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What is the Future of Remote Work?

The pandemic ushered in a new era of remote work. And there was a huge disparity between how different companies adapted to the change. In this episode, Rob and Topher dive into their experiences with all types of in person hybrid and remote office settings. they discuss the best settings for managing remote teams, how the sudden shift to remote work has affect how we live, and if we should push for an all-remote future.

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What is the Future of Remote Work?

Monet Davenport:
Welcome to Press the Issue, a podcast for MasterWP, your source for industry insights for WordPress professionals. Get show notes, transcripts, and more information about the [email protected]/presstheissue.

Press The Issue by MasterWP is sponsored by LearnDash. Your...

Monet Davenport:
Welcome to Press the Issue, a podcast for MasterWP, your source for industry insights for WordPress professionals. Get show notes, transcripts, and more information about the [email protected]/presstheissue.

Press The Issue by MasterWP is sponsored by LearnDash. Your expertise makes you money doing what you do, now let it make you money teaching what you do. To create a course with LearnDash, visit

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Monet Davenport:

The pandemic ushered in a new era of remote work. And there was a huge disparity between how different companies adapted to the change. In this episode, Rob and Topher dive into their experiences with all types of in person hybrid and remote office settings. they discuss the best settings for managing remote teams, how the sudden shift to remote work has affect how we live, and if we should push for an all-remote future.

Topher DeRosia:
Hey, Rob.

Rob Howard:
Hey, Topher. How’s it going?

Topher DeRosia:
It’s going great. Today we’re going to talk about the future of remote work, and I have some really good questions for you to kick it right off with.

Rob Howard:
Excellent. We have been doing remote work for a long time, so hopefully I’ll have some good answers for you.

Topher DeRosia:
Yeah, let me ask you that. I’ve been doing it for 12 years now, almost 13. How long have you been remote?

Rob Howard:
So I started freelancing from a home office in 2005, so it’s been a long time. It’s been basically my whole career. I had very few office type jobs early on, so I’ve always by nature enjoyed the home office life, and I’ve even had chances to do the big office thing and chosen not to over the years with different business partnerships and stuff like that. I’ve always liked it, and of course, the world changed very rapidly a couple years ago and work from home became a thing that everybody was doing, whether they were experienced or not, or whether they liked it or not.

Topher DeRosia:
Yeah. I did about 13 years at a desk in an office at some point in my career.

Rob Howard:

Topher DeRosia:
So we all know COVID pushed many into remote work abruptly, and many people individually are finding it to be a better work style. They’re like, “This is better than me at the office.” But I know some corporations are saying now we need to get everybody, get everybody back in the office. What would make a company choose that? Why would they choose not to keep their people remote if they already are because of COVID?

Rob Howard:
So I think there are some benefits obviously, to the company, and I think there are some drawbacks, especially if you are just not used to managing people who are not physically in front of you. So I think that’s the majority of where CEOs and other leaders are saying, “Hey, I don’t feel like we’re as productive. We got to get back to in-person.” I think what they’re saying in large part is, “I can’t tell what you’re doing and it’s harder to manage this group of people because we’re not in the same room together.”

For me, I’ve always been operating and working that way, so it wasn’t really a change. I can get in their heads and be like, “Yeah, that would be hard.” But that was not a change for us, so in a way, the companies who were already remote actually ended up being light years ahead in terms of their management skills because there is a very different management style and set of behaviors and mindsets that you need to manage people who are not in the same room or even in the same city as you.

And then of course, we have companies that manage remote workers who are all over the world in Asia and South America, and Europe and North America. So there’s a lot of different skills and techniques for that.

I think the first people I heard saying it were the JP Morgan, Wall Street folks who were like, “We got to get back into the office and crush it with our investment banking work, and that has to be done in person.”

It reminds me of the movies where everybody is in a room and they’re screaming on their phones and they’re selling stocks, and it’s a mad house atmosphere.

And then you also hear it from Silicon Valley. Twitter and Elon Musk tried to bring people back, then they abandoned that idea, but they’re certainly not the only ones who are doing that. And I think that there definitely has been a push to get workers back in the office who are doing these, quote unquote, knowledge work, office work type jobs.

And I think it’s mostly a question of tradition and surveillance. That would be the two big things that I think are pushing people.

They won’t say that out loud. They’ll say, “Oh, we’re more productive in the office,” but you ask them for data to support that, and that data is minimal if nonexistent.

