The Serial Side Hustler: How to Successfully Execute Multiple Gigs

Currently a third of the U.S. workforce is made up of gig workers, and in the last year alone, over 57 million Americans claimed to work some type of freelance job. This trend is expected to become more prevalent, as it is estimated that by 2027, more than 50% of the U.S. workforce will depend on freelance work for their full-time job. A seemingly accurate estimation as currently, 80% of side hustlers work 1–3 jobs at a time. These “serial side hustlers” are changing the workforce landscape as they create new opportunities for themselves rather than depend on a traditional employer.

Whether you are a seasoned serial side hustler or are new to the game, these tips can help you run your businesses and juggle your ever-growing responsibilities.

Benefits and Challenges of Serial Side Hustling

33% of the U.S. workforce is gig work.

Serial side hustling can be incredibly rewarding. Working multiple jobs can help your finances, fulfill your passions, and give you skills that can help you perform better within your full-time job. However, serial side hustling does come with its challenges. The hardest part is managing your workload and prioritizing your time. Whether you are a serial side hustler with a day job or are a full-time gig worker, finding the perfect combination of jobs for your life can take time.

Scenario One: You Have a Side Hustle and a Day Job

The primary reason that full-time workers pursue side gigs is to improve their financial situation. A recent study from Payoneer revealed that the average hourly rate of gig workers is $19 an hour–more than double the national minimum wage in the U.S.–making a side hustle a helpful choice for those in a financial bind. Though side hustling can relieve money issues, it can come at a cost. A few of the primary challenges of having side hustle and a day job are:

  1. Lack of downtime. Combat this issue by scheduling time for relaxing and de-stressing. 
  2. Lost time with loved ones. Because you have less time, plan special days with your partner, kids, family, or friends.
  3. Decreased day job performance. To avoid a dip in your work performance, timeblock your days so that each side hustle has assigned time slots.

Scenario Two: You Side Hustle Full-Time

While the definition of side hustling is having jobs outside of your full-time job, many have ditched their 9–5 to pursue full-time side hustling. Now
10% of gig workers claim side gigs as their primary income. To master the art of serial side hustling, consider the scalability of every gig you start. For example, instead of just walking dogs, think of ways to start a dog walking company. This way of thinking can help you make more money and take you to new levels of success. A few of the primary challenges are:

  1. Lack of structure. Use time management tools and scheduling to create work days that work for you.
  2. Creative burnout. Don’t be afraid to take an afternoon off for a walk or a talk with a friend to recharge.
  3. Missed deadlines. Juggling multiple jobs can be confusing. Try creating separate planners for each job.

Best Gigs for Serial Side Hustlers

10% of gig workers claim side gigs as their primary income.

Side hustles can range from a time commitment of a few hours a week to more than a full-time job. Almost half of freelancers log 40+ hours per week for their side gigs, so if you have other commitments, a new gig can dramatically change your weekly workload. Before you jump into a new job, take an honest look at your schedule and come up with a game plan for managing your responsibilities.


If you have a marketable skill, a freelancing side gig is a great route to take. Freelancing is extremely scalable and if you are passionate about your work it can be very fulfilling. To attract clients, focus your efforts on an accessible website that features past work, reviews, and contact information. Some freelancing options are:

  • Graphic design
  • Writing
  • Event planning
  • Programming
  • Animating
  • Consulting


If you are a hands-on person, adding a side gig in the service industry is a great option. This massive industry has experienced a 5.4% growth over the last five years and it is projected to continue as consumers seek personalized experiences. Some service industry side hustle options are:

  • Foodservice
  • Cosmetic services
  • Child care
  • Cleaning
The average wage for gig workers is 2x the national minimum wage.


Over the last 15 years, smartphones have allowed for an app-based industry to emerge. Now that 81% of Americans have smartphones, services such as food delivery and ride sharing can all be fulfilled with the touch of a finger. Companies like Uber and Postmates have captivated the industry and have provided great side hustle opportunities. Some other app-based side gigs are:

  • House sitting
  • Dog walking
  • Courier service (Postmates, Uber Eats, Grubhub)
  • Ride-share driving (Uber, Lyft)


For busy side hustlers who can only squeeze in a few hours in the evenings and on weekends, online gigs are the way to go. Whether you run a blog or fill out surveys for extra cash, there are endless opportunities that can fit any lifestyle. Here are some other online options:

  • Blogging
  • Virtual assistant
  • Focus groups
  • Copy editing and proofreading
  • Surveys and reviews

Whether you are a veteran serial side hustler with several gigs or a newbie who is juggling jobs for the first time, the most important thing to do is always look for opportunities to scale into your own company. This mindset can help you turn small opportunities into functioning businesses.

Sources: Payoneer | PYMNTS | Forbes

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