When the pandemic locked the world indoors, most people struggled to balance work and home life. But for Jessica Winder, a 37-year-old HR executive from Las Vegas, it became the perfect opportunity to pull off something extraordinary. As reported in Business Insider’s as-told-to essay, Winder took on two full-time remote HR jobs simultaneously in 2020 — and managed to save over $100,000 (around ₹88 lakh) within a year, all without anyone finding out.
Her reason was simple but pressing: she wanted to clear her credit card debts. “I already had one job going into the pandemic, and I decided to pick up a second. With nowhere to go and nothing else to do, I figured — why not?” Winder told Business Insider .
The secret hustle
It started as a short-term plan. Winder promised herself she’d juggle both jobs for 90 days, just long enough to pay off her dues. But once she realized no one noticed, her goals expanded — from clearing credit cards to saving for her wedding, honeymoon, and even her relocation to Las Vegas.
Both jobs paid six figures, and since she kept her lifestyle modest — same car, same apartment, minimal indulgences — her savings multiplied rapidly. “I didn’t change my lifestyle at all. Besides eating out more often, everything else went straight to savings,” she said.
The chaos behind the calm
Behind the scenes, her double life was far from easy. As a senior HR professional, she managed meetings, projects, and communication across two companies daily — sometimes even at the same time. “One day, I had to be in two meetings simultaneously. On one laptop, I had the camera on; on the other, I stayed muted and off-screen,” she recalled.
Her days stretched from 8 a.m. to 8 p.m., filled with meetings, emails, and after-hours catch-up work. The constant switching left her drained and anxious. “Even now, I keep Slack notifications off because the sound still gives me anxiety,” she admitted.
Learning, earning, and outsmarting the recession
For Winder, the experience wasn’t just about the money. It became a form of career insurance during uncertain times. “During the pandemic, a lot of my friends got laid off. I thought, if one job lets me go, at least I’ll still have the other. It felt recession-proof,” she told Business Insider.
The double employment also became an unexpected career accelerator. One role focused on employee training, while the other specialized in workplace relations — giving her practical exposure across two distinct HR domains. “That kind of cross-training just doesn’t happen in one job,” she noted.
The breaking point and the lessons learned
After a year of 12-hour workdays and endless meetings, Winder finally decided to quit her second job. She had cleared her debts, built a substantial financial cushion, and tested the limits of her endurance.
Looking back, she says she wouldn’t repeat it now that she has children. But for someone single and ambitious, she admits it can be worth it — if done responsibly. “You could have 10 jobs if you’re willing to get the work done,” she said, while warning that discovery could lead to being fired from both roles.
Her reason was simple but pressing: she wanted to clear her credit card debts. “I already had one job going into the pandemic, and I decided to pick up a second. With nowhere to go and nothing else to do, I figured — why not?” Winder told Business Insider .
The secret hustle
It started as a short-term plan. Winder promised herself she’d juggle both jobs for 90 days, just long enough to pay off her dues. But once she realized no one noticed, her goals expanded — from clearing credit cards to saving for her wedding, honeymoon, and even her relocation to Las Vegas.
Both jobs paid six figures, and since she kept her lifestyle modest — same car, same apartment, minimal indulgences — her savings multiplied rapidly. “I didn’t change my lifestyle at all. Besides eating out more often, everything else went straight to savings,” she said.
The chaos behind the calm
Behind the scenes, her double life was far from easy. As a senior HR professional, she managed meetings, projects, and communication across two companies daily — sometimes even at the same time. “One day, I had to be in two meetings simultaneously. On one laptop, I had the camera on; on the other, I stayed muted and off-screen,” she recalled.
Her days stretched from 8 a.m. to 8 p.m., filled with meetings, emails, and after-hours catch-up work. The constant switching left her drained and anxious. “Even now, I keep Slack notifications off because the sound still gives me anxiety,” she admitted.
Learning, earning, and outsmarting the recession
For Winder, the experience wasn’t just about the money. It became a form of career insurance during uncertain times. “During the pandemic, a lot of my friends got laid off. I thought, if one job lets me go, at least I’ll still have the other. It felt recession-proof,” she told Business Insider.
The double employment also became an unexpected career accelerator. One role focused on employee training, while the other specialized in workplace relations — giving her practical exposure across two distinct HR domains. “That kind of cross-training just doesn’t happen in one job,” she noted.
The breaking point and the lessons learned
After a year of 12-hour workdays and endless meetings, Winder finally decided to quit her second job. She had cleared her debts, built a substantial financial cushion, and tested the limits of her endurance.
Looking back, she says she wouldn’t repeat it now that she has children. But for someone single and ambitious, she admits it can be worth it — if done responsibly. “You could have 10 jobs if you’re willing to get the work done,” she said, while warning that discovery could lead to being fired from both roles.
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