But I think the idea that a manager should know basically what you’re doing or be able to look at you all the time and check on you is definitely a part of that, and I think that’s an old school idea that obviously, isn’t necessary and isn’t really even good for a lot of employees and a lot of managers, but that’s how people are used to operating so they’re eager to get back to that.

There’s also challenges just around geographical pay structures as well, which I think companies are quietly struggling with. So this question of, “Okay, If we’re in San Francisco and I hire you, you’re going to get paid an outsize salary because of the nature of the housing market and the cost of living in that particular city.”

So if you look at these companies that are based in… [inaudible 00:05:07]

Topher DeRosia:
And then you move to Oklahoma.

Rob Howard:
Yeah. If these companies are based in California, they’re often pegging pretty high salary numbers because they are assuming that that employee needs to rent or buy home in that area. They’re going to be exposed to all these higher cost of living things.

But like you said, you moved to Boise, you moved to Oklahoma, and all of a sudden you might have been getting paid $350,000 at Google, but maybe 50% of that was really a San Francisco location bonus or increase.

So obviously, the companies are struggling to figure out… It’s hard to give somebody a pay decrease when they move. That’s just not good for morale. But they’re also saying, “Well, if we could hire people anywhere, why are we paying exorbitant rates, because based on this peg to this general location?”

Topher DeRosia:
Why do we even have an office in California in San Francisco?

Rob Howard:
Exactly. So obviously, there’s several ways you can go from there, but one of the ways you can go is, “Okay, everybody just has to show up in San Francisco.” And that’s obviously not the only city, but it’s certainly the biggest spot in the tech world where this is happening. But I think you could say the exact same thing about Wall Street and people living within commuting distance of Manhattan and stuff like that.

Topher DeRosia:
One of my previous jobs was at a company called Big Commerce, and they were an everybody in the office place.

I was remote, but out of 800 employees, less than 1% were remote. It was really, really rare. And I would go to the office maybe quarterly and spend a week, and I experienced some people that actually thrive in the office environment. They really did well talking to people face-to face, just get up, walk down the hall, ask them a question, go back to your desk, that sort of thing. And so I can see where there’s room for not remote work, but then again, there are people like me.

So then when COVID hit, they all split up. Of course, everybody went home. And now that it’s over, some people are going back to the office, but certainly not all.

Way more than 1% are staying at home now, because for those people it works better to stay home.

Rob Howard:
I think it’s also a different skill set. So the skill set you described, managing by walking around, it was actually innovative in the ’50s and ’60s, this idea of we should be a community of employees. That’s something that emerged in Silicon Valley in the Hewlett Packard days many decades ago.

And that style is not incorrect, but it is a completely different skill set from what we do, which is managing a remote team. And there’s different tools, there’s different techniques and strategies.

One of the things that I do is even with 20 or so employees, I do a lot of one-to-ones with every employee. And that is a component of a remote management strategy that I think works to get the best parts of the management by walking around system without requiring everybody to be in the same place. And there’s other stuff like that too.

And we’ve even seen just being good at using Slack and other asynchronous tools is a skill set, and we’ll often start working with a client or another organization, and we’ll be like, “Oh my gosh, nobody here at this other organization knows what they’re doing with these tools.”

And you actually see people who get frustrated by asynchronous communication. So they haven’t developed that skill set of communicating effectively via asynch yet, and they’re asking, “Hey, can we just hop in a quick call, or whatever?”

And that’s where you get friction between a team that’s all in on remote work and a team that’s still learning.

That being said, I think for me, the benefits outweigh the negatives by a lot. And I think the biggest benefits really flow to the people who don’t want that 60 plus hour per week work week structure.

So if you have young kids, or if you just have a life that it does not include 60 to 80 hours of office time per week and two hour commutes back and forth into the city, there’s 100 reasons that you might not want that lifestyle. And what remote work does is opens up the opportunity to achieve these higher value career goals or aspirations without necessarily having that requirement to do the brutal commute and the brutal hours in the office, and spend time away from your loved ones, or ignore your physical and mental health in exchange for more time in the office and you’re sleeping under the desk and stuff.

That’s a very common archetype in the Wall Street and Silicon Valley lifestyles, pre-COVID.

