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A moonshot, according to the ubiquitous WikiPedia, is a “is an ambitious, exploratory and ground-breaking project undertaken without any expectation of near-term profitability or benefit and also, perhaps, without a full investigation of potential risks and benefits.”

In other words, it’s a long-term goal with the hope of success, but also the awareness that not every outcome lies within our control.

I was thinking about this while reading a series of “moonshot proposals” from people who are working on big projects.

The collection includes a lot of what you’d expect (which is to say, a lot of writing about ambitious, noble projects, especially in regards to science and technology). My favorite, though, is from Tyler Cowen, who often has an unconventional take or just a unique perspective. In his essay, he begins by noting that:

“My goal is to be the economist who has most successfully used the internet as a platform to foment broad enlightenment. As I see it, the internet is changing everything, and most intellectuals (and also businesspeople) still are underestimating the import of this reality.”

He then goes on to lay out a series of deliverables he contributes in pursuit of this goal. Namely, he writes a daily blog (for 14 years and counting!), produces a popular YouTube channel, publishes books every two years, hosts conversations with other intellectuals, etc.

The specific items on that list aren’t that original on their own. What’s...

This is the last chance to get your ticket for an all-new adventure.

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

Each year, 1,000+ people from 30+ 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 this 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 (2011-2017), and watch your choice...

In many of the talks I’ve done, I’ve noticed that one topic comes up over and over: failure.

What’s your biggest failure?

Are you afraid to fail?

How are people able to recover from failure?

Even though I have a daily podcast that tells success stories, I believe we can also learn a lot from failure. And here’s the thing: I don’t know if the learning objective is always to “bounce back.” Some failures may be, well, permanent. (Philosophical question: if it’s so easy to recover from a setback, is it really a failure?)

In any case, I’d like to hear from you. I won’t share anything you write without your permission, and if I ever do share, you can be anonymous if you’d like. But don’t hold back. Maybe your failure story will help someone else avoid a similar mishap, or maybe the act of naming it will help you move on.

Oh, and this is an open topic. Your failure can be about any aspect of life, whether work, personal, or somewhere in between. I might get more specific later on, but for now I’m curious to see how people respond to the broader question.

—> Share Your Story About Failure

If you have a story about failure, will you tell me about it? And will you share this link with someone you know who...

Even if you’ve never read Homer’s Iliad, you’re probably familiar with parts of the story. Much of it is about heroism and valor, but it’s also about choice.

Here’s an alternate history interpretation of a choice that Achilles faces:

I have an idiosyncratic take on Book 9 of the Iliad. The Iliad is the story of Achilles is the great warrior on the Greek side in the Trojan War. He gets mad at some slight, and he goes back to his tent to sulk, and the Greeks start losing. So then they send emissaries to his tent to say, “Please come back.” And he says, “No.” Then, the Greeks start losing some more. Eventually, he comes back, and he gets killed. That’s basically the story of the Iliad. Book 9 is where they send the emissaries to say, “Please come back,” and he says, “No.” He gives this speech, this response that is weird, where he says, effectively, “The prophecy is that if I go back to fight here, I will die here. My name will be immortal. If I don’t go back to fight, I’ll go home and live a long life and will be forgotten.” He chooses to go back and be forgotten. Then, later, he changes his mind because his friend gets killed. I think the existential examination of this Greek warrior and this heroic culture that clearly valorizes heroism...

I recently bought my first lottery ticket in something like 15 years.

The purchase happened on a whim, as I was walking down the street in California. When I passed by a convenience store, I thought, “I should go inside and buy a lottery ticket.” And so I did.

To a lottery novice such as myself, the process was a little confusing. Apparently there’s not just one lottery… there are many! Not being familiar with the pros and cons of various options, I asked the clerk for the cheapest one.

Then, for the price of a single dollar, I was given a slip of paper containing a series of numbers.

I understood that this slip of paper had a value that was yet to be determined. Most likely it was worth $0, but there was a chance—however slim—that it could be worth much more. When the winning numbers are announced, hundreds of thousands of tickets like these would immediately become worthless. But of course, one or more tickets could be worth millions.

I bought the ticket on a lark and didn’t really have a plan at first. But then, before I left the store, I knew what I would do next: nothing at all.

I’d hold on to the ticket, but never check the numbers to see if I’d won.

If you’re going through a dark night of the soul, you might as well pass the time in a beautiful place.

That’s what I was thinking as my hour-long Qantas flight from Melbourne began its descent to Sydney. Australia has long been a place of joy and peace for me, and Sydney in particular. Ever since I first stumbled into town five years ago, when I was denied boarding on a flight from Brisbane to Nauru (long story), I’ve been coming back every chance I get.

This time felt different because, well, I’m different. I’ve been judging the days on a 1-10 scale, and I get excited—at least moderately so—when I feel higher than a 3.

And so as the flight lands in Sydney and I take the airport train to the city, bracing myself against an onset of anxiety, I begin my self-talk.

First, a disclaimer: you can’t motivate your way out of sadness. It’s not a matter of saying “Self, cheer up!”

