How to Cultivate Your Side Hustle
Nick Loper left his corporate job after his side hustle – a comparison shoe- shopping service – took off. But he wasn’t done hustling. He started Side Hustle Nation, a blog offering resources and community for aspiring entrepreneurs, and the Side Hustle Show podcast as a side hustle to his main business.
“The most fun part of my work is hearing about the super-random and creative was to make extra money, such as a portable hot tub business,” says Loper, who is based in Seattle.
For some people, a side hustle is about getting paid to do something they already love such as concocting recipes or making unusual craft pieces. For others, the hustle starts with a touch of frustration about the demands of their job or the lack of career progress. Either way, a side hustle can be a source of income, a source of satisfaction, and sometimes even a path to becoming a full-time entrepreneur.
From Side Hustle to Successful Gourmet Food Purveyor
Andy LaPointe says the food industry is in his DNA: His four uncles all owned pizza franchises where he worked alongside his cousins. But it was the 9/11 terrorist attacks that served as the catalyst for LaPointe and his wife to start Traverse Bay Farms, a gourmet food business based in Northern Michigan.
“I was traveling 150 days a year as a registered investment advisor for a large financial institution and knew many people in the financial services industry who were impacted by 9/11,” LaPointe says. “My wife and I decided we needed an exit from the corporate world, so we chose the food business because it was something we could start relatively quickly that would provide recurring income.”
The couple started with concentrated cherry juice for athletes, since 70% of the cherries in the U.S. come from the region in Michigan where they live. They now offer an array of products including jams, mustards, and salad dressings.
“My wife was making the products during the week, and I focused on our business on the weekends,” LaPointe says. “When I was traveling for work, I would drop off samples and flyers in between appointments.”
LaPointe was transparent with his managers and colleagues about his side hustle for compliance, and now many of his former clients and coworkers buy his products.
Making Music Work
In 1995, Michael Nova, CEO of Nova Custom Label Printing, a branding and marketing company based in New York City, worked by day for an event planning firm and on nights and weekends as a musician. His initial target audience was fellow musicians.
“I worked on this on my off-hours and on weekends. Everyone thought it was a great idea and referred me to others, so after a few years I took the leap and quit my full-time job.” Today, Nova’s clients include well-known corporations such as American Express, BMW, Google, and L’Oreal Cosmetics, as well as U.S. government agencies.
In addition to running his main business, Nova has a new side hustle as founder of RiseUpEight.org, a global community of people who have overcome challenges and want to inspire others. “At one point in my business I was close to bankrupt, stressed, and very ill, and I had to borrow money to get back on my feet,” he says. “I founded Rise Up Eight more for community than for profit to share my story and other people’s stories about how to be more resilient.”
Loper says the most lucrative side hustles tend to be those with some built-in time leverage, where you can create something once and earn from it over and over, such as an online course or content business.
“The trick to a successful side hustle is seeing the potential in what you’re passionate about,” says Kraig Kleeman, CEO and founder of The New Workforce, a Chicago-based outsourcing company. “That’s how many side hustles start – out of pure love, and sometimes, a pinch of frustration with what’s already out there. I’ve heard stories of side hustles born from the most straightforward ideas, like a quest for the perfect cup of coffee or an app that solves the most niche problem. It’s not just about making an extra buck but filling a gap only you’ve spotted.”
Tips from the Trenches
Whether you’ve started a side hustle, want to begin one, or are looking to have leave your full-time job, there are some key considerations.
Start with “why.” When Loper asks guests on his Side Hustle Show podcast what kept them going for months of investing their time without earning revenue, the answers he gets demonstrate the deep-rooted motivation that people need for a side hustle.
“I get answers like, ‘I was afraid to stay where I was,’ or ‘I hated having to ask my boss for time off,’ or ‘My son was being mistreated in a daycare and my boss told me that I needed to handle my personal problems after work.’”
Adopt an experimenter’s mindset. You don’t need to know steps two to ten to get started, Loper says, but if you can position step one as an experiment in your mind, it seems easier to take action. He recommends testing out a side hustle for 30 days to see if you like it and if it will get results.
Think about what will happen if your experiment is successful. People tend to think about downside risks, but focusing on the negative can sometimes overshadow the equally important upside. Ask yourself, "If this side hustle works reasonably well, would that be a win for me personally, professionally, and financially?" he advises.
Manage your time. Kraig Kleeman, CEO and founder of The New Workforce, a Chicago-based outsourcing company, says discipline and planning are the secret sauce to time management. “It’s about setting boundaries and sticking to them,” he says. “I remember one side hustler telling me they treated their hustle like a second job. Every evening, from 6 to 9, they worked on their passion project. Weekends were for market research and networking. And hey, if your side hustle is what you love, it will feel like something other than work.”
Be Transparent. You should let your employer know about your side hustle if it's required, which is common in government, defense and legal jobs, if there's a chance your boss may find it on their own or through social media, or if there could be any perceived conflict of interest.
Create a financial plan. LaPlante recommends meeting with your financial advisor to review your business and personal finances and your business growth strategy every six to twelve months. He also recommends having twelve months of expenses in the bank before you leave your full-time job.
Making the leap to full-time job. “There’s no one-size-fits-all answer to when to turn your side hustle into your main hustle,” Kleeman says. “Some folks are happy keeping their hustle on the side, a creative outlet that pads the wallet. Others catch the entrepreneurial bug and can’t imagine returning to a regular 9-to-5.”
LaPlante says his trigger for when to leave was when he could fully replace his corporate income with business profits. For him, that journey took eight years. “When you leave the corporate world, don’t look at it as leaving one paycheck for another,” LaPlante says. “Owning a business is a lifestyle change that can be all-consuming. You won’t be able to shut down your mind at 5 p.m.” On the other hand, it offers flexibility.
Nova admits he probably left his full-time job too soon. “It took me years to build up this business and for the first few years I was scrounging in the couch cushions for quarters to take the bus,” Nova says. “I could have done this as a side hustle forever. I probably jumped into it full-time a little prematurely.”
Side hustles are extremely personal, from the motivation to the ultimate goal to the definition of success. Observes Kleeman, “If your side hustle is what you love, it will feel like something other than work.”
