Technology

Alternate Steves: Work From Home

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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)

I wrote earlier about the idea of thinking about my different choices in the past, and how my life may have gone if economic, political, and technical trends had been different. I’m using this idea to explore how work from home may have become prominent well before COVID, with a Steve-that-could have been as a viewpoint.

Work from home has been around longer than many people realize (indeed I was in a pilot in 2005 to do two days at home a week). But what could have happened to make it a real thing much earlier? Let’s check in on an Alternate Steve in a world where Work From Home became a big thing in the 90s.

One thing that makes me feel old in 2025 is how many people who don’t get that working from home wasn’t normal at one point. OK, I’m not exactly young and it’s been “a thing” for 30 years, but I remember. Of course I was also there when things changed, and as dull as “we worked from home more” sounds, it was pretty wild when it became normal.

OK, so flash back to the very early 90s. I just graduated from college, failed to get into graduate school, and was debating how to pursue my coveted academic career. A friend of mine gave me some of the best advice they’d given me by taking me aside, telling me I was being stupid, and to take a year to get an actual job. I could still live and work near campus, I might take courses, but seriously, he suggested I take a break.

So I actually sat down, thought it over, and realized I had a solution – temping.

Temping made pretty good money in the 90s if you had skills with computers and clerical works, and I was a huge nerd who’d just graduated college. I typed fast, knew how things worked, and was game for anything, so I went to a temp agency and a week later started a six month assignment to cover someone on maternity leave, while getting paid the most I ever had been.

(It also helped that me and some of my fellow graduates got a place with a bunch of tiny “bedrooms” and low rent.)

One great thing about temping is that it gives you opportunities to show off and find new things to do. People don’t want to ditch a temp that learns things and it’s not hard to become very vital – you fill in gaps other people weren’t. Around about 1991 or so the start of the Work From Home trend started, and I found myself a gap to fill.

The early 90s were a strange time after the equally strange 80s. There was cynicism from the economic ups and downs of the 80s mixed in with remaining go-go enthusiasm. We had more and more prominent technologies like PCs and (then comical-looking) mobile phones. There was business-worship as seen by books by folks like Iococa. That was all you needed – ironically – for Work from Home to take off.

Companies doing Work From Home got attention in some business mags, spawning what was a small trend. You could save money and not need as much space with work from home! New technologies made it easier! You weren’t limited by geography! You had a competitive advantage! It seems the more it got talked about, the more people tried it.

Also for some reason almost every owner or C-level expert of those companies was some dude with feathered blonde hair.

I was intrigued because of the technology, but had to admit the cultural element was sort of a good laugh. The same feather-haired interchangeable guy might say how he saved money one interview, and talk about Family Values Of Dad Being Home the next. Yes it was hype. Yes, none of the companies I heard of survived past 2000. But it got everyone thinking then doing, and I was intrigued because this was an entire realignment of work and culture.

I liked a challenge I could have an impact, and it was like a puzzle to solve.

So in my temp assignment I decided to “help” with a work from home project. Oh, not me, I had to be in the office (for now)! But other people like execs and my manager and the senior artist. I knew tech, I knew admin, I could help them.

That turned my six month contract into eighteen, and by that time the writing was on the wall – Work From Home went from fad to trend. So with a fleshed-out resume and a sales pitch, I got myself hired at a consulting company that helped companies set up Work From Home. My boss also didn’t have the hair I’d come to be suspicious of – he kinda looked like Oliver Hardy.

Honestly it was wild. I moved to Chicago (along with one of my roommates and a friend looking for a change), and started helping people not have to travel to Chicago. Which was weird, especially considering where I lived in Chicago, but folks wanted our help.

And that meant I traveled everywhere. I met people, coached them, set stuff up, showed them cool things. I did not work from home as much as most of my clients, but I had fun. I didn’t work from home as much as the clients – hell, I usually did a kind of three day/half-day thing. But my hypocrisy aside, it was an adventure.

It was great. It was wonderful. There’s plenty we’re used to now but back then the Work From Home trend had magic:

  • Business Cybernetics got a minor revival in discussing how to organize offices and time. That’s one of the reason you saw “mail vans” picking up company correspondence before email got even bigger.
  • “Work From Home PCs” reshaped some of the market. Light enough to carry (but not a laptop), powerful enough to run basic office software. There was some real precise engineering there.
  • Time of work changed. 9 to 5 had been long dying or dead anyway, but Work From Home really shifted people’s schedules around.
  • Phone companies made bank and were ready to “set your home up for work” and of course charge your employer.
  • OfficeStar actually started in the 90s with their famous Supply Trucks that you see to this day. SNL did MULTIPLE skits about the Supply Trucks being the Home Bureaucrat’s equivalent of the Ice Cream Truck. But hey you need your pens and paper pads.
  • Kinkos created their newly branded Office Centers. These were really just Kinkos, but they had supplies, desks, etc. I don’t think they could have acquired those other companies without this success.
  • Bragging about work from home and competitive advantage was The Thing for various C-levels trying to impress people.

That was the obvious stuff. What I don’t think got or gets discussed enough is how much things changed outside of work. I watched public transport schedules shift and questions of funding come up. Office real estate declined in value, so people moved back to cities. There was a small panic in the early 2000s about the effect on construction companies. None of this was as radical as breathless news made it sound, but it added up.

And I wonder what might happen if it hadn’t? A few feather-haired guys in mags might never have gotten interviewed then what? We keep hauling an hour into work each day?

This is where I’d talk about how things ended, but it didn’t – but what did end was the Work From Home consulting company. I stuck with my employer for a decade, but past a certain point everyone who needs help from people like you got it, and more importantly, companies knew how to do it themselves.

