Maybe We’re Finally Entering Our Era

Nick Vannello

11 Aug 2026 • 11 min read

I read an article recently arguing that the digital economy is beginning to favor people over 50, and I haven't stopped thinking about it. The writer's point was largely about technology and business. Artificial intelligence now produces information, images, marketing copy, business plans, videos, and endless streams of content in seconds. For years, the internet rewarded people who knew how to produce more, post more, and attract more attention. Now everybody has access to tools that do much of that work almost instantly, which raises an interesting question: When information and content become incredibly easy to produce, what becomes valuable instead?

I think the answer might be experience, judgment, perspective, and knowing what matters. It's knowing when somebody is full of shit, when you've seen this movie before, when something isn't worth worrying about, and when something deserves your full attention. Those aren't technological skills. They're life skills, and the more I thought about that, the more I realized this conversation goes far beyond AI or the digital economy.

What if we're entering an era when getting older starts becoming an advantage again?

For much of the past few decades, American culture has been obsessed with youth. Advertising chased it, television celebrated it, and social media practically worshipped it. Entire industries made fortunes convincing us that looking younger was preferable to looking like someone who had lived. Somewhere along the way, many of us absorbed the idea that after 50, our job was to keep proving that we were still relevant.

I don't like that bargain anymore. I don't want to remain relevant despite my age. I want my age to be part of what makes me relevant, because when you've lived for five or six decades, you've accumulated something younger people simply haven't had enough time to accumulate yet. You've accumulated evidence.

You've watched supposedly permanent things disappear and terrible situations eventually end. You've fallen madly in love with people you barely remember now, and you've lost people you thought would always be sitting at the table. You've made decisions you regret and others that quietly changed the direction of your entire life. You've watched fashions return wearing different names, and you've heard younger people announce brilliant new ideas you remember somebody trying in 1987. Hopefully, somewhere along the way, you've also developed a pretty good bullshit detector.

There is value in all of that.

AI Knows More Than I Do, But I Know Things AI Doesn't

I'm fascinated by artificial intelligence, and I use new technology constantly. I have no interest in becoming one of those people who decides the world should stop changing because I've reached an age where keeping up requires more effort. I want to know what's happening, play with the new toys, learn enough to stay curious, and keep moving along with the world.

But I also see something interesting happening. When information becomes cheap and plentiful, experience starts looking a lot more valuable. AI has access to more facts than any human being will ever hold in one brain. You ask a question and receive an answer before you've finished your coffee. Yet information and wisdom were never the same thing, and having access to every answer doesn't mean knowing which answer matters.

Wisdom comes from making a decision and living with the consequences. You get it from trusting the wrong person, staying too long, leaving too soon, losing money, starting over, and falling in love after swearing you wouldn't. You get it from sitting beside somebody in a hospital, burying a parent, walking into a strange city alone, screwing something up, surviving the embarrassment, and realizing life went right on afterward.

You don't download those lessons. You earn them, and if you're over 50, you've earned quite a collection.

We Aren’t Starting From Scratch

This is the part I wish more people our age understood. When you decide to start something new at 55, 62, 68, or 74, you aren't beginning at zero. You arrive carrying decades with you, even when the thing you're attempting feels completely unfamiliar.

Start a business at 60 and you're bringing every boss you've ever worked for, every customer you've dealt with, every difficult personality you've survived, every mistake you've watched someone make, and every lesson you've picked up along the way. Start traveling at 65 and you bring something a 22-year-old backpacker hasn't had time to develop yet. You know yourself better. You know which discomforts are worth tolerating, which ones aren't, and which supposedly must-see attractions you're perfectly happy skipping because you'd rather spend three hours drinking coffee in a neighborhood you've never visited before.

The same thing applies when you start dating again, making art, writing, teaching, volunteering, learning a language, moving somewhere new, or finally trying the thing you've been talking yourself out of for 30 years. You might be a beginner at the activity, but you're not a beginner at life. There's an enormous difference between the two.

