When I first spoke to Damien last year, he wasn't having much difficulty secretly juggling three full-time jobs.
Read also in BUSINESS INSIDER
Damien says that on a typical workday he wakes up at 4 a.m., goes to the gym and starts work around 6. Logs in to individual companies at different times, adapting to the three different time zones of his employers. He typically finishes work at all companies around 5 p.m., and despite 11-hour days, he finds the workload usually manageable.
He'd be open to a sixth job, but Damien admits in recent months, after seeing posts on LinkedIn from former tech colleagues about recent layoffs, he began to feel some remorse.
“I don't want to take away all the jobs that are available when there are people who really need them,” says Damien, a millennial living in the Mountain West region of the US. He asked to remain anonymous, and Business Insider confirmed his identity.
Over the past three years, Business Insider interviewed more than two dozen multi-job workers who used the extra income to travel, pay off debt and retire early.
Read also: He was afraid of returning to the office, so he looked for another job. Now he works two jobs
Most of them say the extra money is worth the risk of burnout and career consequencesthough tech industry layoffs and orders to return to offices have limited the number of remote positions they rely on.
Damien talked about how he got his latest position, how he juggles five jobs without getting caught and what his plans are to finally end this stage of his life.
How he went from three jobs to five
In 2021, Damien earned approximately PLN 90,000. hole. per year (approx. PLN 330,000), working remotely in IT support when he received a better offer – PLN 110,000. hole. per year (approx. PLN 400,000) for other remote work. He initially intended to take a higher-paying position, but realized he could do both jobs at the same time and keep it a secret from his employers.
But over the next year, he began to fear that he would be exposed when he noticed that employees from both companies were sometimes attending the same business meetings. In 2022, he resigned from both positions and started a new job, for which he received almost PLN 140,000. hole. annually (over PLN 500,000).
In 2024, he added a second full-time remote IT job with an employer that he believed was unrelated to his other jobs.
In early 2025, Damien won his third job. However, he was still actively looking for new positions in case one of the current ones expired. Nothing came out for a while, which he attributed to the cyclical nature of IT recruiting and the general slowdown in the tech industry.
In September, after about six months of searching, he landed his fourth full-time job. A few months later, he was approached by a recruiter, which led to his fifth job. By March 2026, one of his long-term contracts ended, but he replaced it with another position, keeping his total at five full-time jobs.
Damien says that working multiple jobs completely changed the financial situation of his family and allowed his wife to quit her job. His main motivation is to provide his family with financial security and to become independent from one employer. That fear was especially acute last year, when he struggled to find a replacement for his third job.
— I remember thinking, “Wow, if I were really out of work, it would be six months before anyone would contact me.” – reveals.
It made him feel less guilty about having multiple jobs.
How he juggles five jobs and avoids suspicion
Damien, who has won most of his jobs through direct applications, thinks he can juggle five jobs because his employers overestimate the amount of work his responsibilities require. He understands why some companies reduce jobs to improve efficiency.
— Companies are probably thinking, “We have so many people doing nothing, so we need to be a little more disciplined.” – says.
Damien admits that he was testing whether generative AI tools could help him perform his duties faster, but so far he hasn't found many practical applications. In his opinion, this is due to the large amount of contact with people and the need to practically solve problems in his work.
Although he still fears getting caught, he has ways of avoiding suspicion. He said he created a program that made his computers appear active and delivered high-quality work.
— I just don't give people a reason to feel they have to monitor me – he explains.
Life after working multiple jobs
Damien said he managed to maintain a certain work-life balance because he doesn't work after hours. 5 p.m. and spends the evenings with his family. He usually sleeps about six hours a night – about as much as his body allows him to anyway.
In recent months, however, he has focused more on generating passive income through real estate investments, building long-term wealth and potentially starting his own company. He hopes that thanks to this, he will be able to give up working multiple jobs over time. He added that while the extra money allowed him some luxuries, he eventually “ran out of things to buy.”
— I don't want to work this way for the rest of my life – says.
The above text is a translation from American edition of Business Insider
