11 min 14 sec

WEEKLY RECAP: What Was Your Biggest Side Hustle Failure?

In our twenty-first weekly recap, we'll highlight the lessons learned in this week. Also: more listener Q&A!
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Notes from Chris

Episode 148

Each week, there will be a new question and an opportunity for you to share your side hustle journey on the show!

I've had a lot of people ask about side hustle failure stories, so I want to know—what has been your biggest side hustle failure?

To send in your response either leave me a voice message, call our Side Hustle Hotline at 844-9-HUSTLE (844-948-7853), or make a voice memo on your phone and email it to me at podcast@sidehustleschool.com


Our listener questions for this week come to us from Libby in San Diego and Gavin in Victoria:

  • Like many of our listeners, Libby has a passion project, and she decided to use a platform that she heard about in a previous episode to make money for it. Unfortunately, this has had the opposite effect and has been an expensive venture. She's also not really driven enough to reach a point where it's making a profit either, so she's wondering whether she should stick with it and give it a year or abandon it entirely.
  • Gavin is looking to take his artwork and photography to the next level by putting it on t-shirts, mugs, and canvas, but he's having a really difficult time getting an online presence. He often finds that he's so consumed with perfecting every aspect of his website that it's challenging to focus on the bigger picture and is looking for guidance.
Listen to the Weekly Recap for a more comprehensive look at this week's Listener Q&A. Also, if you have a question you'd like answered, send me a voice message. Your question may be featured on the show!

NEW: You can now call in from your phone and leave me a voicemail! Dial 844-9-HUSTLE // 844-948-7853 and leave a message with your comment or question for the show.


If you're artistically inclined like Gavin in one of today's listener questions, here are a couple of resources to help you reach a larger audience online.

  • Society6: If you're artistically inclined, Society6 may fit the bill. You can sell your designs on a variety of items including laptop sleeves and travel mugs
  • Shopify: Shopify is offering a 21-day trial and exclusive discount for all Side Hustle School listeners


    Here are some quick highlights for each episode this week. Listen to this week's recap for a more comprehensive highlight reel.

    • Ep. 142 - In this episode, we feature a teacher who used a starter platform to save up enough money to almost completely fund her honeymoon, and it's a great example of how your income on the side can go toward something fun or different from just paying your regular bills
    • Ep. 143 - Tired of battling split ends and hair breakage, a fashion and lifestyle blogger switches to satin pillowcases. She then learns to make and sell her own, earning six-figures annually
    • Ep. 144 - If you've ever wondered how to use Facebook Ads to further your business, you'll definitely want to check out this episode featuring an online marketing pro who helps an orthodontist bring in 13 new patients and $65K in new revenue spending only $500
    • Ep. 145 - A unique delivery service side hustle featuring a university employee who uses her logistical savvy to deliver IKEA enthusiasts their goods at greatly reduced rates
    • Ep. 146 - A Kansas City-area mom and her 10-year-old son invent an unconventional (but essential) product for young male athletes that brings in more than $5,000 a month
    • Ep. 147 - A love of 1920s-style photography allows a Texas woman to leave her day job and bring in multiple six-figures with classic “recreations” of a faraway time
    Inspiration is good; inspiration combined with action is better. Now get back to work!

    Yours in the revolution,


Side Hustle School Live:

Make a plan to start your hustle in 28 days or less.

You need more than one source of income. This in-person workshop (NOT available online) will show you exactly how to set up your first—or your fifth—hustle. We just added two more dates to the lineup for August! Here's where I'll be next:

  • Washington, D.C. - June 8th
  • Atlanta, GA - June 10th
  • Portland, OR - August 19th
  • Anaheim, CA - August 20th

Don’t See Your City? Let me know where you live! I’ll use your input to decide on future workshop locations. If we get enough people together in your city, I’ll be there.

Here's what's coming up next...

Each week I'll feature more stories from people who are starting side hustles without quitting their job. Here's a sneak peek of what's coming next week:

  • A side hustler who moonlights as a balloon artist
  • A couple in Canada who help other Americans immigrate to the Great White North with their informative e-book based on their research
  • How a search for the perfect engagement ring leads a software engineer in Baltimore on a mission to discover the logarithm for the ideal sparkly diamond. Along the way, he creates an affiliate side hustle with major potential.

Do you have a side hustle story you'd like to share? Fill out the Side Hustle School submission form and your story may be featured on the show!



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Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

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Quote of the Day
"What do successful side hustles have in common? They help someone AND have a profitable business model."

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To infinity and beyond,

Chris Guillebeau