Maybe Experience Is Becoming Cool Again

I don't think youth is losing its value, nor would I want it to. Young people bring energy, new ideas, different assumptions, and a willingness to question things the rest of us stopped noticing years ago. We need that. But they need something from us too, and perhaps we're moving toward a healthier arrangement where one generation doesn't have to become invisible for another one to matter.

I see hints of this everywhere. People in their 50s, 60s, and 70s are starting businesses, traveling alone, creating communities, going back to school, dating, making videos, writing newsletters, moving abroad, and learning new technology instead of running from it. More important, they're beginning to talk about aging without treating their age like an apology or something they need to disguise.

That interests me far more than looking younger. I don't want to be mistaken for 42. I want 62 to look like a hell of an interesting age to be, and I want the same thing when I'm 72 and 82. If I'm lucky enough to get there, I intend to give 92 a respectable attempt too.

This Is What Dorothy Is About

The Dorothy Society was never supposed to be a place where older people sit around talking about getting older. Quite the opposite. I'm far more interested in talking about what we're doing with all this experience we've accumulated and where we're going next.

I want to know where you're going, what you're learning, who you're becoming, and what opinion you've changed after believing it for 30 years. I want to know what you've finally stopped caring about and what you've suddenly started caring about again. Most of all, I'm interested in the parts of ourselves we put away years ago because work, family, money, fear, responsibility, or somebody else's expectations got in the way.

Perhaps one of the great gifts of getting older isn't wisdom at all. Perhaps it's permission. At some point, you realize there are fewer people left whose approval you need, and you begin asking a different question. Instead of wondering what everyone else will think about the life you want, you start wondering why you're still allowing everyone else to have a vote.

The world around us is changing at an astonishing speed. AI will change how we work, technology will change how we communicate, and younger generations will change culture in ways we don't fully understand yet. None of that requires us to move aside. There's still a seat at the table for people who have been around long enough to remember several previous versions of the table.

We don't need to pretend we're 30 to deserve that seat. We don't need to master every new platform, collect millions of followers, dress younger, talk younger, or desperately prove we're keeping up. We need to show up with what we've spent decades accumulating: curiosity, experience, stories, judgment, humor, perspective, a few scars, and enough humility to admit we're still learning.

For years, aging has been presented as a gradual process of becoming less important, less interesting, and less necessary. I think we're beginning to see how ridiculous that idea was. In a culture overflowing with information, perhaps people who have spent decades learning what to do with information are becoming more valuable, not less.

Maybe this isn't the period when we fade quietly into the background. Maybe the world is finally catching up with something we should have known all along.

Maybe we're entering our era.

And Dorothy, I have plans.

I read an article recently arguing that the digital economy is beginning to favor people over 50, and I haven't stopped thinking about it. The writer's point was largely about technology and business. Artificial intelligence now produces information, images, marketing copy, business plans, videos, and endless streams of content in seconds. For years, the internet rewarded people who knew how to produce more, post more, and attract more attention. Now everybody has access to tools that do much of that work almost instantly, which raises an interesting question: When information and content become incredibly easy to produce, what becomes valuable instead?

I think the answer might be experience, judgment, perspective, and knowing what matters. It's knowing when somebody is full of shit, when you've seen this movie before, when something isn't worth worrying about, and when something deserves your full attention. Those aren't technological skills. They're life skills, and the more I thought about that, the more I realized this conversation goes far beyond AI or the digital economy.

What if we're entering an era when getting older starts becoming an advantage again?

For much of the past few decades, American culture has been obsessed with youth. Advertising chased it, television celebrated it, and social media practically worshipped it. Entire industries made fortunes convincing us that looking younger was preferable to looking like someone who had lived. Somewhere along the way, many of us absorbed the idea that after 50, our job was to keep proving that we were still relevant.

