Chris Pyle spends the entirety of his workdays wearing a white tank top and boxer shorts, sitting in a recliner.

It’s an unusual setting for a mechanic, but a profitable one. Pyle started answering strangers’ questions about their gas and diesel engines on JustAnswer as a side hustle in October 2006.

It was quickly lucrative: He made $500 in his first month, then doubled it in November, then doubled it again. He quit his full-time $75,000-per-year job at Ford Motors when JustAnswer outpaced his salary in 2012, Pyle says.

Pyle made $170,500 in 2023, an average of $14,200 per month, on JustAnswer, according to documents reviewed by CNBC Make It. His monthly income is more than three times as much as the national median monthly side hustle earnings and mechanic’s salary combined.

The job has also shaped his life: He and his wife bought a 34-acre plot of land for $130,000 in Dickson County, Tennessee, where he lives with his family. Pyle also bought an RV and is building a second home, largely by himself, on the property — all funded by his JustAnswer work.

While he works eight to 10 hours per day, seven days per week, he sets his own schedule, allowing him to be present for his family, he says.

“I was a Cub Scout master for eight years … I was a soccer coach,” Pyle, 45, tells Make It. “I could log off right now and go play a video game with my son, or go swim in the pool.”

Here’s how Pyle built his clientele and stays successful on JustAnswer.

Pyle discovered the side hustle organically: Ford hired and trained him as a transmission tech, and funded his certifications. He was virtually researching how to fix a transmission and found an answer supplied by another mechanic on Just Answer, he says.

He signed up and started answering a handful of questions in the afternoon after work, he says. He liked the challenge of diagnosing a motor he “couldn’t see, touch or smell,” and realized he had a knack for virtually helping people solve their mechanical problems, he says.

After he made $1,000 in his second month on JustAnswer, he took his wife to the mall, gave her half of the earnings and said, “Do not come back with any cash in your hand,” Pyle recalls.

He spent his half in 15 minutes at Bass Pro Shop, he adds.

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As Pyle’s earnings became more consistent, he realized he could use the side hustle to fund more than just mall runs, he says. He started spending more time on the platform. By 2012, he was spending three hours answering close to 40 questions per day, he says.

“For six years, my paycheck was very consistent working here,” Pyle says. “I was like, ‘Well, if I throw in some more hours, that [check] will increase.’”

Pyle’s JustAnswer paycheck remains consistent and has increased every year. He has the most work in the summers, he says, when people are mowing their lawns and traveling.

His schedule remains flexible in that he can log on and off whenever he wants — but because he is paid by the answer, he still has to work at least 40 to 60 hours a week to maintain his income, he says. He works every single day, including Christmas and birthdays.

Pyle doesn’t mind the tradeoffs. His working hours on JustAnswer have helped him build a career, home and life without a boss, he says.

His earnings also support his wife, who quit her nursing job, and their two sons, who she homeschools, Pyle says. While he has to file his own taxes and pay for his family’s medical insurance, he also can write off things like his phone, internet, his HP laptop and 10% of his utilities bill, he says.

There are some cons, though. Despite his 12 years working on the site, Pyle is not an actual JustAnswer employee. The platform reviews its “experts” on a weekly basis, and their grade affects how much they make per answer. The company does not openly share the criteria, but Pyle says his answers and customer service skills usually receive a high rating.

Still, he has no plans to drastically change his day-to-day work, he says. Once Pyle’s house is finished, he wants to cut back on his JustAnswer work, but he’ll likely still be online at least 30 hours per week, he says.

“I have zero plans to go back for a real job, unless I’m the boss,” Pyle says. “Between my work attire and the environment that I work in, [life] is pretty good.”

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Jessica Jackson was afraid of heights when she first started her job as a wind turbine service technician — now, she spends most of her days working 300 feet in the air.

Jackson, 37, is a technician at Vestas, a wind turbine manufacturer, in Bee County, Texas, and earns $73,000 per year.

Climbing the turbine tower “isn’t as scary as you’d think,” she tells CNBC Make It. The tallest turbine on the wind farm Jackson works on is about 350 feet above the ground. It takes her less than 10 minutes to get to the top.

“Once you’re up there, you get to see the best views: You’re watching birds fly, eagles, hawks,” she says. “You get to see planes fly by. You get to see as far as you can see. It’s beautiful.”

Jackson has one of the most dangerous jobs in the world. The Labor Department reports that wind turbine service technicians have one of the highest rates of injury and illness of all occupations.

It’s also the fastest-growing job in the U.S., with employment in the sector expected to almost double over the next decade.

