrison Ford’s brilliance) aside, sometimes I want to know the odds. Actually I definitely want to know the odds, because I’m someone that likes to plan things, evaluate success, and plan for contingencies. I say this as a person who has debated with himself on “what day of the week does the week really start” kind of planning.

The odds, to me, a professional Project Manager (which I suppose means I’m worth listening to), are a way to calculate what to build. They let me evaluate success, plan for contingencies, and make something solid. If I do things right, the odds barely come into play because the plan, risk assessments, and options are all in place.

The odds are, at best, a tool, a way to get better, a way to improve. For all my world of flowcharts and checklists – professionally and privately – my world is one of solidity. I deal in how and results and measurements. From personal zines to environmental systems, it’s about results

But right now it seems society is more and more about playing the odds. As my friend Serdar put it once, more and more aspects of our society are coming to resemble a casino. The problem is casinos aren’t about building things, and that’s the problem.

As of this writing there are plenty of discussions about Kalshi, Polymarket, and other activities that are “prediction markets” which are really just gambling. That’s it, they’re gambling, and you can’t call it anything else. Draft Kings may have led the way with sports betting, but now we have prominent gambling companies. Call it what it is.

Our society is a casino. But it has been for awhile.

The stock market is not the economy, as we’re often reminded. It is, to an extent, about playing the odds and estimating chances. Now any economy is going to have some of that, as will any part, but if you ever looked at overvalued stocks and wondered, it’s not about the economy in many cases. It’s about the odds that something pays off, and it’s why some investments in companies that don’t do anything pay off, because people think they can sell before they loose.

Then there was Crypto, which really is just a stock on the blockchain. Then there was the NFTs, which thankfully crashed and burned then sunk into a swamp, that was gambling as well. Now we’re just to plain almost-honest gambling. It’d be refreshing if it wasn’t so prominent, so pathological, and in more and more cases it seems about people manipulating odds.

It’s all been a bit of gambling for decades – centuries? – but now it’s all gambling front and center. Bets and odds and manipulation. Know what it isn’t? Doing something with measurable achievements..

Where’s the plan? The results? The thing built? The thing made? Something that gets something done, that helps people, that can be felt, seen, touched, used? Where’s something I can break down into a Kanban backlog, where I can say “yes, here is a distinct result.”

But it’s a Casino. It’s about playing the odds, getting money, and that’s it. Nothing to be built, to be made, to be achieved. If you can manipulate things (say, with a bit of insider political information) so much the better. Why do something that has a role, a result, a history when you can just get paid for wondering what the body count is in a train wreck?

Play the odds enough and that’s all you can do. Look for the gamble, the payoff, the high. You just slosh money around and play the odds. That’s it.

The Casino economy is forgetting how to do things, and forgetting the value of doing things for and with people. And as a Project Manager, a person, and a citizen, I hate it.

Steven Savage

Book Review: Enshittification by Cory Doctorow

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(This column is posted at www.StevenSavage.com, Steve’s Tumblr, and Pillowfort.  Find out more at my newsletter, and all my social media at my linktr.ee)

Ever read a book that was very obvious but also a must-read? Well that’s Enshittification by Cory Doctorow.

You’ve probably heard the term Enshittification before because Doctrow made it famous. It’s a term to describe how things get worse and worse as they’re exploited, usually technology companies that were Doctrow’s initial targets. Well this is the book about why everything seems to be worse in the technology world. Companies locked us and their customers in and are squeezing us for every dime.

There’s very little in here that’s a surprise. But at the same time you’ll have a much better grasp about why your phone overheats when you go to web pages, why you get spam, and why your damn dishwasher has an internet connection.

Doctrow dives right in by discussing case studies of companies and services that Enshittified. None of this is going to be news to you in general, but the specific instances he invokes are eye-opening. You probably have at least one tech company you complain about and though it’s bad, it’s actually probably worse.

After giving you some examples that you’re all-too familiar with Doctorow then explores the Pathology of Enshittification. Simply put, there are usually social, government, and financial processes that keep companies from making their products worse. If you break those then, someone is going to start messing with the system, exploiting their locked-in users as much as they can.

