How to make your side hustle work for you

Elisa Irvolino, full-time ultrasound tech, has an alter ego: Her friends call her the Latina Martha Stewart, she said.

Irvolino, 54, has worked in healthcare for decades. But for about 20 hours per week, the Patchogue resident is also the content creator behind the lifestyle brand Sazón y Corazón — which, in English, translates to "seasoning and love."

On her website and social media channels, she posts Latin American recipes, a lifestyle blog covering everything from self care rituals to travel tips, podcast episodes about Latino culture, and organizes events like a Bad Bunny bingo brunch and cooking lessons, often hosted at local libraries. 

It doesn’t bring in a ton of extra cash, the Patchogue resident said, but she’s still taken steps to protect her business from any potential tax or legal complications. Irvolino, for instance, has registered her business as an LLC, purchased liability insurance for her in-person cooking classes, and at the end of each month, is careful to set aside about a third of her supplemental income each month to pay come tax season.

“It is difficult,” she said, but “I don’t see it so much as having a second job. It’s more following my passions.”

But as more Long Islanders take on side hustles to make extra money or pursue passions, experts say those second jobs can come with hidden risks — from tax surprises to legal conflicts and burnout — that can undercut the financial upside if workers aren’t careful.

The difference between earning extra money and creating new financial and personal problems often comes down to how well workers plan for taxes, avoid conflicts with their primary job and set limits on how much they take on.

Tax and legal complications

Working two, three or more jobs can pose unexpected financial complications for workers trying to make a few extra dollars, experts said.

For example, someone with two or more jobs who loses their main source of income may not qualify for unemployment assistance, said Alexandrea Ravenelle, a sociology professor at the University of North Carolina at Chapel Hill whose research examines the gig economy.

“What people don’t realize is that our unemployment system is not created for people to make their own safety net,” she said. “In the worst case, your safety net is actually going to cause you to fall through a hole in the social safety net that we have in the U.S.”

Besides unemployment assistance, people working as independent contractors might also forgo workplace protections like compensation for injuries, or sick leave, she said.

Tax complications are another possibility for multiple jobholders. For instance, it’s common for people who have two jobs to underpay their taxes because neither job is taking into account their entire income, said Manny DeFreitas, a certified financial planner and public accountant based in Jericho.

People also might overpay Social Security taxes, he said, although that can be recovered as a credit on federal income tax returns.

If you're running the risk of overpaying your taxes, go to your employer and fill out a W-4 to change your withholdings, he advised.

“As people make more money, they lose deductions and they lose credits. So having that second job may not be as impactful as they thought it was going to be,” he said.

If you’re planning to work multiple jobs, it’s important to come in with a game plan — including an exit plan, Ravenelle said.

“You never want to find yourself in a situation where you’ve picked up this additional job and then it turns out that now you’re going to have to continue working that additional job” to pay the tax liability it creates, she said.

A side gig can impact your primary employment

Workers in New York should be careful that they aren’t picking up side hustles that could pose a conflict of interest to their main job, said Raymond Nardo, a Jericho-based employment attorney.

The state has a legal statue protecting second jobs, but employers can fire a worker for coming in late or not getting work done as a result of a second job, he said. It’s also illegal to do work for one job during paid hours for a different job.

“That would leave an employee vulnerable to a claim where the employer could sue the employee and get their money back because the employee has breached their duty of loyalty,” he said.

That second job might not be legally protected either if it’s too similar to your primary job, and you run the risk of sharing trade secrets or soliciting customers that would have otherwise gone to your main employer, he added.

For example, he said: “A guy works at an architect firm and wants to take clients privately at night. That’s a square conflict because any work in that sphere should be done through your employer.”

Plus, splitting focus and loyalties can cause things to fall through the cracks and lead to burnout at your primary job, said Sam DeMase, a career expert at ZipRecruiter.

“You might also experience reduced enthusiasm for your main job if your side hustle is more motivating,” she said. “Your boss can pick up on that energetic shift and potentially perceive you as checked out and that could result in less opportunities for key projects, promotions and raises.”

Isolation and stress

Juggling more than one job can come at a cost to workers' personal lives, experts said. Especially for gig workers, working too much can be isolating.

“There's an opportunity cost to constantly working,” Ravenelle said. “You’re kind of a ghost in the night ... Nobody has a work wife or work husband when they’re doing gig work and part-time work here and there.”

And if you’re too busy working, you have less time for your social life, she pointed out. For young people without a partner, juggling hours around the clock can make it difficult to date.

“That takes a lot of time investment, whether that’s time on dating apps, time out at social events to meet people, networking, going to friends’ parties and social gatherings,” DeMase said.

Even basic tasks like cooking or cleaning might fall by the wayside, she said. That's why, to protect your well-being, it's important to plan for breaks to reset and relax.

Try to schedule time off between jobs, she said. And, when you do have down time, “do things that fill your cup.”

“Fuel your personal relationships. If you’re really into working out, do that. If you love reading, do that. Do things that really make you happy,” she said.