“Working in this field is hard, but it’s rewarding,” says Jackson. “I love what I’m doing, so it makes the job not seem like a job as much.”

Here’s how Jackson earns $73,000 a year as a wind turbine service technician in Texas.

Before she became a wind tech, Jackson was a stay-at-home mom for 10 years.

After she and her husband separated in 2019, when her youngest child started school full time the following year, Jackson decided to return to the workforce. But she was worried her opportunities — and earning potential — would be limited without a bachelor’s degree.

DON’T MISS: The ultimate guide to acing your interview and landing your dream job

She enrolled in college online part-time in 2017 but didn’t finish her bachelor’s degree in environmental science from the University of Arizona until 2022.

“Not having a college degree [yet] and being a single mom was hard,” says Jackson, who has four children between the ages of 10 and 21. “I was getting passed up for jobs that I had the experience and skills for only because I didn’t have that degree.”

Jackson’s ex-husband was working as a wind tech and recommended her for a job at Blattner Energy, a renewable energy contractor in northern Texas, installing tower wiring.

While you don’t need a bachelor’s degree to become a wind turbine service technician, some jobs might require you to complete a 2-year technical program or apprenticeship. Others, like Blattner Energy and Vestas, will provide on-the-job training for new hires.

Vestas’ training covers best practices for the turbine’s electrical equipment, technical procedures like bolt torque and tensioning as well as first aid and safety protocols.

Jackson quickly fell in love with the hands-on aspects of servicing the turbines, the quiet peace of working in the wind.

“It felt good knowing that when a turbine was fixed or ran more smoothly, you did that, just seeing the immediate results of your efforts,” she says.

Working in a field that aims to help the environment was another perk that attracted her to the job.

“Wind turbines produce clean energy that goes to a grid, which then powers your homes, businesses, cell phones, TVs .. it’s awesome,” says Jackson. “I tell my kids all the time: Do something you love, but also do something that helps others and helps the environment.”

That job introduced Jackson to Vestas, where she started working in February 2020.

Jackson gets to work at 7 a.m. and ends her shift by 5:30 p.m. She works five days a week.

Every day on the job is different but starts with a problem.

“What I’m working on changes every day depending on what error code, or problem with the turbine, you’re coming in to,” Jackson explains. “The wind turbines are smart, they’re basically computers and constantly communicating to us what is going on with them.”

Comparable to cars, wind turbines have sensitive electronic systems, generators, pumps and other critical components that are susceptible to freezing or breaking down. Jackson’s job is to inspect, maintain and repair such parts as needed to keep the turbines running and producing power.

Vestas has 66 turbines on the farm where Jackson works. She’s typically responsible for one turbine per shift, but some days, it could be several.

The hardest part of her job is the climb. Jackson has to scale a narrow, metal ladder inside the turbine and pull herself through a hatch at the top to access the turbine’s nacelle, which sits atop the tower and contains the machine’s main parts. It’s a vertical climb nearly 30 stories tall.

“Cutting any corners with safety could be the reason why I don’t go home that day,” says Jackson, who wears gloves, glasses, a helmet, harness and other protective equipment on the job. “Once you’re up there, you’re in your office and ready to work. Everything else is easier.“

She might have been scared of heights when she first started, but after practicing the same climb nearly every day, sometimes multiple times in the same afternoon, Jackson says she started to trust her equipment and “got a lot more comfortable climbing such high heights.”

Jackson plans to work as a wind turbine service technician until she retires in her 70s, if not sooner.

The job might be physically demanding, but Jackson says spending so much time outside on the farm — and climbing the towers — has helped her feel “stronger and healthier.”

She’s working toward getting promoted to a level-three technician at Vestas, a role that pays about $80,000 a year, then will train to become a lead technician after that, a role that pays about $100,000 a year.

“Having this job has given me financial stability and freedom, enabling me to afford activities that will make my children happy, like signing up for a basketball league, while still saving money every month,” she says.

As Jackson continues to climb the ranks in her career — both literally and figuratively — she hopes more women and non-degree holders will join her field.

“I’m extremely grateful for my job, I love what I do,” she adds. “If I was doing something else, I probably would not be as happy.”

Do you have a creative or nontraditional career path? We’d love to hear from you! Fill out this form to be considered for a future episode of “On the Job.”

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Kristen Faulkner ended a 40-year-drought for the U.S. in the Paris Olympics — in a sport she picked up for fun six years ago.

On Sunday, the 31-year-old became the first American rider to win gold in the women’s road race since Connie Carpenter did so in the 1984 Los Angeles games. 

Faulkner grew up hiking and rowing in Homer, Alaska, a small city on the Kenai Peninsula, and joined the women’s crew team at Harvard University, where she graduated in 2016. 

