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Dreading the Holidays? It’s Not Just You.

Do you find yourself dreading the holiday season, or just not excited about it? If so, I promise you're not the only one. 🎄❌

One report from the National Alliance on Mental Illness suggests that 64% of people with mental health issues feel worse during the holidays.

Whether you have a diagnosed mental illness or not, you might just be sad, depressed, or anxious during this time. This is ... normal.

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Always Ask for What You Want: A Lesson in Asymmetrical Risk

TLDR: An asymmetrical risk is one where the potential reward greatly outweighs the potential loss. Identify and take more of these risks.

Every so often, a news article that offers "expert advice" on getting upgraded at the airport makes the rounds. Inevitably, the advice includes something about how you should "dress well and ask nicely."

Real travel experts always roll their eyes at such advice. These days, almost all upgrades are handled through computer systems based on elite status, travel disruptions, and other automated factors.

The travel experts then write their own articles explaining why the advice is dumb, and the process repeats a few months later.

I'm with the real travel experts: the advice on asking for upgrades is just clickbait. Yet I can't help but remember a time many years ago—way back in 2007, I think—when I was traveling from Copenhagen to Chicago.

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Change Your Future to Rewrite the Past

“People think that only the future can be changed, but in fact, the future is continually changing the past. The past can and does change. It’s exquisitely sensitive and delicately balanced.” -Keiichiro Hirano, At the End of the Matinee

When we think about time, we tend to divide it into three dimensions: past, present, future. We also tend to accept certain beliefs about each dimension without much questioning.

The present time is the "here and now." It's what's currently happening. The future, alternatively, is what will happen. It's what will come to be.

Unlike the present and the future, the past is locked in ... right? Short of inventing the elusive time machine, there's not much we can do to change the past. We simply have to accept it and move on. Or do we?

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The Greatest Story Ever Sold đź’µ

Two weeks ago, I wrote about how money mistakes are temporary. My main argument was that unlike other kinds of mistakes, money mistakes rarely have permanent consequences.

I'll return to that in this post, but first let's consider a few things that have happened this month:

  • We've all been hearing about NFTs, also known as "non-fungible tokens," also known as digital art that can be reproduced over and over but sells for a ton of money. The NBA has sold $230 million on these intangible "items." An artist sold one for $69 million the other day, and I'm sure that record will be broken soon.
  • The price of a single Bitcoin, another modern invention, has risen to more than $60,000. Like NFTs, Bitcoin is also completely digital. There is no such thing as "a Bitcoin" you can carry in your pocket or store in your safe deposit box at the bank. Everyone who trades Bitcoin or other digital currencies simply accepts that it exists.
  • The U.S. government has passed a law enacting a $1.9 trillion stimulus package. Put another way, the U.S. government has printed $1.9 trillion more dollars. This was on top of another $2 trillion they printed last March. And presumably there's more where that came from!

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The Courage to Change Your Mind

Here's a helpful filter to know when to worry: does something sound too good to be true, or does it sound so bad that people give up and stop thinking for themselves?

Either way, when everyone around you agrees, it's worth asking some questions. Questions like: "What’s really going on here—and who is threatened by disagreement?"

Consider it an opportunity! When it comes to Coronavirus life, an astounding amount of groupthink is currently taking place. It’s as though everyone is taking the collective temperature (no pun intended...) before deciding what they believe and how they should act.

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If You Find Yourself Dreading Appointments You Made Long Ago, Start Asking “Would I Do This Tomorrow?”

You know the feeling you get when an appointment approaches on your calendar and you’re not looking forward to it? Maybe you’re even dreading it?

Ugh. I totally forgot about that, you think. But I guess I need to to do it, since I agreed long ago.

We've all been there. Some of us find ourselves there all the time. The good news is, there’s a trick to make that happen less and less.

It comes from understanding that when someone asks you to do something you don't really want to do, you’re more willing to agree if it takes place far into the future. You tend to think, “Oh, that’s a long time from now. I’m not thrilled about the idea, but sure, I can do that.”

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7 Questions to Ask When You’re Feeling Stuck

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.

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Welcome, New Readers! What The Art of Non-Conformity Is All About

37847813471_2cfc03e1df_z 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.

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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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Be Careful of Telling Your Origins Story Over and Over

The time came for the interview and I logged into Skype with my headset. After a few minutes of small talk, the host pressed the record button and began with the usual question: “Tell our listeners a little about you… how did you get started?”

It’s a fair question. The only problem is that I’ve answered it over and over—and over and over. Whenever I have a book out, I do at least 50 podcast interviews and usually another 50 radio interviews. At least 30% of the time, this is the first question that’s asked.

When you tell the same story over and over, two things happen. First, you get really good at telling it. You know what to say and how to say it. Second, because you hear the same question and give more-or-less the same answer each time, you rarely deviate from the course.

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The Reviews Are In! Attendee Blog Posts and Memories from WDS 2016 (Round 2)

Every year for six years, I’ve been part of a team that produces an annual gathering in Portland, Oregon. It’s a lot of work and a lot of fun. Rather than share my own recap, I usually prefer to let our attendees share their perspective—so without further ado, here's our second batch of reviews! (See Round 1 here)

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The Reviews Are In! Attendee Blog Posts and Memories from WDS 2016 (Round 1)

Every year for six years, I’ve been part of a team that produces an annual gathering in Portland, Oregon. It’s a lot of work and a lot of fun. Rather than share my own recap, I usually prefer to let our attendees share their perspective. All of these posts are unfiltered and uncensored—take a look and learn more of what WDS is all about!

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Just Because It’s Supposed to Work Doesn’t Mean It Will

Dan finished his education degree without ever stepping into a classroom.

After he graduated, he realized he didn’t like teaching and wasn’t good at it. The very first day of student teaching, where the goal was to serve as an intern before accepting a full-time position, he knew that this was not the career for him.

You’re probably thinking: hey, that’s life! He just had to stick it out, and then he’d be fine. And it’s true, sometimes there’s a learning curve on the road of purpose. We’re supposed to challenge ourselves, and it takes time to gain real-world skills.

This was different, though. Dan really didn’t like teaching. It felt uncomfortable and unnatural. He knew he could probably soldier on through the internship, but he didn’t want to go any further.

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If Everyone Becomes a Non-Conformist, Won’t We All Be Conforming?

I used to get this question a lot, sometimes framed in skepticism but other times just curiosity. The simple answer is that not everyone wants to become a non-conformist, or any other particular means of self-identification. Plenty of people are happy with the way things are, which is the definition of conformity. It’s not always a bad thing.

It’s also like asking, what if everyone wanted world peace? It would be wonderful If everyone wanted world peace, but not everyone does. People generally operate in their own interests, and some people benefit from conflict and strife. It’s no surprise that the world is full of constant conflict.

Being a non-conformist, or just a rebel in general, isn’t about fighting for the sake of fighting. Nor is it usually about rejecting an orthodoxy or culture. When it is about those things, the rebellion is usually superficial and short-lasting.

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Lessons in Non-Conformity from Sesame Street

A reader sent me this fun video from a long-ago sketch on Sesame Street.

I love the turning point right at the halfway mark: Dan would do everything that Stan did, until one day he decides to make a change.

“Hi, I’m Dan. I decided I’m not going to do everything that Stan does anymore."

Isn’t this exactly how it works in life? You go along with the crowd, playing follow the leader and keeping your head down. The status quo is maintained—until it isn't.

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