Pearson - The End of Jobs: Money, Meaning and Freedom Without the 9-To-5

Its only when the tide goes out that you learn whos been swimming naked.

Warren Buffett

Hello sir, you want special massage? A pretty Thai girl smiled as she framed the spa menu between slender arms.

A hundred feet ahead, wearing Croc flip flops, cargo shorts, a San Miguel tank top, Dan Andrews didnt look like a typical multinational company CEO. Then again, no one at the Dubliner bar table fit the bill. I had just started working with Dan to manage the online marketing for a portfolio of eCommerce stores he owned with his business partner, Ian.

Next to him was Travis Jamison. 6 4, a former bodybuilder in a white v-neck and fitted jeans with brown leather oxfords, Travis ran two multinational businessesone manufacturing supplements, and the other selling online marketing services.

The trio was completed by an American woman. Curly haired with a bright Balinese skirt, whiskey in hand, head cocked back in a laugh, Elisa Doucette ran a content editing business for writers and authors.

They all turned to me as I approached the table. Welcome to Asia, Dan nodded.

Thanks, I replied gratefully.

The waitress walked up to the table, You want drink?

Whiskey.

As she turned to leave, Dan informed me: We were just talking about the conference this weekend. Weve sold out. There are going to be seventy-five entrepreneurs coming.

The way he said it, you would have thought he was announcing U.S. gold medalists. A whole seventy-five people at a business conference.

It was by far the smallest business conference Id ever heard of.

As the night wore on, more conference attendees trickled into the Irish pub.

There was Jimmy who, with his partner Doug, was working to start a company selling travel gear. The pair of Kiwis had met at an exchange program in Canada and, over a North American road trip, agreed to alternate short-term stints at jobs and living off of savings, working to launch their company. At the time Doug was still at his job in New Zealand and Jimmy was fresh off the plane from the Philippines where he had been working on sourcing moisture wicking, wrinkle-resistant dress shirts.

Jesse Lawler, who had spent his twenties living in Los Angeles directing independent films, had given up trying to raise money for movies, taught himself to code, and started doing freelance software development building iPhone Apps a year earlier.

Dan Norris had a years worth of savings from selling his web design company, and was in the process of building a software startup, Informly, designed as an all-in-one dashboard for online businesses.

What was going on? Id read popular books like The 4-Hour Workweek about entrepreneurship. I even had some friends freelancing or running small companies. But I didnt quite get it.

Two years later, in 2014, the small conference had grown by 400%, from seventy-five to three hundred entrepreneurs.

I had been managing a couple of Dan and Ians businesses. I had grown the eCommerce business, which sold fold up, portable bars to caterers and hotels, by 527% over the same two-year period that wages for jobs in the U.S. were growing 0.5% per year.

Jimmy was back, and Doug had quit his job in New Zealand. The travel shirt idea had been put on holdgetting shirts custom tailored in the Philippines is easier said than done. Instead, they had raised $341,393 through a Kickstarter campaign for their Minaal travel backpack at the end of 2013 in just thirty days, so theyd shifted focus to the faster growing product line.

Jesse Lawler was back. His freelance software development had grown from a one-man show into a software development agency for iPhone Apps, run from his house in Vietnam. In between drinking coconuts, he was funneling the profits from his agency into building his own product suite and hosting a podcast about smart drugs used for cognitive enhancement.

Dan Norris was back. He had spent nine months and nearly his entire savings trying to build Informly. Two weeks before he needed to get a job to support his family in Australia, he had launched WP Curve, an outsourced service for software development, on pace to do over a million dollars in revenue in 2015.

Its hard to square these two-year stories with the stories of my friends from college over the same period.

Back in Columbus, Max had graduated with me and was working at one of the bigger accounting firms in town. He was anxious in the wake of his two-year performance review. Hed placed third out of five in his department despite working fifty- and sixty-hour weeks in the months leading up to tax time in April. He felt grateful for the 3% cost of living raise hed gotten each year. His girlfriends parents were proud. He was putting in his time.

Julian had gotten into one of the nations top law schools. Hed done well and, as a result, had already gotten a position with a top San Francisco law firm. Like most people starting a career in law, he was planning to spend the next three to five years working long hours, sometimes eighty- to one-hundred-hour weeks at the firm, to build a reputation and pay off his student loans. He eventually wanted to start a family and hoped to move to a smaller, more affordable city where he could take a position with better work-life balance.

Marie had gotten into medical school straight out of college and was in the process of choosing her specialty. Shed always wanted to be a family practitioner, but Medicare and insurance reimbursements for primary care doctors like family medicine and internists had dropped so low, she feared there was no way she could pay back the loans and make a decent living. Instead, shed opted for Anesthesiology, fingers-crossed that reimbursements wouldnt continue to fall for specialist physicians.

What was going on? Whats the difference between my friends from college and the three hundred entrepreneurs now emigrating to Bangkok in flip flops?

From the outside looking in, both groups were intelligent and hard working. Why was one group living in fear of the threat of job loss, unreasonably long hours, and shrinking wages, while another was so overwhelmed by new opportunities they dont know what to do?