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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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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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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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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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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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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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For All the Things You Can’t Control, Remember “This Too Shall Pass”

elijah-macleod-400010 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.

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Thirty-Four

A man in San Francisco jumps or falls on the subway tracks. As the train approaches, the passengers all around him unite to warn the train's conductor, who’s able to slow down and prevent disaster.

The man’s life is saved—maybe not forever, but at least for a day.

I recently saw this video of CCTV footage from the incident being passed around, showing exactly what happened. There's no audio, but you can perceive the commotion and urgency of passengers frantically waving for the train to stop.


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Going Back to a Hard Place

Imagine revisiting a place you’d been long ago during a hard time in your life. Maybe that time was long, long ago, and the place far, far away. Or maybe it was last week, and the place is the coffee shop down the street.

Whatever the story, you walk in and experience an unpleasant flashback. You remember what happened when you received bad news, that thing that someone said, or whatever the hard time was about. But it’s not just about the memories. You can feel it. The anxiety tightens, and maybe you’re short of breath.

There's no doubt about it: that thing was hard! Not just a little hard, but hard in a life-changing way. Back then, during the time of the hard thing, you had no idea how you'd recover. You couldn't fathom ever being "okay" or normal again.

But maybe there’s also something good about this experience, the one that feels so unpleasant at first.

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Evening Rituals

I have one or two drinks with dinner, rarely any more.

Before bed I make a cup of herbal tea and take magnesium. Sometimes I have a square of dark chocolate.

I sit with my thoughts and my calendar. I look at my tasks. I do this in digital and analogue form. There is pen and paper and phone and MacBook Air.

I determine the priorities for the next day, with the knowledge that there can only be so many. There may be thirty things to do, but only two to three are truly critical.

In fact, it’s hard to do three. Often it’s just a maximum of two. Choosing more is a recipe for procrastination, if not outright failure.

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The Movie of Your Life, Part II

A while back I wrote about the idea of your life as a movie, with you as the director. When you go through your archives in post-production, you might stumble on a scene that feels particularly surreal.

In those times, you may want to ask yourself, “Why did I put this scene in my movie?"

With the benefit of perspective, I realize that some of the scenes in my movie are a little surreal. Looking back on those scenes, it's easy to wonder, “Did that really happen?”

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The Myth of the Self-Made Man

Arnold Schwarzenegger on being a self-made man:

“I always tell people that you can call me anything that you want, but don’t ever, ever call me a self-made man. It gives the wrong impression, that we can do it alone. None of us can. The whole concept of the self-made man or woman is a myth. I would have never made it in my life without the help.

I want you to understand this because as soon as you know you are here because of a lot of help, then you also understand that now it’s time to help others. That’s what this is all about.”

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”If You Can Invest in Someone Else’s Company, You Can Invest in Yourself”

On an upcoming episode of Side Hustle School, I tell the story of someone who obtained a patent for a special kind of mittens for runners. Unlike a $100 Startup, getting a patent is not an easy or cheap process. It look several years and more than $5,000.

Still, she stuck with it because she believed in the idea and was convinced of its value. When she asked one friend where she was going to get the money, he said, “Do you own any stocks?” She said yes.

“If you can invest in someone else’s company,” he told her, "you can invest in yourself. Sell the stocks!”

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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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