You've made the budget spreadsheet. You've done the version where you cut streaming services and switch to store-brand everything. The numbers still aren’t lining up the way you need, and at this point the only line item left to change is income.
About 35% of people working side hustles say they need the extra income for regular living expenses like rent and groceries. They have plenty of company: roughly 8.6 million Americans work more than one job.
Karen Southall Watts helps people in exactly this situation. She works in workforce development at Alamance Community College in North Carolina, and coaches people of all ages and walks of life. Her caseload used to include people exploring side businesses out of curiosity. Lately, the conversations look a little different. "Less of 'I always wanted to see if I could sell my hand-painted birdhouses,'" she says, "and more of 'we're not going to make rent.'"
Most of the people Watts coaches hope the second job is a temporary stopgap while they search for full-time work with benefits. That’s a worthwhile goal, but it only works if the second job fits into your lifestyle.
Before you start looking for a second job, ask yourself three questions.
You have more marketable skills than you think. Watts recommends thinking about who comes to you for help in everyday life. "When somebody has a question about ‘whatever,’ what is that ‘whatever?’" she says. "Are they coming to you for recipes? A ride to the airport? Advice on how to not have all their tomatoes die?"
The person everyone calls to troubleshoot their Wi-Fi has tech support instincts. The one who organizes every family reunion has event coordination experience. Your second job should connect to something you already know how to do, even if nobody has ever paid you for it.
A second job changes everyone's schedule, not just yours. "You might think picking up a job as an Uber driver in the evenings would be really great," Watts says, "but then you find out your spouse can’t be the full-time parent in the evenings." You have to look at not only what you know how to do and what's available, but also what the people in your life can tolerate. "It doesn't do you any good to pick up a second job if by the end of the first week everyone in your household is miserable."
Burnout from your second job can put strain on both you and your family. In a survey of 1,000 side hustlers, 65% reported burnout at least some of the time. Watts says that self-care should be a fixed line item in your schedule, same as grocery shopping. It doesn’t have to be fancy or expensive. It might look like a five-minute gratitude meditation before bed or a walk outside after dinner. Whatever form it takes for you, it’s worth prioritizing.
Watts works with a lot of clients who are tempted by roles that look like they'd fit a tight schedule but would put too much strain on their bodies, like overnight stocking, warehouse shifts, and unloading trucks. Those jobs are right for some people, but not everyone.
"It looks like it'll magically fit into your schedule and they're desperate to hire people, but you have two replaced knees and sciatica. Is that really going to work for you?" she says. "If your doctor knew you were applying for that job, would their head spin around?"
Being honest with yourself saves you from trading income for medical bills.
Your next step: Write down your answers to all three questions, and use that list to filter your options.
When you’re looking for a second job, think about the kind of schedule, energy, and commitment your options require.
If you're still testing whether a second job is the right move, start with something you can easily walk away from. These roles are what you think of when you think “side hustle.” They let you set your own hours, require little upfront investment, and won't penalize you for stepping back:
Watts recommends this category if you’re still weighing your options. "You can sign up to be an Uber driver or to do grocery shopping and delivery," she says, "and you can just as easily walk away from that if you decide it doesn’t work."
One thing to know: delivery and rideshare are the most common side hustle categories, but net pay after gas, vehicle wear, and platform fees tends to run lower than the posted rate. Make sure you have realistic expectations and are ready for a little extra vehicle maintenance.
If you're working a second job anyway and are looking to change careers, it’s a good idea to get something besides a paycheck out of it. These options pair income with skill-building:
Some of these roles are useful for building skills, some are better as a stepping stone. Even if it’s not your dream job, Watts says "you might think, ‘maybe I could do it for this chunk of time while I finish getting this two-year certificate, and then I can go do something else.’"
Large corporations tend to be more flexible with scheduling than small businesses because they have a lot of people working there. "They might let you take all your Thursday nights off so you can pick up that accounting class," Watts explains.
Temp-to-hire roles can also help you build your career. You get paid while testing an industry, you build verifiable experience on your resume, and some assignments lead to permanent offers.
If you're holding a full-time day job, you need something that happens outside those hours. Watts points her clients toward creative and judgment-based work, like:
"A lot of creative work doesn't happen in the nine-to-five hours anyway,” Watts says. If you’re a writer, artist, or have any kind of niche expertise, you can build a client base during evenings and weekends. Watts has seen clients turn specialty gardening into weekend farmers market income, while others turn sales skills into independent consulting.
Watts also sees demand for roles that require human judgment, like online customer support. While entry level customer service roles are dwindling as companies switch to AI agents, "AI bots can only do what the model knows," Watts says. "When you ask the question the model doesn't know, it gets stuck in a loop. If you've got customer service skills, there are still off-hours jobs where the technology has failed and they need a human."
Remote and low-physical-demand roles might work well if caregiving, a chronic condition, or a long commute makes in-person work impractical:
Many of these roles are easier on your body than physical gig work, and can pay as well or better. "If you’re thinking, ‘I can't stand on my feet for eight hours and fry French fries,’" Watts says, "or ‘I don't have the ability to sit for a long period because if I don't get up and walk around, my arthritis is going to make my whole body lock up,’" remote roles with flexible pacing are a strong fit. Just be sure to watch out for scams and fake postings, which are more common for remote jobs.
Watts recommends the same first step for anyone who isn’t sure where to begin: go to the library. "Whatever community you're in, if you've got an issue you need to work out, start at the library," she says. Many libraries now employ business and career specialists who offer free job coaching, and community colleges often have free or low-cost workshops, career planning services, and connections to financial aid for certificate programs.
Staffing agencies are another free resource worth considering, especially if you've been out of the job market for a while. Even the “get-to-know-you” conversation you might have with a recruiter is helpful. "Those little practice conversations can be incredibly valuable," Watts says. "The hundredth time you do that, it's so much easier than the first time." Staffing agencies also tend to specialize in certain industries, so they can help you find a role that fits your experience and lifestyle.
Your next step: This week, look up your local library's career services and check whether your community college has a workforce development center. Find a staffing agency that specializes in the kinds of roles you’re looking for, and submit your resume.
Watts sees a pattern with clients who've been juggling two jobs for months: the second paycheck helps, but they're running on fumes and the bills are still winning. At that point, the question becomes "what can we do to make your life not only financially viable, but so you're not miserable as you're moving forward?" she says.
If that sounds familiar, it's worth checking whether the real problem is your primary job. Look up what your role pays in your area using the Bureau of Labor Statistics Occupational Outlook Handbook or Glassdoor. If the number is significantly higher than what you're earning, a raise conversation, a promotion, or a job change could do more than a second shift ever will. A staffing recruiter can show you what's out there at your experience level, including contract and temp-to-hire roles that often move faster than a traditional job search. Sometimes the smartest "second job" is a better first one.
Talk to a Kelly recruiter. We’ll show you roles that fit your skills and your schedule, whether you need a second income or a stronger first one.