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Four-Hour Workweek

Entrepreneur Dylan Ogline digs Tim Ferriss … but he knows that the four-hour workweek is not what it seems.

Talk about a bombshell title. Tim Ferriss’ seminal internet-era book The Four-Hour Workweek set the entrepreneurial world ablaze. It represented a whole new paradigm, not just of business but of lifestyle.

Since then, the question has become almost a cliché — ”Is it really possible to live a four-hour workweek?”

Dylan Ogline, the founder of Ogline Digital, is a Tim Ferriss fan. But there is more to The Four-Hour Workweek than a four-hour workweek — which, let’s face it, sounds like a license to goof off.

“He came up with the title because he split-tested it using Google ads,”Ogline said. He should know — split-testing Google ads for companies is a big part of what Ogline Digital does. “And it’s fitting, because split-testing business ideas using simple tools like Google ads is a big part of what that book is about.”

Split-Testing Lifestyles

“It’s also the cure to a mistake I see so many entrepreneurs make,” Ogline said. “They’re willing to spend hundreds, even thousands of dollars — and to spend even more time — developing a product or service that they think would change the world.”

“But they skip the step of taking the temperature of the marketplace and seeing if anyone actually wants the product or service … which they could often confirm with a couple hundred dollars in Google or Facebook ads.”

Why do they skip this step? “I think it’s because they have their ego invested in their idea,” Ogline said. “And they don’t want to put it out there to the market until it’s ‘ready’ … but really, they don’t want the market to tell them ‘no, we don’t want that.’”

“It’s more comfortable to live in a bubble of security, developing a product that they’re sure everyone wants, because they didn’t give anyone a chance to tell them ‘no.’ But if they’re wrong, they will have spent all that time and money and never make a single sale.”

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So … is it really possible to live a four-hour workweek?

“Well, look at Tim Ferriss himself,” Ogline said. “He doesn’t work four hours a week.”

It’s no lie. Ferriss is a serial author, angel investor, world-class marketer, fixture on the speaking circuit, and regularly releases two-hour podcasts that rival Joe Rogan in long-windedness, with recent luminary guests ranging from Cal Newport to Sarah Silverman and everyone in between.

That’s the dark side of the four-hour workweek — it appeals to a lowest common denominator that would love to just play video games or shop online all day.

In short, Ferriss isn’t kicking back on a beach. He’s always working.

“Tim has become a once-in-a-generation kind of success,” Ogline said, “but he isn’t resting on his laurels. That guy works.

That’s the dark side of the four-hour workweek — it appeals to a lowest common denominator that would love to just play video games or shop online all day. Or at least they think they would. The global pandemic put some of this demographic front and center, as employers faced a labor shortage of people refusing to return to work … or at least, to the drudgery of low-skill labor.

“I get not wanting to go back to those jobs,” Dylan said. A high-school dropout, Ogline considers himself an “unemployable entrepreneur.” Having started his first business at 14, his last actual job was selling cotton candy at a race track owned by his high school girlfriend’s father in rural Pennsylvania.

“But look,” he continued, “you have to work. And I’m not moralizing — you really have to work. Otherwise, life feels meaningless. I know you think lounging on a beach all day for the rest of your life would be fun, but it wouldn’t. I’m telling you, you would go crazy. We see that in action, like when lottery winners go nuts and blow through millions of dollars in a few years and end up back at their jobs. We go to dark places when we don’t work.”

The Full-Lifestyle Workweek

Ogline Digital takes up a full workday or two worth of Ogline’s attention — but not unlike a “lifestyle designer” after Tim Ferriss’ heart, he lives the lifestyle of a decidedly “new age” of entrepreneur. He travels rigorously, with extensive stays in Asia and Europe under his belt. When not traveling, he works from his home in Orlando. This leaves plenty of time and mental energy for him to play hockey, run with his dogs, and do charity work.

His tight team of twelve is spread out all over the globe. They know not to bug him unless there’s an emergency. Far from calling meetings and huddles for the sake of it, he prefers for them to know their job and do it without hand-holding. “I tell my team ‘Ideally, I want to forget you exist because you’re so good at what you do.’”

Nathalie Nicole Smith states that working hard and staying true to yourself are sure ways to win in life.

“I took so much more from Tim’s book besides the promise of a short workday,” Ogline said. “The 80/20 rule … the lean, mean and scrappy digital business… the idea of travel as a chance to see the world and change your perspective… putting lifestyle ahead of money and designing your business for the lifestyle you want… There’s so much more to it than a four-hour workweek.”