For more than a decade, the iPod Classic was an icon of mainstream culture. But it was one song that didn’t remain the same.

Three months ago, the device, which at that point hadn’t been updated in about five years, finally fell from its long-standing place on Apple’s shelves. The iPhone had taken its place, and then some.

But a funny thing happened on the way to obscurity: Longtime fans of the device came out of the woodwork, and suddenly there’s a run on the devices on eBay. They now cost as much as a high-end iPhone 6 Plus—without a data plan.

It’s odd how nostalgia works, doesn’t it? Like old-school Nintendo nerds and vinyl record addicts before them, they simply appreciate the pureness of the old-school technology. More power to them.

My wife is kinda like that. She only got an iPhone because her employer said she needed to. She was otherwise perfectly content with her old feature phone, and even now she’s not big on apps. She’s not alone in that sentiment: Iggy Pop and Anna Wintour are among the most famous clamshell diehards.

This highlights the ultimate technology challenge many organizations face: When do we let go of the legacy? And how do we balance the old with the new? I’d like to pose this in terms of a thoroughly disrupted technology that we’re basically stuck with: the phone book.

Phone books: They’re like the AOL CDs of of the 21st century. (Justin Sullivan/Getty Images)

The Phone Book Problem

Some people still need phone books. The problem is, most people don’t. They’re just not a part of most people’s lives anymore, thanks to the cluster of wires you’re using to read this article.

That leads to scenes in cities where piles of books sit in front of apartment complexes, untouched. It’s a huge waste of time, money, and resources for everyone involved.

If you’re the phone company, how do you tell the difference between people who need phone books and people who don’t? And how do you cater to both? Do you print fewer copies? (Or, if you’re required to print all those copies by government regulators, do you ask for looser regulations?) Do you put most of your resources into your website or into apps? And will your advertisers stay along for the ride if you change your strategy? At what point does it cost more to print and deliver the books than it does to bring in ad revenue?

And as for the people who still want or need a copy of the Yellow Pages, how much do you cater to them? Thus far, many phone companies have chosen to cut the books down from Bible-sized tomes with white pages to novellas without.

The next challenge for phone companies: If it makes sense to stop printing phone books, how do they get the diehards to join the 21st century? It’s a lot to think about. And none of these problems have easy solutions.

The goal for associations is to blaze a trail without kicking up so much dust along the way that your members and employees can’t follow you.

The Great Disconnect

The example of phone books really gets down to the push and pull of technology in general. You can see it in a lot of places, like the feet-dragging that preceded the death of Windows XP and the lingering discomfort many IT departments still have with BYOD.

It bleeds into regulatory questions about emerging spaces like the internet of things and mobile payments. Heck, technologies can’t even ride off into the sunset without lots of hand-wringing.

Every organization has this tension between embracing the new and letting go of the old. For associations, it varies by space: Associations in the tech industry, for example, are more likely to embrace the latest and greatest by their very nature. Other industries may be too small or niche to benefit from the extra costs that come with getting everyone in front of the curve. If your members are barely even using smartphones, it might be a little early for you to launch an app—but you can certainly tell them why they’d benefit from the upgrade.

I write about the early adopters a lot in my blog posts, because they define our industry’s future path—and associations can prove stronger by leading the way rather than following behind. But it’s dangerous to focus only on early adopters in your organization, because you may find yourself on the wrong side of the bell curve.

Likewise, you’d be making a mistake to let the way you’ve always done things define your future path. So the goal for associations is to blaze a trail without kicking up so much dust along the way that your members and employees can’t follow you.

Keep handing out the phone books, sure—but make sure you’re only handing them to the people who really need them.

Yes, people still use phones like these. (iStock/Thinkstock)