Stay-To-Work Is Again And It Might Value You A Nice Fortune

Since 2009, I’ve been writing in regards to the significance of working to stay—accumulating wealth to obtain monetary independence and freedom. However regardless of years of advocating for this way of life, I’ve come to comprehend that convincing individuals stays an uphill battle. As an alternative, I now have new proof that live-to-work is again and stronger than ever!
“Stay to work” describes a mindset the place an individual’s life revolves primarily round their profession or job. Individuals who “stay to work” usually prioritize their work above private pursuits, relationships, or leisure. Their identification and self-worth could also be carefully tied to their skilled achievements and productiveness.
I perceive the significance of “dwelling to work” while you first graduate from faculty. Constructing a profession and establishing monetary safety usually require dedication and lengthy hours. Nevertheless, there comes a degree when we have to determine what actually issues and when sufficient is sufficient. In any other case, we danger trying again with remorse, wishing we had the braveness to prioritize our happiness and stay life on our personal phrases.
My Begin Of Wanting To Work To Stay
A few years earlier than retiring from finance in 2012, my spouse and I had been speeding by Venice, Italy when an older couple stopped us and stated, “Take it gradual and go searching. There’s no hurry to get to the place you’re going.” At first, I used to be shocked, however then I noticed they had been proper. We had been speed-walking by town like New Yorkers in Midtown Manhattan.
Once I lastly constructed up the braveness to barter a severance and depart my job, I spent late mornings sitting in Golden Gate Park, studying a e-book or just having fun with the second. It was an exquisite feeling—not having to endure rush-hour site visitors simply to sit down in conferences all day. Although I earned 85% much less in my first yr of retirement, I used to be happier as a result of I used to be free.
Ultimately, I might lastly benefit from the public parks and providers my six-figure tax payments had been paying for over the previous decade. It felt good to interrupt free from the live-to-work mentality—the relentless pursuit of extra money and better standing. Looking back, it was bizarre to let go at 34, however I do not remorse it at 47 at the moment.
Work-to-Stay (FIRE) Is Getting Pushed Apart Once more
I shouldn’t be too shocked that the work-to-live philosophy is fading once more. In any case, I wrote the submit Why Early Retirement/FIRE Is Changing into Out of date, which argued that elevated office flexibility had diminished the urgency to retire early. If I solely had to enter the workplace 2-3 days per week, I doubtless would have labored no less than 5 years longer.
Simply final week, I performed pickleball from 2 – 3:45 PM with somebody who works at Uber. He advised me his firm solely requires staff to be within the workplace on Tuesdays and Thursdays, giving him a four-day weekend. This season, he’s been snowboarding in Lake Tahoe nearly each week. On Fridays and Mondays, he takes video conferences till about 11 AM, will get in six runs on the slopes from 11:30 AM to 1 PM, after which logs again in for work.
Spending time on the pickleball and tennis courts led me to imagine that extra individuals had been embracing versatile work. Nevertheless, assembly a number of people with relaxed schedules is one factor—seeing how individuals spend their cash is one other. And from what I’ve noticed, probably the most critical professionals—those dwelling to work—are literally doubling down on work submit pandemic.
The fact is that almost all of my noon pickleball companions fall into two teams: individuals of their 20s and people over 50. The youthful crowd are all renters with out children, whereas the older group both runs their very own companies, has a working partner, or lives frugally on authorities help.
Proof That Stay-to-Work Is Again And Stronger Than Ever
Probably the greatest issues to return out of the pandemic was widespread distant work. Past eliminating commutes and pointless face time, it additionally allowed individuals to save on housing prices by shifting farther from metropolis facilities. This development is among the explanation why I have been investing in heartland actual property since 2016.
In San Francisco, it can save you 40%–60% on hire or residence costs simply by shifting 3–5 miles west. Through the pandemic, 1000’s relocated to thoroughly completely different cities to chop prices. Personally, I advocate for much less drastic measures—relocating inside your metropolis to cut back bills whereas preserving the identical wage, skilled community, and faculty district on your children.
However what shocked me just lately was seeing two houses with no views promote for effectively above asking costs on San Francisco’s rising west aspect. They bought for greater than the houses accessible with ocean views. I had toured each properties extensively and estimated their ultimate promoting costs. I do that for each property I go to to maintain my pricing forecast expertise sharp.
