Side Work and Freelancing: Advice From Side Hustlers

The idea of taking on a side job or freelancing isn’t anything new. “Side hustles” have gained increased popularity in recent years, and the current health crisis has put second jobs and gig work in high demand. 

Kelly Strain, Content Marketing Manager at GigSmart, explained how COVID-19 has impacted those looking for work on the company’s platform. “Our daily demand is up 25%, and the average hourly pay rate across all gigs has increased from $17 to $22,” she noted.

With increasing opportunities for gig workers and freelancers growing, the timing for pursuing a side hustle couldn’t be better. We’ve collected advice from freelancers, gig workers and entrepreneurs to help your side work get off to a great start.

Why Get a Side Hustle?

Having a second source of income comes with many benefits. Some find joy in a particular hobby and find ways to monetize it, using their side hustle as a creative outlet or a way to hone new skills. 

While passion projects are fun, many side hustlers pursue their second gigs for the financial benefits. If you’re in debt, a side income can help provide the extra money that you’ll need to pay it off. You can also put that extra cash towards your emergency fund, or use it to reach a different financial goal faster. Side hustles can also provide you with additional support should something prevent you from working at your primary job.

Shaun Morgan, who teaches full time and works as a notary signing agent, entrepreneur and personal finance blogger at Simply Know Money on the side, credits his side work with helping him gain more personal freedom and career options. “By taking on this side hustle, I was able to save enough money to move to a different state where I could make more money as a teacher,” he noted, “which would mean that I wouldn’t need my side hustle as much to cover the bills. Without my side gig, I would still be working in the same place slowly slipping into debt because I didn’t have the income to cover my costs.”

Consider Your Time and Energy

Before committing to a side job, consider how much time and effort you can put into it. Do you have an open schedule outside of your primary job, or will you only be able to dedicate a few hours a week to side work? Are you wiped out after your regular work day but able to find motivation to work extra on weekends, or are you able to keep working for a few hours after you clock out?

Caleb Riutta, who works full time as a roofer while providing SEO services at Dusk Digital on the side, noted that aspiring side hustlers should consider the  amount of energy they can dedicate to extra projects. “A side gig should be something that you enjoy and that is also worth your time. So you have to ask yourself, ‘Will I be able to stay motivated to do this gig after a long workday? Is it a viable hustle, will the time spent be worth the monetary gains?’”

It’s also a good idea to evaluate your talents, skills and interests  that could be profitable. That way, you can jump right into your work rather than spending the time and money to learn a new trade. 

Kalyn Franke, who juggles a full-time position while managing multiple blogs, has turned her love for baking and decorating cookies into a solid side hustle. “I started cookie decorating for fun, but quickly realized I could make money from it once my friends and family wanted to order some,” she said. “I fill orders for people in my local area who want cookies for special events, birthdays or just because.”

If you’re short on time, you can still make an income on the side with creative thinking and the right skill set. Dane Kolbaba stays busy as the co-founder of Watchdog Pest Control, but uses his SEO and marketing skills to help other business owners in his spare time. “I had a few plumbing websites built in different cities, and I forward the calls to plumbers in those cities in exchange for a set fee per month,” he explained. “We agree on a price, and I don’t do much else. My expenses are low, profit is high, and I don’t work much at it.”

Keep Your Primary Job in the Loop

Some companies have restrictions, like noncompete agreements or noncompete clauses, that may limit the type of work you can do outside of your office. These rules are usually set to protect trade secrets and keep employees from taking any training they’ve received at the cost of the employer to a competitor company. Breaking noncompete agreements can put your primary job at risk, so it’s best to review what you signed when starting at your primary job before making any big side hustle moves. 

In addition to making sure that your side hustle isn’t violating any company rules, you should also take care to manage your time well and not let your hustle interfere with your main job.

Adam Sanders began his side work as a teacher, program leader and reentry advisor at San Quentin State Prison while balancing his full time work in the tech industry.  Now working full time as the Director of Successful Release, he emphasized the importance of maintaining your level of performance at your primary job. 

“Many bosses and employers have no issue with their employees taking on a second job as long as it doesn’t impact their work,” Sanders explained. “The moment that your side hustle begins to take away time, effort, or quality from your main job, things are going to get difficult.”

