Want to Start a Side Hustle? These Stories Will Inspire You to (Finally) Take Action

Do you dream about crafting a sustainable, flexible full-time or part-time job fueled by your true personal or professional interests?

You're not alone. Many of us are continually seeking a change from the 9 to 5 grind. If only we had the extra time, ample resources, and a brilliant idea, we would get started, right?

Caila Zappala is living proof that even with the constraints of a busy schedule, it's not unrealistic to hope, plan, and work for a new and fulfilling career. And hers started from a side hustle.

Zappala was working full-time as an IT project manager in New York City when she started teaching neighborhood group fitness classes in the mornings and evenings. She followed this routine for several years until she realized her love for fitness and helping people trumped what she was doing in the office, and her budding interest and expertise in prenatal and postnatal health could dramatically improve lives.

"Getting up and going into the office started to feel torturous because my heart and focus were truly somewhere else all day," she explains. "I was mentally creating my new day to day well before I made that jump." 

Now a PregnancySāf Elite Coach with additional corrective exercise certifications, Zappala is a trusted resource for new and expectant mothers, sharing her knowledge through one-on-one training, group classes, social media, and a podcast.

She left her IT job just a few months before the pandemic, so like most business owners at the time, she had to quickly pivot to become an online virtual training business. Thankfully, her skills as an IT professional helped her to transition quickly. 

Her advice to readers is the perfect prelude for the other stories that will follow: You've got to give it a try!

"Otherwise, you'll just always wonder," Zappala says. "I feel like we wait until things feel 'that bad' to make a change. This side gig to full-time adventure has been one of the most difficult yet most rewarding experiences of my life. I wouldn’t change a thing about it because I’ve learned so much about myself, my business, and dreams for the future!" 

Benefits of a side hustle

Also called a side gig, side job, or microbusiness, a successful side hustle has the potential to create space in your life for one or more of the following:

• A passion-guided project dictated by you alone 
• A new hobby or area of expertise — or income for the hobbies you’re already pursuing
• Additional income to supplement what you’re already earning 
• Replacement income for your current job 
• The flexibility to pursue interests or to rest from over-busy-ness 
• A fulfilling business partnership with a friend or family member 
• A novel trajectory for your day job or other new career opportunities

Basically, if you want to earn more money outside of the 9 to 5 or if your day job just isn’t fulfilling your need for creative expression or autonomy, you could benefit from starting a side hustle. 

If you’ve considered starting a side hustle of your own, this guide — full of real-life examples from people in the trenches of supplemental entrepreneurship — will excite, educate, and empower you to do so. 

Download and print our companion worksheet to jot down your own ideas as you follow along. 

Pick a lane: Identify side hustle opportunities

1. Create the resource or service you wish you had

What would make your life easier? 

When marketing manager Giuseppe Frustaci wanted to learn how to drive stick shift (a manual transmission car), he struggled to find a teacher. "Driving schools don't offer it, and it was really hard to find a friend or family member who had a stick shift car and was willing to teach,” he recalls.  So about a year after he learned how to drive stick shift, he took advantage of the lack of resources available by creating one himself.

His stick shift driving lesson business began as a side hustle in 2017. He partnered with someone who had a stick shift car and wanted to make some side money teaching, put up a website, and ran some ads on Google. 

Frustaci established his business as an LLC for legal protection reasons but didn’t file as a corporation because he doesn’t expect to raise money or grow the business much more. “Although it has now become my full-time job," he explains, "I just don't see investors wanting to invest in what could be considered a dying art.” 

But that doesn’t mean the customer demand isn’t still there. Since the summer of 2018, Frustaci’s business has grown to be in 48 cities nationwide with 170 instructors and has sold about 2,000 lessons. And Stick Shift Driving Academy continued to thrive during the pandemic since there was a surge of new instructors looking for side gigs of their own. 

2. Improve upon a product or service you already use

What improvements could you make, big or small? 

Scott Penick had always wanted to start a business but never knew what it should be. And as an attorney, he didn’t have a lot of extra time to devote to a side project, so he put it off. But when his dad passed away from cancer in 2019, Penick realized that he needed to stop waiting for the “right time” and take action, even if it meant the risk of failure. 

