I Spent Less Than $500 Last Year for Housing–All While Living in Some of the Most Expensive Cities in the U.S.

Lori Anderson’s 2021 divorce gave her a green light to make a change she hadn’t realized she was ready for. 

The long-time Boston suburb resident gave herself permission to travel, departing for Colorado immediately, just for a change of scenery. 

But she realized quickly that although the divorce had left her with “a chunk of money,” it was “not enough to live on.”

She returned to Boston, got a job, and started pet sitting for friends to make extra cash, often $80 a night per pet. As her apartment lease neared completion in June 2022, she happened to go for a walk with a friend, who asked her if she had ever heard of Trusted Housesitters. 

She hadn’t, but went home, hopped on the site, and a whole new adventure began.

House sitter for hire

The site connects pet sitters with pet owners. Sitters apply for sits, ranging in duration from days to months. Pet owners can interview candidates, then select a sitter who will stay in their home. Both pay a membership fee to the site, but no money is exchanged between homeowner and pet sitter.

Anderson, 63, liked the idea of using Trusted Housesitters as a means to explore Maine, Vermont, and New Hampshire–all states she was considering moving to. 

Right away, she found a six-week sit in the tourism hotspot of Stowe, VT. Fifteen people had already applied, and she was hesitant to spend $120 joining the site if she wasn’t going to get a gig.

She slept on it and, in the morning, completed her profile and applied. “Within an hour, he responded,” she says of the pet owner. “He said I was exactly what he was looking for.”

The owners were a couple in their 50s and had mainly received applications from twentysomethings who, they said, were “just looking for a place to crash so they can play.” This couple saw Anderson’s age and that she had owned three homes, raised two kids, and was now an empty nester with no pets.

“Once I got that sit, I thought, OK, I am going to do this,” she recalls.

The next stay was a cat sit for five months, November to April, at a Christmas tree farm in New Hampshire. Cats require less care, which allowed Anderson to frequently hike the White Mountains.

“It was unbelievable.”

A new lease on life

Initially, Anderson thought she would be a pet sitter for a few months. But one trip led to another. For the next two years, from June 2022 to March 2024, she did 17 sits in Massachusetts, Vermont, Maine, New Hampshire, California, Washington state, and Vancouver Island British Columbia.

Along the way, she learned she could be picky. She doesn’t choose sits with more than two dogs and avoids pet owners who have no reviews on the site. She describes herself as very clean and only wants to stay in well-kept homes.

“If any reviews say the house is just a little dusty, I avoid those, as that means it’s probably more than just a little dusty,” she says.

After two years of traveling, she wanted a break, returning to Boston—and steady employment.

“In two months, I was sick of it,” she says. Morning walks became uninspired, always around “the same reservoir.”

She realized quickly how much she values novelty. She spent 14 months—April 2024 to June 2025—in her hometown, which allowed her to spend every Sunday with her mother, 87, and also time with her son.

“I wasn't miserable—I just knew this wasn't the lifestyle for me,” she says.

She also couldn’t justify the numbers. She was spending 35 hours a week inside working, and “wasn’t making enough to pay my bills.” She didn’t have any streaming services, debt, or anything extra—just rent, food, and phone.

Come June, nomadic life beckoned once more.

A new routine—and reality 

In the last year, she has completed another 18 sits in Massachusetts, Maine, New York, California, Washington state, Florida, and Colorado.

In the last 365 days, she spent 286 nights at 17 pet sits for 21 pets, 40 nights split between house stays with 11 friends and family members, and 34 nights camping at 17 campsites. She has been living for free, paying only $494 for five nights of accommodation in the past year.

Most of the house stays have been easy, aside from one where she broke her own rules because the dates lined up with what she needed. The sit was three weeks in Seattle, for one cat.

“I didn’t love the pictures [of the home], and they had only two reviews,” she says. Nor did the family interview her. She applied, and they immediately accepted—no questions asked.

She arrived and found that the bathroom in the photos was not the one she was allowed to use. The family had posted a photo of the primary bathroom, which they had locked off during her stay. The available bathroom was tiny, so much so it was difficult to turn around in the shower.

“It was worse than camping,” she says.

The family had also cropped a photo from a balcony to highlight a Space Needle view. They had strategically removed the highway from the photo, so it came as a surprise that the home had freeway noise.

Hardest still, Anderson realized only upon arrival that the listing had not included any photos of the living room. She arrived to find no couch, just a mattress on the floor with pillows. The kitchen had wooden chairs, but those were the only place to sit in the home. 

She completed the sit and left an honest review.

“I started with the positive—that the cat was great and the couple was nice. Then I said here are three things that bothered me, but they might not bother you. One was the very small bathroom, one the highway, and the last was that there was no comfortable place to sit.”

Anderson was already at the next home in Tofino, on Vancouver Island, and had already received a five-star review from the family when the homeowner read her review of him. He immediately messaged her on Whatsapp.

“He said he was furious. He said they came back to the messiest house and that it was so bad they had to pay a cleaner $300. He said there was cat poop all over the floor.”

Anderson was shocked. But, back when she started, she got into the habit of recording videos of the home and pet when she left, proving the health of the animal and the state of the home.

She messaged the man back, saying she was sorry he felt that way. She also let him know she had filmed a video of the home and the cat right before she left.

He never replied. It was a minor setback, and hasn’t changed her love of the platform.

Right now, Anderson is taking another break, staying in California for a few months to help her son and his wife, who have a newborn.

She doesn’t know how long she will stay, and that’s part of what she loves about this lifestyle—the freedom.

With housesitting, she is “outside all day, not in front of a computer.” She is “not bringing money in, but my output is so little.”

She recognizes that with her savings, it would be foolish to travel Europe in the traditional way, paying for hotels or other accommodation. This way of traveling allows her to live out her version of retirement, traveling the country cheaply, doing more with less.

“It has really been a gift,” she says.