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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