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.

DON’T MISS: The ultimate guide to earning passive income online

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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European workplaces are known for having generous paid time off policies, some of which encourage taking weeks at a time away during summer.

Embracing that mindset was a big transition for Alex Ingrim, 36, who grew up in the U.S. but has spent the last 17 years living and working across France, the UK, Malta and now Italy.

“I’ve grown up with the American perspective that your career is really important,” Ingrim tells CNBC Make It. “And then I’ve worked within European companies where they encourage: Hey, make sure you spend time with your family. Take all of your holidays — don’t leave holidays on the table just to show that you’re a hard worker. That’s not going to get you anywhere here.”

Leaving lots of vacation days unused is “not respected or valued,” he adds. “You just look like someone who is not taking enough time off.”

Ingrim has worked for financial service companies across Europe, which typically provided 25 vacation days per year on top of around 10 public holidays.

He’s currently the president and co-founder of Chase Buchanan USA based in Florence, where he provides financial guidance to roughly 70 clients on moving from the U.S. to Europe.

Helping clients adjust to a new work culture comes with the territory. One thing Ingrim often tells clients is that discussing work in social settings isn’t as common.

“If you go to a party in the U.S., one of the first things people do is ask each other what they do for work,” Ingrim explains. In Europe, “I’ve been at parties for three hours, and I don’t know what anybody does for a job. We have neighbors [and] I have no idea what they do for work.”

Work is a small part of your life and identity, Ingrim says: “You talk about other things at parties that are usually a little bit more interesting, like food or vacations or sports, whatever it may be — but you talk about your interests personally, not what you’re doing at work.”

The social norm reflects an overall culture that prioritizes life outside of work more so than the typical U.S perspective.

“It’s not as culturally acceptable to put your career ahead of your family and other priorities in life” like hobbies, travel and other pastimes, Ingrim says.

Overall, he says he’s happier living in Italy than in the U.S. He started his time living internationally when a college study-abroad trip to France led him to meet his wife, Louisa. Deciding to live in Europe to be together “was a great choice,” he says.

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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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In February 2024, I returned home to Los Angeles after the adventure of a lifetime: exploring 18 countries across South America and Asia in 18 months on a trip that cost me $34,000. I had quit my dream job as a video journalist to heal my burnout and find happiness beyond traditional measures of success and prestige.

When it was over, I went from chasing waterfalls in Indonesia and whizzing through the rolling green countryside of Vietnam on a motorbike to staring at my computer screen at home, watching the job rejections roll in. 

In some ways, I felt more lost than ever.

I’d jumped back in the job market at a particularly tough moment, as thousands of journalists were getting laid off. The future of my career and income were uncertain. That’s a scary feeling at 34, when you often feel pressured to buy a house, have kids, and save up for retirement.

These circumstances would have made me unhappy and ashamed a few years ago. I no longer had the cool job or the epic, Instagrammable life around which my self-worth used to revolve. Instead, I was home and unemployed.

But my sabbatical taught me four key lessons about happiness that helped keep me positive, confident, and self-assured despite the challenges.

For years, I thought working my dream job would bring me the ultimate happiness. But I couldn’t shake the burnout and anxiety. 

Then I thought going all in on travel — the thing I’m most passionate about — would fulfill me. But eventually, the novelty wore off. Exhausted from constantly being on the go, I longed for the comfort and stability of home. 

I realized that I won’t find lasting happiness unless I’m living a life balanced between adventure, rest, productivity, and learning.    

Now that I’m home, I have new career and financial goals. A few years ago, I would’ve sacrificed everything to achieve those, while applauding myself as a go-getter and a hustler.

But now I pace myself and do my best to maintain a personal life and gym and meditation routine. I’m enjoying the journey instead of racing to a finish line that probably wouldn’t be everything I imagine it is. 

I never felt like I had enough success or money while living and working in Los Angeles and New York City. But in South America and Southeast Asia, where I encountered mind-boggling levels of poverty, I realized how privileged I am.  

Even many average neighborhoods didn’t come close to my standard of comfort. A lot of the locals I met had never left their country because they couldn’t afford it.

I realized that as an American renting an apartment in LA, I live an unfathomably luxurious life compared to much of the world. 

While freelancing and job hunting in a very difficult market, I was tempted to slip back into feelings of inadequacy. But the perspective I gained while traveling reminded me that I already have — and am — more than enough. 

Before returning home, I spent nearly two months in Bali. I found true work-life balance and a magical, extravagant, free-spirited lifestyle I’d never experienced.

I began freelancing and applying for jobs from beautiful cafés and restaurants, while enjoying a slower pace of life, surrounded by lush nature and stunning views. 

A few years ago, I felt like I needed a big brand-name employer to define my value. I would have despaired at the rejections and lack of opportunities. But my experience in Bali inspired me to value well-being over prestige and money. I saw what life could be like, and it had nothing to do with a dream job. 

I decided to stop burning myself out trying to force my way back to a “perfect role.” Instead, I would pursue a job that offers flexibility and quality of life, while channeling my passion for video journalism into becoming a creator with my own YouTube channel.

I went from feeling helpless to empowered.

My sabbatical was partially inspired by the travel influencers I followed on Instagram. I was jealous — my life felt lame in comparison to the epic, picture-perfect lives they seemed to lead. 

But behind the scenes, globetrotting is a lot messier. You don’t see the burnout, fatigue, loneliness, and sadness many travelers experience.

After realizing firsthand that nothing is as glamorous as it seems, I stopped aspiring to be like others and began to prioritize my own needs. I decided to sleep in and relax at cafés in Cartagena, for example, instead of hustling to embark on a Caribbean island boat tour I didn’t really want to take. I don’t regret it.

Nowadays, I spend most of my time working on my computer, going to the gym, running errands, and seeing friends and loved ones in low-key places. There’s barely any fodder for Instagram posts. 

I see others leading more outwardly enviable lives, personally and professionally. I’m happy for them, but I don’t feel bad about myself. I know I’m exactly where I need to be — no matter what it looks like to anyone else.

Helen Zhao is a former video producer and writer at CNBC. Before joining CNBC as a news associate, she covered residential real estate for the LA Business Journal. She’s a California native and a proud USC Trojan and UCLA Bruin. 

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