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If you’re new to this blog, one of the things I write about is travel hacking—the art of having incredible experiences that would otherwise be unobtainable for most people.

It’s a bit different from budget travel, which tends to focus on staying on hostels, flying on low-cost carriers (LCCs), etc. Travel hacking can not only help you travel, it can help you travel better.

I stumbled on this world by accident. I just wanted to learn to travel for less, and then I got upgraded on a transatlantic flight. When it happened again a year later, I was hooked. Then a couple years later, I began my quest to visit every country in the world.

Travel hacking allowed this experience to be much, much cheaper. I can say with confidence that a full third of the 11-year project was either free or nearly free thanks to miles and points.

If you’re like most people, you know a little about frequent flyer miles, but you may not know a) how to earn large amounts of them over and over, and b) how to best use those miles and points for incredible trips. That’s what it’s all about!

So here are five things you can do right away. Most of them are completely free, and two are low-cost.

1. Make sure you’re a member of at least 3 mileage programs.

You should never board a paid flight without a mileage...

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.

Practically speaking, after a few moves you might not be able to take small enough steps to continue “halfway,” but technical speaking, if you only moved halfway, you’d never arrive.

As a ten-year-old, my mind was blown. You’ll never reach the wall if you only move halfway, even if you spend 1,000 years moving over and over?

Yep, even then. Furthermore, the margins get tighter and tighter. Once you’ve played your first big moves, any other distance becomes marginal. The first time you move halfway across the room, you’ve made a ton of progress. The tenth time, not so much.

I thought about this story as I thought about my lists.

See, I am a list person. I live by my lists. When I’m at my office, I have two screens: the laptop...

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:

Do you ever feel stuck? I’m pretty sure we all do at some point. Feeling stuck is like feeling afraid: it happens to everyone, but not everyone gets past it. You win by getting unstuck, not by skipping the process entirely.

When you feel stuck, asking why is often helpful. But just asking “Why am I stuck?” doesn’t always work, because feeling stuck can be more of a general sensation than a specific ailment.

So here are a few other questions that might help you figure things out. Ask them to yourself and see what your self has to say.

1. What do I know to be true?

Ask yourself what you believe beyond any doubt or skepticism. It might be a short list of five items, or it might fill several pages in a journal. Whatever it is, it’s your truth.

Your truth could be different from other people’s. In fact, it probably will be. To understand this, think about a major world problem: climate change, a refugee crisis, lack of clean water, girls’ education. Which of these do you think is the most important to address?

If you ask five people, you might get five different answers. But are any of them wrong? Not really—they are just each person’s truth.

2. What are my guiding values?

When answering this question, be sure to be specific and exclusive. Choosing values...

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. I wrote about Paula in the appendix of SIDE HUSTLE—she’s my go-to expert on rental properties, a topic I know little about, but one that often comes up in the small business world.

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.

Here’s some of what she said that resonated with me:

“The revolutionaries who came before us – the people who shook the worlds of architecture and music and food and art and technology – they thought bigger than the crowds, and that’s why their work … outlives them.

Do you want your grandkids to remember you for writing articles on “5 ways to save on car insurance?”

If your goal is to leave a legacy – not just make a buck or two, but to leave behind work that represents your time on this earth – you cannot...

2018 Tickets are now on sale—join us!

Here’s our next superhero from WDS 2017:

Agapi Stassinopoulos is a best-selling author and speaker who inspires audiences around the world. In her previous book, Unbinding the Heart: A Dose of Greek Wisdom, Generosity, and Unconditional Love, she shares the wisdom from her life’s adventures and experiences. In her new book, Wake Up to the Joy of You: 52 Meditations and Practices for a Calmer, Happier Life, she takes readers on a journey and inspires them to let go of what doesn’t work and instead create the lives they really want.

Beginning and ending her keynote with joy and dancing to the delight of the WDS 2017 community, Agapi challenged us to claim everything we want with ‘chutzpah’ because we’re good people and we deserve it. Agapi shared her belief that each of us carries the light that the earth needs right now.

“I’m about dominating the world with the open heart. Dominate the world with your light.”

“Because we’re doing good work, it doesn’t mean that we have to suffer. Do you hear me? Loud and clear?”

“No does not mean a thing! I am a ‘yes’ woman, and I’m going to hear all the no’s in the world until I get to my yes.’”

Here’s our next superhero from WDS 2017:

Benny Lewis is the language hacker, National Geographic Traveler of the year, author, YouTuber and charming Irish lad behind the hugely successful Fluent in 3 Months blog and international best selling book. For a decade and a half he has traveled the world, immersing himself in local cultures and learning local languages. He can speak 7 languages fluently, and can get by in many more, despite the fact that he only spoke English at the age of 21.

