Join a Supportive Community and Create a New Source of Income


Join the Side Hustle Society and Create a New Source of Income

Link: Side Hustle Society

Short version: my new training program (the first I’ve made in 3 years!) is now available for registration. Join during the introductory launchone week only—before it closes for at least a month.

-OFFER ENDS January 16, 2018-

And here’s the slightly longer version…

It only took me six months to finish what I started.

Last January 1, I introduced Side Hustle School, a daily podcast that promised to show listeners how to make extra money without quitting their jobs. In our first year, Side Hustle School produced 365 episodes that were downloaded millions of times (more than 12 million in total).

I also heard from a ton of listeners. From thousands of emails to in-person meet ups in 40 cities, all along the way I heard what people like you are looking for most of all.

What I’ve heard more than anything else is that you want support. You want to get feedback about your idea, and you want to connect with one another!

You also want a step-by-step process that guides you from start to finish in creating a new source of income.

Well, help has arrived! Side Hustle Society will help with both of these issues. When you join the Society, you’ll get that step-by-step process in the form of 35 short audio and video modules. You’ll also get access to a community of people just like you, where you can bounce ideas off one another and get advice from experts.

Learn more or register now

After one week, we’ll close registration and not accept any new members for at least a month (and likely at a higher price). This is so we can focus on serving and rewarding the inaugural members—perhaps including you.

I spent more than six months designing this program (thanks for your patience), and I know it can help people who are looking for support in starting their hustle.

To your success,


Chris Guillebeau

P.S. To be clear, this program isn’t for everyone. I only want people to join who are absolutely serious about making their side hustle dream a reality. If that’s not you at the moment, no problem—you’re more than welcome to continue to enjoy the free show that comes out every single day.

If, however, you do want to take action and create a new source of income in a short period of time…. GET READY!!! This new program will help, and I’ll do everything I can to support you along the way.


Decide for yourself what you want, then find a way to make it happen.

Where Do Side Hustle School Stories Come From?

Side-Hustle-Stories- Chris-Guillebeau

Every day on Side Hustle School, I tell a different true story of someone who creates a new source of income without quitting their job. Sometimes people ask, “Where do the stories come from?”

Great question! Many of them come from our listeners and readers. Do you have a side hustle? If so, I’d love to hear about it! We’ll feature some of the stories far and wide to 40,000 daily listeners.

—>Tell Us About Your Side Hustle 

If you don’t have a project like this yourself but know someone who does, will you send them this link? Maybe we can help them get more business, and they can also help a lot of people by sharing their story with people who are starting out.

Meanwhile, the SIDE HUSTLE book has been out in the world for more than a month, and I’m hearing from people every day about projects they’re starting.

Side-Hustle-Tour-Georgia Side-Hustle-Tour-San-Francisco Side-Hustle-Tour-San-London

I hope it helps you create more freedom for yourself. Do you have a hustle yet?

SIDE HUSTLE costs $25 or less and can help you in a very practical way.

Get your copy now:

Barnes & Noble
Local Bookstore


Decide for yourself what you want, then find a way to make it happen.

201 More Stories of People with Day Jobs Creating Side Hustles

Listen to Side Hustle School:

in iTunes or Stitcher
on the website
—somewhere else (it should be available almost anywhere you listen to podcasts…)

On January 1, I began a new project: to share a story every day of someone who starts an income-generating project (a “side hustle”) without quitting their day job.

The project failed and I decided to give up. Just kidding! We are relentlessly moving along, publishing story after story—and it’s getting better and better!

I recently completed the first 100 200 300 days. There’s much more to come, but I’m excited about everything I’ve learned since beginning back in January.

If you’re just joining in, you can also catch up on any recent episode from the links below.

Here’s the list and links to the first 100 episodes.

Download all episodes from each month:



Side Hustle School – Week 15:

Side Hustle School – Week 16:


Side Hustle School – Week 17:


Side Hustle School – Week 18:

Side Hustle School – Week 19:

Side Hustle School – Week 20:

Side Hustle School – Week 21:

Side Hustle School – Week 22:

Side Hustle School – Week 23:

Side Hustle School – Week 24:

Side Hustle School – Week 25:

Side Hustle School – Week 26:

Side Hustle School – Week 27:

Side Hustle School – Week 28:

Side Hustle School – Week 29:

Side Hustle School – Week 30:

Side Hustle School – Week 31:

Side Hustle School – Week 32:

Side Hustle School – Week 33:

Side Hustle School – Week 34:

Side Hustle School – Week 35:

Side Hustle School – Week 36:

Side Hustle School – Week 37:

Side Hustle School – Week 38:

Side Hustle School – Week 39:

Side Hustle School – Week 40:

Side Hustle School – Week 41:

Side Hustle School – Week 42:

Side Hustle School – Week 43:

I’ve been so happy to see the show finding a good home with the right people! A new episode arrives each morning at 6:01am EST. As promised, much more is on the way.


Decide for yourself what you want, then find a way to make it happen.

Welcome, New Readers! What The Art of Non-Conformity Is All About


I’ve had a lot of new people join my blog recently, mostly from all the media coverage about my new book. Welcome!

If you’re just joining, here’s a quick explanation of what all of this is about. I started this blog wayyyyy back in 2008. My mission is to help people live unconventional lives, especially through self-employment and travel, but also the general theme of non-conformity.

At the time I started, I was pursuing a big quest to visit every country in the world by my 35th birthday. I achieved that goal and wrote a book about it called The Happiness of Pursuit. I also wrote a book called The $100 Startup, and my newest book is SIDE HUSTLE.

But enough about me. What can you find here on the site? A lot of things, but let’s focus on three areas:

1. Side Hustle School

My latest project is a daily podcast (7x/week, no breaks) and a new book that provides a plan for you to go from Idea to Income in 27 Days. In other words, it will help you create a new source of income without quitting your job.

