【Schoolmistress 2】

Few free resources will help you get a side-hustle off the ground like a podcast. The Schoolmistress 2inspiration, insights, lessons, and exposure to new ways of thinking make a world of difference—and I can vouch for that. I spent three years and hundreds of hours listening to side-hustle podcasts while commuting to and from my full-time job.

Some podcasts led me through the beginning stage of my travel-writing side hustle, from finding a lucrative market to learning from others’ mistakes. As I honed my side-hustle path, inspiration-driven podcasts helped me push past imposter syndrome. Now, even three years after I successfully made the leap, I often return to these podcasts to cultivate new side hustles and off-shoot businesses to keep my career fresh.

If you’re in the market for a side-hustle podcast, here are eight shows that helped me go from dreamer to dream job.

For Side-Hustle Ideas: The Offbeat Life

Debbie Arcangeles spent years trying to find a career that aligned with her passions and life goals: travel, art, and photography. She now helps others pursue non-conventional lives through coaching and her The Offbeat Lifepodcast. This show features hundreds of interviews with bold changemakers who chose the path less traveled. It simultaneously helps listeners uncover new and unexpected career avenues while providing motivation for those in their early side-hustle stages.

For a Dream Job Reality Check: Quit Your Day Job

At age 40, Alisha Fernandez Miranda took a career turn no one expected: She went on sabbatical from her CEO role and signed up for not one but fourunpaid internships. Like many, she wasn’t feeling fulfilled, so she tried on some new dream industries for size: theater, art, fitness, and hospitality. Her podcast, Quit Your Day Job, is an offshoot of this career experiment. She interviews everyone from actresses to life coaches to learn what their careers are really like. The result? A podcast that will help you understand the behind-the-scenes of dream careers, with advice on how to break in.

For Supportive Community: Location Indie Podcast

If you’re surrounded by people who choose a more traditional 9-to-5 life, it can feel daunting to pursue your own thing. At best, no one understands what you’re going through. At worst, they tell you it won’t work. That’s where the Location Indie (LI) podcast(indie as in independent) comes into play. LI, a networking and skills-building community for those living off the beaten path, reminds you that you’re not alone in this journey. The LI podcast hosts Travis Sherry and Jason Moore spend hours talking all things side hustles and location-independent careers, with guest appearances from other members of the LI community. 

For Before-and-After Stories: Magic Lessons with Elizabeth Gilbert

While Elizabeth Gilbert is no longer recording new episodes of her Magic Lessons podcast, it’s a must-listen for anyone who needs inspiration through real-life side-hustle success stories. In Magic Lessons, an offshoot of the “Big Magic” book, Gilbert and guest experts help creatives from all walks of life overcome their fears and hurdles to pursue their dreams—then she checks back in with them months later to hear where their journey’s taken them.

For Business Logistics: Side Hustle School

Perhaps the most nuts-and-bolts podcast on this list is Side Hustle Schoolfrom author and entrepreneur Chris Guillebeau. In Side Hustle School, Guillebeau interviews side-hustlers about their business journey, both good and bad. He and his guests tackle everything from finding a viable market to advertising, overcoming embarrassing failures, and reaching that coveted milestone: making the first $1,000.

For Inspiration: Don’t Keep Your Day Job

Cathy Heller’s podcast Don’t Keep Your Day Jobis part side-hustle inspiration, part life coaching. It’s exactly what I needed during the scariest moments of my side-hustle days, particularly as I got closer to the big jump from side-hustle to full-time career. Heller helps you see and understand the purpose behind dream-chasing through heart-to-heart interviews and solo inspiration sessions. Each guest brings a new, expansive perspective that swaps that internal nay-sayer for a passionate, more confident voice.

For Creatives: Chase Jarvis Live

If you’ve ever wondered how renowned creators like Chris Burkard or Jimmy Chin went from aspiring artists to household names, tune into The Chase Jarvis Live podcast. Jarvis, an author and photographer, interviews the world’s most renowned artists and business owners to help listeners peek behind the scenes and realize they, too, can chase those lofty goals. Come for the big-name interviews, stay for the solo shows where Jarvis answers the exact questions creatives are struggling with, from handling work ruts to prioritizing the work that matters.

For a Sustainable Business Mindset: Deliberate Freelancer

Getting a side-hustle off the ground may take long hours and seemingly endless leg work, but if you want it to last for the long term, you need a healthy business mindset. Enter the Deliberate Freelancerpodcast by writer and editor Melanie Padgett Powers. The Deliberate Freelancer centers on sustainable and healthy business development. Episodes discuss everything from mental health and outsourcing to creating smart habits and learning to say no. It’s a must-listen when you’re ready to take your passion from side-hustle to long-term project or career, with tips and wisdom to ensure this path best serves your needs.