questions : The Art of Non-Conformity

Life

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.

Life

Develop Your Dominant Questions

One time, Will Smith was working on a film set in Toronto. It was the middle of winter and they were shooting night scenes, so the actors and crew worked 6pm to 6am. Brrr! 🥶

During breaks, Smith could have huddled in his trailer, complaining about the bitter cold. Instead, he ran around making jokes and delivering hot chocolate to crew members. He acted on a question that he later explained is constantly on his mind: How can I make this experience more magical?

Working in the cold sucks, but the job had to be done. Rather than complain about it, and rather than just endure it, Smith set out to make the experience better (or "more magical") for everyone else.

Life

Would You Live Your Same Life Over Again?

Among other things, the German philosopher Friedrich Wilhelm Nietzsche was known for an outrageous mustache that frightened away potential soulmates. He also said a lot of outrageous things, which caused him to be shunned by much of society at the time.

One of those things was a simple, provocative question: “What if I had to live this life over again—would I be able to stand it?”

Life

What is the bravest choice you can make right now?

If you want to be more courageous, you have to make brave choices. Sounds simple enough—but how do you know which of those choices to make next?

When I first thought about the question for myself—what’s the bravest choice I can make right now?—I didn’t have an obvious answer. And that felt a little discouraging!

It was like being in a room with inspiring people, all talking about the big important projects they’re working on, and when my turn comes I say something like “Oh, I don’t know … I’m pretty much doing the same stuff as always.”

Life

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.

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.

Life

Is a Quest Better if it Helps Others?

I got an interesting question from Allan about the nature of quests: I really enjoyed “The Happiness of Pursuit.” It appealed to the adventurer in me. I understand that you are encouraging others to pursue whatever quest they are passionate about, but my question is, “Do you notice that people who pursue quests that give…

Travel

Questions and Answers on Travel Hacking

A few weeks ago I mentioned I had created a page on the site that lists current airline mileage credit card bonuses. With just a couple of new cards, you can earn 100,000 miles or more—and then book round-trip plane tickets all over the world. Much to my surprise, card bonuses have continued to get better and better over the past couple of years. It's never been easier to earn a large stash of points or miles that you can quickly convert to plane tickets and hotel stays.

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Life

Questions to Ask When the World Isn’t Going Your Way

Even on the path to your ideal world, things don’t always go the way you would like them to. All of us learn of bad news from time to time. The stock market will crash, or an expected job opportunity will disappear. Something that has always been easy suddenly becomes hard. It happens all the…