I knew it was over at some point around year nine. We all did. When I got an offer to be a Technology Manager for the city, I don’t even know if my boss and I said out loud what was going on. That was over twenty years ago. Funny, I really only worked at two paces in my career, and the city is as big on Work from Home as anyone.

Now? Now Work From Home is so normal. It’s expected. Almost anyone I know with an office or creative type job is only in the office like two or three days. Being in the office full time gets you more money (you’d be surprised how many states have laws on that). It’s all so normal.

But I remember those wild times, getting off the bus in Chicago with a backpack full of paperwork, or me and Charlie parking the van so we could unload computers. I remember having to fly out to New York on short notice because of a new client engagement. I remember something new every day in our little world of the Work From Home People. I remember offices getting more and more uninhabited.

It’s all standard now. And I think that’s good, if a bit less exciting than when I was young.

Steven Savage

Different Times, Different Mes

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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)

One of my obsessions for while has been to ask what the world could be like if our combination of technology and culture had taken different directions. In 2024 a friend said that it felt like nothing new or really good had been invented in 15 years, especially internet-wise. That has had me reviewing all the different choices and events that have led us to where we are now from a technical-cultural standpoint, and how it might be better.

So I started reflecting and asking what did I want to see? Where could things have gone different – and gone better?

That led me to some speculations of course, such as if there had been more social media regulation, or if certain technologies had becom popular at different times. But know what really got interesting?

Asking who I’d be if things had been different in the worlds of technology and culture.

This started by me imagining a world where the internet B.S. of today had never arrived – something I may write about. I tried to imagine myself in a world with different technologies, a world more environmentally conscious, a world where we weren’t doomscrolling. It was essentially writing speculative fiction in my head, but the mental exercise hit hard.

I can see how in some cases I’d have been the exact same kind of person, just using different technologies. I could see how I’d also be different a few twists and turns in the economy and I’d never have become a programmer. I could see how I’d also be the same- because I in many cases I’d still be a Project Manager, even in a semi-Solarpunk, not-quite-utopia I imagined.

Relating a possible future to a possible me, helped me grasp such trends and potentials much better.

This led me to another speculation – I began asking about what my life would be like in the case of particular technological divergences. That has proven to be a great way to understand our world the way it is and what it could be?

What if Work from Home had come early (and believe me it was seeded earlier than you think)? Or phone companies had seen things like AOL and come up with competition? What about prefab homes returning? What would it take to have technologies be different, culture be different, and what would I experience?

I find that idea of imagining “being there” really helped me understand impacts – and unintended impacts. It also helped me understand a few things about myself – such as my ability to get enthused about cool stuff even if it is kind of dumb.

I may actually write some of these ideas up and make a series of it. What can I speculate en and learn from using my knowledge of technology and history? What can I share – and what can we discuss – about possible worlds to understand this one.

But if I write it or not, I want you give it a shot. Ask about “historical divergences” you can imagine, and who you’d be if they happened. Especially if it’s about a better world – since you might be surprised at who you are even in a more ideal place and time.

Steven Savage

But What If It’s Not Worth Doing?

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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)

OK this isn’t another post on AI exactly. I get it, there’s a lot of talk of AI – hell, I talk about it a lot, usually whenever Ed Zitron goes on a tear or my friends in tech (IE all my friends) discuss it. If I was friends with Ed Zitron, who knows what I’d write.

The funny thing about AI is that it’s about automation. Yes it’s complex. Yes it’s controversial. Yes, it lets you generate pictures of Jesus as a Canadian Mountie (Dudley Do-Unto-Others?). But it’s automation at the end of the day. It’s no different than a clock or a pneumatic delivery system.

And, referencing a conversation I had with friends, when you automate something on the job or at home, let’s ask a question – should you have been doing it anyway?

First, if you get something you have to automate, should it be assigned to you? If something really isn’t part of your portfolio of work, maybe someone else should do it. Yes, this includes things like home tasks and that includes the shelves you have not and almost certainly will not put up.

A painful reality I’ve come to realize is that many people take on tasks someone else can do, and often do better. However due to whatever reason it drifts up to them and of course they stick with it. Worse, the really good people often would be better at it, and maybe even have more time and hurt themselves less.

A need to automate something often says “I don’t need to do it and I may be bad at it” and the task should move up or down or somewhere else. I’m not saying automate, it, I’m saying reassign it – to someone that may automate it anyway, but still.

Secondly, and more importantly, if you have a task that can be automated it’s time to ask if anyone should be doing it period.

Anything really important needs a person, a moral authority to make a decision. You have both the decision making skills and the ethical ability to make the right decision. Automation certainly doesn’t have the ethical element, and if it doesn’t need your decision making skills . . . why are you or anyone doing it.

The task might be unnecessary. It could – and trust me I see this a lot – be the result of other automatic generation or other bad choices. It may be a signoff no one needs to sign off on, an automatic update you don’t need to be updated on, or who knows what else. I honestly think a lot of work is generated by other automatic processes and choices that could just bypass people anyway.

But there’s also the chance the task is unneeded, shouldn’t exist, or really a bad idea. Look if the task is assigned to you, a competent individual with good morals, and you want to automate it maybe it just should never have existed. Much as good Agile methods are about making sure you don’t do unneeded work, process is the same.

Whenever something has to be automated, it’s a good time to ask “why did it come to me anyway?” Because the answer may save you time automating, instead letting you hand it off, change how things work, or just ignore it.

And that’s not just AI. That’s anything.

Steven Savage