If you had the option to live in Palo Alto, Pacific Heights or Hillsborough – where would you choose and why?

Funny how things change as life goes on.

10 years ago, the last possible place I’d want to live is Hillsborough. It doesn’t have the full benefits of warm weather you get on the Peninsula, and it has none of the amenities you get in SF. And unlike Palo Alto, it’s anti-walkable or even bikeable. All you get are big houses clinging to the side of a hill which look impressive but often mean a weird yard it’s hard to even use if you can afford anything there.

But life goes on.

Now, I’m a startup world guy with kids in school. My business life is in SF, but the kids want the benefits of a suburban life. The train in Palo Alto is nice, but it doesn’t really match up to an unscripted life as well as you’d hope.

So now I sort of wish we lived in Hillsborough/Burlingame. Easy to get into SF, without all the trade-offs of living in SF with kids.

The Bay Area has evolved into SF-connected segments that are so far from each other they will drive you nuts. Try going from Jackson Square to Mountain View for a meeting. Man.

Hillsborough-Burlingame-etc. may be the best family-friendly trade-off.

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Published on January 28, 2018

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