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Managing Your Business

How to Be a Successful Serial Side Hustler (and Why It’s a Good Idea)

How to Be a Successful Serial Side Hustler (and Why It’s a Good Idea) | Swyft Filings

The 21st century looks to be the age of the side hustle. The gig economy currently makes up a third of the workforce, and it seems like the number of gig workers will only increase. A report by Freelancers Union and Upwork indicates that over 50% of the workforce will be freelancers by 2027. So with everyone and their mother on the side hustle train, it might be time to consider buying a ticket.

What Is Side Hustling?

The main idea behind side hustling is working one or more side jobs alongside your main job. Most side hustlers look to gig jobs or freelance work. Only 10% of gig workers go all in and ditch their full-time employment in favor of full-time side hustling.

Serial side hustlers run multiple side hustles at once. Maybe you work a full-time job, write freelance articles, and run deliveries for an app like Postmates. Maybe you’re a bartender at a restaurant, pick up driving gigs through Uber, and develop websites on the side.

Why Have Multiple Side Hustles?

There are serious benefits for the serial side hustler. From extra income to developing new skills, here are some reasons you should consider being a serial side hustler.

You Can Bring in a Little Extra Income

It’s not greedy to say you need some extra cash. Whether you’re stashing away some funds for early retirement, saving to buy a house, wanting some additional disposable income, or just trying to make ends meet, side hustling can be a great way to bring in more money. The average hourly wage of freelancers is $19 an hour, which is significantly above minimum wage, so the side hustle game is nothing to sneeze at.

If your full-time job isn’t enough for you to reach your goals, taking on side hustles might be just what you need. 

Your Day Job Sucks

If you’re unsatisfied with your full-time job, you’re not alone. A Gallup report indicated that 70% of Americans hate their jobs. It could be that you can’t find a career in your chosen field, you find your work unstimulating, or your boss is a colossal jerk.

Side hustling can give you the opportunity to explore work you’re passionate about while developing skills that could lead you to a more interesting full-time position. You could even expand one or more of your side hustles into your own business.

You Want to Develop New Skills and Explore Your Passions

The best thing about side hustling is that it can be a way to pursue skills and passions that you otherwise wouldn’t be able to within the confines of your full-time job. Think about some of your favorite hobbies. Is there a way you can monetize them? 

By turning your passions into a side hustle, you have the opportunity to make money from things that bring you joy. As you gain experience from pursuing your passions professionally and develop new skills, you could eventually turn your fun side hustles into full-time work or even start a business doing what you love. 

How to Be a Successful Serial Side Hustler (and Why It’s a Good Idea) 2 | Swyft Filings

Tips for Serial Side Hustlers

Serial side hustling can be a bit like a complicated juggling act, and it can be challenging managing your time and resources to make sure you don’t drop any balls. Whether you’re considering taking the leap to become a serial side hustler, or you’ve already got multiple side hustles up in the air, here are a few tips to successfully play the game.

Organization Is Key

Being the one in charge of managing your own side hustles can be liberating, but it’s also a big responsibility. Moving back and forth between multiple gigs and different roles might be exhilarating, but it’s crucial to stay on top of time management and track your finances.

With multiple side hustles on your plate, you need to manage the time you devote to each efficiently. Block out the hours you’re planning to spend on each gig ahead of time, preferably at the beginning of each week. Try writing out time blocks by hand in an old-fashioned planner, or use any number of scheduling apps available online. 

By carefully planning out your week ahead of time, you can confidently get to work knowing that you’ve scheduled time for all your gigs. Be realistic when creating time blocks. If you give yourself too little time to complete your tasks, you’re only hurting yourself.

Gig work and freelancing also lend themselves to a whole different experience when tax season rolls around. Extra income is all well and good, but being audited for improperly filing your taxes can be a painful experience. It’s essential to document your earnings and expenditures for each gig carefully. 

Consider opening a separate bank account or credit card for each of your side hustles. Keep any receipts for any business expenses. It may be a good idea to file taxes quarterly to stay ahead of the game.

Think Scalability

For each side hustle, it’s critical to keep one eye on the future. Look for ways you can scale your gigs into something that brings in more income. If you’re a freelance video editor, you can work on scaling that into your own post-production house. If you sell baked goods at pop-ups, consider flipping that into your own catering company.

Work on developing skills that can lead you to new and better opportunities for future success and a more steady income. While you work as your own boss side hustling today, you may create a future where you’re the boss for your own team of employees.

Be Purposeful

Setting goals and intentions when going into side hustling should be a priority. Ask yourself what you’re looking to get out of the experience. What are you working towards? Is it a certain amount of money saved, a solid web of networking, or are you looking to start your own business? 

With a purpose in mind, you can confidently move forward with your side hustling without feeling like you’re spinning your wheels with no direction. Think critically about what you want to do with all the time you spend hustling, and you can more easily reach your goals.

Focus on What You’re Passionate About

Money is important, but it shouldn’t be the only consideration when taking on different side hustles, or you can very quickly make yourself very unhappy. Enrichment is key to successful serial side hustling. If you focus on gigs you enjoy, you won’t find yourself struggling as hard. 

If you love animals, pursue a side hustle of dog walking or pet sitting. If you’re itching to express your creativity with a paintbrush in hand, you won’t get anything out of driving for Uber instead.

By focusing on your passions and letting them be your driving forces, you can take on the burden of multiple side hustles without feeling as much of a strain. If you work on making money doing something you love, it won’t feel like work at all.

Avoid Burnout

Burnout is common among serial side hustlers. It’s easy to get stuck in a rut and feel yourself waning if you work endlessly and without reprieve. That’s why it’s crucial to schedule off-time and give yourself a break now and then. Focus on maintaining relationships with friends and family or just giving yourself time to relax.

Practice self-care during your time off. Going on relaxing walks, reading that new mystery you’ve had your eye on, or taking yourself out to your favorite restaurant are just as important as the hustle itself. If you neglect your physical or mental health, you’re only going to suffer and burn out. 

Breathe, be kind to yourself, and you’ll be okay.

Formalize Your Businesses With an LLC 

As you scale up your side hustles, you’ll want to form an LLC (or, considering you’re a serial side hustler, several LLCs). It’s easier than many assume and offers some tax benefits, meaning you get to keep a little bit more of your hard-earned side hustling money. 

But the primary reason to start an LLC is asset protection. If you’re just doing business as a sole proprietorship and get sued or owe debts, the courts can take your personal assets, including your car, home, and savings. An LLC offers protection by legally separating your work finances from your personal finances.

Know When to Let Go

Being a serial side hustler can be all-consuming, and you might wear it like a badge of honor, but you also have to recognize when it’s time to give up the hustle. If you’re intentional about your side hustling and have concrete goals, it can be easy to determine when the time comes to move on. 

But if you’re at it for years with no end in sight and you’re dreading every day, you should seriously consider letting go. It’s not worth it to continue if you’re not finding any joy. Put yourself first and know when you need to hang up the side hustle cap.

Know When to Go All In

Of course, the best reason to give up serial side hustling is when one of those side gigs becomes successful enough to become your new full-time job. Maybe your hand-stitched handbags are getting enough hype that you can quit driving for Uber, or your part-time writing gig is so fulfilling that it makes sense to devote more of your time to it.

If you find that unicorn side hustle, it may be wise to let some of your other hustles fall by the wayside while you devote your full time and energies to that profitable passion. Getting paid for doing what you love is every side hustler’s dream. Go make it a reality.


When you’re ready to take your side hustle to the next level, head over to our incorporation guide to get started creating your own business.

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