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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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Can You Master “People Skills” By Reading a Book?

Have you ever wished that you could decode people? Do you want a formula for charisma? Do you want to know exactly what to say to your boss, your date or your networking partner? You need to know how people work.

As a human behavior investigator, Vanessa Van Edwards believes that people skills should never be considered "optional." Over the past decade, she's studied the hidden forces that drive our behavior patterns in her lab, the Science of People, and she's developed shortcuts, formulas, and blueprints for getting along with absolutely anyone you may encounter.

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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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It’s Not My Birthday

Despite what Google or Wikipedia tells you, today (April 4th) is not my birthday. Last year on this day I got a flurry of messages from people all wishing me a joyous celebration.

“Thanks,” I’d reply, “but it’s not my birthday."

I finally developed a working theory of what happened. I’m not positive it’s true, but it’s something that feels comforting, so I’m going with it.

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Limited Time: Earn Up to 180,000 Hilton Points with Special Offers

Link: Get 100,000 Hilton Points (with $75 annual fee)
Link: Get 80,000 Hilton Points (with no annual fee)

There's big news in the travel hacking world this week: a limited-time offer to earn a lot of hotel points has arrived. To be precise, there are actually two offers, one for an increased signup bonus amount (from 40,000 points to 75,000, which is great), and an even better one that gets you a whopping 100,000 Hilton points. Yeah, no kidding!

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Couple Earns 1.8 Million Frequent Flyer Miles, Sets Out to Visit 100 Countries

Nate Buchanan and his wife Kara had been talking about traveling for years. They finally stopped discussing and started planning. Before they left, they travel hacked their way to 1.8 million frequent flyer miles, which they’re using to travel to 100 countries.

I had been mildly obsessed with the idea of full-time travel for a few years. But in January of 2015 we were sitting at Dairy Queen, and something was different about this conversation. We were seriously discussing what it would take to make it a reality, and not just dreaming about "what ifs."

It’s so easy to discuss theoretically. Reality is, there's never an easy time, and we finally realized that there would never be an easier time than right now. We don’t have kids, we rented an apartment, and both of us were in a position where stepping away from our jobs wouldn’t be the end of the world. We finally decided we would take 2016 to travel full-time and see as much of the world as possible before we settled down.

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Swiss Man Finds Dream Job Mushing Sled Dogs in Alaska

Sven Haltmann went from a miserable office job existence to living his dream life in Alaska, with not just one but two dream jobs. He now spends his winters mushing and his summers running a hostel, meeting guests from around the world.

I used to work for a health insurance company in Switzerland. Even though I loved everyone that I worked with, I hated the job so much that I wanted to shoot myself in the head every Sunday thinking about the start of a new week.

Since I was only 20 and already miserable, I knew I had to do something different to change the path I was headed down. I applied as a tour guide in Greece, got the job and worked on the island of Crete for three years during the summer. Unsure of what to do during the winter, I applied to work for a dog musher who competed in the Iditarod trail sled dog race.

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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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Earn 430,000 Miles from the Best Current Travel Card Offers

Every year I earn well over one million Frequent Flyer miles and points. About 250,000 of them come through actual travel, but the rest come through travel hacking: the art of seeing the world on a budget.

One of the easiest ways to earn a lot of miles all at once is through credit card signup bonuses. When managed carefully (i.e., you pay your bills on time), there's no downside and you can keep the miles coming for a long time.

We've had a bunch of new offers recently, and it's been a while since I've done a roundup. This post contains the best current card offers. If getting each one, you'd earn 430,000 miles!

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“Everything Is Figoureoutable:” Notes from Paris to Doha

On a recent trip, I had to get back to Doha from Paris, a 5 1/2 hour flight. I was transferring via an initial connection from Zurich, and I booked the Zurich flight to arrive less than an hour before the Qatar Airways flight departed.

You might think that’s cutting it close, and it was. In the worst of times, Charles de Gaulle airport can be an absolute nightmare to navigate for transit. It’s not unreasonable to walk more than a kilometer between terminals, and some terminals are reachable only by an extended bus ride. Add long security lines (no PreCheck!) to that equation, and it’s not unreasonable to allow 2-3 hours for a connection.

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Even When You Aren’t Sure What to Say, Don’t Be Silent

I recently had the honor of introducing Emily McDowell and facilitating a Q&A session with her at Powell’s for her new book, There Is No Good Card for This.

You probably know Emily’s work even if you don’t know her yourself. She’s the creator, designer, and entrepreneur behind a line of greeting cards and related products, all with the goal of serving “the relationships we really have.”

Here are a few of her popular cards (order yours online or from one of 2,000 stores around the world):

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