Work : The Art of Non-Conformity

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101 Stories of People with Day Jobs Creating Side Hustles

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

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How Do You Know If Your Idea Is Worth Pursuing?

Creative people usually have no shortage of ideas of things they'd like to do. The greater challenge is: how do you know which ideas are worth pursuing, and which should be abandoned or just put on hold for now?

Here’s one way: consider the amount of time you spend thinking about the idea, even as you go on to other things.

I don’t just mean when you have an idea and you think about it a lot the same day. I mean when you have an idea, and you think about it for a while before putting it aside... and then it comes back to you the next day. Then a week goes by, and you realize you’ve thought about it almost every day.

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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.

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

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.

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 in this post.

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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 SHS 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 cities, 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.

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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.

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Advice for Students and Jobseekers: When Experience Comes Your Way, Take It

Whatever hands-on experience you can get, take it, and take more than you think you can handle. Don’t limit your writing experience to the typical classroom workshop environment, where egos can be fragile and stakes are low.

In this advice, Jane Friedman is specifically referring to undergrad students who are pursuing a creative writing degree. It’s good advice for them, and there’s more from her here.

I think this lesson applies to beginning careers of all kinds: When you’re starting out or trying to establish yourself in an unfamiliar industry, whatever experience you can get, take it.

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Announcing SIDE HUSTLE SCHOOL: A Daily Project for 2017

Big news!

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.

Subscribe in iTunes

Get daily emails

Suggest a city for a new workshop series

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.

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Instead of Manufacturing Hype, Just Start Doing Great Work

I got a call to do some filming for a marketing agency in Los Angeles. I had the date open and it sounded interesting, so I decided to go.

The filming took place in a Beverly Hills mansion, probably the largest single-person home I’ve ever been in. On the way in I waved awkwardly to the car valet who was hosing down a Porsche, then said hello to the personal chef chopping vegetables in the kitchen.

All over the studio, which looked a bit like what I’d imagine a porn set to be, there were whiteboards set up with verbal cues. Most of them related to the science of persuasion: scarcity, limited-time offer, feel better about yourself.

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Get Your First 1,000 Email Subscribers

Also known as: Why I Fired My Email List Provider

Link: Get Your First 1,000 Email Subscribers

For more than 8 years I used the same email provider. At one time, long ago, they were the best in the business. As the years went by, they became… well, definitely not the best. I had countless frustrations, including one time where the whole system was down for several days and the company only acknowledged the disaster after people complained.

Still, I resisted change, because change is hard—or so I thought. Over the past few years, a good friend of mine named Nathan Barry has been developing a new service that promised to fix many of the frustrations I had with the larger company that slowly declined over time.

I was skeptical at first, because, well, change is hard. But I finally decided to give Nathan’s service a try, and I was impressed right away. It’s much, much better than every other service I’ve seen, and depending on how you use it, it can be cheaper too.

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Build a Business Where You Can’t Get Fired

Link: Webcomic Entrepreneurs

A while back, a friend of mine who worked in publishing was laid off. He was at the height of a career and by all accounts had done an excellent job for his employer. He lived in New York City, perhaps the center of the universe for many things, but definitely not known for being affordable. Oh, and he also had a large family, with at least two kids who would be going to college soon.

When he was laid off, I thought, “Wow, if that can happen to him, it can happen to nearly any employee.”

Thankfully, he’s landed on his feet and now works in a senior role with another publisher. Still, what if there was a better way?

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Being Able to Ask “What’s Next?” Is a Sign You Are Happy in Your Work

During the Born for This tour, people would occasionally ask how you know when you have your dream job. It was an easy setup for a joke: “If you have to ask, ‘Am I happy?’ you probably aren’t.”

Still, even when you’re satisfied in your work, it’s nice to get reinforcement of that fact from time to time. There are several big and little signs that can provide that reinforcement:

At the end of the day, you experience the feeling of knowing that today matters
You work towards a long-term goal while still appreciating the present
You generally look forward to the morning or whenever you begin your work

Here’s another one that I’ve been pondering lately. When you finish a task or project, do you experience a sense of accomplishment—or do you only feel relief?

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“I Write To Create Something That Is Better than Myself”: Reading Karl Ove Knausgaard

Like a lot of people outside of Scandinavia, I discovered Karl Ove Knausgaard's epic, extended memoir series a few years after it was a huge bestseller in his native Norway.

So far in my reading, the six-volume, 3,600 page (!) series has covered the extremely intimate and granular experiences of childhood, burying his alcoholic father, leaving a marriage and entering a new relationship with a woman who suffers from bi-polar disorder, all in a kaleidoscope of words and paragraphs about what could be termed the joy and trauma of ordinary life.

Yep, I'm a fan.

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Be Careful of Telling Your Origins Story Over and Over

The time came for the interview and I logged into Skype with my headset. After a few minutes of small talk, the host pressed the record button and began with the usual question: “Tell our listeners a little about you… how did you get started?”

It’s a fair question. The only problem is that I’ve answered it over and over—and over and over. Whenever I have a book out, I do at least 50 podcast interviews and usually another 50 radio interviews. At least 30% of the time, this is the first question that’s asked.

When you tell the same story over and over, two things happen. First, you get really good at telling it. You know what to say and how to say it. Second, because you hear the same question and give more-or-less the same answer each time, you rarely deviate from the course.

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“The Beauty Is That It Could Fail”: A Real-World Story of Risk

The new host of Prairie Home Companion steps in after forty years of someone else running the show.

Toward the end of the meeting, Thile suggested a new idea. He wanted to perform a live request every week with his new house band. The rules: A minimum of two of the players should have heard the song, but none could have previously played it.

Rowles liked it. Hudson looked wary. Someone else said, “It could fall flat.”

Thile pointed out that its flopping could be entertaining as well: “It’s Evel Knievel.”