The Serial Side Hustler: How to Successfully Execute Multiple Side Hustles

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’s estimated that by 2027, more than 50% of the U.S. workforce will depend on freelance work for their full-time job.

That’s 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 to earn money rather than depend on a traditional employer.

Whether you are a seasoned serial side hustler or you’re 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’re a serial side hustler with a day job or 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 earn extra money and 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 current minimum wage — making a side hustle a helpful choice for those in a financial bind. Though the extra income from side hustling can relieve money issues, it can come at a cost. A few of the primary challenges of having both a side hustle and a day job include:

  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, time block 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. Currently, 10% of gig workers claim side gigs as their primary source of income.

To master the art of serial side hustling, consider the scalability of every gig you start. For example, instead of just being a dog walker, think of ways you could start a dog walking company. This way of thinking can help you make more money and improve your own success financially. A few of the primary challenges to full-time side-hustling 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 go out with a friend to recharge.
  3. Missed deadlines. Juggling multiple jobs can be confusing. Try creating separate planners for each job.

Choosing the Right Side Hustle

Choosing the right side hustle can be a daunting task, especially with so many options available. However, by following a few simple steps, you can increase your chances of success and find a side hustle that aligns with your interests and goals.

Align your interests with your side hustle

When choosing a side hustle, it’s essential to consider your interests and passions. Ask yourself, “What do I enjoy doing in my spare time?” or “What am I good at?” By aligning your side hustle with your interests, you’ll be more motivated to put in the time and effort required to succeed.

For example, if you’re passionate about photography, you could consider starting a photography side hustle. You could offer your services to local businesses, events, or even start a photography blog. By doing something you love, you’ll be more likely to stick with it and make it a success. As an added plus, photography can be a very workable side hustle since most people need photos taken after business hours or on weekends.

Assess the financial viability of your side hustle

Before starting a side hustle, it’s crucial to assess its financial viability. Ask yourself, “Can I make enough money from this side hustle to justify the time and effort I’ll put in?” Consider the upfront costs, potential earnings, and competition in the market.

For instance, if you’re considering starting a freelance writing side hustle, research the going rate for freelance writers in your area and calculate how much you can earn per hour. You should also consider the costs of marketing yourself, equipment, and software.

Schedule Your Side Hustle for Success

Once you’ve chosen a side hustle, it’s essential to schedule it for success. Create a schedule that works for you and your day job, and stick to it. Consider setting aside a specific time each day or week to work on your side hustle.

For example, if you’re starting a side hustle as a virtual assistant, you could schedule two hours each morning to work on client tasks. By having a set schedule, you’ll be able to stay organized and focused, and make progress on your side hustle.

Managing Multiple Side Hustles

Managing multiple side hustles can be challenging, but with the right strategies, you can succeed. Here are some tips to help you manage multiple side hustles:

Create a business plan for your side hustles

When managing multiple side hustles, it can be helpful to create a separate business plan for each one. This will help you stay organized, focused, and ensure that each side hustle is working towards your overall goals.

Within each business plan for each side hustle, outline your goals, target market, marketing strategies to attract potential clients, and financial projections for your business expenses and potential profits. This will help you stay on track and make informed decisions about each side hustle.

Set a strategy to balance your workload

While you can’t plan out exactly how each day will go, you can set yourself up for success by making a loose plan for how you’ll spend each day. For example, you might decide that you’ll spend an hour or two each day focusing on your side hustles to answer emails and chat with clients, and then have a dedicated side hustle “work day” on the weekend.

If you can, be sure to allow for some downtime for yourself, too. Never having spare time can lead to burnout, decreased performance in all of your jobs, and more. A day off here and there can leave you refreshed and ready to tackle the challenges ahead.

By following these tips, you can choose the right side hustle and manage multiple side hustles successfully. Remember to align your interests with your side hustle, assess its financial viability, and schedule it for success. With the right mindset and strategies, you can turn your side hustle into a successful and profitable business.

Best Side Hustle Ideas for Serial Side Hustlers

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

When exploring side hustle ideas, it’s important to consider the variety of options available, as side hustles can range from a time commitment of a few hours a week to more than a full-time job. A lot 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.

Freelancing

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 popular freelancing options are:

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

Teaching Your Skills Online

If you’re an expert at a marketable skill like the ones we’ve listed above, it might make sense to set up an online course to pass on your skills to other people. Online platforms like Udemy, Coursera, or Teachable can be great places to build a course, market it, and get paid for your expertise.

The best part? Once you’ve got the course up and running, there’s minimal upkeep and your course can generate passive income for you. Likely, you’ll need to invest just a few hours each week to market your course and double-check that your content is up-to-date.

Services

If you are a hands-on person, adding a side gig in the service industry is a great option. More and more customers are seeking help with essential tasks like making meals, child care, and cleaning, so there’s a wealth of opportunities. That said, it’s important to have realistic expectations and be wary of the notion of easy money. While service industry side hustles can be lucrative, they require effort and dedication, and there are no shortcuts to financial success.

Some service industry side hustle options are:

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

App-Based Services

Over the last 15 years, smartphones have allowed for an app-based industry to emerge. Now that an overwhelming majority of Americans have smartphones, in-demand 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 great app-based side gigs are:

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

Online Businesses

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
  • Social media account manager

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

Disclaimer: The content on this page is for information purposes only and does not constitute legal, tax, or accounting advice. If you have specific questions about any of these topics, seek the counsel of a licensed professional.

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