As meal replacement shake fans, Penick and his wife decided to create some of their own. “As we learned more about nutrition and read labels more closely, we started to realize that a lot of the meal replacement shakes were not all that healthy and that even the healthiest ones could be better, he explains." They started researching and making a chart of potential ingredients and their macronutrient profiles to determine the perfect nutrition shake formula.

At the same time, they shopped out potential manufacturers for what would become Soul ShāXe — name idea number 94. 

The Penicks formed Soul ShāXe as an LLC, which would provide some insulation from personal liability without adding a lot of complexity to their finances with taxes. And they decided to begin by selling their product direct-to-consumer online to allow for enough margin to be profitable without needing to sell tens of thousands of units per month through a wholesaler. 

The moment of truth was placing their first order for production. “It was a five-figure bill, and we did not have that kind of money just laying around, but we did have equity in our home,” Penick recounts. “If you are married, you absolutely have to have your spouse's buy-in on this; but we took out a home equity line of credit to fund the first production run. It was nerve-wracking and exhilarating at the same time.”

But just as they were getting ready to place the order for the first production run, the pandemic hit, prompting fears about the home equity, stay-at-home orders, and job security. 

They decided to look at the situation this way: “Some people are going to hide and push pause for the duration of this pandemic. If those people are lucky, they will come out of hiding at the status quo, wipe their brows, and be thankful they survived. Others are going to decide that this is a time to be bold, forge ahead, and grow through the adversity. We decided to grow.”

They have received overwhelmingly positive feedback from customers so far, and the goal is to continue to get the word out to prospective customers. 

Soul ShāXe’s biggest challenge is standing out in a crowded online market. Based on what he’s experienced, Penick would have made one decision differently when starting out: order less inventory upfront, invest more in marketing, then find a way to finance inventory to meet order demand.

3. Test your concept before investing a lot of time and money 

You may not need to come up with a new idea at all. What successful business models do you see that you might want to replicate? 

 

Nick Loper is not only an experienced side hustler but also an entrepreneurship expert. He is the founder of Side Hustle Nation and has been helping a community of people earn more money and build businesses they love since 2013. As a former zone manager for Ford Motor Company, his original corporate getaway vehicle was a comparison shopping site for footwear. 

It was three years of nights and weekends before Loper felt comfortable leaving his full-time job to focus on his side gig. Years later, he started Side Hustle Nation to showcase this “lower-risk brand of entrepreneurship” and the stories of others getting it done. Loper has directly interviewed and interacted with thousands of other side hustlers over the years, so he's identified countless tips and guiding principles that can aid aspiring side hustlers.

Along the lines of starting small with your business concept, it makes the most sense for most side hustles to start as sole proprietorships. "Unless there are specific licenses and registrations required in your local area, sole proprietor status is automatic when you start to make income outside of your job," Loper explains. "An LLC may afford you some personal liability protection, but probably won't save you money on taxes since it's a 'pass-through' entity." As your business grows, consider incorporating as an S-corp or an LLC with an S-corp election, which should allow you to save on some self-employment taxes.* 

Loper aims to teach business concepts through others' experiences via his podcast and blog but also through sharing his own struggles in various ventures. "A classic failure of mine in this space was rushing to sell my condo in Atlanta when I moved across the country," Loper laments. It could have been a cash-flowing rental, but he was afraid of the prospects of trying to manage it remotely. Loper continues, "Turns out, there's this thing called property management built to solve that exact problem! Odds are, someone somewhere has already overcome what you're struggling with, and so your job as the entrepreneur is to seek out those solutions." 

*Not intended as legal or tax advice. Consult a CPA or other tax or legal professional as you consider business registration. 

4. Look for existing opportunities within your network of family and friends

Could any of your connections use some assistance with their own projects? Think about the personal and professional conversations you’ve had recently.  

“I had always wanted my own business but struggled to find the right combination of product or service with high demand, accessible market entry, steady supply line, and the ability to bring a value-added component into the mix," explains Jay Jermo. "Honey was the perfect find and, in truth, it found me.” 

