Saturday, July 25, 2026

Every Generation Gets the Same Mountains

Recently, a childhood friend tagged me in a Facebook post linking to a YouTube video called Why Nobody Wants to Visit the Poconos, Pennsylvania Anymore. I clicked expecting a little nostalgia. I grew up there, after all, and figured I'd spend half an hour recognizing familiar places before getting on with my day.

Which is not where this story goes.  Stay with me, this is a long one.

For years, I've worked with researchers, inventors, and founders trying to turn ideas into companies. One of the hardest lessons to teach isn't how to launch a product; it's convincing people not to become one-trick ponies. A first success is wonderful, but it can also become a trap. Once customers love what you've built, it's only natural to spend your time making it better, faster, cheaper, or easier to scale. 

What's much harder is imagining that the thing people love today might not be the thing they'll want tomorrow, which is how one-trick ponies are made. Not because people lack talent or ambition, but because success has a way of narrowing our imagination. We become so busy refining what works that we forget to ask what might come next.

Now- back to the video.

Growing up, I never thought much about the resorts that dotted the Poconos. Buck Hill Inn, where I celebrated my senior prom, was less than a mile from my house as the crow flies. Mount Airy Lodge sat on my route to school, and I drove through its grounds nearly every weekday from fifth grade until I graduated from high school. They weren't destinations to me. They were simply part of everyday life.

I wasn't surprised to learn Buck Hill was gone or that Mount Airy had become something else; I already knew both of those things. What surprised me was seeing their history laid out end to end. For the first time, I wasn't thinking about them as places I happened to know but as ideas. Each represented someone's answer to the question, Why would people come to the Poconos?

When I was growing up, the answer seemed obvious. The Poconos were where people went on their honeymoon- it was, after all, “The Honeymoon Capital of the World.” That identity felt so established that it was easy to assume it had always existed. (spoiler alert- it hadn't, because before honeymooners came wealthy families escaping the summer heat. Before them came visitors seeking fresh mountain air and the promise of better health) After the honeymoon era waned there was skiing, water parks, casinos, hiking, outlet shopping, and countless other experiences. The mountains though, never changed. What changed was the imagination of the people who looked at those mountains and saw new possibilities.

Once I started looking at the resorts that way, I realized I wasn't really watching the story of a vacation destination anymore. I was watching generations of entrepreneurs answer that same question in completely different ways. For a while, each of them had the right answer, but every answer had a shelf life. The entrepreneurs who realized the answer had changed wrote the next chapter. The ones who assumed yesterday's answer would always be enough eventually became part of the previous one.

That doesn't mean the Poconos rose and fell for a single reason. Changing travel habits, affordable airfare, economic shifts, competition from other destinations, and countless other factors all played a role. But what struck me was that every new chapter seemed to begin with someone who saw possibilities the previous generation hadn't. They weren't necessarily better hotel operators or better business people. They simply looked at the same landscape and imagined a different future.

Many of the resorts that had defined earlier eras never made that leap - not because they were lazy or incompetent, but because, in many cases, they became exceptionally good at delivering exactly the experience they had promised for decades. Their challenge wasn't so much a failure of execution as it was a failure of imagination. Resort owners kept refining yesterday's answer while a new generation of visitors was hungry for today's answer, and by the time they recognized it, someone else was already imagining tomorrow's.

I see versions of that story all the time in the innovation world. Founders become attached to products, universities become attached to programs, and organizations become attached to services that once set them apart. None of those things are inherently bad; in fact, they're usually the result of years of thoughtful work and genuine success. The danger comes when that success convinces us that tomorrow will reward us for becoming even better at yesterday's answer instead of challenging us to ask what will tomorrow's look like.

That's why I spend so much time warning founders about becoming one-trick ponies. I'm not suggesting they abandon successful products every time a new technology appears or a new trend catches everyone's attention. I'm encouraging them to protect their imagination, because the companies that endure aren't always the ones with the best first idea. They're the ones that continue asking what comes next, even while their current answer is still working.

By the time the video ended, I realized it hadn't made me nostalgic at all. It reminded me that innovation isn't simply about creativity or clever ideas. It's about protecting your imagination. It takes imagination to create something new the first time; it takes even more imagination to recognize when the world has changed and to ask a different question before someone else does.

Ultimately, I realized I hadn't been watching a video about the Poconos at all. I'd been learning about entrepreneurs.

The video mentioned several times “the mountains remained.” What changed was the answer to a simple question: Why would people come here? One generation answered with grand hotels, another answered with honeymoon resorts, skiing, casinos, water parks, and outdoor adventure. None of those answers lasted forever, but each reflected someone who looked at the same mountains and imagined a different future.

Watching that history unfold reminded me that the people who shaped the Poconos weren't necessarily the ones who built the biggest hotels or operated them the best. They were the ones who realized the old answer was losing its power and had the imagination to offer a new one.

I think that's the hardest part of innovation. It isn't inventing something once. It's refusing to believe your first success is your last answer. Whether you're building a startup, leading an organization, or trying to reinvent an entire region, today's success can become tomorrow's blind spot if we're not careful. The work isn't simply making yesterday's answer better. It's recognizing when the answer has changed - and having the curiosity to imagine the next one before someone else does.