Every day I’m side-hustlin’. But are you? On my podcast When To Jump, I’ve talked with many side-hustlers — some who have transitioned their gigs into full-time roles, others who have kept hustling as a passion project.
No matter where you choose to take your side projects, you can use these 5 tips from hustlers who made them work.
1. The first step is the hardest
The first step is often scary, but small steps can go a long way. Nivi Achanta wanted to impact education reform but wasn’t sure how to start. Inspired at a networking event, she made a simple website about Get Schooled, the education podcast she planned to host. She was surprised to see both how easy it was to get started and how many people wanted to support it.
“A jump doesn’t have to be this big, scary thing,” she says on the podcast. “Just by doing this thing I had the idea to do, it’s gaining traction. When you have this idea you’re really passionate about, people are willing to help out any way they can.”
2. Move in the right direction, even if you don’t know your final destination
When Chris Guillebeau set out to volunteer in West Africa, he didn’t know it’d be the start of his quest to visit every country in the world (yes, all 196). After achieving his goal, he was left wondering “what now?” On When To Jump, he shares how this experience, which he’s called “a period of rapid growth,” gave him a vision to hop to the next thing, eventually inspiring him to start the Side Hustle School podcast.
Though Chris has never had an end-game when it comes to his career, he emphasizes listening to the voice in your head and following the path it leads you down — even if it means you’re in free fall for a bit.
3. Wait for the right moment to take your side hustle full-time
Nick Martell and Jack Kramer, Co-CEOs of MarketSnacks (a millennial-focused business news newsletter), worked on their side hustle for 6 years before taking it to the big leagues.
Frustrated by the lack of digestible news when it came to the business world, the two began writing a daily newsletter, and since they both had full-time finance jobs, that meant working in any and all spare time — on their commutes, after work, even during vacation. But they didn’t mind. “When you’re motivated by loving what you’re doing, it’s a powerful momentum,” says Martell.
On the podcast, they share how their side gig — and the drive and mental stimulation it provided — even improved their performance at work. Gradually, they gained confidence that MarketSnacks could not only solve a problem in the business news space but keep them motivated and financially stable, so they took the leap and haven’t looked back.
4. Bring your ideas to life, even if they fail
Most people have heard of Airbnb, but do you know the man behind it? Co-founder Joe Gebbia joined When To Jump to talk about his entrepreneurial experiences and the importance of bringing your ideas into the world.
“Anytime I spotted an opportunity,” says Gebbia, “I developed this muscle of bringing it to life.”
He shares the side hustles he started and stopped before hitting it big with Airbnb. But even Airbnb took some time to catch on. It’s okay if every idea isn’t “the one.” What matters is getting into the habit of putting your ideas out there, and using this resilience to never stop creating.
5. Run your own race
Whether you’re just starting your side hustle or have been at it for a while, one thing holds true for all hustlers — work at your own pace. Bestselling author duo Christina Lauren (AKA Christina Hobbs and Lauren Billings) went from writing fan-fiction to having 14 New York Times bestsellers, and they attribute it to doing things their own way. While they never planned to become full-time authors, the pair spent a fair amount of time trying to get their first book in the hands of readers.
“When you see those stories of success that feel like they happened overnight, they usually didn’t,” Lauren explains on When To Jump.
For some people, it happens in a matter of months, for others it takes a decade, but the only thing you can (and should) do is focus on achieving your own success, not the rate at which others are reaching their goals.
Looking for more tips about changing your career? Check out the When To Jump podcast on Apple Podcasts or wherever you enjoy podcasts. Hosted by Mike Lewis, who left his comfortable job in finance to become a professional squash player, the podcast features advice from inspiring entrepreneurs and side hustlers who made the leap.