Ten years ago, Jermo was just making ends meet while working for a bank, and in search of an opportunity. He found it when he stopped at a cousin’s house on a tour around the state to connect with friends. Jermo’s cousin, who is a commercial beekeeper, had created some flavored kinds of honey he was selling at a local market and suggested Jermo sell them in the Detroit area. 

One farmer’s market gig turned into eight, and eventually, four flavored honeys turned into 70. He created a webstore for the honey products, memorable branding, and has since expanded to selling different floral types of honey from around the world. He says, “Now this is all I do, and the idea of going back to a day job is a distant memory.” 

Jermo operates as a sole proprietor of his eCommerce store because there is a tax advantage at this stage. Sales are direct to consumers, so he can capture more margin without involving third parties. For marketing, he includes customers on a mailing list to engage future and repeat sales. 

Suit up for the race: Start your side hustle 

5. Join a community of like-minded entrepreneurs for ideas and support 

Who do you know who does what you might want to do? Enter keywords on a search engine or social media to pinpoint relevant groups. 

Content creator Jessica Ashcroft knows the value of strategic pivoting, a diversified skill set, and, above all, community. 

Ashcroft started her own blog as a way to document her life as a newlywed. When fashion blogging started gaining traction, she switched up her blog focus to include fashion content. And after having her first baby, she transitioned her blog one last time to a pregnancy and motherhood blog. 

Through the years, Ashcroft has found ways to keep up with the ever-changing rules, best practices, and strategies of succeeding in the blogosphere. "Blogging has a steep learning curve," she explains. "You have to know SEO, website design, HTML coding, marketing, photography, and social media — on top of the actual writing."

Aside from trial and error, one thing that has helped her expand her knowledge of these topics and others has been joining online blogging groups. That's her top piece of advice for individuals pursuing a side hustle: "Try to find a community of like-minded entrepreneurs. I've learned so much from the Facebook groups I'm in with other bloggers that I would not have known if I was going about this on my own." 

While she tried to spend as little money as possible initially, Ashcroft realized that to make money you have to spend money. So she used some of the income she was making from her work-from-home job in the finance sector to pay for monthly costs to improve her blog and expand its reach. 

It took some time to get there, but Ashcroft eventually started making a full-time income from her blog via sponsored blog posts as well as monetizing blog traffic through an ad network. At that point, she felt it was time to leave her other job so she could use her time to be doing what she really loved: blogging. 

And things are only looking up from here: Ashcroft has started a second blog, this time featuring favorite family recipes, with hopes to get it qualified for her ad network as an additional source of income. 

As a full-time teacher, Shaun Morgan wanted a side hustle to earn some supplemental income, but most things he looked into required too much time or capital upfront. He listened to Nick Loper's Side Hustle Nation podcast as a place to learn about new opportunities.

One day, he heard a notary public loan signing agent, Mark Willis, talking on the podcast about his work. "The job is flexible, pays well, and it takes very little start-up capital," Morgan explains. "I was sold.” It wasn't long before he had a notary business of his own. 

Notaries get paid for walking people through documentation, including mortgage documents, and making sure everything is completed and signed correctly. 

To get started, he needed to take just a few steps: 

1. Become a registered notary
2. Establish a sole proprietorship
3. Acquire a printer and other basic office supplies

It cost Morgan just shy of $2,000 in startup capital, which he put onto a 0% interest promotional credit card. 

Since it is a business that hinges on perfection, Morgan relies on the Loan Signing System, a community the aforementioned Mark Willis created for notaries seeking help when starting out: “I recommend that anyone just starting out in business find a group of people they can turn to for support and advice because of how invaluable that is.”

And now? “Having this side hustle has given me more flexibility to pursue other goals, such as starting a blog." 

6. Utilize in-person and phone communication to maximize your impact 

What are your networking connections, skills, and assets? Jot down the individuals and organizations that come to mind. 

As a cocktail enthusiast, brand strategy leader Jessica Miller saw the explosion of ready-to-drink cocktails hitting the market and felt there was an opportunity for a wine-based cocktail that paid greater attention to flavors and had higher alcohol content like a true cocktail. 

