A remote work prognosticator predicts what’s next


Editor’s Note: Each week Maynard Webb, former CEO of LiveOps and the former COO of eBay, will offer candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at [email protected]

Q. Nearly 10 years ago you wrote a book about leveraging technology and working from wherever. That’s pretty much happened because of the coronavirus. What will work look like when it’s over? 

-Founder of an early-stage company

Dear Founder, 

I can’t believe that we were talking about the future of work 10 years ago. We knew that technology and behaviors were changing in a way that put employees in charge of their own destiny instead of having a company own their destiny, which is how it was when I started my career. Personal empowerment was getting stronger through the past decade. Then the pandemic happened and put everything on steroids. As a result, we have seen more change to the ways we work more quickly than ever before. 

While we used to have to move to a new geography for a job, now people can live anywhere. A confluence of events and progressions in technology have made all of this a reality. We have all figured out how to make remote working work. And we are enjoying the benefits of wasting less time commuting and gaining more time to spend in ways we choose. 

As we all learned in 2020, it’s hard to perfectly predict what will happen but I am sure we will not be snapping back to the workplace of before. That has been changed forever. Employers and employees now know that the ability to work from wherever is real. Furthermore, companies have adjusted on the fly and will continue to as they seek out new approaches and practices that are better suited to today’s world.

Looking ahead I believe we will see:

  • Companies blend in way more flexibility. Employees will value flexibility and expect employers to honor it far more than they have done historically. For employers this opened up more talent pools that they can source workers from—that’s an incredible advance. 
  • It’s not going to be either/or—either you go to the office or you work from home. It’s going to be totally different. Companies and people should feel their way into it what works and what people want. People are leaving the cities in droves buying houses in the suburbs as kids are being home schooled. Homes that were once satisfying are less so when with everyone crammed in the same space. Our cities and towns will change as people can choose to live where they want—near family or by the beach or in the mountains, rather than having priority number one be living close to the office. Many people no longer have to choose between having a great job and living where they desire. 
  • Business travel will forever be changed. We all know it’s not necessary to fly across the country or the world for a meeting. I have found it easier to get to top executives when meeting remotely because it’s less of an ask on people’s time when they don’t have to travel for meetings. 
  • When we can get back to seeing people safely, we will return to lots of in-person time. That is not something that will ever vanish. There is a certain amount of creativity unleashed and energy unlocked that happens when people are all in room. When we can do that without fear again it will be amazing and more appreciated than ever. 


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