In 2016, the Oxford Dictionary named “post-truth” as its “Word of the Year.” At the time, AI generated content was crude and easy to spot, and when it was presented as “real” no one took it seriously. There were plenty of other things to worry about: Brexit, the Panama Papers, the deaths of David Bowie, Prince, Muhammad Ali and John Glenn, numerous European terrorist attacks, Creepy Clown sightings, and the election of a US president who was (and still is) enamored with social media, a platform many of us had already noticed was having a significant detrimental effect on society in general. Fast forward nine years where I just saw a very convincing video on the internet from Jake Paul announcing that he was gay and releasing a makeup line. Except that video wasn’t real, but thousands, possibly millions thought it was.*1
What can we do?
I am asked constantly by my family, friends and clients how we are supposed to trust what we see and hear on the internet. Given just how far we have “advanced” in generating fake content that is essentially indistinguishable from reality, they are understandably concerned if not outright scared. We are far past the point of mainstream media priortizing objectivity and truth over profits. It’s clear we have plenty of politicians and leaders for whom truth is an inconvenience rather than an ideal, and the world’s richest men who are in charge of our technology seem hellbent on squeezing every last cent out of us, at the cost of our security, privacy and integrity. Unfortunately, none of us (as far as I know), is someone with enough clout and money to move this particular needle in any significant way, but we can all do something: You can continue to value truth and scientific knowledge and hold others to that same ideal. There so many ways to pursue this in your daily life that are beyond my capabilities to share with you, but there is definitely one thing I can call out in this blog: if you are going to consume content from social media (let’s face it, it’s not going anywhere anytime soon) don’t be lazy about it. Don’t just assume because someone you know on the internet posted something, that it is automatically true or to be taken at face value. We are already past the point of being able to say, “Seeing is believing,” without having to second guess ourselves, and we already know there are plenty of “people” on social media who are there purely to exploit anyone they can. We are tired. We are overworked and under overwhelming stress, and the internet is so conveniently apt at showing us exactly what we think we want to see. If you are going to value truth, you must be mindful that your social media feed is carefully tailored to show both want you want to see as well as what they want you to see, and their objective, in the end, is always profit and power frequently at the expense of truth. Knowing this is indeed half the battle, and the other half will be you, holding others accountable to truth as you hold yourself.
As a start for my own quest to seek truth on the Internet, I have found a service called Ground News (https://ground.news) that brings you the news as well as the reported bias of the news sources. I have found it useful in determining if the article I am reading might have some bias, and from that, determining if what I have read be helpful in finding out what actually is happening.
Another site that does something similar is AllSides (https://www.allsides.com/unbiased-balanced-news), another news aggregator run by a public benefit corporation, a concept that I wish were applied to many more corporations, especially the ones that seem to have a stranglehold on our daily existence.
Image by Pablo Jimeno from Pixabay
- I don’t want to give the “creator” any more internet clicks than they are already getting. If you want to see it, you know how to find it. ↩︎
I’ve written about this topic before, but it’s nice when major publications back your viewpoint. One of my favorite authors has a new book forthcoming, and as a sign of the times the title – which may have been scandalous in a previous, perhaps more innocent age – gets straight to the point: “Enshittification: Why Everything Suddenly Got Worse and What To Do About It“. And because everything these days is meta and Mr. Doctorow’s book isn’t even out, I read an advanced review of the book that contained praise as well as some criticisms which I think are valid and troubling to consider when asking the most important question.
What can we do about it?
In case you didn’t read my previous blog about this or don’t remember it (because we all have enough to worry about already, so I get it), “enshittification” is the concept that all good online services and websites will eventually be ruined by our society’s relentless pursuit of profit. The advanced review as it appears on the Current Affairs website does a pretty good job of explaining this topic, and if you don’t intend to purchase the book, I think the article provides enough of an overview for you to spot this trend in the world around you, which may or may not improve how you may feel about it. I’m going to read the book for myself before I render my own praise or criticism, but I have similar concerns to the reviewer’s when it comes to answering the question that you have all asked, “What can we do about it?” It sounds like Mr. Doctorow is calling for grassroots efforts and government intervention to counteract future enshittifications (the author seems to think it’s already too late for the likes of Amazon, Facebook, Netflix, etc. and I agree), but from where I’m sitting it seems like getting help from the government isn’t on the menu at the moment, and our grassroots are divided as we fight to maintain healthcare, livelihoods and just basic human decency. So what is my recommendation to you if your technology feels “shitty?”
