
Millions of Americans grapple with the question of where to retire every year. And it’s no wonder many struggle with the decision, considering how many factors are in play.
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Millions of Americans grapple with the question of where to retire every year. And it’s no wonder many struggle with the decision, considering how many factors are in play.
As markets whipsawed through a turbulent first quarter, American workers didn’t blink: They kept saving for retirement — even while watching their 401(k) balances get smaller.
Courtesy of Jeremy Smith
As a businessman, Jeremy Smith never liked the term “downsizing.” When a CEO uses it, it doesn’t tend to be good news.
When it came to retirement, though, Smith and his wife were excited to eventually trade their house in San Ramon, California, 35 miles east of San Francisco, for a smaller, more affordable home to grow old in.
But the couple ultimately opted to upsize their living space — if not their mortgage payments. They ended up leaving California behind and buying a much larger — and much cheaper — place in Oregon.
Smith, who founded a food brokerage company called LaunchPad, wasn’t quite ready to retire in 2021. But watching home values in California skyrocket in 2021, he decided it was time to sell. First, he listed his South Lake Tahoe vacation home, which he’d bought just six years prior for $540,000. The house sold the same day in April 2021 for $1.2 million, all cash and over the asking price.
The sale convinced him to put their primary East Bay house on the market, too. That home, which Smith bought in 2010 for $600,000, sold for $1.5 million.
At first, the couple considered retiring to someplace in Southern California, like Malibu or Manhattan Beach. But their home sales suggested to him they needed to buy their next place outside of California’s hyper-competitive, extremely expensive market.
“I felt like it’s one of those things where you throw a quarter in a slot in Vegas, and it pays $1 million, and you don’t stay at the casino. You get that money, you get the hell out, and you go home so you’re not tempted to spend it,” Smith said.
Smith’s wife, a native Oregonian, pushed for Portland. So they decided on the small city of West Linn, a quiet suburb just south of the city.
When they realized how much more affordable Oregon was, they opted for a home almost three times the square footage of their San Ramon house, but at half the price. They bought the place for $750,000 in June 2021, while mortgage rates were still low.
“I didn’t realize the tremendous cost of living savings that we would get by moving to Portland,” Smith said. “We wound up getting more for a lot, lot less, which allowed us to invest back into the stock market.”
Courtesy of Jeremy Smith
Despite loving the Portland area in many ways, Smith misses California. He yearns for warmer weather, sunshine, ocean views, and living closer to his three children and grandchildren. He says he visits about four times a year to see his kids and doctors.
“I miss the hell out of California,” he said. “Yes, it’s expensive, but it’s a magical place.”
Still, he loves being surrounded by Oregon’s many rivers and Lake Oswego, where his wife kayaks regularly with her friends. And the food is excellent in Portland, he added.
And while Smith may have left California, he’s still surrounded by Californians. He estimates that 12 of the 14 homes in his gated neighborhood are owned by people who moved to Oregon from California. Many came to Portland for a more affordable retirement, and some still have homes in the Golden State.
These days, he spends his time walking his two French bulldogs, eating out with friends, and chatting with neighbors. “It’s nice to be able to joke around and talk about all the fun stuff in California,” he said.
But he’s still adjusting to some of Oregon’s quirks.
“I’ve never seen so many damn beards in my life,” he joked. “And you’ve got to get used to flannel shirts.”
Do you have a story to share about home selling, buying, or moving? Contact this reporter at erelman@businessinsider.com.
Kelly Benthall
My plan had always been to retire at 65 — grind it out, climb the ladder, and finally enjoy the freedom. But plans change, especially when your body starts flashing warnings you can’t ignore.
Last year, at 53, I retired early with my husband — not because we had meticulously planned every detail, but because the cost of staying in the rat race — mentally, physically, and emotionally — had become too high. Work had always been a source of pride, but it was also a source of stress and, at times, serious health consequences.
For more than 30 years, I helped companies ranging from startups to giants such as Shell and Chevron navigate strategic change. I had spent those decades taking on more responsibility than was reasonable, absorbing the pressure, and expecting little in return. Over time, I internalized stress as a normal part of success — until my body forced me to stop.
