From the Editor’s Desk: To Don’t (Premium)

Every once in a while, I come across a formalized description of something I’ve just been doing already, and it’s always a nice bit of affirmation. And so it was a few weeks ago when I saw an article (that I can annoyingly no longer find) about creating a “to-don’t” list instead of a to-do list.

No, not literally: an actual to-don’t list is a ridiculous idea. But the idea here is that we spend a lot of time focusing on the positive things we can change or accomplish in our lives, be it a to-do list, a New Year’s resolution, or whatever. But it is equally useful to be mindful of what you don’t want to do or want to avoid. That is, this year, I’m not going to do … something. Whatever it may be.

I like this because I stumbled upon the value of thinking like this a long time ago. If you’ve read enough of these Monday morning missives, you may recall that I have horrible parents and that it was a revelation to me when I met my future wife’s parents and realized that one could treat their own children like adults. In my wife’s parents, I found a positive example, a “to-do” for parenting. But my experience with my own parents was equally useful and informative as a “to-don’t” for parenting. There are good and bad examples, and you can learn from both. And I did.

I’ve also learned from interacting with some of you that many of these lessons are specific to the individual. For example, as a long-time traveler, I’ve honed my habits around packing and how I travel when flying, and I have a very specific way of doing things. Among them is the notion of traveling light which, among other things, dictates that I will never check a bag. For me, this “to-do” of traveling is reinforced every time I go anywhere. And on those few occasions in my life when I was forced to check a bag, how doing that was likewise a “to-don’t” of frustration and wasted time.

Others feel differently. We have friends who travel at least as much as we do, and they have gone on some incredibly adventurous trips, and they very much prefer bringing many more things with them when they travel, and so they check their bags every time. To me, this is a wrong-headed focus on the “what if” of travel, as in I have to bring an umbrella, because what if it rains. But to them, checking bags and potentially not having something they might need is stressful. As stressful to them as waiting for a bag at an airport is to me. To each their own.

But that’s sort of the point: as our experience with anything grows, the habits we develop are comprised of both positive (“to-do”) and negative (“to-don’t”) learnings, and both impact us equally.

I was thinking about this when Microsoft announced its AI-based Bing chatbot a few months ago and Yusuf Mehdi, intriguingly, used the example of using AI to create a five-day itinerary for Mexico City, a place in which my wife and I have invested an enormous amount of time and money. And so I’ve used this same example in my own experiments with AI for obvious reasons: I know this place well enough to know whether the advice it regurgitates makes sense.

And here’s what I’ve observed: creating a list of the best places to visit in Mexico City and the surrounding area is easy, as is filtering that list so that it’s weighted to the top sites, ensuring that you will have a good experience no matter how many days you’re there. But here’s where AI has always fallen short: Mexico City is a huge place, bigger than any city in North America, and some of the top sites in the area are both time-consuming to visit and very far from each other. And Bing and other AI-based tools have consistently created itineraries that, if not impossible, would surely lead to frustratingly long days.

To prove this point to myself again—these things do improve time, of course—I just asked the Bing chatbot for this exact bit of advice. And what I was told to do in one day are two activities that couldn’t be physically further from each other, and both of which could take up an entire day: visit the Teotihuacán Pyramids, which are about 90 minutes from the historic center of Mexico City and then visit the National Museum of Anthropology, which is in Polanco, on the far opposite end of the city, a drive that could take one hour during rush hour. Those are two great activities, but for two different days, and if you really want a spectacular Teotihuacán experience, consider a hot-air balloon ride over the pyramids too, which will make for an even longer day with a very early start. But totally worth it.

That AI will figure out this problem is both obvious and beside the point: knowing what not to do, in this case on what might be your only trip to a very specific place, is just as important as knowing what not to do. And please don’t get me started on how horrible your day will be if you try to do these two things back-to-back.

Anyway, I’m not sure who came up with this originally, but it’s an interesting and useful way of looking at things, one that turns the notion of “negativity” on its head. No wonder I like it.