Settling The Work From Home Debate Once And For All

One of the most significant developments to come out of the pandemic, if not the greatest, was the shift to remote work for millions of employees. Beginning in March 2020, businesses quickly adapted out of necessity, keeping their operations afloat with employees working in pajamas from their living rooms.

However, this golden era of remote work was short-lived. By the first quarter of 2022, investment banks and other old-school employers began calling employees back to the office, starting with a few days a week. As the pandemic faded, the demand for office presence grew, and today, corporate giants like Amazon are requiring employees to return five days a week.

The reason? It’s clear: when left to their own devices, many employees naturally slack off. At a minimum, without direct supervision, productivity tends to decline.

As a 12+-year shareholder of Amazon, I was pleased to hear the news as Amazon's share price surge higher after the announcement.

A Unique Perspective on Remote Work as a Retiree

Since retiring from investment banking in 2012, I’ve had complete freedom to design my days. Before the pandemic, I could easily play tennis at any park or club during the late morning or after a nap without hassle. But once lockdowns lifted around July 2020, my once-empty courts were suddenly packed.

Curious, I began talking to the players, expecting them to be retirees like myself. To my surprise, none of them were—almost all were “working from home” with a wink and a nod.

Many were out there for hours, with little concern about their managers tracking their day-to-day activity. Armed with a phone and a noise-canceling headset, they made the most of their freedom.

I’ll admit, I was envious. Imagine getting paid to not really work! Many of the 20- and 30-somethings I played pickleball with daily were all enjoying the same luxury. It made me consider coming out of retirement just to experience that level of flexibility!

As an on-the-ground researcher of employees who work from home, it's clear to me that many tend to take advantage of the lack of supervision. It's a rational response to the environment

If you ever visit Larsen Playground on the west side of San Francisco on a weekday, you’ll find the courts packed with young professionals under 40. They are taking advantage of the lingering work-from-home privileges that remain in the tech industry.

Mostly youth working from home at 1pm on a Friday Playing pickleball
Mostly <40 working from home at 1pm on a Friday. All 8 courts packed with 15 minute waits.

Work-from-Home Is a Dream for Employees

It's no surprise that employees overwhelmingly prefer remote work. For many, the worst part of their job was the commute. In my own experience, crammed buses and delayed rides were a daily annoyance.

The flexibility that comes with working from home—being able to pick up and drop off kids or fit in a midday workout—is a huge benefit for many, especially parents. It’s a setup that employees and managers alike want to preserve.

Everybody rationally wants to get paid to work the least amount possible. Let’s accept this fact. Anybody who says otherwise is being dishonest or just virtue signaling.

However, for those early in their careers or looking to climb the corporate ladder, working from home is a career-limiting move. The reality is that the people who are seen, who interact directly with decision-makers, tend to get promoted. Being out of sight too often means missing out on key opportunities that could secure your financial future.

The law of entropy applies here too: when left unchecked, things tend toward disorder. Do you think your room naturally gets cleaner or messier? Over time, working remotely can lead to less focus and diminished output, which explains why terms like “quiet quitting” have emerged as employees resist being pulled back into the office.

Hybrid work from home policy
Amazon’s Hybrid work from home policy

Return to Office Requirement Is a Way to Reduce Headcount

Make no mistake, employers who now require in-office work are using this opportunity to get the least motivated employees to voluntarily leave. Employers see this as a double benefit—it reduces the number of less driven workers and saves them from paying a severance package.

When HR managers see their worst-performing or most entitled employees updating their LinkedIn profiles with #OpenToWork, they’re secretly thrilled! As a former manager myself, one of the hardest parts of the job was getting underperformers to voluntarily leave. We’d have to put them on a PIP (performance improvement plan) for documentation and legal purposes, followed by the difficult conversation 3-6 months later if there was no improvement.

One of the main reasons why negotiating a severance package is possible is because it’s so hard to lay off an employee, even if they’re not that great. By initiating the idea of leaving, you save your manager the trouble of firing you. In turn, if you handle the conversation well and offer a smooth transition, you’re much more likely to receive a severance package.

