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5 Tips For Launching A Successful Side Hustle (For Real This Time)

Side hustles fizzle out for all sorts of reasons. These five entrepreneurs share how they developed their own into full-fledged startups.

5 Tips For Launching A Successful Side Hustle (For Real This Time)
[Photo: rawpixel.com/Unsplash]

You promised yourself this was the year you’d finally launch–and sustain–some sort of side project, be it picking up a few freelance clients, launching a blog, podcast, or YouTube channel, or setting up an e-commerce shop. One day in the hopefully not-too-distant future, your side hustle might even grow into a full-time business.

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But before you can get there, you’ll need some focus, diligence, and a dose of strategy. On my podcast, I’ve asked lots of successful entrepreneurs who’ve built successful businesses that originally began as side projects how they’ve managed to do it. Here’s what five of them told me about pulling it off.


Related: Starting A Side Project This Year? Here’s How To Make It Successful


1. Get Constant Feedback (And Start Early)

Author and life coach Susie Moore has been on the receiving end of hundreds of pitches from side hustlers around the world since she began research for her book, What If It Does Work Out? A common mistake she’s seen many side hustlers make is rushing to market with a product they’re excited to launch without fully vetting it from a customer’s point of view.

That’s understandable; many side projects arise out of passions and interests rather than market needs. But, as Moore points out, “Without clarity on what you’re creating and its direct connection to tangible results for your customers, you’re not likely to solve a real problem in their lives.”

Moore’s solution? Start asking for input early. She explains that regular feedback from your first customers is the only way to make sure you’re building something of value to your audience. Moore recommends constantly soliciting objective feedback, encouraging constructive criticism, and carefully drawing insights from everything your customers have to say.


Related: Everyone Has An Opinion About My Startup–Here’s How I Handle That

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2. Be Flexible On Your Strategy, But Not Your Mission

Caroline Ghosn has grown Levo, the professional network for millennials, to more than 8.6 million members since launching it as a side project in 2011. She has had to pivot the brand multiple times in order to stay competitive and relevant to her users.

Yet that’s convinced her of one thing: “Never compromise on your ‘why,’ but be flexible about the ‘how.’ The way in which you accomplish your goals and help your customers’ needs to be very flexible depending upon how those customers are reacting in real time,” Ghosn explains. “This is especially important when you’re building a side business, because your time is so limited, and it’s tempting to take shortcuts, but the second you change your ‘why,’ you become a different company.”


Related: Your 5-Week Plan To Starting A Side Hustle Over Your Lunch Break


3. Fall In Love With The Problem You’re Solving

Those are Steli Efti’s exact words. (“Don’t fall in love with your idea,” he adds.) Efti, the CEO of sales CRM platform Close.io (I’ve done some freelance work for the company, in full disclosure), says he’s seen too many side hustlers “spend months building what they believe to be the next game-changing product during their nights and weekends outside of work. But then they launch, and nobody buys.”

Efti chalk up this “painful” error to inexperience rather than lack of skill. It’s often more comfortable to build a business in a space you’re already familiar with, hoping that will insulate your precious idea from critical feedback–which, as Moore points out, is exactly what it needs. Efti advises a subtle shift in mind-set: “Choose instead to fall in love with the problem you’re trying to solve for your customers.” This can help you validate that your side-business idea (your “how,” in Ghosn’s phrasing) is actually tackling a problem worth solving.

4. Build For The People You Know

Michele Romanow knows how easy it can be to chase random market opportunities that present themselves. You may be tempted to build a product you feel is lacking within a market you don’t fully understand (or have a deep interest in), the founder of financing platform Clearbanc shared with me, but that’s often a risky move.

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Romanow’s advice to mitigate that risk? “Create for the people you know best.” She suggests starting with “your own personal network,” since you’re more likely to understand their problems better to begin with. “Then do something creative and unique to really capture their attention and begin getting feedback on what you’re building.”

5. Don’t Wait For Inspiration

Business consultant and author Tara Gentile knows that waiting for the perfect idea to come along is the quickest path to never actually building anything. Her advice? “Don’t waste time waiting for inspiration. Start with what you know today.”

Gentile advises using the skills you’ve developed to take on freelance projects first–and then use those as an opportunity to get paid while learning more about your target customers (for future endeavors). “Instead of spending lots of time waiting for a flash of inspiration or investing in learning marketing techniques, let your colleagues, friends, and family know that you’re offering one of your core skills on a project basis,” she recently explained to me by email. “You’ll be surprised how easy it is to find an initial set of projects–new and better gigs will come from those first contracts.”

It takes some legwork, sure. But the rest is just patience.


Ryan Robinson is an entrepreneur and writer. On his blog, ryrob.com, he teaches over 200,000 monthly readers how to start and grow a profitable side business. Join him on Twitter at @TheRyanRobinson to chat more about business and side projects.

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