Take matters into your own hands. If you have the option to use something else, do so and make sure you tell the losing platform why you moved (even if they will probably never read your feedback). If changing the technology isn’t an option, perhaps take a moment to clearly identify the crappy part for the purposes of determining if it’s something you have control or agency over (maybe a new setting or change in interface), or if it’s out of your hands, such as the price going up. If it’s out of your control, focus your energy on working around or through it, or changing something else so that you can eliminate it altogether. Using technology is unavoidable for most of us, but there is no reason to feel like you are a hostage to it, and the best way to manage this is to change the things that you can control, and asking for help or sympathy (or both!) on the things you can’t.
I’ve been working in tech long enough to remember when “automation” meant macros in Excel and AI was still the stuff of sci-fi. Today, artificial intelligence is everywhere—from customer service chatbots to advanced data analytics, predictive modeling, and content creation. It’s no longer a niche tool; it’s a foundational layer in how businesses operate. And while this explosion of AI capability is exciting, it’s also incredibly risky—especially for those who treat it like a shortcut instead of a tool.
Let me be clear: AI is not magic. It’s not intelligent in the human sense. It’s powerful, but it’s only as good as the data it learns from and the intent behind its use. I’ve watched companies implement AI without understanding how it works, leading to biased outcomes, false insights, or compliance violations. They feed it flawed data, make strategic decisions based on unverified outputs, or worse, let it replace human judgment entirely.
The danger lies not in the technology, but in the overconfidence that often accompanies it.
AI should augment decision-making, not replace it. When misused, it can erode trust, amplify existing inequalities, and expose companies to significant legal and reputational risk. If you’re using generative AI to write content, ask yourself—how do you verify it’s accurate? If you’re using AI to screen job candidates, are you confident it’s not introducing bias?
As a consultant, I encourage clients to treat AI the same way they would a junior employee: train it, supervise it, and never let it act without oversight.
The future of AI is promising, but only if we use it responsibly. Those who blindly chase efficiency without understanding the tool may find themselves solving one problem and creating five more. So take the time to understand what AI is—and more importantly, what it isn’t.
Want help making AI work for your business—safely and strategically? Reach out for a consultation.
Author’s Note: This blog post was written by ChatGPT using the following prompt, “Write a short blog from the perspective of an experienced technology consultant about the rising use of AI and the dangers it poses for those that use the tool incorrectly.” I did not touch-up or edit the text provided by that prompt in any way, shape or form other than to copy and paste it into this website. Anyone who’s followed my blog for awhile or knows me personally might have smelled something fishy, or maybe not. In reading the above, I can definitely say that I have written plenty of articles just as bland. Interestingly, ChatGPT included the last, italicised bit – it’s clearly been trained on plenty of marketing blogs like this one. I know that many of you actually read my blogs for my personal take on technology. If I were to feed my own AI engine the past 10 years of my articles so that it could perhaps get a sense for my writing style and personality, do you think it could produce more blogs that would be indistinguishable from what I wrote with my own two hands and one brain?
Image courtesy of TAW4 at FreeDigitalPhotos.net
Most of you have known about this aspect of Internet life for awhile now: everything we do is tracked, even in “incognito” mode and behind VPNs. And while some of the obvious indentifying bits of your transactions may be obscured by privacy tools most don’t even bother to use, everything we do is logged, categorized and analyzed down to the minute and individual, and across years and world-wide demographic groups. Any which way the data can be sliced, diced and sorted, it has and will be for the forseeable future. Data has been the gold-rush of the 21st century for several years now, and you’ve most likely started to sense the bubble of information that seems to follow you everywhere you go.
What on earth are you talking about?
By now, you’ve probably heard the term “algorithm” used to discuss various things, like search results, or page rankings, or advertising. Unless you happened to be immersed in a profession that deals with them all day long, you probably only have a vague sense of the impact algorithms have on your daily life. I could go on and on about how it works, but the easiest way to demonstrate how effective it is will be just to show you.
