Reporting Back on the First Set of Side Hustle Workshops

When I started Side Hustle School, the main commitment was the daily podcast, which is still going strong 60+ episodes in. People are responding to it very well, and I’m having fun. Yay!

But I don’t do small very well, so in addition to the daily show, there’s also a traveling workshop series and an upcoming book. I recently completed the first set of workshops and I learned a lot.

Here are a few reflections based on stops in four cities: Vancouver, Seattle, Portland, and Phoenix

(And yes, eventually I’ll be expanding eastward… more on that at the end.)

  • Most of the people who are coming don’t already have a side hustle and haven’t experimented in this world as much as I expected. Which is totally cool! There are a lot of possibilities when you’re just getting started in the world of hustling, and I’m excited to work with people who are brand-new
  • Nearly a third of the people who came to the first set flew in from elsewhere, including a guy from Puerto Rico who came to Seattle, and two people from Chattanooga who came to Portland. I did not expect this! I originally assumed that these would draw people mostly from the cities where they take place, but obviously, I was wrong. The mix of locals + out-of-towners is great, especially for the weekend events where people make friends and end up doing things together later
  • Speaking of that, I’m still not sure which format is best: weekday evenings or weekend mornings. When I initially designed the series, I had some of each one, on the theory that more people would sign up for one and therefore I’d learn which was best. However, the signups so far have been split almost perfectly even. Hmmmm
  • The schedule creates some issues for me. I’m naturally a morning person and go to bed around 9pm or 10pm at the latest so I can get up and work early. Therefore, for me I think I did a better job on the weekend mornings than I do for weekend evenings. But again, it’s not about me so if there was a strong preference for weekday evenings, I’d adjust to that
  • I want to make sure I’m teaching what people need. Based on everything I learned from the first set, I’m remixing a lot of the content and structure for the next ones. I’m excited to see this evolve and continue to roll out
Oh, and we made a fun video at the Portland workshop. Check it out and see if it might be a good fit for you!

Coming up next:
  • Los Angeles: Thursday, March 16th @ 6:30pm
  • Denver: Tuesday, March 21st @ 6:30pm
  • San Francisco: Thursday, April 6th @ 6:30pm
  • Austin: Saturday, April 8th @ 9:30am
  • New York City: TBD (but soon!)

And of course, more on the way. You can vote for your city on that same page, and if we have enough interest, I’ll make a plan to come!


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