She didn’t start competitive cycling until 2017 when she moved to New York to work as a venture capitalist. 

“I still needed that outdoors fix that was such a big part of my life,” the Olympian told NBC News in a recent interview.

Faulkner wasn’t even supposed to compete at the 2024 Paris Olympics but was called up to Team USA in early July after Taylor Knibb resigned her spot in the road race to focus on the Olympic time trial and triathlon events. 

“This is a dream come true,” she told reporters after the race. “I’m still looking at that finish line sign wondering how my name got there.”

Faulkner signed up for an introductory clinic for women’s cycling in New York City’s Central Park and by 2020, she was racing for Team TIBCO-Silicon Valley Bank, then the longest-running professional women’s cycling team in North America. 

In early 2021, she quit venture capital to commit to the sport full-time — a move that she assumed would be a brief detour from her career. 

“I was like, ‘This will be a two, three-year thing,’” she told the Wall Street Journal. 

Instead, Faulkner, who now rides for the American Continental Women Team EF-Oatly-Cannondale, said she’s developed an even deeper passion for the sport:  the competitiveness, the camaraderie with her teammates, even the constant grind of training. Faulkner, who now lives in San Francisco, rides around 50 miles a day. 

She told the Associated Press that her career as a venture capitalist has been instrumental in her success as a professional athlete.

“I learned how to calculate risks and assess risks,” she said. “In a race I take that mindset with me: What is the risk-reward ratio? Knowing when to go all in.”

Faulkner almost didn’t make it to the Olympics. 

Last year, she was struck by a car while on a training ride in California, and fractured her shin bone — an injury she feared would end her cycling career, she told the Wall Street Journal. She took a break from riding for about three months. 

“I said I’d only do the road race if I felt strong and felt I had a chance of a medal,” Faulkner told the Associated Press. “I knew that it would be a really tough race but if I was racing, I was racing to win. That was a promise I made to my team pursuit teammates.”

The 98-mile road race starts and finishes in Paris, stretching along several hilly routes and ending at the Trocadéro, with the River Seine and Eiffel Tower in the background.

She’s mentioned in several interviews that her Alaskan upbringing instilled in her the strength and resilience she needed to overcome that injury and trust herself to compete on a global stage. 

“It’s never a matter of if I’ll keep going, it’s just a matter of how,” Faulkner told NBC News.

Now, Faulkner is aiming for her second Olympics medal — in team pursuit, where she will race on a track with three of her U.S. teammates against cyclists from other countries. The event begins Tuesday with qualifying.

Her gold medal win, although unexpected, is a childhood dream fulfilled for Faulkner, who has said that she’s wanted to compete in the Olympics since watching the Sydney 2000 Games at home.

“I thought it was an amazing thing to see,” she said in an interview with Global Cycling Network back in March. “At that moment, it became my life goal to go to the Olympics.“

She continued: “It’s never been about reaching a certain level of credibility in the sport, it’s been about that little girl inside of me and what dreams she had when she was a kid.”

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Earlier this year, Sam Dogen quit his job.

For most people, that wouldn’t be much of a story, but for the millionaire founder of Financial Samurai, a couple of details stand out.

For one, it was his first gig since 2012.

Dogen, 47, has lived as a retired, stay-at-home dad since 2012, boosting his annual passive income to about $380,000 by 2023 through a mix of stocks, bonds, real estate and other investments. He returned to work late last year after selling a big chunk of his portfolio to fund the purchase of a new home.

That he stayed only four months at the new gig is its own story — but it’s also worth noting that by leaving so abruptly, he bucked a piece of his own advice: “Never quit your job,” Dogen says. “Get laid off.”

That’s what Dogen did more than a decade ago. Rather than leaving, he engineered a layoff that netted him three months of his base salary plus a low six-figure severance check. That money, combined with the $80,000 a year he was earning in passive income at the time, allowed him to transition into early retirement.

If you’re considering leaving your job, here’s Dogen’s best advice to follow in his footsteps.

How you manage leaving your job is going to depend on your specific circumstances. For Dogen, 2012 marked the end of his rope after 13 years in the investment banking industry. He’d built enough passive income outside the office to feel comfortable leaving, and he knew he wanted to go.

DON’T MISS: Achieve Financial Wellness: Be Happier, Wealthier & More Financially Secure 

He also knew the kind of power he wielded as an employee on his way out the door. “As a previous boss myself, the worst thing that can happen is when an employee of value quits and gives you two weeks notice or less,” he says.

Here’s how to leverage that power into the job departure you want.