Assuming you have either a TikTok or YouTube account that you have used for at least a few months, try opening up a browser tab to either site while you are logged in, and another incognito tab while are not logged in. Even minimal use of an account will drastically change what the site presents to you on the front page. Now think about everywhere you log in: Facebook, Spotify, Amazon, Netflix, Gmail, Instagram. All of them have extremely specific and voluminous data profiles on every aspect of how you use their site, and they are constantly feeding that data to algorithms that constantly inform what and how content is presented to you. While this can be pleasing or even comforting at first, it also has the knock-on effect of not showing us things we don’t want to see, even when it may be important for us to have that exposure. Humans, in their “default” state, will gravitate to what is comfortable and familiar, and the internet continues to reinforce this is as vicious, feedback loop that is definitely turning out to be detrimental to compassion, curiousity and emotional growth.
Interestingly enough, most data algorithms also seem to follow a well-known phenomenon known as the the “Observer’s Effect” where the properties of the observed object change just because it is being observed. You can be certain that the minute you try to poke at the algorithm surrounding you on a particular platform, it will definitely observe you observing it, and depending on that platform’s intent for your interactions with it, will alter itself to maybe make it less obvious that you are being manipulated. Now wrap your head around that and add the fact that nearly all of our “news” is coming from platforms that actively know you are watching and can adjust what you consume based on agendas that most likely involve monetization and not just sharing information, and you get a sense for just how far down the rabbit hole we have fallen.
Image courtesy of TAW4 at FreeDigitalPhotos.net
We’ve discussed in previous blogs how technology things seem to be getting worse from just about every angle, whether it’s cost, quality or security. We can attribute a large chunk of this downward trend to the increasing profitability of cybercrime, which is itself a vicious, amplifying spiral of escalation. The more we try to keep ourselves safe, the more complicated it becomes to do so, and most regular folks don’t have the training or endurance to keep up, especially if you are a part of the growing elderly generations that are forced to use technology they barely understand just to stay alive and keep in contact with friends and family. With the recent (in my opinion ill-advised) downsizing the Cybersecurity and Infrastructure Security Agency (CISA) much of the this country’s organizational strength and operational efficiency in cataloging and combatting cybersecurity threats will be abandoned.
What this means for all of us
Regardless of whether you are a big or small organization, CISA’s leadership and work provided foundational guidance on all existing cybersecurity threats while constantly researching, investigating and publishing information on new threats as they discovered. One of the main reasons that governments exist is to provide funding, resources and scaled force for tasks that cannot (and should not) be handled by smaller groups or for-profit institutions, such as military defense, mail delivery, and national security. As has been demonstrated time and time again, for-profit companies cannot be trusted to put people before profits, and security oversight is definitely not something you want to enshittify. And yet, that is exactly where we are. In the absence of CISA leadership, organizations, whether they be ad-hoc coalitions of state-level agencies or, most likely, for-profit companies in the security industry, are now scrambling to fill the gigantic, CISA-shaped hole in our nation’s cybersecurity. Let’s be clear, security for small businesses was already well on its way to becoming difficult, expensive and onerous. Eliminating national leadership will most definitely lead to a fracturing of an already complicated security framework that will most assuredly weigh very heavily on those who can least afford to shoulder a burden that was formerly carried by those trained, equipped and funded to do so.
Two years ago, in 2023, Microsoft announced that over 36 million people were still using Skype daily to communicate via video and chat. The app was 20 years old at that time, and has been in Microsoft’s hands since 2011 when they bought it from eBay for $8.5 billion to replace their own popular (but less capable) Live Messenger service. On May 5, after 14 years in the trenches, Microsoft has shut down the service and has given users 60 days to move their content (contacts and messages) to the free version of Teams, or lose the data forever.
What this means for you
If you were a diehard Skype user hoping that Microsoft wasn’t going to make good on it’s February promise to close Skype permanently on May 5th, you are probably wondering what to do next. Fortunately, it seems that logging into Teams with your Skype credentials will ease the transition by automatically bringing over your chat history and contacts, because, in case you didn’t know, your Skype account was actually a full-blown Microsoft (personal) account all along. Unfortunately for many, the Teams replacement for Skype is not a feature-for-feature substitute, with the main loss being the ability to make phone calls to land lines and mobiles that don’t have internet access. This well-known “life-hack” trick was assuredly what kept Skype popular in face of the various other video chat apps that have come to dominate the space, and probably one of the main reasons Microsoft decided to shut down Skype in the end. If only a fraction of the 36 million Skype users were using Skype to make cheap or free long-distance calls, Microsoft was leaving a large amount of money on the table, even by their standards. Rest in power, Skype. You were a handy bit of software for many people.
