In an age of artificial intelligence, digital transformation, and cloud-first everything, one would expect our work tools to become lighter, smarter, and easier to use. And yet, for many employees across industries, the opposite feels true. What used to be accessible in a few taps now requires multiple logins, a corporate VPN, and sometimes an entire course just to learn where the right button is.
Take, for example, the shift from WordPress to Adobe Experience Manager in a corporate setting. WordPress, for all its limitations, allowed users to edit and upload content from almost any device. Log in, verify your identity, and you were in. But with Adobe’s enterprise solution, that same task now demands a VPN connection, a desktop browser, and sometimes IT assistance. The process has become heavier, not lighter, in the name of security and control.
This isn’t an isolated case. Many enterprise decisions that are justified as upgrades end up making daily work more complex, not less. The tools grow, the steps multiply, and the learning curve steepens. Progress is still declared, but the user quietly pays the price.
VPN and the Legacy of Control
The Virtual Private Network (VPN) was once a cutting-edge invention, a digital drawbridge that allowed remote employees to cross into the private world of their office network. In an era when everything lived behind firewalls and on-premise servers, VPNs made sense. They extended the perimeter of trust just enough to let you in, provided you passed the right checkpoints.
But times have changed. Most modern work now happens in browsers, not file shares. Tools like Google Workspace, Microsoft 365, Slack, and Zoom do not require a tunnel to the office. They rely on identity, not location. And yet, VPNs persist. Not because they are the best tool for the job, but because enterprise infrastructure moves slowly. Risk-averse IT departments continue to use VPNs as a blanket solution, even when better models exist.
The rise of Zero Trust architecture reflects this shift in thinking. Under Zero Trust, no user or device is assumed to be safe just because they are on the company network. Every access request is verified in real time, based on identity, device posture, and context. This model promises more precision and less friction. But for many companies, the path from VPN to Zero Trust is a long one. Systems are entangled, legacy applications still require network-level access, and procurement cycles are sluggish. So the VPN remains, a relic of a fading architecture.
Artificial Intelligence and the Illusion of Help
Meanwhile, the technology landscape is being flooded with promises of artificial intelligence. Security vendors now offer digital twins that supposedly monitor your entire infrastructure in real time. Productivity tools come with smart assistants that autocomplete your sentences, summarize meetings, and generate slide decks. The term “copilot” has become the new badge of innovation.
On the surface, this sounds like salvation. Finally, machines will take care of the repetitive and tedious. But look closer, and a pattern emerges. Many of these AI-powered tools are not replacing complexity. They are accommodating it. They become guides, not simplifiers. They help you find the right form, not eliminate the form altogether. They help you automate the steps, not question why the steps exist.
In a sense, AI becomes a polite assistant in a dysfunctional house. It offers convenience, but does not challenge the structure. If the software environment is already overgrown with menus, permissions, and workflows, AI just learns to work around them. The real transformation is postponed. And the user remains trapped in a system that still demands too much attention.
The Ritual of Certification
Enterprise software has always required training, but in recent years, this need has turned into a mini-economy of its own. Adobe offers certificates for completing courses on Experience Manager. Microsoft provides badges for mastering Teams, SharePoint, and Azure. Salesforce has its own ladder of certifications. What these certificates often reflect is not a mastery of ideas, but an ability to operate within a convoluted toolset.
These badges are rarely about innovation or critical thinking. They are more like licenses to survive. Proof that you can endure the UI. Proof that you know which obscure setting to toggle. In some cases, they even become job requirements. A person is not hired for their insight, but for their ability to click through the enterprise maze without getting lost.
This creates a strange dynamic. Software becomes harder, training becomes longer, and the organization rewards those who can endure the pain. It is not unlike bureaucracy in the old sense. Knowledge of procedure replaces knowledge of purpose. The software becomes a system of rites, and the certificate is your priesthood.
Maintenance as Employment
One consequence of this trend is the proliferation of roles whose primary function is to maintain or mediate these systems. Support desks, admin teams, digital operations specialists; entire job families now exist to handle the friction that enterprise software creates. They are not building value. They are managing complexity.
David Graeber famously called this phenomenon “bullshit jobs.” These are jobs that exist not because the work is necessary, but because the system has made it necessary. In the context of enterprise software, this means jobs that revolve around provisioning access, troubleshooting VPN issues, resetting passwords, approving user flows, or managing configurations that probably shouldn’t exist in the first place.
The problem is not the people. It is the system. In a better environment, those same individuals could be solving real problems, helping teams create, analyze, or communicate more effectively. Instead, they are caught in the logic of upkeep. Their labor is real, but its purpose is circular.
The Real Cost of Complexity
The cost of these systems is not just monetary. It is cultural. Complexity breeds dependence. It trains users to defer, to avoid experimentation, and to fear change. When tools are hard to use, people stop asking if there’s a better way. They adapt, even when it hurts. They learn the script and stop questioning the play.
In this way, enterprise software becomes a kind of invisible authority. Not through surveillance or coercion, but through sheer inertia. The difficulty of the system becomes a reason not to think differently. And this mental habit seeps into teams, meetings, and decisions. Innovation becomes boxed in by tool limitations.
Even the language starts to shift. People no longer talk about what they want to do. They talk about what the system allows. They stop designing solutions and start designing workarounds. And the organization, as a whole, forgets what clarity felt like.
Quiet Signs of Change
Yet, despite this bleak picture, something is starting to shift. The frustration is growing louder. Users are no longer content to be trained endlessly just to use a content editor or a calendar tool. Designers and developers are paying more attention to experience. Startups are launching lighter, simpler alternatives that challenge the giants. Even large enterprises are beginning to experiment with no-code platforms, headless CMSs, and identity-driven access.
Zero Trust is gaining traction. More tools are decoupling security from network location. Mobile-first workflows are finally being respected. And AI, in some cases, is being used to truly reduce steps, not just mask them. The dream is not dead. But it is fragile.
The real breakthrough will come not from more intelligence, but from more respect. Respect for the user’s time. Respect for their attention. Respect for the idea that tools should fit into our lives, not consume them. That simplicity is not childish, but deeply mature.
Returning to the Human
It is strange to think how far we have drifted from the promise of technology. Computers were meant to make things easier. Software was supposed to extend our abilities, not our burdens. And yet, in the corporate world, the dominant feeling is often fatigue. Not from the work itself, but from the systems we are forced to use to get to the work.
When you need a VPN just to correct a typo. When you need a certificate to click the right button. When AI becomes the workaround, not the solution. These are signs that something is broken. Not because of bad intentions, but because of accumulated assumptions that were never questioned.
We need to ask better questions again. What is this tool for? Who is it serving? Can a child understand it? Can a new hire feel empowered, not intimidated? These are not technical questions. They are human questions.
And perhaps that is where hope lies. Not in the next feature or the next platform, but in the return to clarity. In remembering that technology should be a window, not a wall. That work should be meaningful, not maze-like. That the best systems are not the ones that certify us, but the ones that quietly disappear when we no longer need them.
Image by Andrew Martin
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