Communicate your unhappiness

Get the ball rolling by letting the right people know that you are unhappy with your current role, Dogen says.

“You basically have to talk to HR or talk to your direct supervisor, say, ‘I’m not happy here, I’d like to make some changes,’” he says. “Ultimately, I’d like to leave if these changes are not met.”

In doing so, you create a win-win situation, Dogen says, because there’s a chance that your superiors are willing to meet your needs.

“They might give you a raise. They might give you more flexible hours. Sweet!”  he says. “No employer wants someone whose heart is not in it anymore.”

Offer to ease the transition

If your company can’t meet your demands, pivot the conversation toward the possibility of you leaving while making life easy on your employer.

“Let’s figure something out,” Dogen says you might say. “I’m willing to stay as long as possible to help make the transition. But in light of that, let’s talk about a severance package.”

Dogen stayed on for two months after having this conversation with his boss in 2012, spending that time training his junior hire and introducing him to his clients.

If you’re willing to do something similar, “more often than not, your employer will work with you — especially if you’re a better than average employee,” Dogen says.

Negotiate a layoff

Ask if your company is planning on doing a round of layoffs, and if you can be included. Under the WARN Act, companies with 100 or more employees (fewer in some states) must provide 60 days warning before conducting a mass layoff. In lieu of that warning, firms owe compensation to the affected employees, generally equivalent to 60 days of base pay.

On top of any WARN Act pay you may receive, Dogen suggests negotiating further for a severance payment. “The standard is one to three weeks of pay for every year served,” he says.

And negotiating a layoff, rather than quitting, goes beyond a cash payout, Dogen says.

“If you get laid off, you get unemployment benefits. You get a severance package, deferred comp, subsidized health care. You get tons of stuff that gives you a huge financial runway for your next endeavor.”

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Ramit Sethi, self-made millionaire and star of Netflix’s “How to Get Rich,” says that renting is unfairly dismissed as “wasting money” because “it’s going to a landlord” rather than building wealth.

But when you pay rent, “you’re not throwing money away,” Sethi tells CNBC Make It. “You’re paying for a roof over your head. You’re paying for a landlord to maintain your residence and you’re paying for the convenience and flexibility of being able to leave at the end of your lease.”

When looking at homes as an investment, renters commonly overlook the “phantom costs” of owning a property beyond the monthly mortgage payment.

This includes closing costs, property taxes, insurance, utilities, homeowners association fees and repairs. Mortgage payments are also front-loaded with interest, often as high as 80% during the first few years of the loan.

“People say they don’t want to throw money away on rent,” Sethi says. “Well, I don’t want to throw money away on interest.”

Sethi has rented homes in expensive cities like Los Angeles and New York simply because the costs of owning were too high. 

“I’ve made more money renting than I would have owning,” he says, referring to investments made with money that could have been spent on a down payment and phantom costs for units similar to the ones he rented.

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That doesn’t mean that buying a home can’t be a good investment, he says. Considering that home values have increased by 85% since 2010, many Americans have built wealth by owning a home.

However, we “have become accustomed to irrationally high appreciation in real estate markets,” especially during the run-up in home prices after 2020, says Sethi. This can lead people to assume that owning a home is the best way to build wealth, even though stocks have historically outperformed home prices.

“If people believe that a housing shortage will cause higher prices for decades, that’s a perfectly respectable bet to make,” he says. “But you also need to calculate your alternatives. How much would it cost to rent and invest differently? How much capital would be tied up in a down payment?”

There are lifestyle considerations that go into buying a home, too. Those could include a number of things, such as expecting to move within a few years, needing a bigger place for a family, wanting to change neighborhoods or simply needing the “flexibility to switch jobs at the drop of a hat and increase your income,” says Sethi. In that case, renting might be a better fit because it keeps your options open.

In Sethi’s experience, homebuyers don’t always examine the opportunity costs of acquiring property, especially once they’ve decided that they want to own their own home.

That’s because homeownership is viewed as a major achievement and a key part of the American dream, something “deeply embedded in the American psyche,” he says. This can lead to shortsightedness about a property’s true value compared with other investments, like 401(k) plans or stock index funds.

“I speak to couples that often tell me that the money in their retirement account does not feel real. They’ll say, ’I mean it’s there. But I can’t really touch it [like a home],” says Sethi. “There’s something mesmerizing about about a physical thing that we can see and touch.”

Since purchasing property is one of the biggest decisions that people will make in their life, Sethi advises buyers to “carefully run the numbers,” including phantom costs, before they make a decision.

“The American dream is not simply buying an expensive purchase that represents over 100% of your net worth and drains your finances because of phantom cost that you didn’t predict,” he says.

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