15 min 3 sec

Weekly Recap: Have a #HappierLaborDay!

In our thirty-fifth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A!
#HappierLaborDay Getting Started Ideas Lessons SHS Check In Weekly Recap

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Notes from Chris

Episode 610

In Gretchen Rubin’s most recent episode (Ep. 184—listen to it here!), she included a number of tips and ideas about how to have a Happier Labor Day (#happierlaborday).

I’ll just note that my philosophy is that the meaning of life is not to stop working and sit on the beach. That’s fine for a few days or a week, but then what do you do?

Surely the answer is to find meaningful work, something that you believe in and can look forward to.

If I think about times of career satisfaction vs. dissatisfaction, most of the satisfying times came when I was challenging myself in some significant way, doing something new, or embracing a quest of some kind. The times I was dissatisfied were when I tried to do something I wasn’t good at (and didn’t want to do), but I felt like I had to for whatever reason.

Or I was otherwise striving in some way that felt inauthentic.

So my challenge to you today is that if you feel dissatisfied, let’s mix it up somehow! Promise yourself that you’ll do something by the end of the day to make a change.

If you're interested in learning more about Happier Labor Day, check out today's Weekly Recap and head on over to Gretchen's podcast page!


This is a new segment we're trying out with the help of side hustlers that we've featured in the past. Today, we have an update from Jake Posko, who was featured very early in the show on Ep. 23.

When we featured Jake back in 2017, he was advertising "the World's most awesome guitar lessons," and he also found a way to bring in passive income through referrals on his website, Severn River Guitar.

Listen to the Weekly Recap to hear from Jake and learn what's happened since he was 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. 604 - An ad executive turned teddy bear manufacturer creates a military-grade sleep system for children, earning $100,000 in sales and making a lot of people beary happy
  • Ep. 605 - Hungover after a night of hosting a party, an Australian accountant comes up with an unusual cleaning service that goes on to earn $30,000/year part-time
  • Ep. 606 - What starts as a collegiate adventure in getting around the legal drinking age requirements leads to a mission that turns trash into cash
  • Ep. 607 - A digital marketing manager finds success by growing her dollhouse drop-shipping website business—all without paying for advertising, and by working only one hour a week
  • Ep. 608 - After experiencing the frustrating moment of not having a witty reply for a rude stranger, this event organizer launches a website to share the best comebacks for every situation
  • Ep. 609 - After a painful breakup, an account manager becomes a new spokes-person for side hustling by reselling bicycle gear
Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


We want to hear from you!

The best part of Side Hustle School is our community, and around 20% of our episodes come from listeners. Are you working on something and want to share it with us and our audience? If so, we want to hear from you!

Head on over to our online submission page, and we'll be in touch if your story is chosen.

And if you're still working on something but have some questions, we want to hear from you too! Most Weekly Recap episodes include Listener Q&A.

Call the Side Hustle Hotline at 844-9-HUSTLE (844-948-7853), record your question and send it to podcast@sidehustleschool.com, or just send us an email!

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:

  • This CPA was burned out on office work, so she turned her efforts to an Etsy business—but it wasn’t long before she was hitting the books again, just in a more creative way. Her new spreadsheets help Etsy sellers and earn a six-figure income for her
  • In search of a side hustle, two Australian friends learn to import toothbrushes from the U.S., earning $30,000 in profit
  • And 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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Quote of the Day
"I was dissatisfied whenever I tried to do something that didn’t feel like myself, or when I tried to do something I wasn’t good at and didn’t enjoy—but felt like everyone expected me to."

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To infinity and beyond,

Chris Guillebeau