• Erik Boquist, 27, has made a side gig out of helping older adults improve their tech skills.
• He charges $50 an hour, offering personalized guidance.
• Boquist said he enjoys the work because the older people he helps are grateful and "so sharp."

This as-told-to essay is based on a conversation with Erik Boquist, 27, who lives in Sutton, New Hampshire, and travels the US and beyond working as a house-sitter with his girlfriend. Boquist also does video editing. His latest side gig is showing people, many of whom are older, how to level up their tech skills. Business Insider has verified his identity and that Boquist has earned money from these efforts. The following has been edited for brevity and clarity.

I started thinking about training baby boomers on technology because of the simple tech tasks my mom needs help with and because I saw glimpses of my dad's workflow. Those were huge revelations.

It was everything from how they email, surf the web, and watch videos on YouTube. There might be simple things they don't know about, like changing the playback speed or using the arrows to go ahead or back five seconds.

My mother lives in a 55-plus community, and one day, after helping her, she said, "Erik, you should be doing this for everybody here."

Boom. She was right. If I'm going to help the community as much as possible, I just have to let people know I would be willing to talk with them.

My role is often vetting what they're hearing and then making money off researching it and determining if it's legit.

Other times, it might be simple things like someone wanting a box of markers to do crafts. I ask whether they've thought about Amazon and whether they have an account. If not, I might help them set it up.

I want the people I'm helping to realize that — whether they're able-bodied or not, they just need to be able to use their fingers. Dude, they're so sharp. You talk to somebody who's 80 years old — I'm not going to generalize, but I'm going to generalize — they can do what younger people can do on computers. I don't want older people's voices to be lost, the wisdom to be lost. I want them to express themselves.

I've been doing this for about six months. One of the things I'm working on now is digitizing the journals written by a woman's brother who passed away. The journals span decades.

She wants to get them into a PDF that can be shared with his friends. We're also thinking of using AI to create an audio recording of the entries. This can bring more remembrance of her brother's life and experiences because they're fascinating stories, and his voice is so interesting. Once it's digitized, she can even then play with text and make songs from the journal entries using AI.

That's why I sit down with people, usually IRL, and ask, "What do you want to do? What have you heard that interests you?"

Outside my parents, the first person I helped was my neighbor, who I always saw walking her dog. I was chatting with her, and she shared that she couldn't listen to audiobooks at night, which she had liked to do, because the battery on her phone kept dying.

I went on YouTube and used various search engines. The question became, "How do I replace a battery for an iPhone 7?" She's using an older phone, but it works for her. I'm not trying to sell her on a new one. Some of the reviews on battery-replacement kits were that the battery died 30 days after they were replaced. So, I suggested she avoid one seller, who was cheaper, and maybe go with an authorized battery replacer, who was $90. She said, "Oh, that's so great to know all this. Thank you so much. Let me pay you for this."

I told her no because it was a great lesson for me. That was the start of realizing, "Wow, that took me about 15 minutes." Then I shared all that with her in about 60 seconds, and it seemed to really impact her.

The business is essentially demystifying tech and bringing more knowledge to people.

It's been a great addition to my workflow. In recent months, I had three consistent clients. We talk about an hour at a time. It's not a 40-hour workweek by any means, but it's meaningful. So it's been four to 12 hours a week since I started, and I love it.

My fee is $50 an hour, and I haven't had the heart to bump it up. People are OK paying for it. Those who have called have been so enthusiastic. They're like, "Oh my gosh, I wish that somebody had been doing the sooner."

Every client surprises me. Someone might say something like, "I hear Bluesky is the opposite of X." Just hearing that brought me to dive deeper into that comparison. It's fascinating.

My girlfriend and I are heading to Seattle soon to house-sit for a family with a pair of beagles. We've been doing it for a couple of years now. There are coffee shops a two-minute walk from the place. I'll put up flyers there and at the grocery store, and we'll see what rolls in.

I've had sessions on FaceTime, but when I'm in person, people seem more likely to ask if I can come back the next week. Then, one of the things we work on is to go from cash or check to Venmo.

• A millennial is on track to earn about $368,000 this year juggling three full-time remote IT jobs.
• He feels no sense of guilt or loyalty to his employers because he could be laid off at any time.
• He said he's spent the extra income on travel, food, and furniture.

Damien doesn't think his employers would be thrilled to learn he's secretly juggling multiple jobs, but he's not losing sleep over it.

"As long as I'm doing my job and what's asked of me, I don't feel any guilt for it at all," said Damien, whose identity was verified by Business Insider but who asked to use a pseudonym, citing fears of professional repercussions.

He added that he feels no sense of loyalty to his employers because he doesn't believe they'd protect him from a layoff. "They can let you go at any point," he said.

Damien, who's in his 30s and based in the Mountain West, is on track to earn about $368,000 this year from his three IT support jobs. Damien is among some of the Americans who have secretly juggled multiple remote roles to more than double their incomes. Over the past two years, BI has interviewed more than two dozen "overemployed" workers who've used their extra cash to travel the world, buy weight-loss drugs, and pay down debt.

To be sure, holding multiple jobs without employer approval could have professional repercussions and lead to burnout. But many job jugglers have told BI the financial benefits have generally outweighed the downsides and risks.

For Damien, the additional income allowed his wife to quit her job while she plots her next career move. Damien has also spent his earnings on furniture, restaurants, and travel.

"I was at a point where I had so much cash, I didn't even know what to do with it," he said.

Gaining confidence in job-juggling

Last September, Damien started a full-time contract role that paid about $150,000 annually, which he worked in addition to his primary job — which paid about $140,000. Damien recently landed a third full-time contract job that will pay him roughly $78,000 between his start date this month and the end of the year, when his contract comes to an end. He plans to keep all three jobs and boost his income further through some part-time work for two other employers.

"I just have a hard time saying no, because I feel like if I could squeeze it in, then why not?" he said.

Damien first tried job juggling in 2021. He was making $90,000 annually working one IT support job and when he landed a new IT position that paid about $110,000, he initially planned to take the higher-earning role. But then he thought about how much free time he had during the workday: his workflow could be so slow that he'd sometimes go to the gym or run errands.

He held both jobs for less than a year, then stopped juggling when he accepted a new position that paid about $135,000 annually.

One of the factors that prompted him to initially give up overemployment was that the two companies he worked for were in the same industry. Damien said there were some "close calls" where he was invited to meetings for his "job A" that included some people who worked for his "job B" employer.

"Any one of them could have looked me up and immediately seen that I also still worked at 'job B,'" he said, adding, "It was just a little too close for comfort."

Around June 2023, Damien became more confident in his ability to juggle multiple jobs undetected and took on some contract work as an IT consultant. Last September, he started a second full-time job.

He doesn't feel guilty about job-juggling

Between his two jobs, Damien said he doesn't work more than 40 hours a week on average, and he's hopeful that this will continue once he starts his third job. He said he's fortunate not to have many meetings but occasionally has two that are scheduled at the same time. When this happens, he uses two sets of headphones simultaneously: AirPods in one ear and over-ear headphones on the other.

Looking ahead, Damien said he plans to continue working multiple jobs as long as his work hours remain manageable. While remote roles can be very competitive among applicants amid companies calling workers back to the office, he's continued to have success securing these types of roles.

"I figure I'll do it as long as I don't feel like it's negatively affecting my life," he said, adding, "I have the time. What else am I going to do?"

Do you have a story to share about secretly working multiple jobs or discovering an employee is doing so? Contact this reporter via email at [email protected] or Signal at jzinkula.29.