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201 More Stories of People with Day Jobs Creating Side Hustles

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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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Pandering Never Builds a Legacy

I’m as guilty as anyone else who says that to build a business, or a blog, it’s good to ask people what they want and then give it to them. It works!

But there’s another side to this thinking, and I heard the counterpoint presented beautifully last week by Paula Pant.

For years, she's published a popular blog about personal finance. But as she shared in a talk, after starting down the familiar path of "Hey everyone, what should I write for you?" she realized that maybe it was better to ask herself what she wanted to do.

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Making Money From More Than One Paycheck Can Help You Follow Your Dreams

36793093064_e8ac576920_z This year I’ve been focused almost entirely on helping people take action. Side Hustle School, my daily podcast, shines a spotlight on people who are creating freedom and security for themselves (and making more money, too).

In my new book, SIDE HUSTLE, you’ll get a 27-day plan to go from idea to income. It’s meant to be as straightforward as possible: follow this plan and you will have something to show for it within a month.

A few people have asked: why is everything so practical? What happened to “follow your dreams”?

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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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Why Ideas Are Not Enough (Or: How to Sell Out Like Iron Maiden)

Link: Perennial Seller

"What if I'm not good at making ideas happen? I just like to have ideas!"

Ever since I started Side Hustle School on January 1, I've heard this question a surprising number of times. And believe me, I know it would be nice if you could just have ideas and then someone else does things.

That's not how it works for most of us, though—even those who are successful writers, entrepreneurs, or artists of all kinds. Ideas gain value not through brainstorming but through the getting-it-done phase that all good work needs.

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This “1-3-5 Rule” Can Completely Change Your To-Do List

Do you have a cluttered and crowded to-do list? Do you try to get everything accomplished, only to burn out and end up feeling further behind? If so, you're not alone.

While reading The New Rules of Work, a new book by co-founders of The Muse, I stumbled on an alternative to-do list strategy that I thought was worth sharing:

On any given day, assume that you can only accomplish one big thing, three medium things, and five small things, and narrow down your to-do list to those nine items.

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The Best Productivity Hack Is to Care About What You Do

I’m heading out to speak at a tech conference this week. The conference will undoubtedly have many smart people in attendance. In fact, I don’t think it’s self-depreciating to assume that most of them are a lot smarter than me. It's just true.

Continuing with the theme of “Is this really what it’s about in the world of productivity?”, a common question I get at these events is “Tell us about your productivity hacks.” This question usually comes from someone who’s not only smarter, but also most likely far more organized than me.

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The Key to Productivity Isn’t More Rest, It’s Intentionality

It's tempting to think this is the answer. Just take it easy. It will come to you.

And sure, maybe it will.

I just know that for me, there’s more to it than "work in the morning, sit around and think in the afternoon." That’s how it’s always, always been.

The answer isn’t only “work hard all the time,” because of course you can work hard all the time on the wrong things. But I don’t think the answer is to coast either.

It’s more like: find the right thing, then give it all you’ve got. A two-step plan, essentially.

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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

Read More

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

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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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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