risk : 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

Risky Decisions That Turned Out Well

Strategy: To increase your risk tolerance, remind yourself of risky decisions that have turned out well.

As with the list of things you've done that few other people have, this is not merely a list of accomplishments. The key point is to identify risks you've taken, bold moves, and other decisions you made that could have gone south but ended up paying off.

Of course, what's "bold" for you may be different from me, and vice versa. But here are a few of mine...

Work

“The Beauty Is That It Could Fail”: A Real-World Story of Risk

The new host of Prairie Home Companion steps in after forty years of someone else running the show.

Toward the end of the meeting, Thile suggested a new idea. He wanted to perform a live request every week with his new house band. The rules: A minimum of two of the players should have heard the song, but none could have previously played it.

Rowles liked it. Hudson looked wary. Someone else said, “It could fall flat.”

Thile pointed out that its flopping could be entertaining as well: “It’s Evel Knievel.”

Et Cetera

“He didn’t have a death wish, he had a life wish”: The Risk-Taking Legacy of Evel Knievel

On a long flight recently I watched a fascinating documentary about Evel Knievel, the 1970s-era stuntsman who set out to jump the Grand Canyon in a motorcycle.

I was only going to watch a few minutes, but I got hooked and kept going. Without spoiling it for you, the greatest lesson I took from the film was that Evel Knievel wasn’t actually that great of a motorcycle rider. He was a decent rider who became an incredible stuntsman risk-taker.

That’s where the fame and fortune came from: he never won a lot of motorcycle races, but he took risks and attempted feats that no one else would dare. Being fearless can kill you, of course, but it also has its benefits.

Life

If You Have No Challenges, Maybe It’s Time to Change Your Life

Have you ever walked around endless airport highway ramps for more than a mile? When it’s after 10pm and you’ve got your carry-on bags with you?

Yeah, so I did that the other night. Short version: when you arrive in DFW and are staying at the off-airport Hyatt Regency, you’re supposed to take the SkyTrain to the C gates, and then hike through the parking garage to the entrance. I’ve done it that way before, and it’s not terribly difficult.

This time I was hanging out in the D terminal, working from my favorite U.S. airline lounge, and I decided to walk outside and skip the whole SkyTrain thing. How hard could it be? I’ve been to DFW, oh, I don’t know—several hundred times if not more. Sure, it’s a big place, and there was that time I got lost trying to return a rental car and missed my flight, but still.

Work

If Plan A Fails, Remember that You Have 25 Letters Left

*My brand-new book, Born for This, is all about helping you find the work you were meant to do. This series explores some of these lessons.

Lesson: Craft backup plans. They will allow you to take more risks and make better choices.

There’s no shame in having a plan B, or even plans C–Z. Use the “if this, then that” method to make a backup plan for every career choice, and then make a backup for the backup. If one strategy doesn’t work, move to the next.

Life

The 50-Mile Race vs. The Cliff Jump

Imagine two scenarios that each require you to take on a monumental task.

In the first scenario, your task is to run a 50-mile race. You’re not quite out of shape, and you exercise regularly, but you’ve never ran anywhere close to that distance. It’s a daunting challenge, likely the most difficult physical activity of your life, and you haven’t even had breakfast yet.

Despite the tremendous challenge, you set off, determined to overcome the odds. You draw on whatever motivation you can muster. Maybe someone told you that you could never run a single mile, so you think of those comments as you place step over tired step on the ground, one foot in front of the other. Maybe you picture your arrival at the end of the race, with a crowd of supporters cheering your accomplishment.

Life

“Taking Risks” Is Not the Same as “Doing Hard Things”

Recently I’ve been noticing that I haven’t been taking enough risks. I don’t want to be complacent! And I always want to be challenging myself.

I’ve also been saying that I don’t feel like I have a big idea or am doing something hard. For a long time, I could immediately identify a major goal I was pursuing that required a lot of attention, investment, and sacrifice.

But in trying to move forward and make some changes, I think I’ve been making a mistake: taking risks and doing hard things are not necessarily the same.

Life

Three Things I Know Are True: Taking Risks

I’ve been attempting to find “true north” in a lot of things lately. This series explores what I’ve found to be true in my own life. Your answers will probably differ; the point is to find what’s true for you.

Today’s topic is taking risks. Here are three things I know are true.

1. Most risk is perceived.

For example, it’s not any riskier to work for yourself than it is to work for a company, and it may actually be less risky. Why would you trust someone else with your well-being? Self-employment is actually a very safe and conservative choice for many of us.

Therefore, it’s very important to rethink the role of risk in your life.

Travel

“Adventure Is Anything that Puts Us Outside our Comfort Zone”: Notes from the Himalayas

Adventure photographer Cory Richards almost died in an avalanche while descending from a mountain in Pakistan, but he lived and the experience changed his life.

In a short (and amazing) video, he shares on “the richness that comes through struggle.”

“I’ve never been comfortable in the place that I’m in. I can’t stop and sit. It’s a constant engine that’s driving me to the things that are unknown to me."

Et Cetera

Playing It Safe Is Riskier Than You Think

From a Harvard Business Review article cited by Tom Fishburne: “Executives and entrepreneurs face two very different sorts of risks. One is that their organization will make a bold move that failed — a risk they call ‘sinking the ship.’ The other is that their organization will fail to make a bold move that would…

Life

Playing Safe or Living Dangerously

There’s a way of playing safe, there’s a way of using tricks—and then there’s the way I like to play.

Life

Conversations: Turning Pro, Bravery, and the Get-To World

This week I've been reading Turning Pro, a new call-to-arms by Steven Pressfield. Here's an interesting section on making a choice:

Sometimes, when we're terrified of embracing our true calling, we'll pursue a shadow calling instead. That shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career involves no real risk. If we fail at a shadow career, the consequences are meaningless to us. Are you pursuing a shadow career?

Life

Intentions, Decisions, and Outcomes

I recently posted a question to readers about what to do in an uncertain airport situation. This was the scenario:

You arrive very late at an airport you haven’t been to before. Security takes forever, but the flight is on time—which means you’re even more rushed. You walk into the terminal and look for your gate: A70. Damn … you’re currently at A18. Above you is an “Express Train” that runs between A1 and A75 with an unknown number of intermediate stops.

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Life

The Need for Change

I talked with my seatmate Rachel on the flight to Singapore. She was 6G, I was 6H—Cathay Pacific Business Class. I was sitting up front thanks to my Platinum status and a big stash of Frequent Flyer Miles. Rachel was up front thanks to the global bank she worked for, which after a brief display of frugality was now back to flying even its junior employees in Business. Rachel was the same age as me. She had traveled to much of the world, but hadn't really seen anything. It was always running back and forth, flying to meetings, going to business dinners, arriving late at night back in the big Asian city where she was based before getting up early for more meetings.

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