Top Work Trends For 2020 And Beyond

Steve Strauss

Part 2 of the “2020 Strategies and Insights for Midsize Companies” series

Register for the Webinar of the 6 trends that every midsize business needs to knowAlthough I don’t practice law anymore (I came to my senses long ago, thank you very much!), I started out back in the day working for a big firm in the big city. I also had a big commute. So after about a year, I proposed that I be allowed to, as we called it back then, “tele-commute.”

Now, of course, remote working is all the rage, but it wasn’t then. So, as it turns out, I was a bit of a forerunner in that regard.

Similarly, I have been writing my online small business column for USA TODAY for about 20 years and have had a podcast for almost a decade, so fortunes have put me at the forefront of a lot of business trends. That is why I was very happy when SAP asked me to write a blog on the top trends I see for business generally, and small business specifically, for 2020 and beyond.

Indeed, tracking trends in business is something that has become a bit of a cottage industry for me, and mostly (although far from totally) I have been right.

And I mention this, not out of ego (well, maybe a little bit) but more because the trends that are coming down the pike will affect a business near you or, more likely, yours. For example, one thing you will see throughout this blog is that the very nature of work is changing; younger workers expect more out of work and their employers.

Are you ready?

Are you ready for flextime and remote work and BYO devices and gig workers and all the rest? Because I can tell you, big businesses are, and as a result, they will snag the best and the brightest if you don’t keep up with these changes and pivot accordingly.

OK, so with that disclaimer out of the way, here is my take on the top trends coming down the pike to a business near you:

The changing of the guard is going to radically change business

I don’t use the word “radically” lightly or often, but it is appropriate here.

For years, generations actually, baby boomers ruled the land. They were – by far – the largest generation ever in the history of the United States, and their effect was seen and felt everywhere: from music to culture to, yes, business.

Woodstock drowned out Don Draper.

But no longer. This year, 2019, saw a changing of the demographic guard – there are now 73 million millennials vs. 72 million baby boomers. Bye-bye, boomer dominance.

In business, the effect is profound.

For starters, millennials do business very differently,

  • As opposed to boomerpreneurs, millennials adopt new technologies easily and quickly.
  • Millennials are generally more comfortable with doing business remotely and virtually.

Similarly, millennial employees expect to not only be able to work virtually and flexibly, but also, they expect that they will be given the tools and freedom by their employer to do so.

So yes, of course, the 9 to 5 era is fading away, and the one of flexible work is just getting started.

Remote work is the future of work

Indeed, whereas work used to be a place where you go, now it is something that you do. That psychological shift is not insignificant because it means that, among other things, traditional ideas of teamwork – being something both physical and tangible – are less obvious and more challenging.

As Stephane Kasriel, the CEO of the remote working platform UpWork, explains,

“At the World Economic Forum, we call this the Fourth Industrial Revolution. The first two revolutions were about mass production. The third turned us into knowledge workers bound in offices. This revolution is about breaking free of geography. It is being driven by the technology to help us do that.

 “People know that place-bound work no longer makes sense. Collaboration technologies, like Microsoft’s Office 365, Slack, and Google Hangouts, along with the ability to find work online via sites like ours, make it possible to work anywhere.”

The good news is that companies are making remote work easier, more productive, and more possible.

It’s all about freedom

This confluence – of millennials, technology, and attitudes – means that your staff will increasingly expect to work when, where, and how they want. They will expect to be remote and to be given the tools and freedom to work this way.

Much of this has to do with the fact that younger workers are increasingly choosing lifestyle over work. They don’t see the work/life balance problem that many older and female workers do; work/play/life is all the same thing for them.

And this also will result in…

The gig economy winning

Karl Marx famously said, “Workers of the world, unite!” These days, a more appropriate phrase may be, “Workers of the world, disintegrate!”

According to a recent survey by Bankrate, nearly 40% of all Americans now do their own thing and have a side hustle. Of course, a side hustle can be almost anything, be it driving for Lyft or selling on Etsy, but whatever the case, the advent of the gig economy means that side hustles are not unusual.

And get this: According to one survey I just saw, the majority of the U.S. workforce will freelance to some degree by 2027. (Of course, the youngest workforce generation is leading the way, with almost half of millennials freelancing already.)

Cities are starting to vie for talent, not for businesses

For ages, cities offered tax breaks and other incentives to try to get employers to relocate to their area.

Enter the Amazon HQ2 debacle.

The HQ2 race only exemplified what an old, outdated strategy trying to lure corporations to a city is.

Instead, what we are increasingly seeing is that cities like Portland, Austin, and the like are highlighting their towns as a great lifestyle choice for today’s top talent, emphasizing things like affordability, nightlife, and sustainability.

Just look at what the mayor of San Jose, California, wrote in his op-ed for the Wall Street Journal, “Why I’m Not Bidding for Amazon’s HQ.” Mayor Liccardo explained:

“Luring new corporate offices like those of Amazon to cities would only perpetuate an unsustainable cycle. The talent war of the future will no longer be between companies, it will be between cities.

 “As technology untethers society, and remote work becomes the norm, people will live in the cities of their choosing, rather than the ones that are nearest to where they work. The cities of their choosing will have a certain “vibe” by offering attractive living options in tech-friendly environments.”

Bottom line: The key to the future of work is lifestyle

The upshot of all of this is that what people are increasingly looking for in this technologically driven society is something more. More freedom, better work, more connections, better choices.

And they are using the digital tools that companies like SAP are creating to forge something altogether new and surprisingly analog: A better, more connected way of working with each other, with employees, with employers, and with customers.

See IDC’s list of top trends for small and midsize businesses in the 2020s. Download the IDC infographic, sponsored by SAP, “The Roaring 2020s – Six Trends Midsize Companies in the Next Decade.” And we invite you to join our upcoming webinar for a deeper dive into each of these trends and what you can do now to take advantage of them. Register for Winning in the 2020s:  Six Trends Every Midsize Company Needs to Know.

Steve Strauss

About Steve Strauss

Steve Strauss is a best-selling author and senior USA TODAY small business columnist whose content and media appearances reach millions. Steve is also an attorney, thought leader, and the author of 17 books, including The Small Business Bible. He can be reached at