I think if you want to do that, more power to you, but I never want to do that regardless of my…

When I was 23 and single, I didn’t want to do that, and now that I have a kid, I don’t want to do that. And it’s like that was never my thing, so I definitely cannot identify with that as a badge of honor. But some people do think that is a power move to work in that way, so they’re certainly welcome to do that, but I think the increased prevalence of remote work opens up more career opportunities for people who don’t want to be, what I would describe as unnecessarily, performatively intense workers.

You want to do good work, but you want to also have a life. And I think working from a home office is conducive to that. Being able to move to a different city that is a better fit for you. It’s not just cost of living, it’s also, “Hey, I actually want to live near my aging parents, and they can’t live in San Francisco. It’s insanely prohibitively expensive, but maybe I moved to the Denver suburbs or I move to New Mexico, or Phoenix or something, and now I have different and better family and social connections in those places.”

Obviously, there’s a lot to unpack there, but I would definitely say that I think the CEOs of the Big Wall Street and Silicon Valley companies probably were overly optimistic about getting people to come back because there’s just a lot of benefits to not having to commute and not having to be physically in a certain chair, in a certain office building.

Even this morning we’re recording this, it’s 10:00 AM my time, and I just finished dropping my son off at school and running errands for an extra hour this morning. That would’ve been impossible if we both had to meet up at a certain office in Denver instead of being in our respective home offices.

Topher DeRosia:
I do have to say, as a developer, some of the most powerful programming I’ve ever done was paired programming, sitting elbow to elbow with another developer and looking at the code together, and there’s a big draw there, but the people I know who do it full time also want to work remote. And so there’s been a bunch of progress made in the last few years for remote paired programming where you don’t have to sit and share a screen. And that’s really exciting. That feeds right into part of the future of remote work.

Rob Howard:
Yeah, that’s awesome.

Topher DeRosia:
I think that’s going to be a huge thing when we work that out.

Rob Howard:
And that’s a good example of the thing where that is clearly a solvable problem like, “Hey, I want to work with Topher to write some code, but we are in different cities.” Obviously, you can figure it out. Using basically the same technology we’re using to do this podcast right now, you could do pair programming or something similar to it.

So that’s the kind of thing where I think earlier in the pandemic, there were a number of people who were just… They would throw their hands up and be like, “Oh, we’re never going to be able to collaborate again.”

But I don’t think that’s panned out in reality. I actually think that thinking about our team and the other remote companies that I know, we’re doing a pretty good job. We’re still creating cool stuff.

I really don’t think that the myth of the spark of creativity that can only happen in a room together has actually been demonstrated to be real over the last few years. And obviously, I can’t prove that an invention that would’ve happened failed to happen. That’s a falsifiable statement. But I haven’t noticed in the teams that we’ve worked with that are, let’s say above average in terms of how good their remote work. They seem to be enjoying life more and collaborating just as much as they would’ve in an office, in my view at least.

Topher DeRosia:
All right. So my next question, we both know many companies that do remote only, and it’s great for them and us, but is it so inherently better that we should work to change society to work that way, to make companies who are perfectly happy in office switch? Do we have any responsibility there? And the specific example I’m thinking of is if everybody worked from home, there’d be a ton less gas burned.

Rob Howard:

Topher DeRosia:
You know what I mean?

Rob Howard:

Topher DeRosia:
That would be great for the environment.

Rob Howard:
Yeah, that’s definitely true.

And I also think it would change the way that we build housing and the way that we choose where we live, which could have positive or negative effects environmentally, but I think certainly, a world with less gas burning vehicles would be a better place in the long term.

I bought an electric car recently so I’m super pumped about never using gas. Obviously, there’s different side effects, but I think it’s overall a better thing.

I think it certainly would be better in some obvious ways, but I’m also hesitant to say that there’s no weird externality that we’re not thinking of that would offset that. But I think for me, I’m pretty hesitant to try to externally force other companies to do something from a societal standpoint. But I think what we can do is say, “Let’s compete and see who gets better employees,” and it makes recruiting easier and it creates better staff and ultimately, creates a stronger company.

And I think what we’re going to see is the companies that have flexibility are going to attract, for lack of a better word, better employees and better talent because of that, in most situations. And I think we’re going to see them thrive in different ways than the companies that are, quote unquote, stuck in the workplace.

And obviously, that being said, even the people who can work from office jobs are still a minority of the total working populations, so there’s still always going to be commuting, there’s still always going to be movement of people within cities and suburbs, and exurbs and everything.

