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Why I Wrote a Book About How to Manage Your Career


I had less gray hair then, but worse haircuts.

Nineteen years ago this week, I went to work for The Washington Post as a fresh-faced intern, as my old work ID above shows. At the end of that summer, I was hired onto the staff in my first real job.


My job was to be a financial reporter, but, in a very real sense, I occupied one spot on a long assembly line. As a young financial writer, I would write an article and hand it off to an editor, where it would be passed in turn to a copy editor, a page designer, the prepress department, then to the massive plants where the newspaper was physically printed, to a series of trucks and delivery drivers who ensured that each morning, a million or so readers of the Post received a newspaper on their doorstep. My article about some obscure company’s earnings woes was typically buried on page E5.


Appropriately enough, I was, in the government's official classification system at that time, a manufacturing worker, because the company I worked for “manufactured” newspapers.


Careers in those days were as linear as the assembly line by which we produced the newspaper.

Many of my colleagues had worked doing the same job, the same way, for years, or even decades.


People who were ambitious knew exactly how to channel that ambition—it was clear what constituted advancement and what boxes to check to get there.


And even if you weren't able to snag a job at The Washington Post, or my current employer, The New York Times, dozens of newspapers in other big cities offered career opportunities and compensation that were nearly as good. The technology of print newspapers created local monopolies that allowed at least one big paper in each city of any size to be highly profitable and offer many good jobs. In career terms, there just wasn’t that big a gap between, say, The Philadelphia Inquirer or The Baltimore Sun and the Times or the Post.


What I didn’t know at the time was that the economics of our industry were about to change, with radical implications for people trying to make a career in it. If you visit the Post or theTimes today, you will find not a single giant assembly line in which reporters feed articles into the newspaper, but rather teams of people with myriad skills creating not just newspapers but a range of products—addictive podcasts, apps optimized for mobile devices, and immersive virtual reality experiences, to name a few.


Indeed, the best work is often done by teams of people with dramatically different skills—a team might include software engineers, graphic artists, data scientists, and video editors, along with more traditional writers like me. That means it’s no longer so obvious what a person should do to ensure they will remain employed, let alone get ahead.


The gap between the top handful of publications and the next tier has widened, both in terms of the number of jobs available and what they pay. In digital media, the handful of organizations with the best products and technology reach readers around the planet, while the old local print monopolies are under severe strain.


And long gone is the old pattern in which people who got hired at a leading media outlet could expect to remain there for decades doing mostly the same job. Those who do stay with an employer for a long time tend to do so by adjusting to the changing strategies, technologies, and ways of working; those who fail to adjust are likely to find themselves laid off.


The more I’ve spoken to people in other industries—friends, sources, business school classmates—the more I’ve been struck by the ways that people who seek a well-paying professional-track career in nearly every sector are grappling with the same challenges: Reinvention of business models due to digital technology; the rise of a handful of successful “superstar” firms; and rapidly changing understandings around loyalty and the level of mutual commitment to an employer-employee relationship.


Even as this epochal change takes place, a lot of our logic and advice about a career that made perfect sense in the twentieth century economy—pick a field, get a job, spend decades getting better and more senior at that job before you retire—just doesn’t really apply.


To thrive, people need to have a much deeper understanding of the economic forces that shape their industry—the kinds of things that at one time only senior executives had to worry about. They need to understand how to work together with people with different types of technical skills, to make great products. Rather than just get better and better and one thing, they need to cultivate adaptability—the capacity to keep acquiring new skills and ways of working as technological and economic forces change.


So I set out to write a book looking at how people can do exactly that. I read lots of work by academics, consultants, and other researchers. But most importantly, I approached many of the big, technologically advanced companies that dominate the modern economy, asking them two questions:


1)What does an ambitious person need to do to have a successful career at your company in the modern age?


2) Can I meet some of the people there who have exemplified that success?


My reporting took me to some of the best-known companies on earth, including Microsoft, Goldman Sachs, General Electric, and Walmart. I also visited smaller enterprises that offered particularly important lessons, learning from the people who make Planet of the Apes movies, Shake Shack cheeseburgers, driverless Volvo cars, and Jim Beam bourbon.


The people I met and the lessons I learned form the core of How to Win in a Winner-Take All World, coming in two weeks from St. Martin’s Press. You can pre-order it now from Amazon, Barnes & Noble, or your favorite independent bookstore.


This project was personal for me. It forced me to grapple with what it means to have a rewarding career, and the successes and failures I’ve had these last 19 years. I hope it helps a lot of other people have more of the former than the latter.

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