I don't like that bargain anymore. I don't want to remain relevant despite my age. I want my age to be part of what makes me relevant, because when you've lived for five or six decades, you've accumulated something younger people simply haven't had enough time to accumulate yet. You've accumulated evidence.

There is value in all of that.

AI Knows More Than I Do, But I Know Things AI Doesn't

But I also see something interesting happening. When information becomes cheap and plentiful, experience starts looking a lot more valuable. AI has access to more facts than any human being will ever hold in one brain. You ask a question and receive an answer before you've finished your coffee. Yet information and wisdom were never the same thing, and having access to every answer doesn't mean knowing which answer matters.

You don't download those lessons. You earn them, and if you're over 50, you've earned quite a collection.

We Aren’t Starting From Scratch

This is the part I wish more people our age understood. When you decide to start something new at 55, 62, 68, or 74, you aren't beginning at zero. You arrive carrying decades with you, even when the thing you're attempting feels completely unfamiliar.

Start a business at 60 and you're bringing every boss you've ever worked for, every customer you've dealt with, every difficult personality you've survived, every mistake you've watched someone make, and every lesson you've picked up along the way. Start traveling at 65 and you bring something a 22-year-old backpacker hasn't had time to develop yet. You know yourself better. You know which discomforts are worth tolerating, which ones aren't, and which supposedly must-see attractions you're perfectly happy skipping because you'd rather spend three hours drinking coffee in a neighborhood you've never visited before.

The same thing applies when you start dating again, making art, writing, teaching, volunteering, learning a language, moving somewhere new, or finally trying the thing you've been talking yourself out of for 30 years. You might be a beginner at the activity, but you're not a beginner at life. There's an enormous difference between the two.

Maybe Experience Is Becoming Cool Again

I don't think youth is losing its value, nor would I want it to. Young people bring energy, new ideas, different assumptions, and a willingness to question things the rest of us stopped noticing years ago. We need that. But they need something from us too, and perhaps we're moving toward a healthier arrangement where one generation doesn't have to become invisible for another one to matter.

That interests me far more than looking younger. I don't want to be mistaken for 42. I want 62 to look like a hell of an interesting age to be, and I want the same thing when I'm 72 and 82. If I'm lucky enough to get there, I intend to give 92 a respectable attempt too.

This Is What Dorothy Is About

The Dorothy Society was never supposed to be a place where older people sit around talking about getting older. Quite the opposite. I'm far more interested in talking about what we're doing with all this experience we've accumulated and where we're going next.

I want to know where you're going, what you're learning, who you're becoming, and what opinion you've changed after believing it for 30 years. I want to know what you've finally stopped caring about and what you've suddenly started caring about again. Most of all, I'm interested in the parts of ourselves we put away years ago because work, family, money, fear, responsibility, or somebody else's expectations got in the way.

Perhaps one of the great gifts of getting older isn't wisdom at all. Perhaps it's permission. At some point, you realize there are fewer people left whose approval you need, and you begin asking a different question. Instead of wondering what everyone else will think about the life you want, you start wondering why you're still allowing everyone else to have a vote.

The world around us is changing at an astonishing speed. AI will change how we work, technology will change how we communicate, and younger generations will change culture in ways we don't fully understand yet. None of that requires us to move aside. There's still a seat at the table for people who have been around long enough to remember several previous versions of the table.

We don't need to pretend we're 30 to deserve that seat. We don't need to master every new platform, collect millions of followers, dress younger, talk younger, or desperately prove we're keeping up. We need to show up with what we've spent decades accumulating: curiosity, experience, stories, judgment, humor, perspective, a few scars, and enough humility to admit we're still learning.

For years, aging has been presented as a gradual process of becoming less important, less interesting, and less necessary. I think we're beginning to see how ridiculous that idea was. In a culture overflowing with information, perhaps people who have spent decades learning what to do with information are becoming more valuable, not less.

Maybe this isn't the period when we fade quietly into the background. Maybe the world is finally catching up with something we should have known all along.

Maybe we're entering our era.

And Dorothy, I have plans.