A birthday cake with a number 2 number 5 candles

25 years ago this month, I moved to Vancouver for love. That meant leaving my graduate-school program and associated work opportunities on the other side of the continent, and the other side of a national border.

I needed some kind of income to keep me afloat in my new city, so I got in touch with a tech author for whom I had previously done a little bit of research. He hired me to help him flesh out an idea for a digital governance research program, and just a few months later, I put my graduate research on hold to become a full-time research director for his Toronto-based company.

That was the beginning of my life as a mostly remote worker. But my experience of remote work in 2023 is nothing like what it was in 1998. Some of that is due to the skills and mindset I’ve developed as a remote worker, but a lot is due to all the ways the world changed in the past 25 years!

Technological innovation is a big part of how remote work has changed over the past two and a half decades, but it’s by no means the whole story. Here are the 25 biggest changes to remote work over the course of my many years working from home (and various coffee shops!)

  1. Mobile phones got good. Once phone signals became clean and stable, I could work remotely and take calls without having to disclose that I’d stepped away from my desk—or even out of the house!—during a remote work day.
  2. MP3s gave work a soundtrack. Reaching the end of a CD used to interrupt my work focus—until MP3s arrived, and it became possible to curate an all-day playlist.
  3. Email became a personal archive. I couldn’t tell you a whole lot of detail about my first decade of remote work, but I can tell you every single thing I’ve done since 2006—which is when I got my first Gmail address, and started holding onto all my emails, forever.
  4. Social media created a virtual water cooler. Remote work was a lot lonelier before the advent of Twitter and Facebook, which kept me company during the day and helped me make new friends offline.
  5. Travel got tricky. In my first remote job I spent one week every month or two in another city, back when air travel was relatively simple; that got a lot more complicated and exhausting in the post-9/11 era of high-security airports.
  6. Skype looped me in. From the era of Skype and WebEx to the current norm of Zoom and Teams, video conferencing changed the nature of remote work by making it possible to see my colleagues, or to talk with a whole group at once.
  7. Offshoring made virtual normal. Once it became common for companies to contract offshore programmers, call centers and other services, it was a lot easier for clients to roll with hiring remote helpers closer to home.
  8. Wifi got fast. Once wifi got fast enough to compete with our house-wide Ethernet, I could move from desk to sofa to bed throughout the workday, and the sheer variety of positions was better for my back than any one ergonomic desk ever could be.
  9. LinkedIn jumpstarted networking. In my early days of meeting remote colleagues, people were weirded out if you’d googled them for some background context; then LinkedIn made it totally normal to show up at a meeting with the backstory already filled in.
  10. Cafés got wifi. Once coffee shops sprouted wifi, working remotely could get me out into my community, instead of staying locked in the home office.
  11. Homeschooling took off. The rise of homeschooling not only gave me (and many other parents) an option if school didn’t work for our kids; it also turned out to be a great way to meet other parents who had turned to remote work as a way of balancing career and family.
  12. Yelp pinpointed co-working spots. In its heyday, the business review site rocked my world by suddenly making it easy to find restaurants and coffee shops with wifi.
  13. Real estate got pricey. It was a lot easier to work from home in the olden days, when even a young couple could afford to rent—or even buy!—a home large enough to provide office space.
  14. Laptop batteries got serious. In the days of 2-hour charges, you could only work at a coffee shop if you landed a spot near an outlet; now I can work all day on a single charge.
  15. Leggings became clothing. With the mainstreaming of “athleisure” wear, working from home meant I could spend my day feeling comfortable instead of constricted.
  16. Data went mobile. From the time I got my first Treo in 2005, followed by my first iPhone in 2008, my experience of remote work was transformed by the ability to answer email or conduct a web search anytime and anywhere.
  17. Step counters moved me. I became very sedentary when I returned to remote work a decade ago—until my Fitbit and Apple Watch got me back into the happiness-inducing habit of regular movement and exercise.
  18. Pot became legal. For many years, an end-of-day toke served as my way of punctuating the remote-work day and shifting into home mode.
  19. YouTube taught us everything. As a parent, I hate YouTube with the heat of a thousand suns, but as a remote worker, it helped me learn key skills—like the knitting habit that replaced my end-of-day pot smoking.
  20. Starbucks got protein boxes. Once coffee shops started serving things other than cookies and pastries, it became possible to camp all day at a coffee shop and stay in your work groove.
  21. Slack gave me colleagues. When Slack became widespread, I found a community of remote colleagues I could stay in touch with throughout the day—in addition to staying in touch with my clients.
  22. TV went golden. As someone who relies on TV to get my work day underway, or to stay focused when my energy lags, the rise of Netflix, streaming and just generally good TV has helped make my remote working life a lot more enjoyable and productive.
  23. Google Docs enabled real-time collaboration. Collaborating with remote colleagues was a nightmare in the era when we actually sent document edits back and forth via email; Google Docs made those changes visible in real time.
  24. Tethering took off. I spent a lot of years shaking my fist at unreliable café wifi until mobile phone tethering became a truly dependable alternative.
  25. Covid made remote mainstream. When offices closed down at the beginning of Covid, remote work changed from niche lifestyle to a new kind of normal. Only the advent of the smartphone rivals Covid for sheer impact on the experience of remote work.

The next 25 years

When I speak about the future of work, I often conclude by reminding people that we are still in the early days of figuring out what a world of hybrid work is going to look like. When I look back at how much remote work has changed in my own 25 years of experience, I get excited about all the improvements that still lie ahead.

And once again, technological innovation is not going to be the whole story.  So much depends on how organizations integrate hybrid and on-site employees; on how our businesses and community organizations adapt to support remote and hybrid workers; and on how we, as individuals, shape our own working lives.

What do you want hybrid work to look like, 25 years from now?

This post was originally featured in the Thrive at Work newsletter. Subscribe here to be the first to receive updates and insights on the new workplace.