I started this project to help everyone who doesn’t necessarily want to “become an entrepreneur,” but does understand how important it is to have more than one source of income. It’s for busy people who believe in investing in themselves to have more security, confidence, and freedom.


Subscribe in Apple Podcasts
Subscribe in Spotify (mobile only)
Subscribe in Stitcher

I’m currently on a 100-city tour to speak to readers about the book. Come say hi! And if you don’t see your city listed, let me know if you’d like me to come.

2. Travel Hacking

I was able to visit every country in the world largely because of travel hacking: the art of using Frequent Flyer miles and other strategies to a) save money, and b) have incredible experiences that would otherwise be inaccessible.

This page provides a good overview of the details:


If you’re just starting to learn about these things:

My #1 recommendation is to get the Chase Sapphire Preferred card. If you do nothing else, this card will get you $625 in free travel right after meeting your minimum spend. It’s a great value, and the same card I used myself every day for five years.

3. WDS

Eight years ago, a small team and I had a crazy idea: invite 480 awesome people (like you!) to join us in Portland, Oregon for a weekend adventure called World Domination Summit.

WDS has grown since then, but the original values of Community, Adventure, and Service remain. Every summer, more than 1,500 people from 25+ countries travel to Portland. In addition to keynote talks in a theater, attendees host hundreds of meetups, workshops, and activities.


Tickets go on sale twice a year. If you’ve never been to WDS, I’d love for you to come—it will change your life.


The central message of my work is that you don’t have to live your life the way others expect. You can do good things for yourself and for others. You can pursue a dream of your own, no matter how crazy it may seem.

Also, you’re not alone out there. People all over the world are doing this in their own way. The revolution continues!


Decide for yourself what you want, then find a way to make it happen.

SIDE HUSTLE: From Idea to Income in 27 Days (The Book Is Out!)


Buy it now: Amazon | Barnes & Noble | iBooks| Your local bookstore
Join me on my 100-city tour.


Hey everyone, the SIDE HUSTLE book is out!

Last year I spoke to groups all across the U.S. and Canada. More than anything else, one topic resonated: how to start a side hustle. 

The more I thought about it, the more I wanted to tackle this topic in depth. I’ve been starting my own side hustles for two decades, and have been writing about them for nine years.

I decided to make this a mission, not just a project. The book is out today, but I’ve been publishing a daily podcast 7 days a week since January 1. Each day, I tell a true story of an employee who creates a new source of income without quitting their day job.

So far we’ve published 262 episodes, with a new one coming out every day. I’ve never worked so hard AND had so much fun.

Now I’m going on the road: this week to Seattle, Los Angeles, San Diego, Portland, and Denver, and then on to dozens more cities in North America and beyond. Come out and say hi!

Side Hustle Book Image

SIDE HUSTLE: From Idea to Income in 27 Days (What’s It About?)

The key message of this book is: don’t quit your job, but do create a new source of income while you’re still there.

A side hustle isn’t just nice, it’s necessary—and there’s a process you can follow to create one.

I created a 27-day plan of action, with one step for you to complete each day. If you follow the plan, you can start your own income-generating project. Don’t take it from me; thousands of people have done it for themselves!

I used a case study format for this book, with lots of stories of regular people who all succeeded using this method.

  • The woman who makes personalized candy hearts for Valentine’s Day, earning $100,000 a year on the side
  • The guy who sets up a website containing fish tank reviews, then never touches it again… but three years later, continues to receive $700 a month in affiliate commissions from Amazon
  • The couple who visits Nepal for their honeymoon then brings back cashmere scarves to resell (donating a portion of the profits to girls’ education in Nepal)

…and many more. I loved writing this book, and I hope you love it too!

How You Can Help

This book is extra special because it basically came about in response to what YOU (or at least many readers) told me over and over.

If you’d like to help, I’d be most grateful. There are three main things you can do:


Where do you spend time online or offline? Wherever it is, let people know that the book is out and why you think they should buy it.

Feel free to use these images and the hashtag #SideHustleBook.





Once you read the book, tell everyone what you learned and what your favorite part was. The best places to post reviews are Amazon and Goodreads. Everyone else in the publishing industry looks at those sites to see what people are saying about books.


Unlike online courses or other business products, the book is cheap. The list price is just $25, and many retailers will sell it for less. Yet despite the low price tag, you can use this model to create a moneymaking asset that can serve you for years to come.

If you enjoy some of the work I do for free (the blog, the podcast, the meetups—basically 80% of what I spend time on), please consider purchasing a copy for yourself, and copies for anyone who you think needs a side hustle.

Buy it now: Amazon | Barnes & Noble | iBooks| Your local bookstore

*If you buy 50 or more copies for a group or organization, please let me know so I can thank you personally. 



Okay, I’m getting ready to hit the road—and I’m excited to begin a new journey. Will I see you on tour? Will you start your side hustle?

Either way, I’ll be cheering you on, and I’d love to know what happens.


Decide for yourself what you want, then find a way to make it happen.

Meet Me Anywhere! Announcing the 100-City* Side Hustle Tour

Hey, everyone!

Two big things today…

My new book, Side Hustle, comes out on September 19. As part of that process, I now have the first batch of cities for my fall tour ready to go. And because pre-orders for the book make a huge difference for authors, I also have a special offer for you.

Chris Vancouver

1. The first part of my fall tour schedule is now online!

I’m incredibly excited to announce that the first 30 cities of my Side Hustle tour are now finalized!

Well, mostly—we’re still working out a few scheduling things. But I didn’t want to keep you waiting any longer… the tour starts next month!