If you know someone who struggles with depression or anxiety, remember this. When people are persistently sad, some aspects of their experience are outside their control. They aren’t always able to access parts of themselves that give them a baseline and protect them from harm.

Still, a little perspective helps, I remember as I hop off the train onto Circular Quay. It’s Australia! If you can...

Greetings from paradise, also known as Australia.

I started writing this post from one of my favorite places in the world: the balcony of my room at Park Hyatt Sydney (check out this photo of the sunrise!). I’m staying here with points earned from the Chase Sapphire Preferred, my #1 recommendation for travel rewards cards.

Normally, the room would cost $900 a night (!), but naturally, my cost is … $0. I’ve been here over and over, usually at least once a year, and every stay has been “funded” through my points from this card.

And it’s not just here. All over the world, I’ve been able to fly and stay for nearly free—all thanks to the wonders of travel hacking.

All of this is possible for you, too! Or at least it is for many of our readers, who regularly write in to tell me about how they used their points for amazing experiences of their own.


The Latest Offers: Earn 100,000 Hilton Points and More

It’s been a while since I’ve written about the latest and greatest travel hacking offers. Here are a few deals that are particularly good. With the exception of the new Hilton card, which I plan to apply for at some point, I have all of...

Join the Side Hustle Society and Create a New Source of Income Link: Side Hustle Society

Short version: my new training program (the first I’ve made in 3 years!) is now available for registration. Join during the introductory launchone week only—before it closes for at least a month.

-OFFER ENDS January 16, 2018-

And here’s the slightly longer version…

It only took me six months to finish what I started.

Last January 1, I introduced Side Hustle School, a daily podcast that promised to show listeners how to make extra money without quitting their jobs. In our first year, Side Hustle School produced 365 episodes that were downloaded millions of times (more than 12 million in total).

I also heard from a ton of listeners. From thousands of emails to in-person meet ups in 40 cities, all along the way I heard what people like you are looking for most of all.

What I’ve heard more than anything else is that you want support. You want to get feedback about your idea, and you want to connect with one another!

You also want a step-by-step process that guides you from start to finish in creating a new source of income.

Well, help has arrived! Side Hustle Society will help with both of these issues. When you join the Society, you’ll get that step-by-step process in the form of 35 short audio and video...

I got an email from a reader who wrote in with a question I’ve heard many times in different ways. Here’s how Andrew, this reader in particular, phrased it:

“I just graduated from college, but still feel entirely lost on what I want to do and where I want to be. I’m only 21 and graduated high school and college a year early, but I just feel like I’m pushing my life along without learning what I want and enjoying the process of it all . I’ve had my highs and lows throughout these years, and I’m starting to get nervous that I’m going to slip low again because I don’t know how to find what I truly want. I’m done with college, but feel more lost than when I started. I’ve been taking the steps to try to find my true passion, but I just get frustrated when I feel like I’m not getting any closer. Do you have any advice? I know you hear this all the time, but I’m not afraid of hard work, I’m just struggling to find out what to pour my motivation and drive into.”

I’m no expert on life—your answers to his questions are just as valid as mine—but here’s what I said:

I don’t think most of us know our true passion or purpose right away. It tends to emerge as we...

What can I say about the Annual Review process that I’ve completed without fail for more than a decade?

This year, I gave up on it and walked away.

Well, not quite—that would be an exaggeration. But to be fully honest (and we shall return to this phrase again), I had a hard time facing it. Eventually I was able to make some progress, which I’ll note below, but the overall sense was one of wistfulness.

Last year was hard, too. And there have been other hard years. This time, however, felt nearly insurmountable.

A challenge became a struggle. The struggle became a crisis, and the crisis became, well, something that approaches a total breakdown.

More on that in a bit too. For now, here are the two principles I’ve been looking to as guideposts:

“A crisis represents an appetite for growth that hasn’t found another way of expressing itself. Many people, after a horrific few months or years of breakdown, will say: ‘I don’t know how I’d ever have gotten well if I hadn’t fallen ill.’” –The Book of Life and “When we make a decision, whether it’s good or bad, at least it’s motion. That motion is what moves us forward. Ironically, whether that motion is in the right or wrong direction, at least it’s giving us some better visibility of the terrain around us and helping...

I’ve always thought you aren’t supposed to try too hard to be liked. You should be nice, of course—but choosing likability as a goal feels odd.

Still, new research shows—and 9 out of 10 dentists agree—that being likable is more important than being “known.”

“People who seek to be likable tend to end up healthier, in better relationships, with more fulfilling work, and even live longer. Status-seekers, on the other hand, often end up anxious, depressed, and with addiction problems.”

This argument continues that the “age of the selfie” reinforces a belief that used to be shed after adolescence, but is now retained into adulthood thanks to the social web and its currency of likes. By pursuing status, we’re forever chasing the high-school clique, the shallow desire to be recognized above others.

Can you have status and be likable? Yes, many people have both—though it seems that status is a byproduct of other factors, not something to be pursued for its own sake.

What does this mean for the independent, goal-oriented person? I think it means we can still have goals, but we should be careful about ones that are merely reflective of some type of comparative achievement.

Instead, we should choose goals that are purposeful, relational, and aligned with a value that challenges us to be better versions of ourselves.