But I think particularly, for the reasons that I mentioned about, just increasing flexibility also tends to increase diversity within an organization and allow people who might otherwise get burned out of a high intensity office workplace to stay and thrive, and build great careers.

To me, that’s really the biggest thing. I think the questions about housing, and traffic and commuting, there are so many different complexities to that.

I don’t think remote work is necessarily a cure all for those things. However, I do think that it is a cure for a lot of the burnout problems and a lot of the sort of… I’m not sure exactly what the word is, but if you think about who is… There’s this huge gap where people start careers in their 20s and 30s, and then eventually, there ends up being a tremendous gap between the earnings and career trajectory of the people who work 60 to 80 hours per week versus the people who work 30 to 40 hours per week.

And you see that in women who take time off after having children. You see that in people who just opt out of the high intensity Wall Street style work structure.

And what you end up with is a divergence that is not simply a linear arithmetic of, “I work more hours and I get paid more,” but it’s in fact, that people in many industries tend to progress to higher levels of the corporate ladder because they are workaholics essentially.

So if we can remove the workaholic advantage, I think that actually is better for everybody because ultimately, when you hear somebody talk about, “Oh hey, I slept at the office last night and whatever,” they always try to frame it as, “Because I’m so dedicated and I’m like, “I want to teach people that you can really be devoted to the mission.”

And I’m like, “What is your mission? You guys build an app where you can type things on the internet. This is not a life altering experience.”

It’s one thing if you’re a medic on the front lines of some really horrible situation where people genuinely need their lives saved, but there is no job where you’re moving stock money or you’re moving code that is worth that in my view.

There’s a lot of delusional statements and behavior around that, and I would love to see the of weird facade of workaholism just start to break down. And those folks who are in that weird world, either are exposed for just BSing the people around them, or maybe they choose a different and healthier lifestyle. I think that’d be better for everybody.

So that’s more of a lifestyle change and a culture change than it is a change to the physical world, but obviously those things all interrelate with one another.

Topher DeRosia:
All right. One last question, pull out the crystal ball. It looks like COVID launched remote work ahead a big step. We were forced into it. Can you think of anything else, societal, financial, business that would give it another shove? Can we advance without thousands of people dying?

Rob Howard:
Hopefully, we’ll never have anything like that happen again.

And I will also say that as you were saying that, it also strikes me that, while I think it worked really well for office work, I also think it worked really poorly for school, for kids, for example.

A lot of kids just weren’t into it, didn’t get what they could have gotten had there’d been no pandemic and they’d been in normal school situations. I think that’s also an inherent flaw in the whole idea of move the world to Zoom.

That being said, I think where we’ve ended up is there’s a bunch of companies now, Zoom being one of them and many others, Slack being another that we talked about earlier, but there’s dozens of these companies now that really are incentivized to make remote work better.

I forget what the exact numbers were, but pre-pandemic, it was in the low single digit percentages, so maybe 2% of people worked from home pre pandemic, and now it’s like 20 to 30 or something like that. Still not anywhere close to everybody, but it’s a lot.

And certainly, if you’re in a social circle where most people are office workers, most of your friends probably work from home.

So I think that we are past the inflection point in growth where it probably will continue to spread and grow, and I think for the reason that we talked about. If you’re applying for jobs and one is remote and the other forces you to come into a building in Chicago every day, which one are you going to choose?

People have even said that they’re willing to pay cuts to work remotely. Most people don’t explicitly want to take a pay cut, but if for example, you’re choosing between two options, the premium value of a remote situation is significant. The Chicago office workplace will have to pay you a lot more to make that worth your while.

So I think that just competitive nature of different firms. Trying different things, getting better at different techniques will ultimately show that, at least for some industries and some types of jobs, and some types of work, you can do remote and be equally as good if not better. And it generally is going to be cheaper for the company in a lot of ways, less real estate costs. And those are clearly not offset by the cost of Zoom, which is much less than the cost of a nice office building. And just more access to high quality workers who are going to be happier at the company because of the remote nature.

That being said, there’s also a ceiling because there really are a bunch of jobs that require a physical presence, so you’re never going to get to a place where you have 75% of people working from home because that would just be essentially a physical impossibility for a big percentage of jobs.

Everything from doctors to people who work at restaurants and stores. It’s all across the income spectrum, all across the education spectrum. There are always going to be physical, in-person jobs, and I don’t think that’s a bad thing.