Trevor Rappleye, who balances his work as the CEO of CorporateFilming with his seasonal work as a D1 College Soccer Referee, advised that side hustlers should manage both of their jobs carefully. “Your employer can’t see you slipping at your main job,” he said. Rappleye also recommended that employees should be honest with all of their bosses regarding their employment.

Track Your Finances and Taxes

Watching your side hustle grow into a profitable pursuit can be incredibly rewarding. While it may be tempting to spend that extra cash or blindly throw it into your savings, side hustlers should track their financial flow carefully. 

“Separate your finances from day one,” advised abstract artist Sillie Mugo, who side hustled as a creative entrepreneur outside of her position at a Fortune 500 company. “This way, you can see how much revenue you’re generating in order to forecast what that would look like as a full-time income.” Mugo’s careful tracking and planning of her finances allowed her to quit her job and work as an artist full time.

Even if you’re not aiming to turn your secondary job into your primary job, you’ll still need to track your finances so that you’re prepared for tax season. Many side hustlers forget that their income is taxable, which can lead to headaches and scrambling down the road.

“First year side hustlers often don’t realize that their earnings are subject to both income tax and the additional self employment tax, which is almost 15%,” noted George Birrell, CPA and founder of Taxhub. “If they don’t make quarterly payments, they could be subject to underpayment penalties, so their tax bill is often close to 50% of what they earned. It is important to take proactive tax planning when taking on a side hustle.”

Whether you do your own taxes or consult with a tax expert, you should have your financial paperwork handy. This includes any bank statements, business records, tax forms, car mileage and receipts relevant to your work.

Beware of Scams and Schemes

Remember the old saying, “if it sounds too good to be true, it is”? This is incredibly true of second jobs and side gigs. Many jobs that promise fast and easy ways to make money may actually be scams, including the following:

A good rule of thumb is to avoid “opportunities” that require you to pay them first. Steer clear of any jobs that ask you to cash unfamiliar checks and make wire transfers on their behalf.

Give It Time and Be Realistic

Side hustles can be incredibly profitable over time, but they won’t make you rich right away. Depending on your pursuits, it may take some time to start earning anything. 

“I won’t make $100k a year freelancing because it is a side hustle,” said Rank Fuse Content Manager Chelsea Roller, who works as a freelance writer outside of her primary job. “To make a lot of money, you generally have to make it your full-time job. However, just because you don’t make a ton doesn’t mean it can’t be a rewarding experience.”

To avoid burnout as your side business grows, try setting small goals to keep you motivated. Have you created and launched a marketing plan? Did you build a website to advertise your services? Have you made your first $100? These are all things worth patting yourself on the back for!

When Your Side Hustle Turns Into Your Main Hustle

Whether planned or not, you might find yourself in a position where your side work replaces your primary work.

Shaun Durkee previously worked full time as an engineer. He was able to rely on his side hustle when he was laid off during the COVID-19 economic downturn. “I started my side business because I wanted to transition out of the corporate world and move into a career I was really passionate about,” he explained. He now works full time with his wife on their business, Alpen Fuel, where they sell backpacking food to fellow outdoor enthusiasts. 

Others find opportunities to transition their side work from contract or part time to a full-time position, as was the case for Melissa Brock. “My original side hustle involved working for Benzinga as a contract editor, which turned into a full-time job,” she said, explaining that she worked full time in college admissions when she received an offer to be the site’s money editor. “I thoroughly enjoyed working with my Benzinga coworkers on a contract basis — and do even more as a full-time employee!” She has also taken on another side hustle, utilizing her writing, admissions and financial experience for her blog, College Money Tips.

If you’ve found success with your side hustle, it may make sense to turn it into your full-time job. “I made the decision to quit my full-time job when my side hustle income surpassed my annual salary,” reported Jayson DeMers, who is now the CEO of his company, EmailAnalytics. “That’s when I knew it was the right time to make the leap and become fully self-employed. My business grew quickly from there, as I was able to dedicate all my time to it after I quit my job.”

Start Side Hustling

There isn’t a clear cut side hustle formula that works for everyone, but there are plenty of ways to make extra cash on the side. If you balance your time wisely, research your options thoroughly, track your finances and pursue work that interests you, you’ll enjoy the added security and money that second jobs bring.