5 Podcasts That Will Inspire You to Work on Your Side Hustles

Riding the tiger.jpg

Experiencing the rough side of creative entrepreneurship?

One of my favourite analogies for the experience of entrepreneurship is the act of riding a tiger.

The people around you are marvelling at the daring venture while you’re on the back of the tiger thinking, “Holy shit! How do I stay on this thing without getting eaten alive!?”

The point is some of the greatest success stories are filled with trials and tribulations.

This binge-worthy podcast list is curated for those days — because we all have them — when we feel as though we’re losing momentum on our creative hustles and are afraid the tiger we’ve taken on is going throw us off its back and consume us.

How I Built This with Guy Raz

How I Built This Podcast

How I Built This is an NPR produced podcast that dives into the stories of the innovators, entrepreneurs, and dreamers behind some of the world's biggest companies such Bobbi Brown, Chip Wilson from Lululemon, to Ben Cohen and Jerry Greenfield of Ben & Jerry’s ice cream.

One of the things I love about the podcasting world is the candid conversations. Host Guy Raz wants to know, “Who are you when you’re on the bathroom floor in the fetal position, crying because you are not going to make it to the next day?”

It speaks volumes to Raz’s interview style because these wildly successful guests want to tell all when it comes to moments of failures, the risks they took to get to their success, and the critical moments in between.

Weird Work

Weird Work Podcast

Weird Work shares stories of people who earn a living in unconventional ways, like writing dinosaur erotica or performing with cats and dogs for Cirque du Sewer— if someone can make a living doing this, it just goes to show there’s a market for nearly everything if you put the work in to find your tribe.  

Magic Lessons with Elizabeth Gilbert

Magic Lessons Podcast

After Elizabeth Gilbert — most known for Eat, Pray, Love—published Big Magic on understanding creativity and how to overcome fear surrounding it, she wasn’t quite through with the topic. Luckily for us, she created this podcast to help artists struggling with creative blocks.

Gilbert consults her fellow writers, artists, and performers for insightful advice that is relevant for so many people when it comes to overcoming fears in the pursuit of living a life with purpose.

The Femails

The Femails Podcast

Hosted by Lauren McGoodwin—the founder of my favourite career blog, Career Contessa, The Femails is a podcast run by women for women diving into topics for building a successful and fulfilling career on your terms.

Not all of us are born and bred to climb ladders at corporate companies. McGoodwin’s guests talk about the failures, triumphs, and lessons in paving their own paths for success.

That Creative Life by Sara Dietschy

That creative life podcast

Sara Dietschy is a professional “interneter”—Youtuber, Blogger, Influencer, and now Podcaster. I followed her when she started out on Youtube filming tech reviews and I was learning how to use my camera.

She’s made a career on sharing her creative process when it comes to photography, filmmaking, and content creating for the web. That Creative Life podcast is a “creative exchange” with successful artists and business professionals in creative industries.

Share your thoughts!

We have curious ears and would love to know your podcast recommendations.


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