I’m sure it’s still a thing for students today, but one of the phrases that always caused a groan in any class that involved solving equations was, “Make sure you show your work.” Whether it was pre-Algebra or Advanced Calculus, the only way you could prove that you actually understood the topic well enough to solve the problem was for you to write out each step of the solution. We had graphing calculators when I was going through high school, but even if we were allowed to use them during tests, more often than not there was going to be at least one instance where the calculator was only there to confirm the answer we arrived at after lines and lines of chicken scratch and piles of eraser crumbs.
There’s a point to this nostalgic indulgence
If you are a business owner or part of the executive team, you will likely be familiar with the technology security questionnaires that accompany your organization insurance renewals. Up until perhaps 2023, checking “yes” boxes on the questions or tossing in vague answers were typically enough to get you through the approval or renewal process, and I’m fairly certain that the application reviewers were just as cross-eyed as you were when filling them out. I’m (not really) sorry to say this “relaxed” approach to evaluating your security standards are in the rear-view mirror for everyone, regardless of the industry you are in or the size of your organization. Insurance carriers are reading your responses and are not taking “N/A” or “No” as an answer when asking if you have various security safeguards in place. At best, you may be encouraged by your insurance agent to, “Reconsider some of your responses,” and at worst it may lead to an outright denial of coverage and a mad scramble to find another carrier for your insurance needs. The insurance industry is already taking a beating on natural disaster claims (something not likely to abate given the world’s general dismissal of climate change), so they are definitely not going to be generous with the next most popular claim: cyberattacks. Don’t given them any excuse to deny a cyber liability claim by just checking a box. Show your work by actually implementing the security standards they are asking about, and if you don’t know where to start, get a professional like C2 on the job as soon as possible.
As of now, Microsoft seems to be holding fast to its promise to end support for Windows 10 in October this year. Old tech heads like me are skeptical as to whether Microsoft will keep its word as the clock ticks down, as we still remember when these same promises were made about Windows 7, for which support and updates lingered for years after its scheduled demise. In case you were worried, the October deadline doesn’t mean that Windows 10 will suddenly stop working, but if Microsoft sticks to its guns, the nearly 10-year old operating system might get the boot much faster than the previous deadline-defying champion, Windows 7.
Hang on, what happened to Windows 8 (or 9)?
For those of you paying attention, you may have noticed that only certain of Microsoft’s operating systems seem to enjoy more staying power than other versions. Since the early ’90’s Microsoft has been infamous for releasing alternating generations of good and bad operating systems, and if you ask any IT professional around long enough to experience at least 2 waves of this, they are pretty much in agreement that the current pairing of Windows 10 and 11 matches the previous cadence of Windows 7 and 8, and Windows XP and Vista, eg. good, then bad, then good, etc. The pattern actually goes back even further but I think you get the point.
What’s changed this time around isn’t that Windows 11 is better than 10. Most folks who have gone through the transition already would probably agree that regardless of what may have been improved under the hood, the Windows 11 experience is not an upgrade over 10. What has changed is the pace of security updates. Windows 10, through most of its early years, was updated on a monthly basis, with a few patches sprinkled throughout, and many companies would hold updates back from being applied upwards of a full 3 months so as to not disrupt operations. Likewise, many software developers would match Microsoft’s slow cadence with their own reserved pace, oftentimes exhorting their customers to delay applying new Microsoft updates too quickly lest they break their own software (which they did, regardless of your pacing).
Today, that’s just not going to fly. The pervasive onslaught of cybercriminal activity has forced Microsoft (and everyone else, to be fair) into an absolute frantic pace of updates. On top of this, the insurance carriers providing what meager safety nets they can for the inevitable cyberattack are now requiring that everyone manage these risks at a rigor previously only applied to much bigger organizations (and budgets). And if Microsoft makes good on their promise to stop updating Windows 10 – let’s face it, they have no good reason to do otherwise – then we will all have very little say in the matter. Windows 11 is what’s for dinner, and a Windows 10 peanut butter sandwich is not an option.
