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Life

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To Win the Lottery, Buy a Ticket and Never Check the Numbers

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 minimart, 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.

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.

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Life

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Under the Unseen Blue Sky in Sydney, Australia

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.

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Travel

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New Travel Hacking Offers: Earn 100,000 Hilton Honors Points & More


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.

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Life

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Don’t Feel Pressured To Find Your Life’s Purpose At Age 21

I don't think you're supposed to know your true passion or purpose right away. It tends to emerge as you embark on different paths.

It's good that you're frustrated—it shows that you understand the importance of the search. But I think the best thing you can do is be open and explore different paths. The truest one tends to appear as you go along, not before you start.

At least that's how it was for me. From a young age I felt exactly what you describe: the idea that I was just pushing my life along with no north star.

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Life

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The Importance of Having a Breakdown, AKA “What Happened to the Annual Review”

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 sadness.

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.

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Et Cetera

Is It Better to Have Status or Be Likable?

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."

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Work

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Where Do Side Hustle School Stories Come From?

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.

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Life

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2017 Annual Review: How to Evaluate Your Life Even When You’re Feeling Sad

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.

There are still several reasons why I’m going to proceed with the review...

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Et Cetera

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Feeling sad on the holidays? Me too. Here’s all I know how to do.

clem-onojeghuo-178228 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.

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Life

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When You’re Stuck in a Hole, Look for Someone to Join You: A Lesson in Empathy

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...

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Life

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A Field Guide to Wandering in the Wilderness of the Soul

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.

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Travel

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5 First Steps for Travel Hacking

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.

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Life

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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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Work

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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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