How IT Stopped Being Boring

The journey from tucked in grey shirts to hoodies

Simon Pitt
Mar 25 · 9 min read
They call themselves the digital team, but they’re just posting pictures of cats to each other, no one seems to have the sides off their computers anymore. Photo by Zane Lee on Unsplash

e’s short, grey hair, mustache, balding, wearing a short-sleeved checked shirt. In his office (which has no windows) is an O’Reilly XSLT book with a Heron on the front. Let’s call him Gordon (the man with the checked shirt, that is, not the Heron).

A few things you should know about Gordon:

  1. He loves comments in his VBScript files. And if you don’t put comments in the right format, that script will be deleted.
  2. You cannot write any code until you know about networking. And Microsoft installer packages. And Configuration Manager. He’ll start by teaching you about Windows NT 4.0, even though that came out in 1996.
  3. It’s his way or the highway. What the sysadmin can give, the sysadmin can taketh away. He has that on a magnet on the fridge. You’re welcome to put your lunch in the fridge, but if it’s there on Friday at 3 pm it will be thrown out. He treats the fridge the same way he treats temp folders on his servers.
  4. You will not be granted admin rights on your computer.
You may not borrow this mug. Photo by Amazon

Gordon’s not a developer, although he writes scripts and codes websites for the company. He’s very strict about them. The text must be 10pt, Times New Roman, black. These websites aren’t for fun, they are business tools, and should be treated as such.

I’ve been writing websites for, oh jeez, over twenty years now. But I’ve worked professionally in some variety of technology for thirteen of those years. By professionally, I mean going into an office where other people are working (or, these days, logging onto a computer in the corner of my room), and then doing software-type stuff in exchange for money.

The going-into-the-office-thing changes the nature of the job. It’s working at scale and with other people, that’s the problem. Writing code, or making a computer do your bidding is easy when there’s one of you and one computer. It’s a fair fight. At work, you start to get out-numbered. In an I.T. department, you might be involved with thousands, or tens of thousands of computers. If you work on a public app, millions of computers might run it. Over the years, hundreds of people could read or edit the code you write. Those other people will add and delete lines and tut about whether you used tabs or spaces. Someone needs to set rules for everyone to play by.

When I first started being paid to do things on computers, you built websites with jQuery (if you even needed dynamic behavior). Gordon is dismissive of jQuery or, in fact, any attempt to add interactivity into web pages. “Being flashy,” he calls it. He had been here where computers were first introduced into the company, had installed the first networks, and understood the technology from the Ethernet cable all the way up. He doesn’t have time for these happy-come-lately people who fiddle around with odds and ends on the top. Especially if that fiddling results in needless extra bandwidth being consumed on his ethernet cables sending information that doesn’t enhance the page. That isn’t proper I.T.

Some best practice jQuery. Photo by Skillcrush

I.T. is about knowledge and rules. You have to have rules because without rules the carefully constructed systems fall apart. So, Gordon keeps a list of applications that are allowed on the network. If you want to use an application not on the list you have to email Gordon, explaining why you want to use it. He will purchase a copy, assess it for safety, and, if it passes, install it onto your machine. And yes, you have to do that for every version of the application. No, it doesn’t matter that Photoshop 6 has been approved, you have to make a separate request for Photoshop 7. So what if it’s written by a massive company? Gordon still has to perform his assessment to make sure Photoshop 7 won’t introduce any viruses onto the network. His network, his rules. The sysadmin giveth and the sysadmin taketh away.

But something strange starts to happen.

Gordon doesn’t use Post-Its. He writes on foolscap. Photo by Daria Nepriakhina/Unsplash

There’s this media department. Gordon doesn’t think much of them, but they’ve taken over responsibility for the company website and they want a load of servers and software. In fact, they want software that Gordon hasn’t approved. Obviously, Gordon says no, but senior management overrides him.

All this media department does is make flashy websites that, let’s be honest, are much slower to load than the ones Gordon made and have a much lower information density. On Gordon’s website, in size 10pt Times New Roman, you could fit four or five hundred words without scrolling. These new sites are all margins and padding and white space. And that is to say nothing of the way the team works. There are post-its everywhere. And every morning they all stand in a circle together and pass a stuffed monkey around. A stuffed monkey!

People say that some of the tools Gordon provided (tools, dammit, not apps) are hard to use, but they’re business tools. People should learn to use them by reading the manual or going on a course if necessary. It’s their job. If you think an airplane is hard to fly then you probably shouldn’t be in the cockpit to begin with. People are paid to learn these things. They’re not paid to scroll through pages with fancy fonts and big margins.

