15 min 15 sec

Weekly Recap: When To Leave a Good Job

In our eighteenth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A!
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Notes from Chris

Episode 491

In today's recap, we look at the concept of when you should leave a good job. I've been thinking about it this week because I'm in the middle of recording an audio version of my first book, The Art of Non-Conformity.

The right time to leave a good job is right before you get tired of it. In the long-run, you’ll do your best work when you’re excited about doing it. That’s why I believe so much in planning for your future, or at least building for a future of choice.

In today's recap, I'll delve into the best time to leave a good job, and how having a side hustle can help you—listen to the Weekly Recap to learn more!


This week, we received a listener email from a side hustler named Sean:

  • Sean: "Hi Chris! I've listened to every episode since day one. Love the podcast and appreciate your insights.

    I currently have a 9-5 but put all of my energy and passion into my other business which I hope will replace my 9-5 very soon (but you can technically call it a side hustle for now).

    I create videos for small, sustainable and socially responsible businesses. Basically, I only do work for companies that I share the same values with. I know—horrible business model!

    To get to the point... You had an episode about a small, organic energy bar company called Mammoth Bar. They seemed like an ideal company to do work for so I reached out. We had a great first meeting, and I created a short animated video for them about their brand and bars. We still maintain a great relationship and they would like more videos in the future. I can send you a link to the video if you are interested.

    Just wanted to share this story with you as a huge thanks! Not only are you inspiring people to create side hustles but also connecting people from around the world.

    [Check out Ep. 219 to hear Mammoth Bar's story!]"

If you have something you'd like to ask me or an update you'd like to share, I'd love to hear from you. Leave me a voice message on the website or call into the Side Hustle Hotline (Dial 844-9-HUSTLE // 844-948-7853), and your question may be featured on the show!


Here's what we heard this week on Side Hustle School! Listen to this week's recap for a more comprehensive highlight reel.

  • Ep. 485 - A graphic designer and pet lover unleashes a side hustle that earns $84,000 a year. Dog-ear this episode!
  • Ep. 486 - She leaves her job to join a startup, then starts a business of her own—and then starts a side hustle to fund the business. Did you get all that? If not, just listen to hear how she earns $250/hour on the side
  • Ep. 487 - This software developer has always been a stock trading enthusiast. When he invests his time into an app to trade more efficiently, the app becomes a hit with other traders around the world
  • Ep. 488 - Two dog lovers create and grow a wiener-dog themed brand that now provides a six-figure income
  • Ep. 489 - A doctor with a voice worth listening to teaches himself the art of voiceover, then goes on to earn thousands of dollars working for some of the world’s biggest brands
  • Ep. 490 - When a designer quits his job at Apple to travel the world, he realizes that his nomadic lifestyle hacks are a hot topic—and a profitable one, too
Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


Join me at the World Domination Summit!

Have you heard of the World Domination Summit? This is a gathering of awesome people—an event that I've been hosting together with an amazing team in Portland, OR every summer for the past eight years.

WDS 2018 is coming up at the end of June (June 26th-July 2nd), and we'll be welcoming people from over 30 different countries. With inspiring keynote speakers, a week full of activities and attendee-led meetups, and two incredible parties, you won't want to miss it!

This is our final wave of main stage tickets so visit our website to get your ticket to this incredible, once a year event! We promise that it's unlike anything you've ever experienced before.

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 couple save $5 for four months to purchase textbooks off of eBay, and they turn around and resell them on Amazon. The best part? This ends up bringing them $68,000 within two years of starting!
  • Two former baseball players create a bat rental service, serving thousands of customers across the country
  • And so much more!

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!

Also, if you're interested in joining the Side Hustle Society, visit our Society page to get notified when it goes live!



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I use this card every day all over the world! ✈️

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Quote of the Day
"The right time to leave a good job is right before you get tired of it. In the long-run you’ll do your best work when you’re excited about doing it."

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To infinity and beyond,

Chris Guillebeau