Link: There Are Two...

Every day on Side Hustle School, I tell a different true story of someone who creates a new source of income without quitting their job. Sometimes people ask, “Where do the stories come from?”

Great question! Many of them come from our listeners and readers. Do you have a side hustle? If so, I’d love to hear about it! We’ll feature some of the stories far and wide to 40,000 daily listeners.

—>Tell Us About Your Side Hustle 

If you don’t have a project like this yourself but know someone who does, will you send them this link? Maybe we can help them get more business, and they can also help a lot of people by sharing their story with people who are starting out.

Meanwhile, the SIDE HUSTLE book has been out in the world for more than a month, and I’m hearing from people every day about projects they’re starting.

I hope it helps you create more freedom for yourself. Do you have a hustle yet?

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

Get your copy...

UPDATE: The Importance of Having a Breakdown

Last year I resisted my Annual Review for the first time in 10 years. This year, what can I say… I guess it’s the second wave of resistance.

Over the past month I’ve entered a season of wandering in the wilderness. I don’t want to sound overly mopey, so I’ll spare you the details. I know I’ll get through it at some point; it’s just hard to celebrate accomplishments or feel festive at the moment.

Still, there are several reasons why I’m going to proceed with the review:

First, the unexamined life is not worth living—at least according to a wise person like Socrates or Bill Murray. Only by looking at things the way they are, not the way we might wish them to be, can we truly set an intention and ensure that anything within our realm of control is aligned with that intention.

Second, joy and sorrow can co-exist. Looking back, I know I can I feel proud of some of the work I did this year. And it’s not just work: I also feel proud of a lot of personal growth as well. I do feel more self-aware than ever, for better or worse (or maybe for better and worse).

Last, in recent weeks I’ve been thinking about this quote a lot:

“You cannot protect yourself from sadness...

Maybe you like hearing Christmas music in September. Maybe you can’t get enough of Rudolph’s story of triumph over reindeer bullying. And let’s all pour another glass of egg nog!

If you’re wearing matching sweaters while stringing lights and singing carols with your family, good for you. I really do mean it. Take joy whenever and however you can.

The thing is, not everyone feels joyful this season. In fact, not everyone likes the holidays in general. Some of us actively dread this season, because it tends to correspond with seasons of sadness.

Sometimes these seasons of sadness are connected to specific events, and sometimes they aren’t. Sometimes we feel alone, even if we’re around good people who love and care for us.

Sadness like this isn’t usually simple. You can’t just tell someone, “Cheer up!” and witness their transformation in front of your eyes. (And unfortunately it doesn’t usually work when you say it to yourself either.)

There isn’t an easy answer for these things, at least not one that I’ve found. Mostly I want you to know that even if you feel alone, you’re not the only one who’s struggling. And there will be a better season at some point, hopefully soon and “just around the corner,” but even if not, it’s still on the way at some point.

In the meantime….

Having some perspective is good. You...

Happy Thanksgiving to all, and not just those in the U.S.! Thankfulness is available no matter where you live. Hopefully pie is available where you live, too.

Here’s a story for anyone wandering in the wilderness—or in this case, anyone stuck in a hole:

A man is walking down a street when he falls in a hole. The walls are so steep he can’t get out.

A doctor passes by and the man shouts up, “Hey you! Can you help me out?” The doctor writes a prescription, throws it down in the hole, and moves on.

Then a priest comes along and the man shouts up, “Father, I’m down in this hole. Can you help me out?” The priest writes out a prayer, throws it down in the hole, and moves on.

Then a friend walks by. “Hey, it’s me,” the man calls out. “Can you help?” And then the friend jumps in the hole.

The man says, “Are you stupid? Now we’re both down here.”

The friend says, “Yeah, but I’ve been down here before … and I know the way out.”

Everyone you meet is fighting a hard battle, and sometimes we need a companion who’s fought the battle before.

Are you stuck in a hole? Hang tough! Can you help someone who’s stuck? Jump in and join them.


-From The West Wing with hat tip to Peter Shankman

-Image by

When you’re wandering cobblestone streets in Europe, stopping at cafes and making unexpected discoveries, it’s fun to lose your way and wander off the well-trodden path. You’re on an adventure! When you’re out on a long run and don’t mind if you take a wrong turn or two, you know that the extra distance is good for you.

But here’s the thing: you’re not really lost in those situations. You’re exactly where you wanted to be, even if you didn’t know it before you took the detour. That’s why “getting lost” feels oddly welcoming.

When it comes to wandering in the wilderness of the soul, however, it’s a different situation. This is the wilderness where you feel truly lost. You lack direction, enthusiasm, or purpose—or maybe all three. You don’t know what to do, and every option you can see feels like two steps backwards.

Amenities are limited in this wilderness. You sprain your ankle on those picturesque cobblestones. Cafés serve overpriced, burnt coffee, and the servers are rude. All you want is to get back on the path, but it’s not so simple. The teacher appears when the student is ready, so they say, but you’re ready to drop out of class.

You curse the landscape, your traveling companions, and most of all yourself. You try to fight your way out, but any opponent you select is a straw...

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...