If you’ve never been to one of my book events before, know that they are a lot of fun. Each stop is both interactive and introvert-friendly. You’ll learn something, we’ll have a chance to talk, and you’ll also meet a lot of other awesome people.

—> Check it out and sign up! 

I’ve been doing unconventional book tours for seven years now, and I love every part of it. Last year I finished the 30-city Born for This tour and thought, “When can I do this again??”

I hope you’ll join me somewhere along the way for this one. Most stops are free, and everyone is welcome.

Sign up and tell your friends!

2. I’d love to send you a free report.

Ever since I started Side Hustle School on January 1, a lot of people have told me that their biggest challenge is finding the right idea. Well, every day on the show, I tell a story of someone who’s found an idea and turned it into a new source of income.

Still, sometimes you just need the ideas. I get it!

With that in mind, I’ve recently created a report featuring some of the best ideas from the show so far. It’s called “48 Hustle Ideas to Get You Started,” and it’s NOT for sale.

My new book, Side Hustle, comes out on September 19. If you pre-order it from any retailer (including Amazon or Barnes & Noble, but also your local bookstore), I’ll send you the report free.

—> Get the report here!


I feel very fortunate that I can write for a living and serve a global community of remarkable people. Much more is on the way!

Yours in hustling,


Chris Guillebeau

Decide for yourself what you want, then find a way to make it happen.

Announcing the Side Hustle Book: Coming September 19, 2017 (+ 100 City Tour!)


Friends and readers!

On September 19th, my new book, Side Hustle, will launch—and I can’t wait to share it with you! I’ve been working on it for more than a year… or perhaps more than two decades, if you count the whole time I’ve been making a living without a job.

After much debate, I can finally show you the book cover, as selected by a panel of readers who had a lot of strong opinions. 🙂

The book builds on the lessons of my daily podcast, Side Hustle School, and presents a step-by-step, 27-day plan to help you create a new source of income without quitting your day job.

More news coming soon, but for now:

  • You can pre-order the book from your choice of retailers. Those retailers include your favorite local bookstore, Amazon, Barnes & Noble, iBooks, or anywhere else you’d prefer. If you pre-order, save your receipt (digital or physical)—I’ll have a special bonus for you later.
  • Join the Street Team and be part of the launch! If you’d like to learn about the behind-the-scenes and join me in making sure that everyone hears about the book in September, sign up here.
  • Note: if joining the Street Team, we’ll ask you to buy at least one copy of the book and leave an honest review.

  • I’ll be doing a 100-city tour throughout the U.S., Canada, U.K., and then eventually the rest of the world. If you represent a company, organization, co-working space, or similar that would like to host an event, let me know. We’ll be announcing cities next month and I’d love to visit as many cities as possible.

All of my work is reader-supported and made for readers. Over and over on last year’s tour for Born for This, I heard that people wanted to learn more about starting a side hustle without quitting their day job.

This book, this tour, and the daily podcast is the answer to that request demand. I can’t wait till September 19th!


Decide for yourself what you want, then find a way to make it happen.

101 Stories of People with Day Jobs Creating Side Hustles

Listen to Side Hustle School:

in iTunes or Stitcher
on the website
—somewhere else (it should be available almost anywhere you listen to podcasts…)

On January 1, I began a new project: to publish a story every day of someone who starts an income-generating project (a “side hustle”) without quitting their day job.

The project failed and I decided to give up. Just kidding! We are relentlessly moving along, publishing story after story—and it’s getting better and better!

I recently completed the first 100 days. There’s much more to come, but I’m excited about everything I’ve learned since beginning back in January.

If you’re just joining in, you can also catch up on any recent episode from the links below.

Download all episodes from each month:

January | February | March | April

Week 1 Collage
Ep. 6 (L): Astrology Calendar Hustle. Ep. 4 (R): Pinning for Cash!
Side Hustle School – Week 1:


Ep. 12 (L): San Francisco Traveling App. Ep. 10 (R): Saddles for Chickens!
Side Hustle School – Week 2:


Ep. 17 (L): Airbnb for dogs. Ep. 15 (R): Digital caricature hustle.
Side Hustle School – Week 3:


Ep. 24 (L): Philanthropic Cashmere Hustle. Ep. 25 (R): Pottery Barn Photography Hustle.
Side Hustle School – Week 4:


Ep. 33 (L): Handmade State Slates. Ep. 31 (R): Ballpark Sweaters!
Side Hustle School – Week 5:


Ep. 38 (L): Astronomy Book Hustle; Ep. 40 (R): TLC Officiant Hustle
Side Hustle School – Week 6:


Ep. 45 (L): The SimpleBra; Ep. 48 (R): Next-Level Tarot Hustle
Side Hustle School – Week 7:


Ep. 50 (L): Belgian Chocolate Hustle!; Ep. 52 (R): Spa-Grade Face Paint
Side Hustle School – Week 8:


Ep. 58 (L): 50 Shades of Grey Hustle; Ep. 62 (R): Gold Panning in New Zealand!
Side Hustle School – Week 9:


Ep. 68 (L): Novelty Pocket Shirts; Ep. 65 (R): Self-Published Romance Novels
Side Hustle School – Week 10:


Ep. 75 (L): British Pork Pies; Ep. 76 (R): Whimsical Sketch Hustle
Side Hustle School – Week 11:


Ep. 78 (L): Jewelry for Social Good in Detroit; Ep. 83 (R): Craigslist Bridesmaid-for-Hire
Side Hustle School – Week 12:


Ep. 87 (L): 20,000/Month Cleaning Hustle; Ep. 90 (R): Karaoke League Hustle!
Side Hustle School – Week 13:


Ep. 93 (L): Juppy Baby Harness; Ep. 96 (R): Instagram Calligraphy Hustle!
Side Hustle School – Week 14:


Side Hustle School – Week 15:



I’ve been so happy to see the show finding a good home with the right people! A new episode arrives each morning at 6:01am EST. As promised, much more is on the way.