The workplace has changed a lot since the ’90s and early 2000s, particularly in male-dominated industries like oil and gas. Back then, I was a minority as a woman, and those who made it to the top endured relentless pressure. Some became champions for equality. Others expected fellow women to tough it out, believing suffering was a rite of passage.
Some female leaders respected my work, but others saw it as a threat.
During an orientation at one of my first jobs, I mentioned my experience in speechwriting to a CEO. He asked me to write his sales conference talks, but my female boss told him I wasn’t interested and offered to do it herself. I later reached back out to the CEO to clarify, and we ended up partnering for years.
And then there were #MeToo moments I can’t believe I tolerated. One boss thought it was appropriate to share his appreciation for Playboy centerfolds during meetings.
The culture shifted over time as companies implemented stronger policies and accountability measures. By the time I reached my final years in corporate life, the culture had improved. But the damage had already been done.
Years of working in high-alert mode left me conditioned to expect the worst, even in safer environments.
Despite disappointments, I kept my foot on the gas. I worked harder than ever, sometimes logging 90-hour weeks, believing that if I just worked smart enough and fast enough, I could outpace the stress.
I was wrong.
One day, I collapsed at work. My blood pressure spiked to 220/180, and I ended up in an ambulance. The EMTs gave me nitroglycerin, but nothing happened. I heard one of them say, “Uh-oh,” before telling the driver to move faster.
That should have been my wake-up call. Instead, I doubled down — cycling through medications in a desperate attempt to keep going.
It wasn’t sustainable.
I had spent my career coaching others to accept change.
The advice I’d given countless others seemed easy when it was someone else’s problem. “Do as I say, not as I do,” I thought. Yet, as I struggled with burnout and my health deteriorated, I realized I wasn’t taking my own lessons to heart. I had built a career around helping people, but I had been afraid to make the same leap myself.
It wasn’t until I spoke with a coach — a free consultation, something I almost canceled because I “didn’t have time” — that I saw my life from a different perspective.
She asked me one simple question: “When was the last time you did something that scared you?”
The question caught me off guard. I had spent so many years operating in a world of controlled risks, where I calculated every move and mitigated every possible failure. But fear? The kind that comes from stepping into the unknown, from daring to disrupt the status quo? It had been a long time since I’d felt that.
That moment unlocked something in me. I remembered who I was — someone who took chances. I had once thrived on new challenges, stepping into high-stakes projects where failure wasn’t an option and leading teams through uncertainty. Yet, I had spent years trapped in a cycle of stress and obligation, mistaking endurance for achievement.
“Sometimes you have to break down to break through,” the voice in my head whispered. That was the moment I decided to retire.
When I finally stepped away from my career, I didn’t fully grasp the toll it had taken on my body. But retirement didn’t just heal me — it gave me a new way of living. My husband and I embraced slow travel, trading deadlines and commutes for long walks in new cities, quiet mornings with coffee, and the freedom to explore at our own pace.
It wasn’t until my first post-retirement checkup that I saw the difference. My blood pressure had dropped, and my stress markers were lower.
My doctor looked at my stats, then back at me, and said: “Your job was trying to kill you.”
Retirement didn’t just save my health. It felt like finally pulling off the highway, realizing I’d been speeding toward a crash. It rewired my brain. What I had once called “drive” was really just a never-ending sprint toward exhaustion.
While work environments have improved in some ways, the effects of years spent enduring stress don’t just disappear overnight. People like me, who became accustomed to overwork and constant pressure, struggle to recognize what a healthy pace actually looks like.
If you feel trapped in a high-stress career, ask yourself: When was the last time you did something that scared you? What are you really working for? At what point will you have enough? How long can your body sustain this stress? And most importantly, what’s stopping you from making a change?
I wish I had asked myself these questions sooner. But the good news is that not everyone has to wait until their body forces them to stop.
Do you have a story to share about retirement? Contact the editor at akarplus@businessinsider.com.
