Gigs, Side Hustles, Second Jobs: The Millennial Way

Let’s get one thing straight: I would LOVE to have one job, then come home and sit on my butt. Juggling multiple jobs in the “gig economy” isn’t fun. But working additional jobs for supplemental income is becoming more and more common and can help you reach savings/debt-paying goals faster. I’m not going to talk about ways to make it big, like creating an app or becoming a landlord, because those often require significant time and start-up cash. We’ll start small, and we’re going to work with whatever time you have available.

Can you reliably work on evenings?

  • Waitressing/bartending/hostessing
  • Overnight receptionist/supervisor/security jobs. My husband works one of these types of jobs at a local university library Friday and Saturday nights midnight to 8am.


  • Babysitting
  • Petsitting
  • Retail
  • Tutoring
  • Refereeing
  • Teaching a class at a community center

Are you available on the coveted weekday?

  • Daily dogwalking
  • Nannying (like babysitting, but with a lot more regularity!)
  • Part-time office work like data-entry, editing, copying, organization

Is there a particular season where your main job slows down or stops?

  • If you have extra free time in the summer, try mowing lawns or other landscaping/outdoor maintenance. You can also look into jobs at summer camps or jobs in university-adjacent businesses where student employees have left for break. Lifeguarding is another option.
  • If your job slows down in the winter, shoveling and snowblowing are great. Retailers also look for extra help in the fall and winter to keep up with holiday shopping.

Is your free time more sporadic? You may have to think outside of the box.

  • Reselling items found at yard sales. You can buy furniture on the cheap, repaint/refurbish it, and sell on Craigslist for a profit. Or you could find cool antique collectibles, research their details and worth, and sell them on eBay where more a knowledgeable buyer will pay a higher price.
  • Selling crafts, either locally or on a site such as Etsy (Make sure your costs don’t exceed your profits.)
  • Ubering or Lyfting (Again, make sure your costs don’t exceed your profits.)
  • AirBnb

Whatever your availability or skill set, I’m confident you can find a side gig that works for you. Network with friends, family, neighbors and coworkers to find opportunities and don’t sell yourself short on skills– you’re valuable!

Just keep in mind that side jobs are still work. You can’t babysit once and expect your car to suddenly be paid off. Consistency is key. Once you’ve found something that works, stick with it. You’ll have more success excelling at one type of side job rather than babysitting, dogwalking, selling things on Etsy, and Ubering and not having enough time to do any of them justice.

What side job do you have? I’m sure there are lots of options I’ve left off the list– what should I add?

A note about freelance writing: It’s weird that I’m a writer and I didn’t mention freelance writing, huh? That’s because writing requires a lot of skill, a lot of mental energy, and takes a lot of time to actually start paying a livable wage. If that’s an area you have interest in and want to spend time on, go for it! But I cringe when sites recommend it as a way to make quick cash.


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