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What It’s Like to Work for the Same Company for More Than 25 Years

In the era of the job-hopper, it seems like more of a pipe dream than a reality, but these guys really did report to the same office for decades

After 30 years of working the arts and culture beat at Newsweek, Ray Sawhill was let go. The magazine had “somehow survived the advent of 24/7 cable news, but the internet was proving harder to compete with,” Sawhill explains. So in 2008, he found himself among the older employees being offered a buyout package.

“Yahoo to that!” the 65-year-old tells me. “I accepted their offer and was able to retire with a small pension and some sweetened benefits at the age of 54. I’ve been a happy, lazy bum ever since. These days I seldom think of the place.”

If the data behind the “job-hopping generation” is to be believed, for many millennials — especially those of us in the media — working at the same company for 30 years is both a pipe dream and a nightmare. Job security is great and all, but many millennials see hopping from company to company as the only way to advance their career.

Which, of course, baffles those from older generations, Sawhill included. “Funny how unusual working for just one or two companies over a lifetime has become, isn’t it?” he says. “It used to be a semi-normal thing. My WWII-era dad bounced between jobs at the beginning of his civilian work life for about five years, then worked for the same company for 25 years until he retired.”

But such steady employment feels more and more like a relic these days, and seemingly impossible in this economy. The same co-workers, same coffee, same commute… for your entire life? Is all that stability and sameness mind-numbing, or does it let people do their best work without fear of being rendered obsolete by a sudden pivot?

I sought out three guys who went to the same office every day to find out.

Ray Sawhill, 30 years at Newsweek

I didn’t set out to have a career. I was a bright kid coming out of grad school in the late 1970s and I knew I needed to support myself somehow, but I also preferred to have a less-boring rather than a more-boring job. A lot of my friends were moving to New York City, and a friend of a friend set me up with an interview for a lowly job answering reader mail at Newsweek. Somewhat to my surprise, I was hired.

Thanks to my Newsweek paycheck I was able to move to Manhattan, where I could get on with my real interests — movies, books, punk rock, drugs and girls. Let’s just say I wasn’t at Newsweek in order to try to have a career as a magazine star. It’s hard for younger people to believe, I suppose, but before the 1980s, not everyone thought of work in terms of “having a career.” Employment-wise, what I was looking for was a bearable job.

All that throat-clearing out of the way, after a year or two of answering reader mail, I spent a few years working as a researcher. Back in those days, Newsweek was great at bringing people along, giving them chances and training them. So I learned the basics of interviewing, reporting, fact-checking and popular-magazine writing. Eventually, I wound up as an arts reporter, mostly covering the book-publishing world but also pitching in regularly to stories about movies, art, dance, etc.

It was a pretty darned sweet and interesting gig — especially given that I’d just kind of stumbled into it. I lunched regularly at ritzy restaurants with people in publishing. I had a wonderful expense account. I attended book conventions, movie screenings, art parties and Broadway openings. And I interviewed and met hundreds of prominent creative people.

Not to mention, the job itself was pretty informal. Most days I could wear jeans. I could duck out for an hour to meet up with a friend who was passing through town. I could take two hours at lunchtime to hit the gym. So while I was putting in more than 40 hours a week, it was a flexible and fun 40 to 50 hours a week.

That’s not to say there wasn’t the usual office-life tedium to contend with: boring meetings, dull stories, late nights waiting around for pieces to be edited. Plus, such a job or career does tend to want to engulf your life, which is something to manage. But given that I had to work for a living, and given that I wanted to sustain a middle-class level of life (i.e., given that I needed to work full-time), I was always aware that I could have done a lot worse.

I did shop myself around more than a few times. Every few years I’d feel tired of my work life, I’d build up a little ambition and I’d head out to have lunch with other editors. I came out of these meet-ups with a lot of individual assignments and freelance work but no one ever wanted to take me on full-time. It probably helped, too, that I was friendly with a lot of pro book, art and movie reviewers, and I didn’t necessarily love what I saw of their lives. They got fired a lot, and they moved from publication to publication a lot. As someone who really liked the way I got more and more vacation the longer I stuck around Newsweek, I didn’t like the sound of that at all.

