decisions : The Art of Non-Conformity

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...

Life

Regret Is an Unreliable Emotion

I have long believed that thinking about regret is a powerful motivator for action. When you're feeling indecisive, trying to figure out if a particular step is a good one, consider how you'll feel if you don't take the step. Often this leads you to what seems like the right direction.

But while mental models can be helpful, most of them also have limits. Lately I've realized there's a flaw in the logic of focusing your attention on the avoidance of regrets. Simply put, regret is an unreliable emotion.

Think about that for a moment—what does it mean?

It means, in short, that regret is both difficult to anticipate and even harder to characterize in retrospect. If you feel certain about your choices in either direction—either looking back or looking forward—you may be basing your interpretations on selectively chosen information.

Life

Habits of Highly Effective Real People

Humans are not machines, and we don’t all want the same things. But we do want to do something purposeful, to use the time we have to the best of our ability—and we also long to discover our authentic selves.

If our lives consist of a series of choices, how do highly effective real people make them? Here’s a short list of characteristics for your consideration.

First and foremost, they know what’s important to them.

I’ve been saying for a while that the greatest productivity hack is to love what you do. It is much, much easier to be both productive and satisfied when you spend most of your time on something you find meaningful.

I often go back to this principle as a compass point. It really does no good at all to become efficient at the wrong things. On balance, it’s actually negative because the more efficient you become, the more likely it is that you’ll continue on the wrong path. Therefore, it’s better to fail quickly at the wrong things, so you can discover the right ones.

Work

How Do You Know If Your Idea Is Worth Pursuing?

Creative people usually have no shortage of ideas of things they'd like to do. The greater challenge is: how do you know which ideas are worth pursuing, and which should be abandoned or just put on hold for now?

Here’s one way: consider the amount of time you spend thinking about the idea, even as you go on to other things.

I don’t just mean when you have an idea and you think about it a lot the same day. I mean when you have an idea, and you think about it for a while before putting it aside... and then it comes back to you the next day. Then a week goes by, and you realize you’ve thought about it almost every day.

Life

When to Compromise and When to Hold Your Ground

At some point, most of us end up settling in a major part of our life. We compromise and make tradeoffs.

We can’t always get everything we want, of course. We can’t always be in total control. But we can certainly get a lot of what we want, and if we prioritize what's most important to us, we can probably get the top things on the list. Just because we can’t always be in control doesn’t mean that we're never in control.

This truth presents a natural question: when should we compromise, and when should we hold our ground and keep fighting for what we really want?

Life

There’s No School for What You Need to Do

At one of the stops on my current tour, the bookstore host introduced me by saying in part “... and Chris earned a master’s degree in International Studies from the University of Washington.” It surprised me a little because no one else has ever mentioned that in any introduction that I can recall.

Sure, it’s public information, but who cares? No one reads my blog because I went to college. No one buys my books or comes to an event because I earned an advanced degree, or any degree for that matter.

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Life

Questions to Ask When Pondering a Big Life Choice

What’s the worst thing that can happen? What’s the best thing that can happen? How do I feel about this choice? What doors will close if I pursue this choice? Why am I hesitant or indecisive over making this choice? If I don’t make this choice, will I always regret it? *** A few other…

Travel

The Confirm Button Never Disappoints

File under: awesome travel advice. On any given week I spend at least several hours in making travel plans. I constantly go back and forth over the various options, sometimes becoming plagued by indecision. I talked about this recently with my friend and fellow wanderer Stephanie Zito, when we were riding around in a taxi…

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Life

Reducing Decisions to Focus Better

From Robert Genn’s recent letter to artists: Choreographer Twyla Tharp’s Creative Habit, describes her morning routine of rising early and going through the same morning rituals; same coffee, same bun. She puts on the same leotards, goes down the same elevator to the same street corner, puts her arm up in the air and gets…

Work

How to Make Decisions

I received a copy of the new book Decisive by Chip and Dan Heath, two brothers and co-authors responsible for the previous bestsellers Switch and Made to Stick.

I've always enjoyed Chip and Dan's work, so when our mutual publisher asked me to share an excerpt of their new book, I was happy to do so.

Check out the excerpt below, or pick up the book for full reading.

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Life

Unnecessary Traffic Lights

Have you ever pulled up to a stoplight and waited ... and waited ... while there was no other traffic in sight?

Three minutes later, the light finally changes, and you pull away ... with no other traffic in sight?

A couple of years ago, this happened to me late at night while I was traveling in the midwest. I sat there and kept thinking: what a useless stoplight. What am I waiting for?

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Life

How To Make Decisions

Much of the time, we don't actually want to make decisions. We want to defer or postpone them, allowing another person or some external event to determine our future. In that case, see how to put off making decisions about your life.

But what about those times when you really do want to make a decision, but you aren't sure of the right one?

Here are three approaches ...

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

An Academic Confession

A long time ago, I sent a thick packet of information to Yale, explaining in considerable detail how awesome I was and why they should accept the honor of my giving them tens of thousands of dollars a year. They sent me back a short, polite letter, saying that while they were happy to accept my initial contribution of $75, they had plenty of other applicants, even more qualified and more awesome than me, all willing to pony up the tens of thousands of dollars for the next few years.

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Life

Everyday Decisions: Should You Take the Train?

Here's 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.

You know if you take the escalator up to the train and catch a ride it could be faster—but remember, you're unfamiliar with this airport.

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