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Since his divorce, Joe Olson has been asking himself the same question he found himself with just after he retired early: Will I have to go back to work?
Though he mapped out his FIRE journey with detailed spreadsheets, he knows not everything goes according to plan.
Olson, who is 36, retired almost seven years ago along with his then-wife, Ali, and they chronicled their journey of financial independence, travel and parenting at AdventuringAlong.com.
The two Las Vegas teachers were living frugally (“like college students”) and supplemented their modest but steadily growing incomes with side jobs like teaching summer school and grading exams. “Every side gig you could think of related to teaching,” Olson told MarketWatch.
Crucially, they also invested in Las Vegas real estate, starting as the housing bubble was beginning to deflate.
They bought their first rental property in 2008, a year after buying the roughly 400-square-foot condo they lived in. They bought a second rental unit in 2009, and two more in 2010.
But the couple was surfing a housing curve without being able to see where it was going.
“After we bought the first few and prices kept falling, I was like, maybe I don’t know what I’m doing, what makes a good real estate deal,” Olson said. So, he borrowed a slew of real estate books from the library and started going to meetups.
In 2010, Olson made a spreadsheet that showed that the income from their jobs left them able to save $4,000 a month after covering their living expenses, including their $330 monthly condo payment.
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He and Ali decided that every time they saved more than $25,000 cash, they would make a down payment on a rental property. When they bought a house, Olson would add to the rental property column on his spreadsheet and subtract from the cash column.
As they bought property, the cash column would grow faster as new rental income came into the mix. Where it once took six months to buy a house, they would eventually be able to buy every couple of months. At first, they managed the properties themselves, hiring out for repairs as needed.
Read: I lost my job at 58. Here’s how I was able to get by until retirement
Using the spreadsheet, Olson said he made a projection 10 years into the future and saw rental income of $9,000 a month.
“I said, this is more than we’re making teaching, so this is pretty cool,” he recalled. “We ended up even doing better than that and quite a bit sooner, years sooner than this projected.”
The Las Vegas housing market would bottom out in early 2012, and in the years that followed, as prices increased, the Olsons unloaded most of their Vegas properties to invest in other markets and did some flips.
“Even though those first few we bought went down temporarily, they eventually rebounded and we started buying more and more and really setting up our path to FIRE,” he said. FIRE, which stands for Financial Independence, Retire Early, is a movement rooted in frugality, high savings rates and investing, whose followers work toward having enough financially to be able to leave traditional jobs.
In 2015, Olson said they weren’t sure they were financially ready to retire, but decided to go for it anyway.
“I never really did the 25x rule, I think it’s way overly conservative,” he said of the general FIRE rule of thumb to save 25 times your annual expenses.
Read: How much do I need to retire? You tell me.
Olson said that at the time he and Ali retired, they had 15 rental units, all single-family houses, and downsized their possessions to what they could fit in two backpacks and a box. They were 29.
Then they hiked the Camino de Santiago in Spain. Ali was pregnant at the time with their first child, Annabelle.
The couple’s next few years were a complete 180 from their previous lives as Las Vegas teachers who shared a small apartment. After stints in Portugal, Germany, England, Morocco and Croatia, they had their daughter Annabelle in Istanbul, traveled to Athens and Krakow, visited family in Seattle and Southwestern California, then explored Australia, Southeast Asia and Japan. They took an RV up and down the West coast of the United States, Canada and Mexico before having their son, Cassian, in Amsterdam.
Once they had their third child, Caitlyn, they decided to settle in Seattle near Olson’s family.
Joe Olson plays the Allowance Game with his kids.
Brian Quist
“We’d been planning for more like the $50,000, $60,000 spending range” in early retirement, Olson said, but moving to a high cost of living area changed things. “Housing is expensive here, everything is expensive here. I probably spend closer to $100,000 now.”
His high expenses are partly the result of the couple’s separation in 2020, which left him and Ali managing two households and Joe paying back refinanced mortgage debt to cover the costs he owed her. Aside from those costs and business expenses, Olson lives on around $5,900 a month, which includes his contributions to charity.
The divorce was finalized in 2021. The couple split their nest egg 50-50, with Ali taking the liquid assets, including cash, investments and retirement funds, and Joe taking the property and paying Ali the difference. They share custody of the kids.
Olson said that while he doesn’t think money had anything to do with the divorce, retiring early gave them time to explore and realize that they wanted different things.
“It very well could be the case that if we had just been going to our normal 9-to-5 jobs and…not really confronted with the existential questions that FIRE gives you of who am I, what do I want, what do I want out of life, we might have stayed together,” he said.
Today, most of his real estate holdings are in Michigan north of Detroit, though he still owns two properties in Las Vegas. Property managers run almost everything.
While his expenses have soared since his low-cost days in Las Vegas, Joe’s net rental income and other passive earnings still cover it all, according to records reviewed by MarketWatch.
One expense Olson has by choice, and increases each year, is charity.
He uses a spreadsheet for this, of course, checking it every December and making lump sum payments in the thousands of dollars by year’s end if he hasn’t met his goals.
He aims to give more than 50% to causes outside the U.S., including antimalaria efforts and the Malala Fund. In the coming years, he hopes to donate at least 1% of his net worth to charity annually, or 15% of his income, whichever is higher.
As a frugal person, Olson admits writing these end-of-year checks can be painful.
So, will he have to go back to work?
Right now, no, but said he may in the future, even if he doesn’t need to for his own sake.
“I’ve decided that I’m going to hit these goals, and I’m going to donate this much money, and if I don’t have the money, I need to go back to work,” he said, “because I’m not OK being like, ‘hey, I’m retired, I don’t work, but also, I don’t have the money to donate to people who really need it.’”
For now, Olson has a schedule of “on weeks and off weeks,” where “on weeks” mean a single-dad schedule of aquarium visits, picnics, and all the life in between, and “off weeks” are downtime to do housework, see friends and spend time on newer hobbies like painting.
He enjoys having so much time with his kids, which is one reason he wanted to retire early in the first place.
“I don’t think about money that much anymore these days,” he said. “Divorce made me think about money, but in general, I’m very privileged in many ways and that is one of them, to not have to stress about money.”
Do you have a FIRE story? Email us at helpmeretire@marketwatch.com.
Brian Quist contributed to this article.