For context, I’m bullish on San Francisco actual property, significantly because of the development of synthetic intelligence. I’m particularly optimistic in regards to the metropolis’s west aspect, pushed by new faculties, property developments, and the $4 billion UCSF Parnassus medical middle transform, which is able to add over 1,400 new jobs.
I believe these two houses are nice—I’m simply shocked they bought for a lot greater than my estimates, when you should buy nicer houses with views simply 0.5 – 1 miles away, for much less.
Instance #1: West Portal Home, San Francisco, CA
This absolutely transformed 3-bedroom, 3.5-bathroom, 2,836-square-foot residence within the West Portal neighborhood bought for $3,125,000 in April 2024. Given my optimistic stance on west-side San Francisco actual property, I projected a 4% appreciation in 2025, bringing its estimated worth to $3,250,000.
It was re-listed in 2025 at $2,495,000 to generate curiosity—just like its 2024 technique when it was listed on the similar worth and finally bought for $3,125,000. Nevertheless, I doubted it will go $750,000 over asking once more. That could be a scary sum of money and share to overbid.
I used to be incorrect. The house bought for $3,435,000—10% increased than its 2024 worth, and $393,799 over Redfin’s estimate.

Why I Had My Doubts It Would Promote For So A lot
The house’s greatest promoting level, based on actual property brokers, was its proximity to the MUNI station. A five-minute stroll to the practice, an eight-minute wait, a 15-minute journey, and also you’re in downtown San Francisco.
However I debated this logic with my actual property agent. “Why would somebody pay an enormous premium for a house simply to have a brief commute to work underneath fluorescent lights for 8-10 hours a day? That doesn’t sound enjoyable. By paying that housing premium, they’re locking themselves into working even tougher to afford it.”
Her response? “What if they’ve to enter the workplace?” Good level. That ended the controversy as a result of it jogged my memory that I am on this FIRE bubble the place I refuse to work longer than I’ve to. Solely a minority of individuals are private finance lovers, whereas the overwhelming majority of Monetary Samurai readers are.
Instance #2: Smaller West Portal House, San Francisco, CA
A single instance isn’t sufficient to declare a development for the brand new yr, however then I got here throughout one other. This 3-bedroom, 3-bathroom residence, 2,230 sqft (600 sq. toes smaller than the primary), was considerably move-in prepared, although its transform was 25–30 years previous. So it did not really feel almost as good as the primary residence. The truth is, I might need to spend $100,000 – $200,000 transforming it.
It was additionally listed at $2,495,000, and I estimated it will promote for about $2.8 million. Once more, I used to be incorrect. It bought for $3,039,159—over $359,000 above Redfin’s estimate, or $1,362/sqft. By no means would I’ve guessed the house would recover from $3 million.
Why the premium? A slight skyline view from the principle bed room and a seven-minute stroll to the MUNI station as an alternative of 5. In a earlier submit, I discussed that proudly owning a house inside strolling distance of all the pieces isn’t all the time superb as a consequence of noise and different disturbances. Being one block farther from the MUNI station, retailers, and eating places might have made this residence barely extra fascinating to patrons.
As soon as once more, actual property brokers confirmed that every one the patrons had been households prioritizing proximity to public transportation. Stay-to-work strikes once more! You might purchase a 300 sqft bigger, absolutely transformed residence with ocean views for 10% much less. Or you could possibly purchase an identical high quality home 1 mile away additionally close to a MUNI station for 33% much less.
Clearly, my recommendation for individuals to search out extra inexpensive houses a bit farther from work appears to be failing. And don’t be concerned, I’ve lots extra examples apart from these two that present how working to stay is again.

The Stay-to-Work Cycle Will Drive House Costs Larger
I’m not saying these homebuyers are obsessive about work—many merely must be within the workplace day by day. Their areas are handy—near downtown, close to transit hubs, and inside strolling distance of outlets and eating places. Once more, these are nice houses in a pleasant neighborhood.
However the actuality is that the necessity to work fuels demand for houses close to workplaces and public transportation, driving costs increased. And as residence costs climb, extra individuals discover themselves working extra simply to afford them. Keep in mind, increased residence costs means extra upkeep, insurance coverage, and property taxes to pay for.
This cycle received’t break anytime quickly, regardless of the private finance group’s finest efforts to encourage extra inexpensive dwelling preparations. There’s merely an excessive amount of stress to earn extra and develop social standing.