Negotiate A Severance If You Want To Quit Your Job

But please, for the love of baby pandas everywhere, never quit your job just because you’re dissatisfied. Always try to negotiate a severance package to help ease you into your next chapter. If you’re planning to leave anyway due to the return-to-office requirement, you might as well aim for a smooth exit. It’s what I did in 2012 and what my wife did in 2015.

Pick up a copy of my bestseller, How to Engineer Your Layoff, if you want to learn how to leave your job with money in your pocket. It’s been revised six times since its release in 2012, with the most recent update for a post-pandemic world. Use the code “saveten” to save $10 at checkout.

How to engineer your layoff - learn how to negotiate a severance package and be free

Work-from-Home Is Suboptimal for Shareholders

While most of us view the work-from-home debate from the perspective of employees, consider it through the eyes of investors—especially if you're working toward building passive income for financial freedom.

Would you prefer to invest in a company that allows employees to work from home five days a week? Or one that requires in-office collaboration and longer hours five days a week?

As a rational investor, the answer is clear: you’d likely choose the latter. More face-to-face interaction and structured hours generally lead to greater productivity, which in turn drives profitability and, ultimately, higher stock prices.

Investing is not an act of charity. You’re taking on risk in the hope of growing your money. And goodness knows investors have lost plenty of money before!

Therefore, as a shareholder, it's reasonable to expect a company to push its employees to be as productive as possible. If a company isn’t focused on maximizing output, you have the right to sell your shares and invest in one that is.

The return to office trend continues to grow. And one investment idea you should consider is investing in real estate in cities with the greatest return to office trend.

Invest in real estate in cities with the greatest shift of employees returning to the office

Solution: Work for a Chill Company, Invest in a Hard-Charging One

So, what's the ideal approach for balancing lifestyle and wealth creation? It depends on where you are in your financial independence journey.

  • Early stages of FI: Work for an ambitious company that requires in-office attendance, and invest in similarly driven companies.
  • Middle stages of FI: Look for a more laid-back employer that offers a remote work option, but continue investing in high-growth, ambitious firms.
  • Late stages of FI: Stick to a relaxed job while maintaining investments in hard-charging companies.

For example, at 28, you might want to work at a fast-growing startup and invest heavily in other promising startups through a venture capital fund. After consulting for various startups, I can assure you that startup employees work harder than most employees at established companies. And this is coming from me working 13 years in banking.

By the time you're 50 and a multimillionaire, you may want to transition to a more relaxed role at a large company or even your local city government, where the pressure to perform is much lower. Meanwhile, you can invest in promising private AI companies that demand their employees work in the office and put in 60+ hours a week. Investing in smart, driven people is the best combination for success!

Act Rationally With Work From Home Policies

Nobody wants to grind forever. Once you’ve achieved a certain level of financial security, it’s wise to transition into a new role with fewer responsibilities and less pressure. You can still collect a paycheck while playing tennis at 3 p.m. if you want—because by then, you’ve already made it.

However, if you haven’t reached that point yet, don’t be fooled into thinking you can coast your way to a corner office. Many eager employees saw their managers and C-level executives enjoying life from Aspen or Hawaii during the pandemic and may have assumed that’s the norm. But the truth is, those executives put in their time to get there.

Ideally, balance your mental and physical well-being by working for a company that offers a flexible lifestyle, while still fueling your financial growth by investing in ambitious, high-performing firms. This approach lets you enjoy the best of both worlds: a peaceful work life and strong financial returns.

Reader Questions

As a shareholder, would you prefer to invest in a company that requires its employees to work in the office or one that allows them to work from home five days a week? Do you have the ideal setup where you enjoy a cushy job with plenty of flexibility while investing your capital in hard-charging companies?

Invest In Private Growth Companies

Consider diversifying into private growth companies through an open venture capital fund. Companies are staying private for longer, as a result, more gains are accruing to private company investors. Finding the next Google or Apple before going public can be a life-changing investment. 

Check out the Fundrise venture capital product, which invests in the following five sectors:

  • Artificial Intelligence & Machine Learning
  • Modern Data Infrastructure
  • Development Operations (DevOps)
  • Financial Technology (FinTech)
  • Real Estate & Property Technology (PropTech)

Roughly 60% of the Fundrise venture product is invests in artificial intelligence, which I'm bullish about. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI! The investment minimum is also only $10 and I've invested $143,000 in Fundrise venture so far and Fundrise is a long-time sponsor of Financial Samurai.