Irfan Khan/Getty Images
Getting rid of a life’s worth of stuff and shrinking your living quarters isn’t most people’s idea of a good time. But Holly Gates had fun saying goodbye to half of her things.
“I’m probably more of a minimalist than I ever wanted to admit to,” the 75-year-old retiree told BI, “so downsizing was a lovely challenge for me.”
Baby boomers have been getting some of the blame for the shortage of larger homes on the market. Many of them are resistant to downsizing — opting to age in place in homes that have exploded in value. And some who want to downsize are having a hard time finding accessible and affordable retirement housing.
But others have gotten lucky, managing to cash in on the booming housing market and trade in for a home that better suits their needs.
Two years ago, Gates and her husband sold their Oceanside, California, home and moved 40 miles south, where they bought a house for less than half the price and square footage. What convinced them to move wasn’t just a desire to downsize. Not ready for assisted living, but eager for community, the couple wanted to live in a walkable, close-knit place full of active people their age.
That’s just what they found at Laguna Woods, a 55-plus community of nearly 19,000 residents just south of Irvine. They have more than 200 clubs, including for music, astronomy, and Badminton, seven clubhouses for golf and bridge players to gather, several pools to pick from, and a bus system that ferries residents to medical appointments and shops. Gates recently celebrated her 75th birthday with 30 neighbors in a shared event space.
“We’re all in this together, and we watch out for each other,” she said. “The enormity of the pluses outweighs the small things, like an extra bedroom.”
The couple sold their Oceanside home for $1.07 million and bought their current home for $525,000, all cash, according to documents viewed by BI. They have to pay a $1,200 monthly homeowners association fee, which covers their property taxes, water bill, and home maintenance, including recent plumbing repairs and a new roof, Gates said. The co-op model removes much of the burden and liability of homeownership.
Courtesy of Holly Gates
Leaving Orange County, California, wasn’t part of Bruce Levin’s plan. But when he got sick and retired from his 20-year career as a chef for Amtrak, Levin realized he wasn’t up to the task of maintaining his 1950s bungalow with a pool in Buena Park.
It was 2021 and the value of his home of about 35 years had ballooned. So he sold it for $730,000 without making any repairs and moved 200 miles north to Central California to live near his daughter and two grandchildren. Mortgage rates were still low, and Levin, a widower, managed to buy an accessible, single-story home for $335,000 in the small city of Exeter. These days, he rides his electric golf cart to a local senior community for lunch and sees his girlfriend who lives nearby.
Levin is healthier now and misses his old neighborhood and taking advantage of his Amtrak pass to hop trains around the state. But he doesn’t think he can live his old, fully independent life anymore. “I’m not like I was, but I’m okay,” he said. “I’m not pole vaulting, I’m not running a marathon. I walk with a cane.”
He added, “LA has become a very young town.”
Like Levin, Hedy Vahabzadeh, 72, and her husband moved to live near their daughters and grandchildren in retirement. The couple sold their home in Houston in 2017 and moved to the Florida panhandle. The couple managed to find an 11-acre piece of land in Freeport and built a new home. “The property was a steal. It was covered in trees. There was nothing around it,” Vahabzadeh said. But her husband “had a vision.”
Courtesy of Hedy Vahabzadeh
Their Freeport home is one story with just a few steps on the front and back porches. “We built it to be comfortable in our old age,” she said.
These days, the area is a sought-after vacation and retirement destination, and Vahabzadeh feels they got in just before demand for homes there exploded. “It’s a comfortable life,” she said. “We’re not trying to keep up with the Joneses kind of people. And we’ve never been that. So we’re just enjoying ourselves.”
Gates, Vahabzadeh, and Levin all benefited from lucky timing. They bought real estate before the demand for — and prices of — homes skyrocketed amid the Covid pandemic. Levin and Gates managed to cash in on the booming market at a moment in their lives when less home was more.
“I’m thanking God that we did this stuff before all this inflation,” Vahabzadeh said. “We were just fortunate.”
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