Barbara Corcoran Says When You Should Quit Your Job for a Side Gig: How To Do It
Written by
Jordan Rosenfeld
Edited by
Molly Sullivan
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Real estate mogul Barbara Corcoran is no stranger to turning a side gig into a day job — she’s made multimillions in real estate investing, starting out with hardly any knowledge of the industry.
With that experience under her belt, Corcoran shared a video on her TikTok channel stating that there is a moment when it finally becomes time to quit your job for your side hustle.
That moment? “The minute your side hustle is able to pay your very basic expenses…”
Experts weighed in on what it takes to get there.
Be Passionate
Before you even begin thinking about the numbers, according to Ethan King, co-founder of stuff4GREEKS.com and Zeus’ Closet, and creator of Simple Success Systems, the “golden recipe” that worked for him and other entrepreneurs he’s mentored starts, “with something you’re so passionate about that you’d do it for free.”
As a college student, King started creating fraternity marketing materials and T-shirts just because he loved design.
“We started stuff4GREEKS as a simple school project, but when paid orders started rolling in from strangers, we knew we had something special,” he said.
Assess Your Financial Capacity
While Corcoran suggests you should leap out of your day job the moment you can pay “basic expenses,” that may not be realistic for everyone.
King said that what enabled him to make the leap that allowed stuff4GREEKS to really take off was that his wife had a stable job with benefits. “This gave us the runway we needed. One year after I went full-time with stuff4GREEKS, the business was doing so well that my wife could join too. We’ve been fully employed by our companies for two decades now.”
Consider Risk Tolerance
According to business coach Charlene Ridley at Unpause Your Dreams, side hustlers need to consider how much they can risk for what return. You need to assess the return on your investment (ROI) and the timeline associated with it to see how realistic it is and how long it might take you to achieve your goal.
“Monetizing your current expertise through things like digital products, courses and coaching/consulting are low-risk, low-cost side hustles. While many product-based businesses require a substantially greater financial investment and depending on the industry and offering can have higher rates of failure with lower ROI,” she said.
Time Capacity
Next you need to be realistic about how much time you have to dedicate to the launch, support and growth of the side hustle without it impacting your 9 to 5 and other obligations, Ridley said.
“While it was once popular (and still is within certain subgroups) to grind toward a goal leaving little time for personal responsibilities, the pandemic, current mental health crisis and current environment show increased rates of burnout and overall lower personal satisfaction levels.”
Keep work-life balance in mind.
Sustainability Is Key
You need to be sure your business can sustain you consistently long term before you make the leap, King said.
“Predictable revenue is key. Make sure you know your numbers at each step of your funnel. Know exactly how much you are spending on ads, what percentage of website visitors become customers and your average order value.”
Leverage Current Expertise
If you’re wondering how to start a side hustle, Ridley suggested leveraging your unique background, experience and expertise to provide a shorter time to launch.
“Couple this with current technology that supports delivery of this expertise through various channels and one can start a new venture in as little as an evening.”
Side hustles that have a tendency to be more lucrative, Ridley said, include digital products, coaching and consulting, corporate training, speaking, courses, specialty photography, service-based businesses supporting the elderly (i.e., companions, home healthcare, etc.) and project-based work.
Be Cautious
Ridley pointed out that social media is “flooded with videos and posts with claims of six figure months in short periods of time,” but this is not average for most people.
“So I would not say it is not wise for anyone to quit their full-time job at the launch of their business in hopes of achieving this overnight success.”
The best approach is to create an exit strategy and plan, she said. “For those with higher corporate salaries, it may not be the goal to replace their paycheck dollar for dollar, they may instead have a particular income goal that allows them to meet their current financial obligations.”
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