According to Susie Moore—coach, rockstar writer, and author of What if It Does Work Out? How a Side Hustle Can Change Your Life—you should start by following a bit of tried-and-true advice: Listen to your heart and you'll probably just know. She says the most important question you can ask yourself is, "If I got the outcome I wanted, does it feel expansive? Does it feel big? Does it feel good?"
That was the deciding factor for her, anyway. While working for a Fortune 500 company in Silicon Valley, Moore found herself asking: "Is this all there is?" And when her soul replied, "Nope!" she left to enroll in New York University's coaching program, started her own life coaching practice, launched an online side-hustle course, and began to interview entrepreneurs like Arianna Huffington, Kris Jenner, and Sara Blakely (AKA the Spanx billionaire) for major publications.
"If I got the outcome I wanted, does it feel expansive? Does it feel big? Does it feel good?"
That said, there are a few practical things to consider before giving up your steady paycheck in favor of a home office and a leggings-only dress code. In What if It Does Work Out?, Moore throws down her sage advice for deciding when to walk away—and it goes far beyond how much you've got stashed in your savings account.
Keep reading for the 5 signs you're ready to trade in your 9-5 for good.
1. Your side hustle is actually making money
Passion is great, but regrettably (*sigh*), it just doesn't pay the bills on its own.
"It's [not] a hustle unless you are making money," stresses Moore. "A lot of us have expensive hobbies that we think are side hustles, but they’re not." Thus, attending boutique fitness classes and reviewing them on your blog could be your hobby, but it's not truly a side gig until you figure out a way to monetize it.
Even after the funds start rolling in, you'll still want to make sure you're earning enough to make your side project your primary source of income. "Focus on matching your base salary or getting as close as you can to what’s going to manage your lifestyle right now," Moore advises. "You have to be making revenue in a way that feels consistent with the lifestyle that you’re used to." Otherwise, it won't be sustainable in the long run.
2. Your day job's taking a backseat to your side gig
With any luck, your hustle will reach some degree of success—and when that happens, it'll inevitably start to siphon love and attention away from your day job. Symptoms of side hustle takeover may include: Falling asleep at your desk, scrolling Pinterest for business ideas while in meetings, or missing your subway stop for work because you're too busy catching up on new client inquiries.
Instead of trying to give both gigs 100 percent, Moore suggests taking this as a sign that it's time to grant your hustle your undivided attention."You’ll be working towards something big versus just filling your days with things that don’t really mean anything to you," she says. (Plus, getting fired for less-than-stellar job performance isn't exactly the best way to launch yourself into self-employment.)
3. You’ve found a tribe that inspires you to aim higher
According to Moore, honing in on your hustle might naturally lead you to outgrow old friendships. "One of the most common [comments] I get as people start to become more and more successful is: 'People are giving me attitude, people are giving me criticism,'" she says.
But when you're navigating the entrepreneurial world, it's crucial to have a support system that's fully aligned with your goals. "You’ll notice that as you get farther along in your business, the new people that you're surrounded with become business partners with you," says Moore.
Luckily, with the rise of all-female co-working spaces, connecting with a like-minded tribe is easier than ever. How to break the ice? Maybe you swap your knowledge of SEO for a quick Mailchimp tutorial—all in the comfort of a gorgeous, millennial pink office space.
4. You've mastered the art of meeting deadlines—even the ones you make for yourself
It sounds obvious, but getting sh*t done is a must if you're going to successfully work for yourself. And as Moore explains, you've got to put due dates on your calendar—and stick to them—to actually accomplish everything you envision. "Any sort of goal without a deadline is just a dream," she proclaims.
Once you've mastered this mentality in the form of consistently meeting self-imposed deadlines, you'll also know you have the willpower to be your own boss.
5.You're willing to push past your fear in pursuit of the unknown
Let's be real: Stepping away from the predictability of a 9-to-5 is super scary. But successful entrepreneurs don't let fear hold them back.
As Moore puts it, the worst-case scenarios in your mind are often far more dramatic than they'd ever be IRL. (After all, if you were resourceful enough to start a thriving side hustle in the first place, you're probably not going to be penniless and living on the street in six months.)
Still not convinced? "The purpose of life isn’t to be safe," she stresses. "The purpose of life is to be expansive and growing." And there's no learning experience quite like naming yourself CEO of your own empire.
Originally published on January 25, 2018; updated July 21, 2018.
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