Winners & Losers from the Work From Home Trend

On March 13th we were awakened by a text message from my daughter’s superintendent informing us school was closed for the foreseeable future. The stay-at-home orders from the governor weren’t too far behind.

Millions of people all across the country were immediately forced to work from home and become part-time teachers.

Considering there was no planning, scenario analysis, technology buildout or meetings involved, the implementation has been impressive. Millions of workers were thrown into the fire of working from home without warning.

Like all trends caused or sped up by the pandemic, it’s still too early to tell how this one will play out.

We do know a handful of big technology companies — Twitter, Square and Coinbase to name a few — have said employees will have the choice of working from home or the office going forward.

Mark Zuckerberg said 50% of Facebook employees could be working remotely in the next 5-10 years. It’s not surprising tech companies are making this shift but I’m guessing other companies will wait to see what their competitors do.

This shift wasn’t that difficult for me because I’ve been working remotely since 2015. I’ve never done so with my kids at home every day but half of the employees in our firm work remotely so we were set up for this type of situation.

I love the ability to work from anywhere but there are pros and cons.

Let’s run through some winners and losers from this trend that is sure to continue in some form.


Established employees. If you’ve been working for the same company for a number of years, hold a high position in the company or have a lot of responsibilities, this is the perfect situation.

If you’re already an established player in your company, the flexibility you get from the ability to work remotely is huge.

This is especially true if you have kids whose schedules crave flexibility. Setting your own hours and working when you are the most productive is a wonderful perk.

People who live in a high standard of living area. Zuckerberg says Facebook will pay less to people who live in a lower standard of living area but I still think you can come out ahead if you move away from a place like San Francisco to a more affordable city.

Unless you make a boatload of money, it’s simply much harder to save in a high cost of living area. The cost savings from housing and taxes alone are likely enough to offer far more financial flexibility. Your chances of personal financial success are much higher even if you make less money.


Young people and new employees. There are top performers and people in certain professions who can come in on day one and be successful in an entry-level or new remote position. But it requires the right skillset and the right company.

I would not have been mature enough to work from home when I began my career. There’s far too much I would have missed out on in the learning process.

Being around your colleagues helps you understand organizational culture, intrapersonal skills, communication, developing relationships, office politics and how to move up through the ranks.

Plus, when you’re young there’s a lot of stuff you don’t know that you don’t know. You learn a lot just by paying attention and being around others.

Young people are well-suited from a technology perspective to work from home but there’s much more that goes into being successful than simply getting your job done.

Unless you’re supremely confident in your abilities, I would be careful about accepting an entry-level remote position without understanding how it could affect your career trajectory.

Extroverts. One of the reasons I enjoy remote work is because I don’t mind working alone. I’ve always been more of an introvert so being in an office by myself allows me to be more efficient with my time.

But there are downsides to this. You miss out on the camaraderie, work events, lunches and dinners, joking around and the ability to pop into anyone’s office or workspace just to chat.

Many of the most successful people in any organization are good at office politics, selling themselves, talking, and using the power of conversation to get their point across.

This stuff doesn’t work as well on a Zoom call with 15 people in little boxes on your computer screen.

There are going to be companies that overreact to this trend because we are living in such interesting times right now. I’m guessing there are going to be policies implemented that will have to be walked back or changed in the coming years as employees and companies adapt.

It’s still too early to jump to conclusions.

Michael and I discussed many of these issues on the podcast this week:

Further Reading:
The Benefits of Working Remotely

Now here’s what I’ve been reading lately:

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