There’s an old joke that you know you're in heaven if the cooks are Italian and the engineering is German. If it's the other way around you're in hell. In an attempt to conjure up a perfect city, I imagine a place that is a mash-up of the best qualities of a host of cities. The permutations are endless. Maybe I'd take the nightlife of New York in a setting like Sydney's with bars like those in Barcelona and cuisine from Singapore served in outdoor restaurants like those in Mexico City. Or I could layer the sense of humor in Spain over the civic accommodation and elegance of Kyoto. Of course, it's not really possible to cherry pick like this—mainly because a city's qualities cannot thrive out of context. A place's cuisine and architecture and language are all somehow interwoven. But one can dream.

As someone who has used a bicycle to get around New York for about 30 years I've watched the city—mainly Manhattan, where I live—change for better and for worse. During this time I started to take a full-size folding bike with me when I traveled so I got to experience other cities as a cyclist as well. Seeing cities from on top of a bike is both pleasurable and instructive. On a bike one sees a lot more than from a freeway, and often it's just as fast as car traffic in many towns.

A "livable city" means vastly different things for many people. In Hong Kong it might mean that your family is in a comfortable apartment while you play in the exciting mercantile world in a glass tower overlooking the harbor. In Dallas livability might mean that you live near an expressway that isn't jammed up, at least not all the time, and your car runs most days. For some it might mean super fast Wi-Fi, the possibility of lucky and lucrative business opportunities and plenty of strip clubs. If that's what rocks your boat then try Houston, though to me that city, oil money made physically manifest, is my worst nightmare.

Here are some things that make a city livable for me:

Size

A city can't be too small. Size guarantees anonymity—if you make an embarrassing mistake in a large city, and it's not on the cover of the Post, you can probably try again. The generous attitude towards failure that big cities afford is invaluable—it's how things get created. In a small town everyone knows about your failures, so you are more careful about what you might attempt. Every time I visit San Francisco I ask out loud "Why don't I live here? Why do I choose to live in a place that is harder, tougher and, well, not as beautiful?" The locals often reply, "You don't want to live here. It looks like a city, but it's really a small village. Everyone knows what you're doing" Oh, OK. If you say so. It's still beautiful.