The New York Times recently announced that it was turning its web site into a pay-to-play operation. Regular subscribers to the newspaper would continue to have unlimited access to all The Times’ online content and archives. But others would have to sign up and pay for a special Internet account.

I sympathize with the Times’ position. As someone who has spent most of his life reading, and working for, print media, I understand how vital it is these days to develop a profitable financial model. People simply don’t read as much anymore. Today, The Times is competing not just with The Washington Post and The Wall Street Journal, but also with HuffingtonPost.com, Politico.com, Slate.com, msnbc.com and a 24-hour, multi-media news cycle.

Inconvenient, I thought, but no problem for me since VMSD has a daily delivery subscription. I would just convert that full-time access to the web site, as they were advertising I could with just one click – or not.

Four days, close to 20 phone calls and maybe 50 apologies and explanations later, I’m still not there. One very polite customer service rep after another has told me they’ve been inundated with requests, they didn’t expect the response, they weren’t set up to handle the volume, they’ve had technical difficulties.

What does this have to do with retail? Just this. Like The Times, retailers are in thrall of all that new technology promises to do. It will make operations more efficient and the stores more exciting and link your digital and bricks-and-mortar operations. Besides, this is what today’s younger demographic knows and expects.

Until it doesn’t work and has the opposite effect than intended. Then it makes customers angry, makes them question your know-how and damages your brand – maybe irreparably.

The New York Times brand is competence. When they tell you they can’t make it work, it’s like learning for the first time that your parents are human and have made mistakes. Of course, learning that your parents are flawed is part of the journey to adulthood. You get over it, learn from it, perhaps become a better adult yourself as a result of it.

But hearing that The New York Times was caught unprepared is like hearing for the first time that there’s no Easter bunny . . . laying eggs . . . COLORED eggs. You don’t get over that so easily. Is there enough damage control to protect any brand from that?