Dylan Ogline is part of a generation leading the way on a new approach to American prosperity.
Dylan Ogline owns his own home in Orlando, but he expects to see less and less of it in the near future.
He spent several months bouncing around between Southeast Asia and Europe before the pandemic, and when border restrictions eased up he was on one of the first flights to Iceland. He envisions a lifestyle where he’s traveling for a month or more, at least three times a year.
“I’m a big fan of Rolf Potts [author of Vagabonding] and Tim Ferriss [author of The Four Hour Workweek],” Dylan said. “I especially love how Tim describes the process of experiencing a new country ‘at a pace that lets it change you.’ Not as a whirlwind five-day tour that’s more stressful than it is fun and enlightening.”
It’s not just his own home that the founder of seven-figure marketing agency Ogline Digital expects to see less of, either. He expects to see less and less homeownership in general … at least, among the Millennials, the Zoomers, and their successors.
The New Coin of the Realm
You can just hear the Boomer moms wringing their hands … the Greatest Generation grandpas rolling in their graves. Not own your own home?! What kind of loser doesn’t own their own home?
But Dylan doesn’t see this from the lens of the gloom-and-doomers, who chalk it up to younger generations being poorer than their parents for the first time ever. He sees it as a fundamental shift of values, and a sign of a new kind of prosperity.
“If they want to own real estate, they’ll buy a rental property,” Dylan said. “Or maybe they’ll buy bitcoin instead.”
“But the new coin of the realm isn’t going to be real estate, or gold, or even bitcoin,” he continued. “The new coin of the realm is freedom.”
“They’re not going to be tied down by a five-bedroom house for a family of three — way more space than they need, with a mortgage they can barely afford, and always the temptation to punish their credit card to put in a new outdoor deck when the current outdoor deck is just fine.”
“I mentored an 18-year-old kid working at Dunkin Donuts not long ago,” he said. “He wanted to learn how to become a successful entrepreneur and make more money, and he didn’t ask me how he could one day afford a McMansion in the suburbs with endless bills. He asked me how he could travel like I do.”
Dylan even remembers, word-for-word, what this Zoomer-aged aspirant asked him after hearing stories of Asia and the like — “Is traveling the world and being completely free as good as it sounds?”
What did Dylan tell him? “It’s better than you can even imagine,” he said, smiling.
A Dream of the Past
What even is the “American Dream?”
We all want a good life, but the phrase “American Dream” brings to mind some very specific benchmarks, with many politicians still tubthump about.
Here are the basics:
- Get a good job with benefits.
- Buy a house in the suburbs.
- Send your kids to college.
- Retire in comfort.
- Leave a legacy.
To Dylan, most of these bullet points seem out of date. “It’s becoming clearer and clearer that jobs are a trap,” he said. “Benefits are hard to come by, pensions are a distant memory, and ‘job security’ is a laughable concept. If your company could automate your job or outsource it to the Philippines, they would do it in a heartbeat.”
“The veneer of ‘company culture’ and ‘we’re all a family’ is wearing incredibly thin,” he said. “And people, God bless them, they’re repaying loyalty with loyalty — people are quicker to change jobs than ever.”
The house we already talked about. Sending your kids to college? Dylan, a high school dropout, points to declining college matriculation rates and the looming college debt crisis. “College is looking even more and more like a trap,” he said, “especially when you can learn valuable skills for free.”
“More and more major employers are no longer requiring degrees, because they know it’s a useless metric for evaluating employees. And that’s great, and it can’t happen soon enough.”
People still want to retire in comfort and leave a legacy, but they don’t want to wait until they are 65 to see Paris or Angkor Wat. And thanks to remote work, they don’t have to.
A Dream Reborn
If the old “American Dream” is a dinosaur, what will take its place? What’s the new dream?
Dylan points out that there is actually a much older version of the ‘American Dream’ that predates the industrialized workforce, and which may ring more true now than ever.
The term “American Dream” was actually coined by James Truslow Adams in his 1913 book Epic of America. He described it as “that dream of a land in which life should be better and richer and fuller for everyone, with opportunity for each according to ability or achievement.”
He was contrasting America with a European social order of rigid class hierarchies, no social or economic mobility. And thanks to the internet, we may be coming back to it.
“The gig economy, the hustle economy, the age of internet entrepreneurship,” Dylan said, “it’s making six-figure business owners out of cubicle dwellers, millionaires out of wage slaves from blue-collar families.”
“And it’s not slowing down,” he said, “it’s only gaining momentum as people use their ingenuity and problem-solving abilities to add more and more freedom to their life, not less.”
“I can’t think of anything more American than that.”