I’ve watched this transition happen gradually and then all at once. It’s remarkable how different things have become. People have left, new people have joined, senior management has changed and budgets have been reallocated. We’re now in a hybrid world. In some parts, there are rigid rules, limitations, and processes. Change requests, reviews, and approvals. And then there’s the world of development. Of scrum, kanban, agile and UX. That’s not to say the new world doesn’t have process — they don’t pass that monkey around for fun — but it’s a different type of process. Less bureaucratic. More cult-like.

Even now, the two worlds co-exist, in a semi-cordial half-peace. It would be untrue to say that we have transitioned from a world of big mainframes and I.T. systems, into a new, user-friendly digital world. Just go into any large company and look at SAP, Oracle Business Suite, or any number of “business” applications they still have.

There’s an update a year to eighteen months away that will change it, I hear. Photo from Wikipedia.

I.T. systems used to require highly trained operators. These were expensive, specialist pieces of equipment that you couldn’t just put anyone in front of. It required a set of skills to be an I.T. Operator. That was a special job, rather than something everyone did as part of another job.

Now, software is commoditized. The ability to use a computer is no longer a specialized, technical skill, like the ability to fly a plane, but a standard expectation of people in the workplace, like being able to read and write. At one point there would have been a typing pool of secretaries who were professional typists. Viewed under one lens, that career has died out: there are no more typists. Viewed another way: we’re all typists now.

Even if you have I.T. rules, it’s not like you can enforce them anyway. Users install applications without admin rights. You couldn’t possibly keep a list of which websites are safe to visit and which aren’t (although some companies try). Having regulations on what webpages you can go to on your computer or smartphone is as strange as having a rule for what words you’re allowed to write with your work pen. And that’s ignoring the fact people use their home computers and personal email addresses for work. And not just any old people. Famously, people with access to the most sensitive information in the country access it through personal email servers and Whatsapp.

This is just how things work now.

But then a ransomware attack hits thousands of computers and costs millions of pounds. All those user stories and post-its can’t save you now, no matter how easy to use your website is.

The point here is not that Gordon is wrong, a silly old relic of a bygone era. Nor is the point that Gordon was right and the script kiddies have taken over the networks. Rather, I.T. has changed. To the extent that it’s a different world and a new set of challenges. The cat is out of the bag, and if you were hired to hold a bag and make sure the cat doesn’t get out, those skills don’t prepare you for cat ownership.

Not going back in the bag. Now he just wants Cheezburger. Photo by Manja Vitolic/Unsplash

We’ve moved from a scarcity of code to an abundance of code. And that requires different skills. I have a pet theory that humans aren’t very good at dealing with abundance. Perhaps this is due to some remnant of primordial hunter-gather instinct, that’s my cod-anthropological suggestion. When there’s a scarcity we hunt for more, ration, innovate and optimize. But when there’s a superabundance we… what? Wade? Panic? Waste? I think the solution to dealing with too much stuff is less instinctual to us. I don’t know if this gets us anywhere, but it’s fun to come up with a unified theory of obesity, climate change, and node modules.

I have a soft spot for Gordon. There is a purity to his approach even if it can be immensely frustrating to work with him. He’s out of time, like someone trying to sell a trebuchet to soldiers during the Second World War.

When he started, it wasn’t just reasonable to lock everything down, it was vital. And the rest of the industry was just the same. Now, if your company website looks like it’s from 1998, you won’t just look old-fashioned, you won’t be able to do business. Out with the grey shirts and in with the pool tables and slides.

When these worlds collide, it’s frustrating for everyone involved. Two groups of people speaking different languages, both able to find justifications for their approaches. In CIO magazines (such things do exist, it turns out) people refer to this as twin-track I.T. For a long time, I’ve assumed that gradually everything would transition to the new, modern, slick I.T. world of cloud services, but actually, I’m starting to think that will never happen. Technology is expensive. It’s, like, really expensive. And difficult, and risky, and inefficient. For every project that goes well, ten fail, and at a certain point, the Director of Finance is going to stop writing those checks.

And so we’re left with a mix of systems. With Gordon’s 10pt Times New Roman pages, butting up against responsive react apps. And that’s fine, actually. Technology has changed and will continue to do so. We are, perhaps, destined now to always exist in a transitional state, with some of our systems in the old world and some in the new world.

As horrible as Gordon’s pages are, he was right about one thing: they do (more or less) still work. And load very quickly over our new fast internet. Even if they’re designed for a 640px screen an impeccably formatted comment in the source says they were last updated in 2008.


Everything connected with Tech & Code

Simon Pitt

Written by

Media techie, developer, product manager, software person and web-stuff doer. Head of Corporate Digital at BBC, but views my own. More at



Everything connected with Tech & Code

Simon Pitt

Written by

Media techie, developer, product manager, software person and web-stuff doer. Head of Corporate Digital at BBC, but views my own. More at



Everything connected with Tech & Code

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store