Decide for yourself what you want, then find a way to make it happen.

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!


Decide for yourself what you want, then find a way to make it happen.

30 Days of Side Hustle School: Cruising for Dollars, Six-Figure Candy Hearts, and Saddles for Pet Chickens

Listen to Side Hustle School:

in iTunes
on the website
—somewhere else (Stitcher, Spotify (mobile only)PlayerFM, CB radio…)

On January 1, I started a daily podcast that will continue throughout the year. I’ve learned a lot, and I’m having a lot of fun.

Best of all, a lot of people are learning from the show and starting their own hustles.

If you’re new to the show, it’s not too late to jump in. You can start listening at any point and not feel left out, but it may help to go back and listen to some of the earlier episodes.

By popular request, we now have a way to download all of the first 30 episodes!

—> Side Hustle School: The First 30 Days

You can then add them to your home library on iTunes, Sonos, or presumably any other player that you prefer.

You can also catch up on any recent episode from the links below:


Week 1 Collage
Ep. 6 (L): Astrology Calendar Hustle. Ep. 4 (R): Pinning for Cash!
Side Hustle School – Week 1:


Ep. 12 (L): San Francisco Traveling App. Ep. 10 (R): Saddles for Chickens!
Side Hustle School – Week 2:


Ep. 17 (L): Airbnb for dogs. Ep. 15 (R): Digital caricature hustle.
Side Hustle School – Week 3:


Ep. 24: Philanthropic Cashmere Hustle. Ep. 25: Pottery Barn Photography Hustle.
Side Hustle School – Week 4:



Side Hustle School – Week 5:



I’ve been so happy to see the show finding a good home with the right people, and I have a lot of plans for the next 335 days.

A new episode arrives each morning at 6:01am EST. Here’s to your hustle!


Decide for yourself what you want, then find a way to make it happen.

Side Hustle Workshops Start Next Week! Join Me in Your Choice of 4 Cities

Link: Side Hustle School Workshops

Next week I’ll be debuting my Side Hustle School Workshop series in four cities: Vancouver, Seattle, Portland, and Phoenix. Come out and join us!

Not in one of those cities? Well, we already have people flying in from several other places, so you won’t be alone… but of course, you can also suggest a stop for your city in the future. To do so, just add your location in the center of that page. You’ll get an email if we schedule something there later.

So anyway, what’s the new workshop all about?

It’s a 2 1/2 hour intensive workshop where I’m teaching a specific method. Everyone who attends will go away with a workbook, a set of tools & resources, and best of all, a specific plan to start their hustle within 30 days.

Specifically, you’ll learn:
  • Discover profitable ideas using the skills you already have
  • Go from Idea to Action: a proven process to get started quickly
  • Master a simple tool to help you choose between multiple ideas
  • Divide your limited time to work only on what’s essential
  • Understand all you need to know about business licenses, bank accounts, and taxes
  • Make more money once you’re up and running (without spending a lot of extra time)

This is a bit different from the free book events I’ve done before. It’s a very small group and everyone will have the opportunity to ask questions.

Not for you? no problem! Feel free to send this on to someone who might need it, and I hope to see you another time.

To your success,


Chris Guillebeau

Decide for yourself what you want, then find a way to make it happen.

9 Life Lessons from Starting a Daily Podcast

So hey—I started a podcast! Yes, it’s true: I’m catching up to the technological age of 2005.

And let me tell you: I’m having so much fun. I feel purposeful.

Readers—many of whom are now listeners—are really enjoying it. And best of all, I truly believe it’s going to be helpful to people.

So that’s great! There really is no downside. I’m glad I did this.

But what have I learned? That’s what this 6,500 word post is about. I’ll share my own lessons and observations, as well as my early advice for anyone thinking of starting their own podcast.


1. First, it takes a *LOT* of time to make a daily 10-minute show.

On average I’d say each episode takes me 3 hours from my side to script and record each draft of the show. Then it goes to a production team in Brooklyn, and they do the audio editing and add the awesome music (thank you, DJ Jayson). They ask for recuts of certain parts, then we go back and forth on the files for a bit.

But that’s just the production! In addition to the most obvious part of making a podcast, I’ve easily spent at least another 2-3 hours a day working on the show since it’s started. That’s 7 days a week, regardless of what else is happening, and whether I’m at home in Portland or flying around the world like I am now while writing these notes.

We also built a website, meaning that I said “Hey, let’s build a website” and then people much smarter than me went to work. Even though I’m just the manager in this process, AKA the least-skilled person, there’s still a lot of ongoing maintenance and active attention required from me.

SHS Homepage
SHS Episodes Page
Ep. 8 – Cruise Vacation Turns Into Highly-Profitable Hustle
Ep. 8 – Cruise Vacation Turns Into Highly-Profitable Hustle

We have show notes for every episode (and we’re working on improving them), a daily email that goes out, a community forum in the works, a traveling workshop series that starts very soon, and … well, much more. I won’t bore you with a list because the work really should speak for itself.

When I think about the past three weeks, pretty much all I remember is waking up to work on something related to the show, then eventually going to sleep at night.

To be clear, I’m not complaining. I love doing this; I’d spend my time no other way and I’m happy to go all-in. I’m just saying: it takes a LOT of time.


2. Gretchen was right, Part 1: A podcast really does reach an all-new group of people!

This lesson comes from Gretchen Rubin, a longtime friend who also happens to be the head of Panoply’s new Onward imprint, which Side Hustle School is part of.

