I’ve talked to hundreds of people about their careers and aspirations over the past few years. The common theme: people are hungry. They want more interesting work, more ambitious environments, better leaders, and more chances to step up. These people are littered all over the world: India, Kenya, Malaysia, Pakistan, and Poland to name a few. The desire to challenge one’s self has no borders.

We have the most educated collection of people on this planet and the best we can tell these people, especially young ones, is that they should channel this ambition into legible paths that result in them being able to add fancy letters to their story like MA, VP, Ph.D., and CEO.

All of this made sense at one point. The industrial economy was incredible. It helped billions move into a middle-class existence while being part of building the future. My father got his start building aircraft engines and spent an entire career being part of a company that grew from $300M in revenue to $75 billion in revenue over 40 years. Imagine being part of something like that! Many people have parents who were to benefit from being part of similar companies.

When I was interning at that same company as an intern in the last 2000s, the excitement was gone. Jobs had been outsourced, people had been laid off over and over, and people were telling me I should try to work elsewhere. I worked with another intern that used to nap under his cubicle every day for two hours. No one even came to our corner of the office and no one noticed. There wasn’t enough work to keep us busy anyway.

I graduated and went to work for GE and found similar sentiment. Senior people seemed happy enough to collect a paycheck but pined for the GE of the past, often saying it was “not what it used to be.” People told me the best strategy was to work hard for a few years, find a cozy job, and coast. I wanted more.

The Industrial Long Boom

Throughout the 20th Century, there were tons of these kinds of companies. Westinghouse, GE, United Technologies, AT&T, Sony, Samsung, Siemens, Toyota, Chrysler, Caterpillar, Xerox, and so on. At one point if you told people you worked at these companies, people would know your life was set. Work at them now and you likely have to put up with an older workforce that is well-compensated but cynical. They forget how fast they were able to raise the ranks and spend their time trying to convince young people that they shouldn’t feel so entitled. “Hard work!” they say. Put the payoff isn’t a pension anymore. It’s a guarantee that you’ll have the same detached stance toward life and work too.

Young people want more.

And in some parts of the economy, they at least find the appearance of it at first. The kinds of companies growing at similar rates to those industrial companies in the mid-20th century are tech companies like Google and Facebook. Except after the glow of landing at one of these companies wears off, the nature of work is different. They aren’t building aircraft engines or rocket ships, they are shipping product design updates for an ad product that sort of generates money on its own.

Most people today work at a computer and create documents or edit other people’s documents. There are a small number of coders that help tweak the algorithms and build new services, but most of the employees work on moderation, project management, coordination, public relations, finance, communications, marketing, and legal work.

Adair Turner has called this “zero-sum” work:

Look around the economy, and it’s striking how much high-talent manpower is devoted to activities that cannot possibly increase human welfare, but entail competition for the available economic pie. Such activities have become ubiquitous: legal services, policing, and prisons; cybercrime and the army of experts defending organizations against it; financial regulators trying to stop mis-selling and the growing ranks of compliance officers employed in response; the huge resources devoted to US election campaigns; real-estate services that facilitate the exchange of already-existing assets; and much financial trading.

There’s nothing wrong with this kind of work but it leaves an inspiration shaped hold in people’s hearts.

People want to get fired up, they want to be challenged, and they want to work on teams that push their limits. But after years of schooling and working in companies where this is so hard to find, people become convinced it doesn’t even exist. Or at least they come to this conclusion after several job changes, flailing about trying to find something that delivers inspiration.

And this is the saddest thing about today’s working world. So many educated people and so little damn inspiration. It breaks my heart to see how many people have convinced themselves that their current job is the best it’s ever going to be.

But deep down if they really were able to admit it, they’d say it: I want more.

“A young man of average ability has been propelled upward so early—and so pleasantly”

Our current workforce is unique in that there is a large mass of older workers who are also working at later ages in life. This has extended the career ladder and made climbing a ladder if it exists at all a much more drawn-out process.

After World War II, if you read about the environment with work, it seems that young people sort of saw leadership positions dropping out of the sky. In William Whyte’s 1956 book Organization Man, he detailed a young man of “average ability”:

Corporations have been expanding at a great rate, and the effect has been a large-scale deferral of dead ends and pigeonholes for thousands of organization men. With so many new departments, divisions, and plants being opened up, many a young man of average ability has been propelled upward so early—and so pleasantly—that he can hardly be blamed if he thinks the momentum is a constant.

The growth rates in this period, and especially in the US, were bananas. There’s a reason they call it the “great boom.” Opportunities were everywhere. Consider another account from a young person in the 1950s:

“We are a young group without mature leadership,” explains a rising young banker, “so we are forced to take on responsibilities that older people usually assume. For the last two years I have been chairman of the board of the church, a job held by a fifty-five or sixty-year-old man in most communities. This gives me a training valuable in business. The church is a corporation with a $50,000 budget, and we’ve had to think about a $100,000 capital loan. How else could people our age get a chance to deal with that much capital? We’re forced ahead of our time.

This simply doesn’t happen to young people. So we pretend like young people are just lazy or entitled. The media invents fake stories saying people are losing their ambition, slacking off at work, resigning en masse, and more.

No! This is all missing it. There is a crisis of inspiration and opportunity!

Optimism Premium

In traveling around the world, I’ve met countless digital nomads, freelancers, and other people who take advantage of geo-arbitrage and are able to work less to meet their needs while living in other countries.

I’ve done this too and many people think these people are lazy and just don’t want to work “normal” jobs. I think people are missing it. Most of these people are highly engaged with the work they manage to create for themselves and if given the opportunity, would move back to their home countries to work in jobs – that is if the jobs were inspiring and challenged them. They don’t have an easy time finding them so they’ve opted out. And are literally trying to create challenging work out of thin air.

I’ve hung out with these people across the world. Digital nomads, crypto people, under-employed freelancers, solopreneurs, YouTubers, vagabonds, and investors. These are some of the most optimistic, energized people I know and are just like the people I talk to all around the world.

They are on their paths because of self-preservation. I was happy to trade a large chunk of my income to lower the odds that I would drift into cynicism in my mid-40s. So are many others.

But there is room for optimism! All of these people have a sense that things are changing and better options will emerge eventually.

I think we are starting to see the beginning of better options in the digital creator world, online communities, online learning, and within tech more broadly. Optimism is trading at an incredible premium and any company, country, city, or individual that can communicate a persuasive version of it will reap the rewards. Elon Musk get dunked on a lot but he understands this. You don’t have to care about his vision for putting people on Mars but at least it’s bold and inspiring.


Just published! The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here


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