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September 6, 2026

by Charles Miller

Several years ago I flew up to Boston to attend a computer security conference that featured some of the leading experts in the field. I was personally acquainted with some of the speakers via email but we had never met in person, so I jumped at the opportunity. As is often the case, a seemingly minor anecdote is one of the main things that now stands out in my memory of that event. One of the most interesting ideas raised during the panel discussion was the contribution by the respected computer security and networking researcher William "Ches" Cheswick. It came as he opined on the inherent conflict between "creepy versus convenient." Everyone wants everything in their life to be convenient, yet convenience starts edging toward creepy when you suddenly realize the extent to which your smartphone is now spying on you.

Cheswick made the point that in past centuries gentlemen of means often had a butler or manservant who ended up being privy to knowing almost everything about his employer. He knew your likes and dislikes, habits, finances; he knew your medical history, dietary requirements, and so much more. He probably knew if you were stepping out on your wife in addition to other intimate details. In short, your butler knew everything about you because that is what was needed to perform his duties; and you trusted his discretion.

Ches went on to say that he was prowling antique book stores hoping to find an old guidebook for butlers that might define what the rules of butlering were in the 18th and 19th centuries because that might serve as a guideline for people designing computer software today. The reason for that is obvious. Today your smartphone fulfills many of the responsibilities that a butler might have performed in previous centuries, it knows more about you than you think it does; and as such it ought to have a code of conduct.

Even after voicing the aforementioned privacy concerns, Cheswick held up his smartphone and said "I WANT my phone to know everything about me." For that sentiment to become commonplace software programmers need to find a way to teach smartphones discretion as well as a sense of morality.

Should your smartphone notify the police every time it detects you have jaywalked? What about a more serious offence such as parking in a handicapped spot? Should it email your cardiologist with a CC to your wife whenever you pig out on a Big Mac with two orders of fries? What about the conversation it overheard concerning certain tax matters? Years ago your butler supposedly knew what his responsibility was if you did something seriously wrong or illegal, but where should the lines be drawn? How do you teach a piece of electronic hardware an appropriate code of conduct? And how do you define "appropriate?"

During that panel discussion it was also pointed up that trusting your cell phone butler will likely be a generational thing. Young people today blithely post the most salacious details of their lives on Facebook thinking there is no downside. Of course that is before they have learned that "the internet is forever" when years later they sit for a job interview or run for public office. Old fogies of my generation are generally more circumspect and wary of who has access to our personal information.

Having a smartphone spy on its owner's activities can provide convenience and personalization, such as targeted recommendations, faster access to information, and potentially improved personal security. It could make daily life work more smoothly by predicting needs or coordinating schedules. The disadvantages are potentially significant and could erode privacy, enable unwanted profiling leading to manipulation through targeted advertising. There is a risk of personal, legal, or financial consequences if sensitive data is leaked or misused. Users may feel less in control not understanding how to manage their digital footprint, and belatedly realize that convenient can be only a step away from creepy.

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Charles Miller is a freelance computer consultant with decades of IT experience and a Texan with a lifetime love for Mexico. The opinions expressed are his own. He may be contacted at 415-101-8528 or email FAQ8 (at) SMAguru.com.

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