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The Limits of Lifehacking: What Happens When You Approach Optimization?

I have a weird memory of my dad explaining math to me when I was a kid. I never actually learned real math, at least once it went beyond how to pocket extra lunch money, and still haven’t learned 30-odd years later.

But my dad was a good storyteller, and often taught me lessons using examples. One time he told me how if you stood across the room and moved halfway toward the wall, and then halfway again, and then kept moving only halfway over and over, you would never actually reach the wall.

As a ten-year-old, my mind was blown. You'll never reach the wall if you only move halfway, even if you spend 10 years moving over and over?

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201 More Stories of People with Day Jobs Creating Side Hustles

Listen to Side Hustle School:
-in iTunes or Stitcher
-on the website
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.

Download all episodes from each month:

JAN | FEB | MARCH | APR | MAY | JUN | JUL | AUG | SEP | OCT

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What If All Your Work Disappeared At the End of the Day?

Over the past ten years, I’ve thought a lot about building a legacy. In particular, I’ve thought about it as it relates to a body of work that you produce and share over the years. This model has kept me going for a long time.

One of the most attractive qualities of writing the blog, starting in 2008 and continuing until now (albeit in several distinct forms), was the idea that I was building a portfolio of sorts. I could write something today, and it would still be around tomorrow, next week, next year, and so on. It would, as I’ve said more than once, “go on to live a life of its own.”

But is that really true?

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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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“We Run Away from Desperation:” Thoughts on Pursuing a Creative Idea

I recently recorded a Side Hustle School episode about Michelle D’Avella, a designer who spent several years building a blog before turning it into a full-time income.

The first year she started her blog, she made $0. Last year, after experimenting with a series of virtual workshops and mentoring sessions, she made $50,000. The success isn’t just about making money, it’s also (maybe even more importantly) about finding work she believes in.

Her advice to others is to create from a place of joy.

"Don’t put so much pressure on figuring it all out, but make sure what you’re doing is something you can feel good about. When we create from joy, people feel it. When we create from lack, people feel it too. We run away from desperation."

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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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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

Audience 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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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.

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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