Subscribe
Notify of
guest


35 Comments
Newest
Oldest Most Voted
Inline Feedbacks
View all comments
Jorge L Polo
Jorge L Polo
4 months ago

Sam,

I workED for almost 40 years for Hi Tech companies (Silicon- not the plastic surgeon type). In 2024 I agree 100% with your statement –> Return to Office Requirement Is a Way to Reduce Headcount.

Ramona
Ramona
4 months ago

As someone who had worked a job and then has been self-employed for 15 years: I loved the idea of WFH, even if I was working from home already for a decade. It’s the best thing happening for many employees. Aren’t they productive? Why is that an issue? Maybe it’s time to work more task-based (achievable tasks, nothing crazy), than just be expected to waste 8 hours at work. Instead of that, let them do their work when they can/want, as long as the “flow” is not interrupted. And those bosses and HR guys who are left without a job, maybe should do something more productive than count how many minutes exployee x spent in the bathroom.

Andy
Andy
4 months ago

I am in the tech industry, we currently have a flexible work policy (so far), but the team I am on is also distributed. My manager is 2400 miles away, my director is 1200 miles away and my VP is 2500 miles away. We have team members distributed around the country. I see 3 of my team every week, but the rest of the folks I see once a year (depending on travel budget)
The challenge here is how do we measure productivity across the board? Even when we are in the office, most of the meetings are in zoom anyways. There isn’t a project where all engineers are located in the same office. Throw in global distributions, many of the teams I work with are in India, Japan, UK and France. Our company is not big enough like Amazon to concentrate one program in one area. (and I can see that in many companies)

Robert
Robert
4 months ago

As an investor I am putting my money into companies that allow WFH. Assuming that butt-in-seat hours = productivity is a fallacy, especially for jobs (like mine, programming) that require a level of concentration that simply can’t be obtained in a buzzing and busy open-plan office. I was one of the highest performing engineers at my company, and I quit due to 5-day RTO. Now they are left with mediocre people who can warm a chair and pantomime busyness but who don’t produce much value. Investors beware!

Robert
Robert
4 months ago

NVIDIA and Netflix are my two favorites. Still letting people be mostly remote. I expect these to outperform AMZN long term!

D
D
4 months ago

The one thing you are missing is the ability of a company to hire the best talent worldwide without having overhead of multiple offices. Our company had 1 office rest was virtual before covid and we had a major competitive advantage hiring the best talent; but after covid nearly every competitor offered work at home. The biggest disadvantage is junior people are not getting properly trained sitting at home. So the best scenario is in-office for junior staff and work at home for top-notch senior staff who prove their worth. Also I suggest having a few different offices across the country/world where staff come together regularly. But our company got addicted to the savings of having zero offices to maintain.

The Social Capitalist
The Social Capitalist
4 months ago

It’s the myth of efficient corporations. One can appreciate that individuals won’t get ahead unless they’re “seen” and we certainly own our own career. But someone playing pickleball while “at work” tells us that person is maximizing their time and companies don’t know how to utilize employees.
Moreover, it tells me not only are employees disengaged, so are bosses. Because companies have decided their only purpose is to make money- so employees are left to only take money. Bravo to them.

GL
GL
4 months ago

Work From Home rewards those who can deliver results most efficiently. RTO actually prolongs the employment of people who aren’t the sharpest or most efficient worker but can put up a good front. Management is fooling themselves that they can flog a mediocre worker into producing the equivalent of a top performer. RTO actually prolongs retention of mediocre workers and is best for those who require a lot of hand holding. If a WFH worker isn’t producing targets then they should either be held to account or made to RTO. Your highest performers will always produce or come in at necessary junctures because they are vested in the work. Poor management or bad management takes the easy way out by mandating RTO 5 days because it is easier than setting accurate targets or evaluating results. Hybrid schedules and living within a 15 minute commute in my opinion leads to the highest productivity. This way you can flex up or down depending upon work needs.

