I moved to Boston in 1982.

 It’s not a huge city and the subway (or “T” as we like to call it) only has five lines. And so it didn’t take me long to get comfortable and find my way around.

That all changed abruptly in 1986.

In the Spring of that year, I bought my first car (a 1970, orange, Toyota hatchback).

 Suddenly, instead of hopping on and off the train and walking the rest of the way to wherever I was headed, I started driving places. That was a problem.

 And not just because the drivers here view traffic laws as well-meaning suggestions (although that certainly didn’t help).

 No, my problem was navigation.

Unlike many cities that are laid out in some type of intelligent grid system, Boston was laid out by (I’m guessing) drunken farm animals with a freakish enthusiasm for one-way streets.

 It was frustrating.

Same city, same streets, new ways

I remember one incident in which my date and I were attempting to drive to a particular restaurant. We could see the building – but we couldn’t get there.

 We went back and forth through the city, sometimes getting closer, but then suddenly we’d be far away again. Once we even got caught in the traffic flow and ended up on the wrong side of the river in Cambridge.

Finally, after about an hour of driving and with the restaurant again in sight, I pushed her out of the car at a traffic light and told her to let me know how dinner turned out. (Yes, if you must know, that was our last date.)

 But then I had a brilliant idea.

Over the next few weeks, I went out several times at three in the morning and drove around the city. No traffic, no pedestrians, no hungry companions.

 It was the same city with the same streets, of course. But with nobody else out there, I could take my time, back track when necessary, and make plenty of mistakes – all with little consequence.

When few people are watching

Thirty-plus years later, I apply this same, “learn important stuff when few people are watching,” approach to the way I market my business.

In other words, rather than going for a big bang with the launch of a redesigned website, newsletter, company blog, podcast or whatever, I don’t go for a bang at all.

 Instead, I tell just a few people and see how it works. Then I tell some more people.

On and on it goes, with whatever it is I’m working on getting tested, tweaked and improved with the input of lots and lots of people. 

By the time I do finally make the big announcement, I’m on version 5.0 instead of 1.0.

Here’s the bottom line. Make your mistakes “at night” when nobody cares and few people are paying attention. You’ll end up releasing something way better and with a lot less pressure to make the right turn, at the right intersection, at the right time.

This article has been edited and condensed.

Since launching Blue Penguin in 2000, Michael Katz has been quoted in The Wall Street Journal, The New York Times, Business Week Online, Bloomberg TV, Forbes.com, The Boston Globe, and other national and local media. He is the author of three books, and has published over 350 issues of “The Likeable Expert Gazette,” a twice-monthly email newsletter with 6,500 passionate subscribers in over 40 countries around the world. Michael has an MBA from Boston University and a BA in Psychology from McGill University in Montreal. He also has a second degree black belt in karate (Kempo), a first degree black belt in parenting (three children), and is a past winner of the New England Press Association award for “Best Humor Columnist.” Connect with @MichaelJKatz on Twitter.

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