Doctrow is pretty much of the opinion that modern corporations would Enshittify immediately, and gotta say, he has a point. Again a lot of this is very obvious, but when you see how many guardrails and limits to keep companies from making you insane for profit are gone, it’s worse than you think. Obvious, just worse than you think.

Then Doctorow does a deep dive on the Epidemiology of Enshittification, the various pathologies and signs and methods. This section introduces a number of useful terms, research, and concepts to help you understand what’s going on – and going wrong. Again, not a lot of it is surprising, but when you see the whole picture the depth is surprising.

To give an example, let’s talk what he calls “The End of Self Help.” We’re all aware of how many companies restricted the ability to repair devices, but the legal restrictions on what you can do with devices and software are probably far more strict than you realize. Repairing, playing with, modifying, or even accessing some devices in an “inappropriate” way can be made impossible or even illegal. Throw in internet-enabled tools and devices, and companies can lock you in and go after people who try to undo said locks.

Think about how that affects business, competition, and removes the concept of ownership. Now take this bit of Enshittification and multiply it by a whole lot of others. As I’ve mentioned a few times a friend decried in 2025 that it seemed technology hadn’t done anything truly new and good for ten years or more, and I kind of agree with her.

(Yay, we have better graphics, great, that’s being used to make Slop AI just like it was used to mine Bitcoin).

Finally, Doctorow looks at solutions. Some of this is the weakest part of the book as the solutions are obvious, but also we face a lot of challenges. Doctorow needed to give people more suggested action paths, communities to get involved in, and so on. The solution are movements and I think he could have done more with that.

And all of this, all of this is familiar. It’s just actually worse and dumber than we expected.

So my recommendation is that this is a must-read book but I’m not sure it’s a must-keep book. You’ll probably “get it” in one read and move on – hopefully after looking at the section on solutions and deciding to take action. So I do recommend buying a hard copy (which can’t be enshittified like a virtual one) and then when done lending it to someone else. Or have your book club do the same.

Let’s make sure this book doesn’t become a timeless classic.

Steven Savage

Purchasing New Overhead

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(This column is posted at www.StevenSavage.com, Steve’s Tumblr, and Pillowfort.  Find out more at my newsletter, and all my social media at my linktr.ee)

When you work in IT if you have a problem, someone has The Solution – for money. Ok there’s free/open source versions but a lot of times people want to pay cash. You don’t get fired for spending someone’s money in too many cases.

There’s always some new piece of software, new module, or new upgrade that’ll solve The Problem. I get this at home as a hobbyist and writer, and I get it at work. My friends who usually work in IT experience the same thing.

However there’s a problem with buying The Solution.

That new software tool or module that will solve The Problem also requires you to follow procedures, and enter data, and do things just a bit differently. Sure you can get customizations or do them yourselves, but usually The Solution to The Problem also adds The Work.

Which, you figure will pay off. Eventually. Yeah you have to track this and add that, but eventually it’ll be more efficient.


Except, then sometimes you add another Solution to another Problem and add more Work. So yeah, you just added a bit more of extra stuff to do, right? It’s worth it! You have The Solutions to the Problems!

Now zoom ahead a few years (or maybe a few months at some places) and you’ve purchased or expanded so many Solutions and added so much Work that you have a new Problem – all the extra Work added to solve the Problem in the first place. Hell, at that point you may have been better off with the Old Problem before you decided to solve things.

We’ve probably all been there when The Work to use The Solution becomes more important than actually solving whatever The Problem was. We may miss the old Problem. We understood The Problem.

Essentially companies and individuals have paid to get more overhead. I’m sure you’ve been there. You may be there now. You may be drinking because you’re there now. Stop that, it’s bad for you.

I think this is because fixing a Problem is hard and requires effort and argument. Making changes needs effort and arguments. The temptation to buy a Solution is both fast and might seem easier at the time. It’s kind of like the old “no one got fired for buying IBM,” whereas the challenges of overhauling The Problem means you have to ask how you got there.

Sometimes I think we need a new wave of minimalism in IT. How can we do more with less? What do we really need to do? How can we scale back to find what we really need to do at a reasonable price?

Because I’m finding that a lot of Solutions just create a new Problem – more Work.

Steven Savage