I think I enjoy interacting with people in person, but also because we do web development, we are fortunate to be able to have a team that is spread around North America as opposed to just being in Denver, for example. And I think that that gives us more opportunities. It gives us the ability to improve the lives of more employees, and their families and their loved ones. I think it’s great for us.

Obviously, if you’re in a position where you’re thinking about, “Should my staff be remote or not,” I would say, “Try it and get good at it, but also recognize that there are a lot of different skill sets at play that you might not have needed to get good at in a physical office space.”

Topher DeRosia:
I agree with you about all that stuff. None of that sounds quite to me like the lunge that COVID was. It’s more reasonable growth through experience.

Rob Howard:
I agree, and I think what’s going to change is that because we are now growing from a higher starting point…

Growing 1% per year if you’re starting at 20% is a big difference than growing 1% per year if you’re starting from 1%.

So I think because we have critical mass now, it will seem like there is more growth even if the rate doesn’t really change. But we’re also going to bump into that ceiling of there’s just only so many jobs that can be converted.

That being said, I think a good example of one that has changed a lot is real estate.

So when I bought my first house 12 years ago, we had to go to a physical place and sign a bunch of paper, and it took three hours, and it was boring and weird.

But now it’s all online. We refinanced our mortgage during COVID and we did it all online. Somebody came to our house wearing a mask and notarized two documents and left. And it was like, “This no longer needs to be an in-person thing.”

And there are people who are buying houses site unseen and filling out all the paperwork on the internet now. And obviously, I wouldn’t do that if I didn’t have to. I’d rather go kick the tires of the house physically.

But all of that administrative stuff that really was done with reams of paper in offices even a few years ago, clearly doesn’t require that anymore.

That’s a good example of one of those jobs where it was convertible, even though nobody was really doing it online before the pandemic, they rapidly figured it out.

I think there is space for that kind of stuff, and online ordering from stores is a similar idea, but at the same time there’s a lot of jobs where people need or want to be physically in a place, so that’s not going to go away.

And ultimately, you can’t remotify every single job. And I don’t think that’ll good for us to do that. But we are really lucky to be in an industry where a lot of people are remote and it’s widely accepted.

And I would even say that being remote already when the pandemic started was a big benefit for us because there was way less learning curve. And since everyone was suddenly remote, there was nobody competing with me who had the fancy downtown office because that was irrelevant.

So weirdly, it actually made the companies that were already remote seem more prestigious, whereas in the past there was definitely this vibe of like, “Well, where’s your office? Oh, you don’t have one? That’s weird.”

I would definitely get that from clients from time to time, and now we never get that because everybody thinks it’s cool that we’re remote and wants to know how we do it.

So that that’s been a big change, but ultimately, we just got lucky that we were positioned for something that suddenly happened. And it wasn’t anything that we predicted. It was just like, Hey, this is how we like to do it, and then suddenly everyone was doing it that way.

Topher DeRosia:
I thought through that question myself and reflected back on that the thing we talked about with there’s less gas burned the more people were from home. And it occurred to me that the government could offer tax incentives to companies to say, “Hey, have more people stay at home in order to reduce carbon burn.” And I don’t know if that’ll ever happen. I’m not enough of an economist to know if it’s even a good idea sort of thing abruptly change it, I think.

Rob Howard:
And where that stuff gets tricky is the city wants people to buy lunch in the city. So they actually, in some ways, benefit from the presence of office workers, because now you’ve got sales tax, now you’ve got property taxes on those cafes and stuff like that. So it’s a tricky balance between, and this is true of all environmental and transportation and housing stuff. There’s this tricky balance between, “We make money off of action taking place in the city through taxes, but we also want less congestion and want less pollution.”

But I agree with you. There’s definitely something there. And I think remote work definitely has… I actually don’t know if it’s actually changed driving a traffic patterns in a positive direction, but there’s certainly an opportunity there to think about what are those side effects that seem not directly related, but actually the number of people going to an office every day makes a big difference towards those different numbers.

Topher DeRosia:
Yeah. Well, that’s all the questions I had you.

Rob Howard:

Topher DeRosia:
You have any [inaudible 00:30:12] out there?

Rob Howard:
We’ll keep working remotely for now until we find a better way to do things. And it is always a pleasure to talk to you, and I look forward to the next time.

Topher DeRosia:
Yeah, me too. See you.

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