First, a quick side note: Gretchen is my hero! I’ve been following her since the blogging dinosaur age when I started The Art of Non-Conformity. Her site, along with one from another friend, J.D. Roth, were early inspirations for me. She is also the only author to have blurbed (written an endorsement for) all four of my books. The fact that I get to work regularly with her now makes me, well, happy.

As for the lesson, when she and I first began talking about the show back in summer 2016, she told me how starting her podcast had brought her a whole-new audience. People had told her that it would, but she was skeptical.

When she told me this story, she was very modest about it, so I’ll translate: her books have done extremely well. The Happiness Project, which I’m proud to own an original advance copy of, has sold millions of copies all over the world. It’s appeared in movies, celebrities regularly share photos of it, and it was on the New York Times list for a ridiculous number of weeks.

Then, she had another runaway bestseller with Better than Before, and she’s gearing up for another big book this fall based on her (also very popular) Four Tendencies quiz. According to the quiz, and to Gretchen herself, I’m a rebel. Shocking, I know! She and I talked about it in this episode of Happier.

Gretchen being interviewed by Oprah Winfrey on her show

The point is that Gretchen had very high name recognition before beginning her show, yet the show brought her another highly-committed and engaged audience. It had a magnifying effect that has allowed her to continue to stay at the top despite great saturation in a field she was a big part of pioneering.

So now back to me: except for the part about very high name recognition—since no one can spell or pronounce my name—and except for those millions of copies sold (I’m approaching my first million, but she will always be ahead…), I’m seeing very much the same effect.

Upwards of 150 people a day are joining the daily email list for the show. I notice a lot of social media comments from people I don’t recognize. I’m hearing from passive readers who are now active listeners. My requests for media quotes and commentary are way up.

All of that to say: if you’re thinking about starting a podcast, it really is a medium entirely of its own. And as a result, if you do it right, it really will attract a very different group of people.

Gretchen Rubin

3. Gretchen was right, Part 2: “A strong voice repels as well as attracts.” 

In my early days with The Art of Non-Conformity, and then with The $100 Startup as well, I received a lot of criticism. I used to regularly get hateful emails from people who didn’t like what I had to say about one subject or another.

But in recent years, the criticism I’ve received has lessened in intensity and volume. Isn’t that great? Well, it’s good for the psyche, I suppose. Whoever said that criticism doesn’t bother them was definitely not a writer or artist.

But it also means that my message became a bit more mainstream over time, and that has pros and cons. The risk is that you have the potential of becoming irrelevant or even obscure, which is probably the worst thing that can happen if you’re trying to put forth a message.

With this show, I’m definitely drawing in a lot more people and a lot more commitment from at least some of those people. And I’m also drawing a lot more active dismissal and criticism than I’ve seen in a while.

And you know what? I think that’s great! Well, at least objectively speaking I think it’s great. I’ll always be a sensitive soul, but that’s where Gretchen’s comment comes in, via her podcasting manifesto: “A strong voice repels as well as attracts.”

When it comes to Side Hustle School, I wholeheartedly believe in the mission, both in terms of intent and approach. If someone hates it or just thinks it’s a waste of time (and there are already plenty of people who do), I’m honestly not that concerned about them.

Please don’t misunderstand: I’m not saying I’m right and they’re wrong.

I’m saying: I know where I’m going with this, and I know who it’s for.

It will be good for some people and not for others, and that’s okay with me. I am 100% committed to the show’s format, the daily practice, and the long-term vision.

4. If You Want to Start a Podcast, Take the Time to Prepare

First: is it worth it? Yes, as long as you have a plan.

It took me about five months of preparation, but not all of that time was active work. Some of it was thinking things through, researching different aspects of the endeavor, working with the partner who handles distribution and advertising, etc.

I probably worked at least two months full-time on it before the debut, but beyond that I’m not sure because as long as I’m working on things I believe in, I don’t really keep up with how I spend my time.

Here are a few things I did:

-Talked with John Lee Dumas and watched his “Podcasting Lessons” series

First of all: super awesome guy! He regularly spoke with me on Skype and texted me advice and ideas.

Much of the podcast series I watched covered topics that were somewhat familiar to me, since I’ve been working online for all eternity more than twenty years. However, it was still very helpful in allowing me to reframe my thinking and approach to a new medium. It also confirmed to me that I was on the right track with what I was planning.

Note: Accomplish your #1 goal in 100 days with John’s Mastery Journal. The Kickstarter starts TODAY and I am making a pledge!

-Experimented in writing draft episodes four months in advance. 

I scripted out at least five episodes and recorded them using various equipment (full list later on). I hired someone on to create DRAFT intro and exit music. This cost a whopping $25 and is most definitely not something I’d do for the real thing, but as an experiment, it was very helpful.

Those first drafts sucked, of course. So did the second. Around the fourth or fifth attempt, maybe three or four weeks into the experimentation phase, I began to notice some potential for finding the right format and voice.

I wrote in a few different environments: Evernote, Google Docs, and Scrivener, the same software I use for writing books. I finally settled on Scrivener because it’s easy to work in multiple sections and move things around.

Like most of my other work, the files sync directly to Dropbox so I can work from any computer.

Sneak peak of my scripts in Scrivener!
Sneak peak of my scripts in Scrivener
Sneak peak of my system!
-Began recruiting stories. 

Since I knew I’d be teaching through storytelling, and since I wanted to do the show DAILY, I knew I’d need to work as far ahead as possible. I put the word out saying that I was looking for interesting candidates.

I did this directly on my site (the form now lives over here—please use that one if submitting) and also through HARO, a longstanding directory that connects journalists with sources. I only use that service once or twice a year, but whenever I do, I’ve been happy with the results.