Perhaps Excessive Earnings Households Battle On Objective
There are additionally individuals who willingly endure a 45-minute commute every manner to drop off their children in school—for the following 8 to 12 years—just because they refuse to surrender the standing of their present neighborhood. As an alternative of shifting nearer and slicing the drive right down to underneath 10 minutes, they keep put as a result of they don’t assume the brand new space is “fancy” sufficient.
Monetary independence is about creating choices, but we’re seeing a shift again towards working tougher simply to maintain an costly way of life. On high of paying a premium to stay nearer to work, many households in large cities need to ship their children to personal faculty, which may simply price between $20,000 and $70,000 per yr per baby. Add on a automotive or two, holidays, positive eating, and supplemental classes for his or her children, and even households making $500,000+ a yr are simply scraping by.
Such households aren’t being irrational—they’re selecting to pay as a result of they imagine the advantages are value it. In different phrases, there is not any have to really feel sorry for them as a result of they will change their scenario in the event that they select. With the assistance of ProjectionLab, we carried out a case examine displaying how a $500,000/yr family went from struggling to having the ability to retire early.
How Many Extra Years Will You Need to Work To Pay For A Extra Costly House?
When you have a million-dollar mindset, saving $1 million on a house equates to ~$42,000 per yr in risk-free earnings—or doubtlessly $100,000 per yr if invested at a ten% return. Personally, I’d a lot quite save $1 million and stay a mile farther away on the MUNI line with a barely longer commute than be compelled to work many extra years simply to afford my residence.
Let’s run the numbers. Say you’ve gotten a $600,000 family earnings—the minimal I’d suggest for comfortably affording a $3 million residence (5X earnings, although ideally, it needs to be 3X). However as an alternative of choosing a $2 million residence only one mile farther, you purchase the costlier one as a result of it feels extra prestigious and handy.
Now, let’s assume you’re a disciplined saver, placing away 10% of your gross earnings, or $60,000 a yr. That’s about 14% of your after-tax earnings of $420,000 (assuming a 30% efficient tax charge). With a 5% compound annual return, it should take you 12 years to avoid wasting $1 million. Holy moly!
Are you telling me you’d quite work 12 extra years simply to stay barely nearer to work, quite than purchase an identical residence a bit farther away for much less and not should work for 12 additional years? That’s a trade-off I wouldn’t make.
A Extra Aggressive Saver Can Sacrifice Much less Time
OK, positive. Perhaps a ten% gross financial savings charge is simply too low for a $600,000 family earnings earner. Let’s say you’re an distinctive saver, setting apart $180,000 a yr (30% of gross, 43% of internet earnings). You’re studying Monetary Samurai, in spite of everything.
Even then, selecting the $3 million residence over the $2 million choice means working 5 additional years—assuming a 5% annual return. And in case you’re middle-aged, these 5 years are far more pricey than in your 20s. Once more, my reply is a tough no!
In case you don’t like these examples since you’re targeted on absolutely the greenback worth of the houses, strive shifting your perspective. Assume in percentages as an alternative. Paying 50% extra for a barely shorter commute will not be value it.
I’ve written up to now about how a large costly residence can derail your path to monetary freedom. Nevertheless, I do not assume many individuals actually care till it is too late. Do the mathematics please.
The Stay-to-Work Mindset Perpetuates Itself
Whereas some maximize work flexibility, others are paying high greenback to make sure they will maintain working. Paradoxically, this live-to-work cycle advantages those that take part in it, as continued demand drives residence costs even increased. In case you purchase into this mindset, the very best factor you are able to do is encourage others to do the identical—as a result of that can improve the percentages of promoting your house for a better revenue down the street.
However in case you’re nonetheless within the wealth accumulation part or are depressing at work, take a step again and ask your self: Are you working to stay, or dwelling to work? As a result of in case you’re not cautious, way of life inflation may entice you within the latter—with out you even realizing it.
Readers, why will we select unenjoyable work over experiencing freedom sooner? Do individuals not run the numbers and notice how the pursuit of a elaborate residence and standing retains them trapped in a piece cycle for much longer than crucial? Do you assume the live-to-work mentality is again? How can we encourage individuals to cease following the herd and think about various existence?
For brand new readers: I lived to work for 13 years in funding banking. I purchased the great home in a elaborate neighborhood, which solely pressured me to work tougher to afford my payments. Ultimately, I made a decision to downsize to a smaller, extra inexpensive residence as a result of I needed to stay extra. Though I misplaced status, standing, and cash, I gained one thing much more worthwhile—freedom.
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Change Your Life For The Higher
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