Making Side Jobs Successful

Aeyrel Twone
6 min readAug 17, 2023


Photo by Annie Spratt on Unsplash

Beginning a side job while you have a regular job can bring big advantages, especially when things are uncertain.

A study by Bankrate in 2019 found that 43 percent of full-time workers in the United States have a side gig. In countries like the United Kingdom, Singapore, and the Philippines, over half of the workforce says they have a second job alongside their main one.

Although “side hustle” might sound new, it was initially coined in African American newspapers in the US during the 1920s. In recent times, this term, along with the idea it represents, has become more popular again due to different reasons. Primarily, the increasing expenses of daily life and concerns about job stability have played a role. These two factors have become especially tough during the COVID pandemic, hitting people of color the hardest.

When her internship at Google didn’t lead to a permanent job like she wanted, Nicaila Matthews Okome, who lives in Washington DC, started her platform, Side Hustle Pro, as a blog in 2016. Now, she’s turned it into a popular podcast where she showcases Black women entrepreneurs who’ve made big businesses out of their side jobs. Her community has almost 80,000 followers on Instagram and is the only podcast focused on this subject for Black women.

“I believe everyone should have a side hustle and different sources of income. But for Black women, it’s even more crucial for various reasons,” states Renae Bluitt, who lives in New York City. She’s the person behind the In Her Shoes blog and is also the creator and executive producer of the Netflix documentary, She Did That.

Bluitt’s blog and movie center on Black women who are business owners, with lots of them beginning as side jobs. She says, “Rather than just waiting for equal pay, we can improve our financial health by making extra income and working harder to ensure and safeguard our money.”

People have various motives for having a side job, naturally. It could be to follow a passion, save for a goal, add to current earnings, or eventually switch to managing your own business. Keep reading for tips from women who have effectively managed both a full-time job and a part-time side gig.

1. Tell your boss about your side hustle

“Is it a good idea to let my boss know about my side gig?” is likely the top question people have, and many tend to keep it under wraps.

Still, Okome suggests that if it’s logical, you should inform your current or possible boss about your side job. It might even help you in your regular work. “I had my podcast on my resume because I believed it demonstrated my skills and I was proud of it,” she shares. Yet, she advises checking your company rules to prevent any clashes of interest before discussing it.

How should you discuss your side job with your boss? According to Christine Michel Carter, a corporate consultant and author of MOM AF in Baltimore, the key is to explain how your personal business actually enhances your performance as an employee. She points out that if you can demonstrate that the skills from your side gig contribute to your main job, having a side hustle adds value.

Additionally, it’s vital to highlight your dedication to your main job. Carter clarifies, “Running a side business doesn’t mean I’m not devoted to my full-time job or my employer.”

2. Ask for help when you need it

The pandemic has shown us that life can be really uncertain. Sharing your daily struggles and situation openly with people can actually boost both you and your business. Make it a routine to let others know where you need help and support.

However, there’s a balance to find between being open and sharing too much, especially with your current boss. Use your own judgment to decide how much to talk about and what to keep private.

“I had to talk openly with my boss about what I needed, like having a flexible schedule,” shares Carter. She’s been open about being a dedicated professional woman and a single mom.

Sometimes, you might need to be honest with your family as well. Carter says, “I also told my kids that I’m a single mom, and they might need to act more grown-up. They understand to make their own breakfast and solve problems themselves. This way, I don’t spread myself too thin and feel pulled in different ways.”

3. Get strategic about your time

If you’re an entrepreneur with a side gig, managing your time well is important, especially if your job is remote now. Rochelle Graham-Campbell began Alikay Naturals with only $100 from her apartment while she was a college student working part-time. Using YouTube, she transformed her side hustle into a successful beauty brand available at CVS, Target, and Walmart.

She acknowledges that handling time was tough at first. What changed things for her was when she began setting aside blocks of time to finish particular tasks on her list. “Discovering your own routine is crucial for making your business work. You have to treat your side gig like a business, even if it’s outside your regular hours,” Graham-Campbell points out. “Time blocking gave me better control over my schedule and my life.”

Time blocking isn’t just helpful for concentrating on your side gig, it’s also great for making sure you get enough rest. Shani Syphrett-Hayes, who works at an advertising agency in New York and runs Jamila Studios on the side, says, “I have to plan my downtime as carefully as I plan everything else. I put my break time on my schedule just like I do with my meetings.”

Burnout is a serious issue, especially for those balancing a job and a side gig. Effective time management helps you take care of both yourself and your businesses. Sakita Holley, the founder of House of Success PR, a beauty and lifestyle PR firm, says, “It’s about finding your pace and doing things that make you happy. Sometimes, you need to take a break from your daily routine and get into other activities to refresh yourself for your work.”

4. Don’t quit your day job until you have a plan

Not everyone who has a side job wants to quit their regular job; you might prefer to keep your 9-to-5. But if leaving is your goal, ensure you’ve saved up enough money. Okome earns money from different sources like sponsorships and digital products, but she saved her side gig earnings for years before becoming a full-time entrepreneur. She suggests having 6 to 12 months’ worth of living and business expenses saved up before you leave your job.

Before you decide to leave your job, Okome recommends considering these questions:

  • “How will I make money?”
  • “Will my money sources last a while, or just a short time?”
  • “How much do I have saved? How much do I need to save to leave my job?”

If you don’t want to leave your regular job, simply relish the freedom of building and learning about a business while you still have a reliable paycheck. And if your side gig becomes successful, you might change your mind. “When your side hustle earns more each month than your job, it’s time to think about what lies ahead,” suggests Okome.

Photo by Microsoft Edge on Unsplash

So, whether you’re content with your main job or dreaming of entrepreneurial success, remember that your side hustle journey is a valuable experience. Embrace the learning and creativity it brings, and if your passion project thrives, you might find yourself at a crossroads, ready to step into a new chapter of your career. Just as Okome advises, keep an eye on the future, and let your side hustle guide you towards exciting possibilities.



Aeyrel Twone

Hi, I'm Aeyrel. I'm a writer and storyteller with a passion for exploring the world around me. I love to write about my experiences and turn them into stories.