I’ve been getting that question ever since moving back here 13 years ago. It’s usually from entrepreneurs or venture capitalists in Silicon Valley, wondering how the home of Route 128, Harvard and MIT seems to keep missing out on the next big thing. If Digital Equipment Corp. and Wang Labs made it here, how come companies like Facebook and Dropbox left?

The stock answer has been that our Yankee heritage has gotten the better of us. We’re always preparing for the next winter, too focused on what we know is next to consider what could be next. Pessimism-tinged realism in an era otherwise filled with technological marvels that were willed into being by unbridled optimism.

But I honestly had believed that things here had begun to change. There seemed to be a groundswell of “Valley-like” entrepreneurship, complete with the requisite networking events (there’s nearly one per night now) and tangible support from elected officials. It’s the reason I’ve spent the past several years answering the “What’s wrong with Boston?” question by saying that the only thing wrong was how long it took us to get things right.

And then came the Olympics.

Well, not literally. The 2024 Olympic Games haven’t come here yet, and seem less likely to arrive with each passing day. What once was little more than an aspirational pipe-dream has quickly morphed into a community piñata, much to the U.S. Olympic Committee’s chagrin.

According to recent poll numbers, more Boston-area voters are against the Summer Games coming to Boston in 2024 than are for it. And these results come even as virtually all of the city’s major political and business figures are in favor, and the opposition has been led by a trio of unpaid, unknown 30-somethings.

To be sure, there are some very good reasons for folks to want the Olympics to stay away. For starters, under IOC rules, the state (read: local taxpayers) would basically have to backstop any financial overruns. Moreover, supporters have yet to put forth the type of granular plan — finances, logistics, infrastructure — that residents must be allowed to analyze before welcoming the world to their doorstep.

But those aren’t the concerns I hear from friends and family, or on local talk radio. Instead, it’s complaints about how Boston just isn’t big enough or competent enough to pull it off. If we couldn’t even keep the subway system running this past winter, how are we supposed to handle the massive influx of tourists? If we couldn’t build a tunnel without becoming the butt of a national joke, how are we supposed to quickly build a temporary stadium that seats 60,000, or any of the other required facilities? And what about the traffic?

It’s the old Yankee mentality all over again. Whatever could go wrong will go wrong, without bothering to deeply analyze the dollars or the sense. And why do we need all this fancy stuff anyway?

As I said, there are some very serious problems with the Boston 2024 bid. But, to me, the larger issue is what the popular unpopularity seems to suggest about our city. We’re still hostage to our own neuroses, and it must be even more evident to outsiders (including investors and prospective entrepreneurs). It’s why the odds are so long that the next great tech company will be built here.

Unless… well, unless we host the Olympics. I think we may really need beach volleyball on Boston Common to prove to ourselves that we can accomplish great things that initially seem too daunting.

So here is my hope: Boston’s Olympics boosters get their act together, and realize that they have leverage with an IOC that really wants an American host city. Get the taxpayer guarantee to go away. Provide a detailed plan that can be analyzed and improved. Win the bid and execute.

Then, and perhaps only then, will Boston be in the proper cultural condition to capitalize on its hometown advantages in the innovation economy. Even if it’s a few decades delayed.

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