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Leaving the corporate world for the Silicon Valley startup game can be akin to walking into a Kafkaesque universe, where nothing is what is seems and the uninitiated must proceed with caution.Chris Majors/Getty Images/iStockphoto

Want to leave your corporate job for the excitement of a Silicon Valley startup?

The notion may appeal to veterans of middle management who have tired of 360-degree performance appraisals and navigating complex, hierarchical structures. However, for the uninitiated, leaving the corporate world for startup-land can be akin to walking into a Kafkaesque universe, where nothing is what is seems and the uninitiated must proceed with caution.

Dan Lyons, a former technology editor at Newsweek, chronicles the lessons he learned after making such a leap in his new book, Disrupted: My Misadventure in the Start-up Bubble. Mr. Lyons' tale starts in 2012, with the familiar scenario of being laid off. After reporting on Silicon Valley for years, he decided to accept a job as a blogger at HubSpot, a company in Cambridge, Mass., that develops software programs for inbound-marketing campaigns.

However, from day one, Mr. Lyons, then 52, couldn't shake the feeling he had made a terrible mistake. He arrived at his new job with no one expecting him and no clear job description. His boss turned out to be someone just five years out of college, whose only experience was an entry-level job at Google and a couple of internships. The average age of the employees was just 26.

These were the first of many clues that he was the odd man out, but realizing that he had just come from a dying industry, he tried his best to fit in, even if it meant embracing made-up words such as "delightion" – used to describe the state of delighting customers – and attending meetings where the company's founder found it reasonable to bring a teddy bear.

Mr. Lyons found himself in a place that, like many other startup companies, doesn't sell a service but promises to change the world, creating a universe so magical that one plus one equals three. In other words, "It's what a bunch of kids in their 20s thought was cool," Mr. Lyons said in an interview.

Believing that your company is not merely about making money, but that there is meaning and purpose to what you do is a prerequisite for working in a Silicon Valley-style startup, Mr. Lyons explained.

"Drinking the Kool-Aid is a phrase everyone in Silicon Valley uses to describe the process by which ordinary people get sucked into an organization and converted into true believers. … How that differs from joining what might otherwise be called a cult is not entirely clear," he wrote in his book.

While the book provides some fascinating, anthropological insights into this new workplace, it also serves as a cautionary tale for experienced employees who are considering making the leap.

For starters, previous industry expertise remains frowned upon. Instead, companies such as HubSpot, Mr. Lyons said, look for employees who are a "blank slate."

"You don't ever want to say around there, 'Well at my old company, we would do this.' No one wants to hear this. Nothing you learned at your old place can help you here. Experience is almost seen as an impediment or as baggage," Mr. Lyons said.

This leads to other problems that he sees as endemic to the startup world, including promoting managers who have no training and an extreme preoccupation with "cultural fit."

"There is this weird fetishization of culture and cultural fit, like the most important thing is working with someone you want to have a beer with. In my generation, if you made a friend at work, that's nice. You weren't going to work to find friends, nor would you expect to find people at work you'd want to hang out with. [To startup employees], work is their social life," he said.

Another startup quirk Mr. Lyons encountered is the notion that every idea is a good idea. He recounted one woman's suggestion to create an automatic blog idea generator, like Mad Libs, that would spit out headlines for customers to write about. On the day it launched, one client complained that when she prompted the system for blog suggestions about cervical cancer, the generator returned with "Five things Miley Cyrus and cervical cancer have in common." The idea was killed, but its originator received a promotion.

Mr. Lyons admits to making some mistakes, and learned that his own personal reinvention could only go so far. (He's gone back to freelance writing.) He observed that many of his contemporaries have made the leap more successfully, but often by transitioning to companies that have a more traditional or hierarchical structure, such as GE or IBM.

So what advice does he have for others in his situation – who find themselves out of work, in a vastly disrupted industry and looking for a lottery-ticket win in a startup that may one day go public?

If you can bite your tongue and deal with the lunacy, you might be okay, he says. But buying into the company's new vision is the best way to survive.

"You can't work there if you stay skeptical. You have to drink the Kool-Aid," he said.

Leah Eichler is founder and CEO of r/ally, a machine-learning, human capital search engine for enterprises. Twitter: @LeahEichler

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