KO
KO
4 months ago

TL;DR Just let me know where I can pick up my UBI check. Working from home is sooo harshing my mellow.

George
George
4 months ago
Reply to  KO

Durham County recently did a pilot UBI program for previously incarcerated citizens to help them get incorporated back into society. Maybe you could give them a call and see if they found anymore money.

JGW
JGW
4 months ago

I keep reading about how great the work ethic is for startups. Ok, great. Let’s remember, 90% of startups fail. Roughly 20-30% in the first year. So, we should all keep that in mind when virtue signaling about the merits of being another in-office Prozac drone. And yes, this definitely includes tech startups. Work smarter not just harder and, worst of all, more performatively.

That said, observing people playing pickleball during the day or whatever doesn’t prove they aren’t working. They may have flexible or non traditional work hours. Even if they say offhand that they’re flexing their WFH privileges to play pickleball, let’s remember they’re in the Bay Area and likely exaggerating to brag or make others feel envious. And remember, they’re saying this to you – a guy who retired in his mid-life with kids and a sustainable passive income. They’re likely being defensive in their response to hide their insecurities. As a Californian, that sorta half-truth humble-bragging is definitely something people love to do here. I wouldn’t doubt they work early or nights or into the weekend.

Companies are enforcing RTO not because the office is more productive. A few online searches will show academic papers that by and large prove the opposite. It’s primarily about reducing headcount, which I agree with in the above post.

So, let’s not jump on the Amazon or Elon exploitation bandwagon here. The office Karens, smelly coworkers, and sexual harassment predators waiting for us to RTO… can wait IMO.

JGW
JGW
4 months ago

I go into the office once a week currently. My in-office day is by far the least productive. Even with headphones on, it’s unavoidable having people bother you with their complaints or gossip.

I would never invest in the companies that have the most working hours/in-office requirements: startups. Might as well as throw my money away given the 90% that fail.

Let’s remember that the startup super-unicorn, Tesla, only exists because of government intervention. Whether it was CA and Fed tax breaks or the government’s market for carbon credits and currently US tariffs on Chinese imports, all those crazy hours they and their dear leader brag about are really for nothing. Cheap Chinese solar, electric vehicles, etc would put them out of business yesterday without the immense government intervention they benefit from.

My main point is that I think we should be very cautious and cynical before falling for the RTO propaganda coming from the likes of Elon or Amazon. They treat their employees like garbage. Why would anyone idealize that? And speaking of banker’s hours, let’s also not forget about Leo Lukenas III. His bank worked him so hard, 80-hour minimums per week, that he died leaving behind a widow with two children. Disgusting. Every single one of his managers should be whipped and jailed.

More time with our families while doing our jobs from home? What’s the problem? People will and very much do slack at the office. Some will do it home. Don’t throw the baby out with the bath water, though.

JGW
JGW
4 months ago

I don’t think adapt is the right word. More like submit… Using WFH technology is adapting. Returning to the office status quo is regressive.

I’ve been with the same company for 13 years. Hybrid for 6. I’ve averaged promotions every two years. Some minor. Some significant. I lead multiple internal and community volunteer initiatives internally. I’m always available for intern season and community volunteer initiatives. The team I’ve been on all these years is a large, if not the largest, revenue generator any given year. We work hard. We primarily work from home. My health and family are the better for it.

My spouse is in tech. Fully remote. He starts at 7am for meetings with Europe. Often finishes his last calls at 7pm or later with Bay colleagues or Asia. His “free time” on weekends is also working. He is not with a startup and yes he works in AI. I fear he is getting burned out even more than he was. His direct boss, who has had RTO implemented in the Bay, has chronic shingles. Other RTO coworkers have come and gone due to stress since then. One recently was fired after poor performance following a divorce.

I read an article this morning on Fortune that the average middle class family works 600 more hours per week than the same household would have in 1975. That if it weren’t for women/dual income households, the middle class in America would have deteriorated.

The point being we are already working more than our parents generation by an average of 600 hours per year. And for less money. Don’t mention pensions… But now you’re advocating we RTO to companies that couldn’t give a fork about us? Please!

