The Cost of Failure

Flying Man Vincent de Groof Falling Down (Image: Old Book Illustrations)

We often judge opportunities based on the potential benefit or “up side” as it’s often called. If we do ‘X’ we get ‘Y’. Typically the risk we consider is simply not getting ‘Y’ if we fail to accomplish ‘X’.

I’ve come to rely on an additional approach to judging both opportunity and risk. I call it the “cost of failure”.

It’s quick, easy, and now one of my most important evaluation tools.

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Right & Wrong


A hypothetical conversation with a hypothetical friend about a controversial topic…

Me: “If you believed CONTROVERSIAL POSITION(*), then you would have no other choice but to believe CONTROVERSIAL RESULT.”

Friend: “No I don’t. CONTROVERSIAL POSITION is wrong.”

Me: “That’s not the point. I’m not trying to debate CONTROVERSIAL POSITION, I’m trying to point out the mindset of the people that disagree with you.”

Friend: “It’s simple: they’re wrong.”

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Happiness is a Choice

I am constantly amazed at the number of people that choose to be unhappy.

And I use the word “choose” deliberately.

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Weight Loss and Meditation

Don’t worry, I’m not about to tell you that you need one to do the other. Far from it.

But in reflecting on my goals and process I stumbled into a concept shared by both.

I don’t have name for it — or, rather, any name I assign seems too limiting — but I can describe it.

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Writing as a Constraint-Based Creativity and Critical Thinking Skill

Placing sometimes artificial constraints on an activity is a fascinating creativity technique. The canonical example might be that Dr. Suess’ book Green Eggs and Ham was written on a bet — a bet that an entertaining children’s story could not be written using only 50 different words. That constraint led to one of the best selling children’s books of all times.

Constraints breed creativity. Create some limits, and see what you can accomplish within them.

The very act of writing is, itself, a constraint. What can you accomplish within the limits of language?

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Everything is an Investment

“Mental models” seem to be the latest and greatest thing. Popularized by folks like Charlie Munger, Ray Dalio, and even the Mental Model of the Month Club, they’re essentially a higher level way of looking at life’s challenges, situations, and opportunities. The 80/20 rule, aka the Pareto Principle, is one example.

I recently realized that I’d developed a mental model of my own that helps me make decisions. I don’t have a fancy name for it, but it’s really nothing more than considering everything an investment of some sort. This, then, helps frame decisions based on expected returns.

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Where I Find Positive News

One of my hats is as the curator of the Not All News Is Bad web site and mailing list. Each day I post one positive story gleaned from recent news.

The criteria are rather simple: besides being relatively recent, the story should be something that most would agree is good news. At a more practical level it needs to make me smile.

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We All Fear What We Don’t Understand

We all fear what we do not understand.
― Dan Brown, The Lost Symbol

I suspect that this quote actually pre-dates Mr. Brown’s 2009 book, but the original source is proving elusive. A longer, perhaps more telling version:

What we don’t understand, we fear. What we fear, we judge as evil. What we judge as evil, we attempt to control. And what we cannot control…we attack.

The author seems to be the exceptionally prolific, and in this case insightful, Mr. “unknown”.

All I can say is that humans apparently don’t understand a great many things.

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Habit Fad

Two days ago I wrote that I’d “techniqued” myself into inaction. I was trying to do so many things, seemingly all at the same time, that I could do none of them well, and some of them not at all.

There’s what I’ll call a fad right now that says improving yourself — be it your productivity, your accomplishments, your health, your whatever — is all about establishing the proper habits. There are a multitude of blog posts, articles, and books on how to go about doing that.

It has a fad-like feeling to me. It wouldn’t surprise me if a few years from now we’ll haved moved on to a different productivity or self-improvement fadtechnique.

And yet, at a practical level, I’m paying attention. Fads often carry nuggets of wisdom.

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The Shallows

As revolutionary as it may be, the Net is best understood as the latest in a long series of tools that have helped mold the human mind.

Last week I finished the book “The Shallows: What the Internet Is Doing to Our Brains” by Nicholas Carr.

It brought a few things in to clarity for me, both with respect to my own ability to focus and dive deep into content, as well as how my audience is being impacted as well.

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We Can Each Make A Difference

We’re being flooded with negativity. Every day, it seems, there’s something newly horrific, upsetting, depressing, embarrassing, or just wrong that comes across our news feeds or in our personal communications.

I think it’s having a deeper impact on our collective well-being than most people realize.

That was brought home to me again this morning when I received the following in response to one of my mailings:

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What Is It About 4 AM?

Four o’clock in the morning is a magical and often anxiety ridden time for me. I don’t know what makes it special, but when I wake up at 4AM there’s a certain consistency in how I frequently feel, or where my mind often goes.

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Getting Away

It’s common wisdom that sometimes you need to “get away” from your normal day-to-day surroundings. A change of scenery, as it’s often called, can bring renewed energy and fresh perspectives.

The problem, so to speak, is that there’s getting away, and there’s getting away.

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Drama Magnets

Over the years I’ve known several people that have more than their share of bad luck; I suspect most of us have.

I use the term “bad luck”, but it really encompasses an entire range of situations, scenarios, and circumstances that – through no visible fault of their own – result in bad things happening to those acquaintances.

My wife and I have started to characterize them as “drama magnets.” It seems that everything could be going along swimmingly, and out of nowhere, some kind of drama finds them.

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In Your Own Voice

One of the problems we have as writers is feeling like we need to continually come up with something new to say.

The problem, of course, is that in so many ways there’s precious little that’s truly new, or that isn’t already being said by others. This is something that I had to face from the start with Ask Leo!. There were, and are, plenty of tech sites answering questions and providing information for the public — often about exactly the same topics I address.

What I learned is that as important as what you say is how you say it. That, in a way, makes it new.

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It’s a Conspiracy!

One of the issues I face periodically on Ask Leo! is that of what we colloquially call “conspiracy theories.”

Be it part of a question, or just a rant, I get comments from people from time to time that are absolutely convinced that there’s a massive government or corporate conspiracy to invade their privacy, steal their information, or worse. Usually it’s of the generic variety — “they’re after us all” — but I’ll occasionally see the more personal version as well — “they’re after me.”

This bothers me in part because these folks are choosing to live a life in fear that is generally unfounded.

What worries me more is that it often prevents them from doing things that would benefit them, or ironically, protect them.

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Accepting What You’re Told

It’s frustrating.

I watch the scenario play out on TV all the time. People are given some information and accept it without question.

Right or wrong, true or false, intentionally deceptive or accidentally misleading. Blind acceptance from someone in a position of perceived power or beguiling intrigue.

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Why I Like Email

Some people hate email.

I love it.

It’s one of the best possible means of communication invented, as far as I’m concerned. And my reasons are very, very simple.

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