Miller and her husband founded their wine wholesale business as partners. They had always wanted to run a business together and were able to launch their side hustle with the financial assistance of a very close friend. Miller says the most difficult aspect of starting a business, if you’re not taking on outside investors, is asking friends and family for help. Aside from the one loan from a friend, Miller tapped into savings, credit cards, and even cash advances on cards with a low-interest rate. 

Of the financial sacrifices involved, Miller says, “All of it can be a bit daunting when you are pulling all of your resources and are leveraged to the hilt, but we wouldn’t have done it any differently! There is a different kind of pressure when you bring on outside investment, and you may lose control or need to compromise your vision.” 

Colony Cocktails is a wine wholesaler, so they sell their products to distributors who sell to retailers, who then sell to consumers. Miller structured her business as an LLC because it offered the best structure as a two-member partnership and with enough legal protections in place. It was also easier for her to apply for federal alcohol permits with an LLC, avoiding the complexities of a corporation structure.

Like Soul ShāXe, Colony Cocktail’s first production run was scheduled right when COVID-19 hit. In Miller’s case, this forced Northern California, where her copacker is located, into lockdown. Thankfully, they were still able to manufacture the cocktails, but they also encountered challenges shipping and sourcing ingredients due to the pandemic. 

According to Miller, pushing through and launching a product during a pandemic was nothing short of a miracle. “It required us to stay nimble, solve problems rapidly and, honestly, inspire our vendors to push harder for solutions as deadlines approached,” she explains. “Picking up the phone and having a conversation with someone helped some of these big companies make an effort to help our little craft cocktail business. There is a humanity that is removed from email communications; speaking over the phone helped us build those relationships and ultimately achieve what we thought was impossible.”

While the business is still challenged by COVID limitations, Miller is finding interesting ways of engaging new consumers on a smaller scale than their preferred cocktail tasting events, such as working with realtors to be featured at open houses.

7. Use a stepping stone side hustle to finance a bigger goal 

What resources do you have to start your side hustle, and what else do you need? How could you come up with the finances you need? 

When engineer Anders Helgeson started working from home in March 2020, he found he could get his work done in a couple of hours and have the rest of the day to work on other projects. With that time and with plenty of motivation, he seized the opportunity to flip couches with his buddy to earn some extra cash. The end result? “My business partner and I fully financed our startup junk removal business last year after spending about 14 weeks flipping couches off of Craigslist and OfferUp,” he explains. 

Their process involved the following: 

1. Scour the free sofa ads on Craigslist and OfferUp. 
2. Pick up sofas that were still in pretty good condition (Both friends already owned small trucks and Helgeson had a spare room for storage in his house). 
3. Vacuum the couches. 
4. Take much better pictures (just with an iPhone). 
5. Repost for sale, priced to include free delivery to discourage people wanting to haggle. 

But just how much can you make by selling free couches? 

In just over three months, they acquired and sold 43 couches at a total profit of $15,870 — enough to pay for the following startup expenses: 

• LLC formation
• Business and commercial auto insurance
• Truck and trailer
• Polo shirts and hats
• Website
• Business cards 

And they had a cushion of money left over for emergencies, which came in handy. 

“I haven't quit my full time job yet, and currently junk removal still sits as a bit of a side hustle for us. However, we are starting to gain traction in San Diego, and I fully expect that within the next year, this will be a full-time job for the both of us!”

Sprint or marathon: Grow your side hustle

8. Be willing to “time hustle” to upgrade your clientele 

What are some to-do items that have the potential to help you grow? Jot them down and work them into your schedule. 

It’s impressive that Rebecca Lake’s six-figure personal finance writing business — involving writing, ad revenue, and affiliate sales — started as a side hustle.

She started freelance writing when she decided it made more sense financially to become a stay-at-home mom rather than pay for daycare for two kids and drive a two-hour commute to work each day. 