Julie Wilder
Ep. 6 – Single Mom Makes $15,000 from Astrology Calendar

Over time I began to see what kinds of stories would be good for the show. Quirky? Absolutely. Inspirational? Maybe, but not in a fluffy way—I wanted lots of details and specifics.

I also wanted a range of stories. First and foremost, I wanted them to be relatable. As I say often on the show, when you’ve never made money on your own before, it’s a Very Big Deal to start getting an extra $500-$1,000 a month that doesn’t come from your job.

But I also wanted them to be aspirational. Many hustles have the potential to make far more than $500 a month, and I regularly hear $100,000+ success stories.

So I decided to go with a mix: some would be about people making $500-1,000 a month in their hustle. Others would be about people making six-figures a year or more with their hustle. My hope was that the show could become both relatable and aspirational.

I also set some parameters about what a side hustle is. This phrase and concept is in the culture more and more these days, so I wanted to be specific about what I mean when I use it:

  • It’s not your full-time gig
  • You may want to turn your hustle into your full-time gig, but just as often, you may not want to
  • It’s not a part-time job; it’s something you have ownership over
Homemade Gin Kit
Ep. 16 – Homemade Gin Kit Sells 75,000 Units

Side note: Despite what their ads will tell you, DRIVING FOR UBER IS NOT A SIDE HUSTLE. We’ll save that rant for later because it deserves an editorial space of its own.

Oh, and one more thing: I wanted to avoid any sort of spammy or circular examples, where there isn’t any real value in what the hustler is making or doing. With that in mind, there are very few (if any) stories of people making money showing other people how to make money. Instead, there are stories of:

Each story is intended to be interesting and educational. With a few exceptions, I’m trying to focus on classic lessons reframed in unusual case studies.

 -Controversial opinion ahead! I did *NOT* listen to other podcasts while developing my own.

I’ll be honest about something that I’m sure some people will disagree with. There’s something NOT on this list that you’d probably expect there to be: I did not “listen to a lot of podcasts before beginning.”

Why not? Well, I’m sure there are best practices I can learn from, but I really did want to create something unique. And the more I worked on it, the clearer my vision became, and the less I felt like I wanted to draw on anyone else’s work, at least directly.

Here’s how I thought about it: as a nonfiction author, I mostly read fiction. I do read some non-fiction as well, but it’s very rare for me to read a modern “Business & Careers” book like Born for This or The $100 Startup. I want to write original books with my own voice, and therefore I’m careful of letting other, potentially similar voices into my writing head.

I’d also note that I’m very familiar with the other side of podcasts, having been a guest on hundreds of them over the years. So it’s not that I knew nothing at all about the concept of podcasting. It’s just that as I set out to create my own, I wanted to find my own way.


5. Good equipment is inexpensive, but there’s more to the process than just buying stuff. 

I sometimes go to a local studio for call-in interviews, but I didn’t want to attempt that with this project. There’s just way too much recording to be done!

My work style is to draft multiple versions of each episode while I’m recording the episode. It’s a messy process that works for me because I know what I want, but it would be frustrating (for both me and an engineer) to do it that way in a recording booth. I’m also an introvert, and I needed space of my own to figure out this new medium without the pressure of other people listening in real-time.

Therefore, I set out to create a DIY solution for the recording side. My home recording setup cost less than $1,000, and here’s what I bought:

Jonathan Fields - 1

Shoutout to my dear friend Jonathan Fields, who talked me through this list and made recommendations along the way. Check out his wildly popular show, Good Life Project!

But here’s the thing: just because you can spend less than $1,000 (and probably less than $500, actually—part of my expenses involved trying different things before I found what worked best for me), that doesn’t mean that’s all you need.

There’s also the production side. This is no small thing!


For that, I’m grateful to Panoply, a large podcasting network and now my distribution and advertising partner. I began talking with their team last summer following an introduction from Gretchen, who was creating the Onward imprint that launched on January 1. It’s a business arrangement with revenue share on the advertising, which will hopefully be sustainable enough for multiple people to work on the show throughout the year.

Why did I work with a network? Well, for me it was a lot like publishing books. Sure, I could publish books on my own, but they wouldn’t be as good. Even as a non-conformist, I’m somewhat a traditionalist when it comes to books. Without a doubt, I know that my work has been made better through a detailed editorial and production process.

So too with podcasting: I was a complete beginner in this world, and I’m still actively learning every day. I didn’t assume that I knew everything, and I thought I could benefit from detailed knowledge and assistance from experts.

Panoply is clear that they’re in to win it, and they expect their shows to have minimum downloads of at least 20,000 per episode. Presumably many of their shows do much more than that. In joining their team I felt like I was playing above my level, and I liked that.

Remember this lesson for both podcasting and life: you never want to be the proverbial big fish in a small pond. It may feel good for a while, but you’ll always wonder what might have happened if you’d tried harder. Step up!

6. Don’t start a “Tell Me About Your Life” show. No really, don’t do it! 

If you want to go down the well-trodden, life of quiet desperation, abandon-all-hope-ye-who-enter-here podcast path, start a show in which you interview people about their life and career. For best results, invite the same people that appear on everyone else’s shows, then ask the same generic questions of them.

Here are some kiss-of-death starter questions for your script:

  • What inspires you?
  • How did you get started?
  • What’s your biggest failure?
  • How do you handle fear?
  • What advice would you give your younger self?

I assure you, anyone who’s ever given an interview will be very familiar with these questions.

OK, so really—don’t do this. Don’t start a generic “let’s talk about life” show. Step away from the ledge!

If you want to have interviews on your show, that’s totally fine, but design a framework for them that is at least somewhat unique. (Note: “How you became an entrepreneur” or “Interview authors about their new books” is not somewhat unique.) You will stand out so much more with a focused topic, and your guests will enjoy it more too.