That said, I do love your blog. It’s been a big part of why I am, knock on wood, on track to retire early. I also see your point about this topic as an investment idea but… I respectfully disagree.

Last edited 4 months ago by JGW
RC
RC
4 months ago

I graduated college in the 80’s during a brutal job market for recent college grads. Through the course of my careers I experienced numerous corporate reorganizations and downsizing, the tech bubble, 9/11, and the great recession of the late 2000’s. All of these events had a profound impact on employment. Fortunately I was never personally impacted in any of my roles. I attributed this to always being visible and continually demonstrating the value I brought to my employers. In short I quickly realized that when the objective was to cut heads I needed to show why mine was worth saving.

If you’re under 35 you’ve likely never experienced a recession during your professional career. Considering that more than a third of workers are in this demographic that’s pretty staggering. But the good times won’t last forever and when the economy inevitably turns the WFH movement will face it’s reckoning. It’s already beginning to happen as more companies are adopting a similar approach to Amazon.

Recessions have a tendency to stop complacency in its tracks. Employees will seek the perceived safety that the office provides fearing that being out of sight will mean being out of mind. And employers will be forced to go through the inevitable headcount reduction mandates and will gravitate towards the low hanging fruit of eliminating roles and people where the value isn’t readily apparent. Will they lose a few remote high performers? Perhaps, but that will be more than offset by having their most motivated employees in the office working on making it through the economic turbulence.

Robert
Robert
4 months ago
Reply to  RC

I have been on teams where those few remote high performers are what stand between the team’s success and its failure. Software project teams are more like basketball teams than we sometimes want to admit: one superstar makes or breaks the team, and those “highly motivated” gung-ho ladder climbers are really just there to provide support and clear obstacles. So managers will sacrifice those high performers at their shareholders’ peril.

Buddhist Slacker
Buddhist Slacker
4 months ago

Beware of assuming you can get a rest and vest government job. That’s not always the case. We are basically 100% in office. Management seems to be reconsidering a bit since everyone is getting hired away so the only tool they have is to offer a little WFH. Maximum two days per week. WFH basically. It’s maximum 20 hours but who’s going to come in for half a day?

Another option would be to grind it out in the government, retire, then do lucrative consulting gigs for two or three times the pay you were getting before. Or get a different job that pays more in ” in government relations” but not lobbying.

I know one person in DC who worked for the federal government in defense contracting. Then she retired and made an obscene amount of money consulting LOL.

Last edited 4 months ago by Buddhist Slacker
Buddhist Slacker
Buddhist Slacker
4 months ago

Generally you would think that a government job would be less stress. Unfortunately I decided to transfer to the highest stress most understaffed department with a bad reputation among workers. This was a rude awakening. Hence my warning. Be careful what you pick even if it’s the government.

The stress level is higher than some PM tech jobs and less than some some when I worked in big tech and the hours can be just as long. We have at least one, sometimes two or three big external audits from regulators each year with corrective action plans required with many deadlines which continue until the next audit. We have various deadlines to meet pretty much everyday from regulators. Union or not, you can definitely get fired for not meeting deadlines which I heartily applaud because teammates not meeting deadlines puts pressure on the rest of us who have to figure out what to do somehow

If I retire now, my pension will be a whopping $546 per month. It goes up dramatically each additional year I stay. I’m currently home sick. I have so many sick days. I don’t even know how many I have. But I’m going to use a couple vacation days because I’m currently capped out and losing 10 hours a month vacation. We have great benefits but if you can’t use them it’s not really a benefit. I’m taking sick days when I need them though. I’m putting my foot down about that. I have to keep up my health because it’s no use being dead LOL.

TK
TK
4 months ago

Such an interesting topic on WFH.

My take, a lot of people have moved since being allowed to WFH.

I think companies could struggle to recruit with so many offering a remote jobs.

