life : The Art of Non-Conformity

Work

What Is Your Personal Moonshot?

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.”

For a long time my moonshot was going to every country in the world. Then I accomplished that goal (without ever getting to the actual moon—it's not a country, after all) and had to figure out what came next...

Life

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.

Life

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.

Life

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.

Life

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.

Life

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...

Et Cetera

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

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.

Life

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.

Life

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?

Life

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.

Work

Pandering Never Builds a Legacy

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.

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.

Life

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

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.

Side-Hustle-Book-Chris-Guillebeau-launch-image-square

Et Cetera

SIDE HUSTLE: From Idea to Income in 27 Days (The Book Is Out!)

Hey everyone, the SIDE HUSTLE book is out!

Buy it now: Amazon | Barnes & Noble | iBooks| Your local bookstore

Support your local bookstore

Join me on my 100-city tour.

Life

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.

Life

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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