If you think I’m complaining… well, OK, I actually am complaining a bit about this. Over the years I’ve done literally hundreds of podcast interviews where people ask me the same questions, starting with “So tell us a little about yourself.”

Here’s the thing: I try to give a good interview, but my life story isn’t going to change from podcast to podcast. As a result, I end up saying the same things and telling the same stories over and over. After a while it can have the effect of phoning it in—which is terrible, of course, and listeners deserve better—but again, the basic narrative of my life doesn’t evolve from any given Tuesday to Wednesday.

Therefore, if you want to ask interesting questions on your podcast… ask anything other than the usual ones!

Hat tip: of all the podcast interviews I’ve done, The Art of Charm requires the most intense preparatory work by far, and it makes for a show that stands tall above many competitors. When they invited me as a guest, they also sent more than a dozen detailed essay questions that I had to answer before we did the interview. Respect!

Chatty Chris

7. Have a CLEAR and SPECIFIC audience in mind.

Think about who is NOT part of the audience as much as who is. For my show, I am deliberately excluding people like me. If you’re “self-employed for life,” as I sometimes describe myself (or “unemployable,” another term I use), you’re not who I’m thinking of every day as I work on the show.

This doesn’t mean those people aren’t welcome—I’ve already had a bunch of notes from listeners who are like me but still like the show.

Francine Jay

No, I just mean that as you make the show, you create the content and direct your attention to that audience. Everyone’s welcome, but you focus on your CLEAR and SPECIFIC audience.

For me I wanted to direct my attention toward employees who don’t want to quit their jobs but do want extra income. 

This is an important distinction, because with Side Hustle School, I’m not teaching people to “be entrepreneurs.” I don’t think everyone should be an entrepreneur, but I do think everyone should learn to think entrepreneurially.

In many conversations with people over the past year, especially on my Born for This book tour, I began to realize what an interesting and largely untapped market this is. There are many resources for aspirational entrepreneurs who want to build a company. But there are surprisingly few for people who just want to create more security for themselves without rewriting the pattern of their entire life.

Audience 1
In Philidelphia, PA for the Born For This Tour

In some ways, I think some people with jobs even feel judged or shamed for not wanting to quit—which is of course ridiculous! For example, my parents are aerospace engineers who’ve spent most of their careers supporting NASA missions. I’m not entirely sure how these things work, but I’m assuming that if you want to be an astronaut, you can’t do that on a freelance basis.

The same holds true for people working in numerous noble professions: teaching, medicine, journalism, social work, etc. And even leaving aside the question of whether some work is more beneficial to society than others, the reality is that a lot of people thrive in more collaborative networks that only exist in companies and organizations.

So yeah, it turns out that not everyone should go straight out and quit their job to backpack in Thailand. Maybe in some ways I feel partially responsible for creating this dynamic, so now I’m partially responsible for correcting it. Who knows! I’ll ask my therapist about this sometime.

In any case, these are my people, the ones I thought about over and over when creating the show: You’re out there and you want to create something for yourself. You’re smart and can work hard. But you’re also busy, and you need some guidance so you don’t waste your time.

100% of my focus is on people who fit that description.

8. Have a hook! Make your show EASY to understand and explain.

The hook is not just for the sake of marketing—though it helps there too—but also for your own sake. Or at least, that’s how it is for me. I love the specificity of it.

My hook was:

  • Side Hustle School will be short-format, with most episodes less than 10-minutes long. My intended audience doesn’t have time to listen to 45-minute conversations
  • I will be the host and there are NO interviews (see above)
  • It will be actionable and interesting (you’ll learn something in each episode, and it won’t be boring)
  • Oh, and … the show will be DAILY

That’s right, every single day in 2017, bitches!

Please note that not everyone thought this was a great idea. (I wasn’t sure it was either.)

When I did the first call with the Panoply execs, one of them said something like: “Wow, a daily show. Five times a week is very ambitious.”

And I was like, “What, only five? Last I checked, there are seven days in a week!”

As I said, I went back and forth about the idea myself. In the end I guess it just came down to my answer to this question:

“Do I want to really go for it? Is this just another project, or do I want to try to give it my all?”

Producing a DAILY episode with no breaks sounded like going to every country in the world, or self-organizing a 63-city book tour to every state and province. The more I thought about it, the more I thought… Hell yeah! Let’s do this!

That’s my only “secret” to a lot of things, by the way. I might not be the first person to think of any particular idea, but when I find something I believe in, I will work very hard for it. This isn’t a groundbreaking secret, but since so few people follow its wisdom, you’re welcome to borrow it for yourself.

Find something you believe in, then give it all you have!

9. What Else? Oh, right: tactics, not strategy

A number of people have asked about this note from my announcement post:

Short version of why I made the show: this is something that people are looking for that I’m qualified to provide. (Also: forget strategy; tactics are the future.)

Listen up: I am no futurist, but tactics really are the future. Watch and see. People are tired of self-appointed thought leaders who opine about everything. They don’t want to be inspired. They want substance! And this is the substance they want: specific, actionable—and even polarizing—instruction, guidance, or case-study driven stories they can learn from.

Yes, of course the world still needs stories; that never changes. It’s just that you can’t coast on inspirational quotes anymore. You can’t leave out the critical “how did they really do it” details. So step it up! If you’ve been trying to get your message out and are struggling to be heard, this is a path that is worth following.

I don’t think I’ll turn out to be wrong about this, but even if I am, will you be any worse off than when people weren’t reading your tweets?

Go make something that has the potential to change lives. That, in the end, is all that matters.


And That’s a Wrap! Only 339 Episodes to Go…

So I started a podcast, and I love it. I’m so glad I spent several months working through the creative, editorial, and logistical issues before the January 1 debut. It made it much better than it would have been otherwise.

