One of my most memorable job interviews ever was one in which I was asked to come up with an answer on the spot to this question: “What are the odds that there are at least two people who live in New York City and have the exact same number of hairs on their heads?” *

It was a programming job; the interviewer was looking for a display of a rational problem-solving. Nonetheless I compulsively said the first thing that came into my head: “One hundred percent. I personally know two bald New Yorkers.”

Smart aleck. I got the job offer, but I knew I hadn’t really demonstrated the thinking they were looking for. I’ve just started a cool book called Guesstimation: Solving the World’s Problems on the Back of a Cocktail Napkin. If I’d read this then, I’d have had the tools to think through that question in the way I suspect the interviewer had hoped.

We’re doing some interesting guesstimation at Yankee Group right now, though, so it will come in handy. As part of some work we have underway to assess the scale and pace of the emergence of ubiquitous connectivity — what we call Anywhere — we’re sizing its impact today and in future. I’ll post again here in a few weeks when it’s finished, so you can see what we have come up with and share some feedback. But at the moment the project is reminding me of the basic challenge of predicting the future: combining art and science in just the right measures. As the book’s authors point out, too many decimal points in a forecast ”are like lying,” since they suggest a level of precision and confidence that these methods can’t possibly offer up.  We’ll round the numbers up to the nearest hundred billion, I promise…

* The current population of NYC is over 8 million, and the average human has 100,000 hairs on his head. so you figure it out.

I’m planning a night at the Oscars. By my reckoning, it should happen around 2010.

A budding Hollywood star, Bridgit Mendler, has emerged in my family. At only 15, she’s won a leading role in The Clique, a film based on the popular teen novels of Lisi Harrison.

Exciting stuff in a bloodline whose only prior notoriety was the publication of the Massachusetts Conveyancers’ Handbook (With forms) in 1984.

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Books: in this age of blogs, IM, and Twittering, so 19th century! But still such a great way to set out an important idea.

It’s not easy to keep up, as the stack on my nightstand will attest, but I’m a voracious reader of non-fiction, particularly those on technology’s impact on us as consumers and business leaders. As I meet with technology executives on both sides of the aisle (developers and deployers, that is!), I’ve probably given out 100 books on these topics in the past two years. One exec who really liked one of my choices for him suggested I start up an on-line book club, so he could find out what else he should be reading.

Fair enough; here it is, via the blog. All you have to do to participate is to take the RSS feed (top-right-hand corner of my main blog page), and then watch for posts in the “YG book club” category. Here are two books I’m reading right now:

• Founders at Work I love story-telling, and I love technology; this book combines the two in an entertaining format, presenting interviews with a wide variety of recent and historical figures in the high-tech startup space.
• Marketing to the Social Web Full disclosure: the author is a friend as well as a member of Yankee Group’s Board of Directors. It’s still a valuable book with advice about how to market in a two-way context to the empowered Anywhere Consumer.

What are you reading these days that I might enjoy?

A personal triumph! I finally finished a challenging, irritating but useful book about forecasting the future. I took on Nassim Taleb’s daunting The Black Swan: The Impact of the Highly Improbable (Random House, 2007) because it seemed like something technology prognosticators ought to understand.

A ‘black swan’, in Taleb’s terminology, is an essentially unpredictable event: the events of 9/11, the rise of Google. It has three qualities: unpredictability, massive consequences, and, most interestingly, ‘retrospective explainability’ — as in, “Well, of course search would be the most important way to dive into the Internet, and of course Google’s approach was better than anyone else’s.”

I’ve spent over ten years building and using forecasts, and answering sometimes hostile questions about them. As I’d suspected from the jacket cover, The Black Swan was an education on how the other side thinks, dripping with attitude: Taleb reviles how humans, including professional futurists, attempt to predict what’s ahead but fall woefully short.

I value having read the book; it offers cogent lessons. One such: You cannot manipulate more information than your past can deliver. Example: a turkey being raised for Thanksgiving will never anticipate — based on his daily feeding — that his end will come quite suddenly. In this case his past has negative value in anticipating his future. Another: Beware the reification of your spreadsheets. Just because a figure appears automatically in a cell doesn’t make it correct.

In the end, though, I asked myself: is it wrong to try to anticipate technology’s future impact on our world? For that’s what I and my technology analyst colleagues do. Here’s where I came out, simply stated:

• We should not stop asking ourselves what’s next — for one thing, it’s too much fun
• While the past is insufficient support, and potentially misleading, it’s still a valid input to that effort
• Pending near-term events, parallel episodes in other domains, and, yes, guesswork also play a part
• If you’re right more often than you’re wrong, you add value

Did you read the book? Share your reactions in the context of anticipating technology’s evolution.