I first encountered Cory Doctorow through his novel Down and Out in the Magic Kingdom which is a vision of our world in the 22nd century where social media rules everything. When it first came out in 2003, it was fascinating and seemingly far-fetched, but here we are, twenty-two years later, living in a world where everyone seems helplessly enthralled with short-form content powered by profit-driven algorithms and relentless thirst for pseudo-anonymous internet validation. Since then, Doctorow has been focusing his energy and writing on the internet and information, spending years as an editor at proto-blog Boing Boing (started in 1995!) before going independent in 2020, and three years later, he wrote about a now semi-famous concept called “enshittification” which describes the process of technology services that start out amazing and then slowly (or quickly) degrade as the platform tries to profit from their viral popularity at the expense of their users.
We can all name at least one
As usual, the internet isn’t quite certain if Doctorow coined the scatalogical neologism, but he definitely nailed the smell wafting off the various services we all know, use daily and once loved unconditionally. Whether its Amazon, Netflix, Twitter, Facebook or TikTok (let’s be fair, that one started out pretty crappy to begin with), every single one of us is subject to services that started out great and have since struggled to prove their continuing worth in the face of seemingly unstoppable profit-making practices and egregious privacy violations. The real problem is many of us can see the crapification happening, but we stick around because there is literally no where else to go. Back in the days before the internet, this was called a monopoly, but now it’s because we can’t convince our softball team to organize games and practices anywhere other than Facebook, our favorite TV series is only available on HBO Max, and a certain online shopping behemoth has literally captured the majority of the industry, forcing everyone to compete in an advertising bloodsport in which the sellers to pay to compete, and we all buy ringside seats because there is no other game in town. Doctorow has been advocating a solution for this but it requires participation (either willing or enforced) by the owners who are profiting from driving their platforms into the ground and for us consumers to recognize when we are being exploited. Back when he wrote that article for EFF in 2023, it seemed like we were making good progress towards protecting users’ rights, but now in 2025, I’m not so sure he’d be as optimistic and let’s be honest, he wasn’t exactly Pollyanna then either.
As you might have guessed, I don’t have the answer either. I do think it’s important to that you know that I know how you feel when you ask me, “Why does (necessary technology service) suck so much?” and that it’s a widely recognized phenomena. It is an important first step to recognize that if something is free, you are the product, and even if you graduate to paying for that service and you are STILL the product (Amazon Prime, I’m looking at you), you can’t just set that recognition aside because it’s easier. In the glorious, early days, we thought the internet would make our lives easier, and it has, but it has also cost us dearly and now the Piper is before us, and this time he doesn’t even have a hand out because he knows we will keep paying. Hopefully, because we all know how the fable ends we are forewarned and can work our way to living our lives outside the pockets of a powerful few. We are all in this together. Keep fighting for your privacy.
Image by Alexa from Pixabay
There have been plenty of rumors about the upcoming retirement of the version of Outlook that most professionals use daily, and a lot of concern from those same professionals about the “new” Outlook, which is very different from “classic” Outlook. The terminology of “classic” versus “new” is actually the official terminology from Microsoft, and “new” Outlook debuted back in August 2024. Much like the famous soft drink who also tried this approach, “new” Outlook has had a frosty reception, and while none of my clients would classify themselves as “fans” of classic Outlook, they definitely prefer it over the new one.
How long do we have together?
Part of the confusion about the impending “death” of classic Outlook comes from the retirement of certain Windows apps that have been a part of of the operating system for over 30 years. Windows Mail first appeared in 1991 on multiple operating systems including Windows 1.0 Microsoft officially discontinued Mail, People and Calendars apps at the end of 2024, and Microsoft has stopped including the apps in Windows 11 as of version 24H2. While most professionals don’t use Windows Mail for their work email, it’s typically the app of choice for everyone’s personal free-mail accounts like Yahoo, Gmail, Hotmail, etc. especially since Outlook installations on home computers were non-existent and only became more commonplace thanks to the pandemic and WFH initiatives.
On top of this, Microsoft is no longer installing classic Outlook in Windows 11 as part of the pre-installed Office 365 suite, and getting the “classic” installer is not immediately obvious, even to the veteran Office 365 user. This may lead many folks to believe that classic’s demise is imminent, but according to Microsoft, they plan to continue supporting classic Outlook through 2029. Will they make it any easier to get that version installed on your new Windows 11 PC? Probably not, but at least we have a few more years with our “beloved” mail reader.
Next post we will look at why “new” Outlook isn’t as popular as Microsoft would have hoped.