12 min 37 sec

Weekly Recap: “Craigslist Wedding Photographer” Strikes Back

In our twenty-fourth 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 533

You are listening to this show because you are interested in making your life better. Sure, you want to make extra money, and that's totally okay! It's totally fine to have that goal (and I think it should be your goal), but you also want to think differently.

You want your tomorrow to be better than your today, and you're working towards something. Maybe you have a specific goal in mind, or maybe it's more general—either way, there's something out there that you need to do. And when you figure this thing out, it is going to make your life better.

In today's recap, I'm going to read you a couple emails that highlight some of our listeners who are taking action.

  • Alain: "I have listened to every episode since January 1st, and one of your episodes featuring a guy who puts a craigslist ad out to start a wedding photography business (see Ep. 9!) really resonated with me. Naturally, I decided to do the same thing!

    I bought a camera, built a website with WordPress (of course), and put an ad on craigslist. 

    It’s been more than a year now, and I am having the time of my life. I get to photograph weddings, birthdays, baptisms, marriage propositions, anniversaries, etc.—essentially, I get to be a part of the best parts of people's lives!

    I don't make $500 every month. I make more during the summer and less during the winter, but it's side hustle. One of many others.

    Thank you for your podcast! I have share it with lots of my friends. One of my friends took inspiration from one of your earlier podcast, the guitar teacher. My friend started teaching guitar and his side hustle is also doing well."
  • Phil: "I just wanted to say how much I enjoyed your book. I'm 22 and in the summer of 2017, I participated in a cross-country bike ride (NYC -> San Fran) as one last hurrah after graduating college and going to work. After the trip, I went to work in rural Pennsylvania for about six months before resigning from my job. I soon realized I had the opportunity to participate in the cross-country cycling event again, and even be the leader of the 20+ students riding!

    When I told my parents of this opportunity they didn't really understand why I wanted to do the trip again, instead of finding another job and saving money. But I knew deep down this trip was what I needed even if I couldn't explain why. Reading your book has helped me better understand my feelings and remind me of the power behind these types of life experiences. Thank you!

    Hopefully, you have the time to read all this, I'm sure you're a busy man. If you're curious about the group I am apart of, check out illini4000.org. We raise money for cancer research and are currently on day 14 of 77 on our 4700-mile journey!"

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. 527 - A dog lover learns to bake and sell superfood dog treats, earning $3,000/month with just $3,000 in startup costs
  • Ep. 528 - Strategy consultants turn a round-the-world trip into inspiration for passive income
  • Ep. 529 - An “involuntary sabbatical” prompts this Polish marketer to investigate the possibilities of apple-based vodka
  • Ep. 530 - A project manager in California lights up a new revenue stream and smokes the competition with his counterculture emojis
  • Ep. 531 - A breakup brings two sisters together to create one happy side hustle
  • Ep. 532 - After feeling burned out from a career at Nike, this merchandiser looks elsewhere for radical inspiration. She then moves her side hustle to Austin, Texas while relocating for a new job
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 the month (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:

  • He wanted to start a side business and put his engineering degree to good use. When he stumbled across two 1950s radios, he found an idea that was right on his wavelength
  • Those long credit sequences at the ends of movies can include a LOT of names—and they also take a lot of time for producers to coordinate. When two industry friends team up to simplify the process, they crawl their way to a highly profitable side hustle
  • 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!



Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

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

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Quote of the Day
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To infinity and beyond,

Chris Guillebeau