Other than some writing she’d done in college, Lake started with no real experience but was able to quickly make a part-time income ghostwriting from home. After her divorce in 2014, she decided to try to grow the side hustle into a full-time business so she could continue to stay home with her kids. 

After about a year and a half after deciding to take her side hustle full-time, she had her first $10,000 month as a freelance writer. "That was the point at which my investment of time hustling and networking started to really pay off," Lake says. "I continued to focus on upgrading my clientele and becoming a sought-after writer. Now my business brings in $20,000 to $30,000 a month, and I still run it with just a laptop and internet.” 

Lake continues, “I didn't invest in any training or special equipment; the biggest investment I made was time. I spent time every day pitching new clients, replying to job postings from job boards, and growing my network on LinkedIn. I was taking care of my two kids full-time, homeschooling them, and running the business solo while living on a single-parent budget.”

Time management has been the biggest challenge to growing Lake’s business. While she works about 25 to 30 hours per week now, it used to be much more than that, and limited childcare options made it imperative that she create routines to get all of the work, mom, and homeschooling tasks done each day. Even with older kids now, routines continue to be imperative to her successful work and home operations. 

9. Be patient as you build (or rebuild) a foundation for growth 

What obstacles have you faced or could you face? What is your plan for pushing through? 

When Kristin Mastoras moved to New York in 2011, she had a great job, but money was still pretty tight, so she used an Etsy design shop she started during college to earn some extra money. She explains, "I was working in pharmaceutical advertising which was not the most creative, so my side hustle was also a way that I could do more work that excited me.”  

It took about four years to grow Miss Design Berry into something Mastoras was able to take full-time, but it was worth the wait. She incorporated her business as an S-corp so she could pay herself as an employee of the business. 

Through the years, she’s encountered obstacles shared by many eCommerce businesses: trademark infringement from competing businesses, online client harassment, and a failed business partnership. 

These challenges make it all the more impressive how far the design business that started as a small Etsy shop has come over the past decade: 

• 2014 — Hired her first part-time employee to help while still working full-time.
• 2015 — Left her advertising job to make her side gig her new full-time gig once she could pay off student loans and earn as much with the side hustle as her former job. “I also really wanted to get a dog, but could not do so unless I was working from home, so this was a big motivator for me!”
• 2016 — Built a team of more than 10 employees.
• 2017 — Brought a partner into the business, which ended up not working out.
• 2020 — COVID-19 dealt a hard blow to the business, dropping revenue by over 50 percent. 

But the story didn’t end there.

Regarding the impact of COVID-19, Mastoras had to pivot and make her design products work for virtual weddings and events as well as rely on help from the PPP and other government assistance. “It will be a long road back to solid ground, but we made it through 2020, and now I know we can make it through anything,” she says. 

10. Start small, but be willing to take a risk when it’s time to go “all in” 

At what point, if any, would you want to quit your day job? Note the financial gains you hope to consistently achieve with your side hustle and imagine what steps you might take personally and professionally when you reach that point. 

While they both had other full-time jobs, Jamie King and her cousin and co-founder worked on building a yoga and fitness community at nights, on weekends, and whenever else they could spare some time. They started what is now Flex & Flow after an "inspiring and wine-filled evening" about 10 years ago.

“I have especially fond memories of the many late evenings and weekends we spent tagging thousands of pink shoelaces and handwriting cards, which is how we initially grew our community,” she reminisces.  "While we both bootstrapped from our own savings, we definitely know how lucky we are to have supportive partners who encouraged us and helped us continue to make our dreams a reality.”

After more than a year of working full-time, investing their own money back into the business, and hustling every spare moment, King knew it was time to quit her job and face the music. 

“It felt like it was time to commit or fail,” she explains. However, she stayed on as a consultant for an additional year to make ends meet and keep floating the business. 

Last year, Flex & Flow’s flagship studio in northeast Portland was forced to close, halting in-person yoga and other fitness classes. However, the business has been providing virtual classes globally with its pay-per-month digital studio membership model. “Ten years and one pandemic later, we're still standing!” says King. 

Ready to work on your own side hustle? If you missed the link at the beginning, here's our brainstorming worksheet to help you take your first steps.