In his opening keynote for WDS 2017, Benny Lewis emphasized that logic trumps luck. Luck is actually beating the odds, seeing the whole picture, and having an open mind. Benny encourages people to make their own luck, to gravitate to situations with unpredictability, and to use math and reasoning to understand situations—rather than listening to the universe or relying on destiny:

“Extremely improbable events are actually commonplace”

“Sometimes when the universe is sending us a message, what we need to do is ignore it”

“Ask yourself, ‘should I try something different’ instead of ‘should I give up’?’”

Want to know more about WDS and how you can join us?

Every summer, over 1,500+ people travel from all over the world to Portland, Oregon for this immersive experience in life, work, and...

Tickets are on sale now –> Join Us in Portland for WDS 2018!

Each year, 1,000+ people from 40+ different countries journey to beautiful Portland, Oregon for a summer gathering known as the World Domination Summit (WDS). It’s an event unlike any other, all focused on a central question, “How can we live a remarkable life in a conventional world?”

We’re doing it again next summer (June 26th – July 2nd, 2018), and the team and I can’t wait to share all that we’ve got planned for this year’s gathering. Each year there are some familiar elements like our main stage talks, opening and closing celebrations, Academies (half-day workshops), activities, and attendee-led meetups.

There’s also a good chance of some surprises and the occasional whimsy and delight. All that’s missing is you.

If you’re new to WDS, take a peek at this quick recap of the 2017 event:

You can also read hundreds of attendee reviews, check out thousands of photos (20112017), and watch your choice of more than 50 talks from alumni...

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...

Our second superhero in our WDS 2017 speaker video series is Mohammed Faris.

Mohammed is an international author, speaker, and leader of a community with more than one million people. He started his journey in 2007 when he became obsessed with the question: “Can faith boost productivity?” Mohammed has since spent the last decade trying to answer this question—from his own Islamic tradition—his popular blog,, and his new book The Productive Muslim: Where Faith Meets Productivity.

At WDS 2017 Mohammed taught us about the missing soul of productivity—leveraging spirituality to boost our productivity. There’s a hidden element of success that, in the Islamic tradition, is called “Barakah.” It can help you do more with less and live beyond your expectations.

“If you’re sincere in making an impact and building a better world AND you’re willing to put in the work hard, that’s the formula for success.”

“It’s not about the dollars and the followers. It’s about long-lasting impact that truly brings benefit to yourself and those around you and society at large.”

“Barakah is doing more with less… If modern productivity is about maximizing your output, then Barakah is about maximizing the impact of that output.”

Want to know more about WDS and how you can join us?

Every summer, over 1,500+ people travel from all over the world to Portland, Oregon for this immersive...

Big news: we’ll soon be releasing tickets for WDS 2018, our 8th annual gathering of creative, remarkable people taking place next summer in beautiful Portland, Oregon. I’d love to see you there!

For the last 7 years tickets for WDS have sold out, so make sure to join the waiting list to be the first to get notified. The next ticket sale is Wednesday, October 25th!

Leading up to the sale, I’ll be sharing speaker videos from this past year’s 2017 event—and here’s our first:

Vanessa Van Edwards is a behavioral investigator and published author. She runs a human behavior research lab where she uncovers the hidden forces that drive our behavior called the Science of People. Vanessa is fascinated by body language, leadership, and charisma. Her innovative work has been featured on NPR, Business Week and USA Today and Vanessa’s new book, Captivate will help you be the most memorable person in the room.

Sitting in the audience 4 years ago, Vanessa vowed that if she ever got to the WDS stage, she would share the full story behind her success. Behind the scenes is years and years of hustle, failure, finding the right people, and building a team. Check out the video below as she shares this story with the WDS community:

“Behind every business, every pretty dress, everyone is wearing a pair of Spanx to...

Just as there are some things that can’t be fixed, there are also some things you can’t control. This fact can be hard to accept for those of us who like to both fix and control things.

You might have a lot of influence, all the autonomy you could wish for, and independence for days—but when it comes to things you can’t control, none of that matters.

I was reading a thread on Quora recently and noticed a recurring theme in what people mentioned as being outside the realm of control.

What other people do.

This is the biggest one. Even if you maintain complete independence for yourself, with no boss and no other accountability, that freedom doesn’t extend beyond yourself. Ultimately, people with free will like to exercise it. You might wish for someone to change, you might even desperately want them to (or feel like you need them to), but their decisions on how to proceed are their own.

What other people think of you.

You can’t control anyone else’s thoughts at all. You may want someone to like you, to think well of you, to earn their favor in some way—but this too is outside your control. Alas!

If you’re seeking approval from someone, never forget that approval is theirs to give or withhold. So since you can’t force someone to think well of you, be attracted to you,...

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”?

Well, the thing is, for nearly a decade now I’ve tried to show people real-world action plans, whether for travel hacking, starting a business for under $100, or just questioning authority in general.

In this case, creating another source of income can help you follow whatever dream you have. It feels really good to get paid outside your normal paycheck.

I don’t want to tell you what your dreams should be; those are for you to figure out. But if you have a dream, you can either follow it or choose to let it die. Which will you choose?

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

Get your copy now:


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: From Idea to Income in...