April
April
4 months ago

As an onsite worker (big lab equipment involved) but with a chance of WFH two days during covid, I prefer to work onsite for better productivity and less distraction. But I have a very short commute and don’t mind talking to colleagues. I observe neighbors building their gardens while WFH, or WFH pickleball players that take 2-hour lunch break in early afternoon, but who knows, they may put into lot of efforts off hours. I do think the flexibility is appreciated especially for employees with family. APAC and Europe employers mandate more onsite days earlier and receive less backlash than in NA, probably because a lot of NA employees have much comfortable homes, longer commute and US lifestyles tend to be more overscheduled and more complex in healthcare/childcare/general services than any other industrial countries. Mandating RTO may increase output in a short period of time for the employers, but it may lead to more burnout in the long run, if the whole society does not address the complex issues in the US that any service is so expensive, so ineffective, and so unavailable.

Buddhist Slacker
Buddhist Slacker
4 months ago

Do you really think it’s the minority that will work the same number of hours when wfh versus RTO? If so, you’re crushing my faith in integrity and humanity LOL. I end up working more hours because I don’t have the cue of certain people leaving as to when to stop. And the emails keep coming at all hours lol. Even though I’m a government employee.

I think even the working climate in the government might be changing. Everyone seems understaffed. Except maybe City and County of San Francisco LOL. And maybe except Santa Clara county. But I have no real insight there. So don’t take my word for it.

Last edited 4 months ago by Buddhist Slacker
George
George
4 months ago

It probably depends on the person. I have worked for a government organization for years and have very in depth knowledge in a couple of areas that has allowed me to easily shift through a couple of different key man roles that require specialized knowledge. This has resulted in me not working very much because I can do much of my work in my sleep, while hardly anyone else can do what I do. Most people in government are lazy and inefficient and won’t do anything to learn something they don’t have to.

Buddhist Slacker
Buddhist Slacker
4 months ago

Also question, you would by definition not see the people who are actually doing a lot of work from home when you are out and about. When I do get to work from home, I’m chained to my computer and I wouldn’t even dream of doing any errands during the day.

What I see is the traffic and Costco is crazy on the weekends and during commuting hours. I saw the traffic gradually come back as the lockdowns lifted. Traffic’ has always been my barometer of economic health and activity and by extension, people not working from home. I drive on the freeways.

Way back when the.com bubble burst, previously it it had taken me as much as a half hour to drive two exits on the peninsula. When the bubble burst the traffic was gone overnight. It was eerie.

So do you really think you can generalize to the entire population by pickleball courts in San Francisco? Of course there’s always going to be slackers but I think the majority are not. I think my freeway barometer is better.

But of course, the few bad apples always spoil things for everyone.

Jamie
Jamie
4 months ago

I can relate to this a lot. I had the opportunity to wfh on some days early in the timeline before covid. It was glorious for me to save 1 hour plus on commute and feel so much autonomy. Did I take advantage of having nobody watching me, absolutely. Even though I slacked in the office to some degree, I could only take it but so far. I definitely upped the slacking and dropped productivity when I was wfh. I still had to hit deadlines and maintain good performance, but my publicized capacity for extra work went down because “I’m still working on xyz” etc.

Your logic on adjusting the type of company one works for as you age vs focusing one’s investment dollars on in-office mandated companies is so true. I definitely prefer to put my money into companies that are focused on productivity and innovation because that’s what drives profits.

WSinTX
WSinTX
4 months ago

However, for those early in their careers or looking to climb the corporate ladder, working from home is a career-limiting move. The reality is that the people who are seen, who interact directly with decision-makers, tend to get promoted. Being out of sight too often means missing out on key opportunities that could secure your financial future.

The WFH crowd is also at the top of our list when RIF’s are necessary due to the continuing deteriorating economic conditions.

Nice article Sam. Well done.

Mike
Mike
4 months ago

I consider myself one of the “OG” work from homers. Started 21 years ago when I was only 16. Back then I was tied to my actual computer using AOL Instant Messenger and ICQ (remember those?) Eventually they made an AIM app for cell phones which began changing the game and loosening the tether. Once cell phones could be used as mobile hot spots, my freedom felt endless.

I began viewing my job not as a 40 hour / week commitment, but rather a “complete all duties in my job responsibilities list and remain on-call for urgent requests.”

Having said that, I spent 15 years at one company, completely out of sight. And in 15 years my income grew from $42K / year up to $48K / year. So you’re spot on with the out of sight / out of mind point.