We hit the 20,000+ downloads per episode goal right out of the gate, and it’s already much higher than that. Whether that trajectory will continue or not is at least partly out of my control, so I’m focusing on the work itself.

And of course, I still have much to learn, and it will continue to get better. I’m committed!

I’m also so glad that listeners (maybe even you?) have found it. As I’ve said on the show multiple times: If you commit to listening every day, rest assured that I’ll be there every day. I will see this through.

Now if you’ll excuse me… I’ve got another 339 episodes to record.

Huzzah! The best is yet to come. 

CG out.

Special thanks: Gretchen Rubin, Panoply team (esp. Laura, Jayson, Sarah, and A.C.), my assistant Whitney who works on the show almost as much as me, Jonathan Fields, John Lee Dumas, everyone who has rated or reviewed the show in iTunes (thank you!), everyone who has shared the show (you are the best!), Taylor Swift, Taylor’s ex-man with the new girlfriend, and side hustlers everywhere.


Decide for yourself what you want, then find a way to make it happen.

Announcing SIDE HUSTLE SCHOOL: A Daily Project for 2017

Hey everyone!

Short version: I’m starting a daily podcast called Side Hustle School. It’s for everyone who wants to create a new source of income without quitting their day job. It will be published, well, every single day in 2017.

I’ve been working on this for a long time and it will be my #1 project in 2017. I’d love for you to be part of it—and if you’re not interested yourself, I’d be grateful if you’d tell your friends who need a side hustle.

Longer version below!

Side Hustle School: Daily Show Starts Now (See: Less Talk, More Creating)

For the past five months, I’ve been working on something behind-the-scenes, without saying a word about it publicly. Doing it that way felt surprisingly refreshing. There was no need to manufacture hype, and no false pressure to live up to.

There was, however, an unbreakable deadline. That deadline was January 1, and the team and I hit it—of course. It’s now January 3, and the project is now off and running with the first three episodes published.

This new project, the one I’ll spend more time on than anything else in 2017, is called Side Hustle School. First and foremost, it’s a daily podcast. By daily, I mean daily. Not 5 days a week, not “most days,” but every single day in 2017.

If you subscribe and make listening to it part of your routine, I want you to be able to rely on it being there. Each episode is short (less than 10 minutes long), carefully thought-out, and action-packed. Every day you’ll hear a new story of someone who’s started a side hustle without quitting their job and by using the skills they already have.

You need a side hustle of your own. By the end of 2017, you can make it a reality.

Why I Made the Show

Short version of why I made the show: this topic is something that people are looking for that I’m qualified to provide, and the more I thought about doing it every day, the more I liked the concept. (Also: forget strategy; tactics are the future.)

There’s no shortage of books that tell you to quit your job and strike out on your own. I should know; I wrote one of them that’s gone all over the world in many different languages.

Abandoning ship is great for some of us, but not all of us. Some people like their jobs. Some people need to keep their jobs for all sorts of good reasons.

Most important, not everyone should be an entrepreneur… but everyone should learn to think entrepreneurially. That’s what Side Hustle School is all about.

Who It’s For: Not “Everyone”!

Back when I started The Art of Non-Conformity, I did so with a deliberately broad group of people in mind. I thought much more about psychographics (values, beliefs, life experiences) than traditional demographics.

Side Hustle School is a little different. For this project, I have a very clear image of the person I’m making it for. It’s not for someone like me, or anyone else who is fundamentally “unemployable.”

There are three specific qualities I’ve been thinking about over and over as I prepared the initial batch of episodes.

  • You’re busy. You work at least one job, and probably some other big commitments
  • You’re willing to invest in yourself. Even though you’re busy, you want to make improvements and achieve goals
  • You’re smart, but you need some guidance. Since your side hustle time is limited, you want to make sure you’re spending it wisely

Again, notice who it’s not for: if you’re trying to launch a huge startup, or if you already have exactly the right balance of life, work, and income, this isn’t for you. It’s for everyone else!

Is It Just a Podcast? Nope.

The daily podcast is produced and scripted—this isn’t a random interview show where I ask people for their life stories.

In other words, it’s a legit commitment. But obviously, we won’t stop there!

Here’s what else is coming down the pike:

  • Side Hustle Workshops (an intensive experience for small groups in different cities)
  • My next book (whoo hoo!) coming in Fall 2017 (you can probably guess the topic)
  • A potentially very large tour to—well—just about everywhere (watch this space!)

I’m very, very excited about this. (So excited that I overuse the words very and excited. I’ll work on it.)

I won’t stop writing on the blog—and I don’t think I ever will—but the blog writing will be a lot less frequent. Right now I’m committing to a 2x/week posting schedule, which is how I started way back in 2008. If I want to post more, I will, but my main commitment in 2017 is to this show and everything related.

How to Help or Participate

Well, first of all—check out the show!

The #1 thing you can do to help is subscribe, listen, and tell others. (Is that three things? It’s meant to be three-in-one.)

Subscribe in iTunes (yes, it’s also on Spotify, Google Play, and all other major outlets)

Leave a rating or a review (and of course I hope you like it, but you can say anything you want)

Help spread the word! Whenever I’ve made something that’s had a true impact on people, it’s because of readers like you

I wholeheartedly believe that everyone needs a side hustle. If you agree, know that I’ll be doing everything I can (literally!) to support everyone who wants to start their first—or their fifth—hustle.

The show is completely free (after the first week or two, there will be one sponsor per episode, with a brief, non-intrusive message). This isn’t a marketing campaign leading up to something else. This is all about helping people. Have I mentioned I’m really excited about it?

Thanks for reading. 🙂 You’re the best!



Decide for yourself what you want, then find a way to make it happen.