The sweetness, however, came to an end in the early 2000s when Newsweek appointed a new arts editor. She and I clashed so hard that I moved out of editorial entirely, sideways into a managerial position. By that point, I’d had a cancer crisis and seen it all in the culture world. I realized that if I could just hold on for five or 10 more years, I’d be able to retire, which sounded great to me. So, for the next six years, I walked around the office with a clipboard as an assistant managing editor, making sure that about a quarter of the magazine was functioning smoothly.

One of the reflections my experience has left me with concerns the difference between a job and a career. In retrospect, I realize that a big part of my frustration — and something I spent all too much energy on — was the fact that for nearly 20 years I was trying to treat a position that should have been a “career” as “just a job.”

I’m sure there were thousands of people who’d have loved to have my position as an “arts reporter.” Meanwhile, I was mainly concerned with trying to minimize the time and energy I put into it. When I shifted over to being a guy with a clipboard, I found myself being much happier and calmer. It was pointless, it was dopey and there was nothing glam about it, but when I went home at the end of the night, I could forget about it. Being an arts reporter for a major magazine was really something that wanted to be a life, not a mere job. I’d always resented that and fought back against it.

Oh well, sometimes it takes us a lot of time to learn what’s really up.

Arthur, 25 years in healthcare IT

I had no plans to work at this company for so long. I needed to get out of an untenable situation at my prior employer, and this was the first offer I got. It was just a place to seek refuge from the storm while I decided what to do next with my life.

Suddenly, it was 20 years later. With continual moves, company acquisitions and the uncertainty of the economy from 2001 through 2011, it’s never felt like I just had the same routine for 20 years. In fact, I never really thought about moving on until I hit 50, when I started thinking I might just ride this out until retirement.

I have co-workers I’ve known for decades. I’ve seen people just out of college get married, divorced, remarried and divorced again. I’ve seen them have kids and then their kids have kids. I’ve also seen a slow erosion of company benefits — pension benefits reduced and then eliminated; 401(k)s emerging as their replacement; health-care costs skyrocketing; and sick time eliminated.

I’m naturally risk-averse and had been with this employer only a few years when 9/11 happened. Over the next decade, the economy was terrible. I saw friends and co-workers lose jobs and barely held onto my own when 75 percent of my area got laid off. I saw people lose pensions and 401(k)s when their employers went under entirely, so I developed a “remain employed” mentality.

Still, I’ve declined a couple of unsolicited promotions over the years — I know from experience that I don’t want to be a manager. Instead, I’ve managed to find a niche where I wasn’t having to work long hours doing soul-crushingly boring work for people who were unpleasant.

Admittedly, though, salary-wise, I’m not a super-high earner. From stuff I found online, I’m a little bit below the average for college-educated people of my age. While I could probably make more money if I job-hopped, at this point, I make enough money to have all the stuff I need and much of the stuff I want. The biggest impact on my financial situation will be how my retirement money grows over the next several years. I laid the groundwork for that 25 years ago, and I’m mostly now just along for the ride.

All that said, I still might have moved to another company several years ago had my employer not offered me the ability to work full-time from home. That was life-changing. I spend most of the day in my pajamas, usually with a cat or two curled up next to me. It’s a very nice way to work.

Ralph, 35 years in tech; retired in 2012

“Silicon Valley” was starting up when I graduated. You can probably “read between the lines” and determine where I worked, but I can’t mention the name of the company name because my retirement package required me to sign a non-disparagement agreement.

I started in the late 1970s. I can’t say I planned to stay in the job for my entire career, but I did plan on working for the company for as long as it made sense. My duties changed continually (including work on a design team that designed some of the first internet servers and some of the first networking products), which is part of the reason I stayed. I also came from a family where my grandfather and father worked for the same companies their entire career. It was the norm for me.

I did, from time to time, interview with other companies just to see what was out there. I never left because the companies I interviewed with didn’t offer anything better than what I had. In fact, company turnover was minimal because, back in the day, they treated employees very well. We had a reputation in Silicon Valley for being one of the best, if not the best, companies to work for. If I had my name tag on and was in a grocery store, people would come up to me and say I was lucky to work for the place and that they heard it was a great place to be.

The people I worked with were like an extended family. We had BBQs, pool parties and “off-sites” at a lake. My manager would even take us out to lunch at a pizza place, where we’d have a beer-drinking contest. It was a great time, but we never got into any real trouble whooping it up — this was a long time before liability lawsuits.

Overall, we had great leadership in the 1970s through the 1990s. Our founders were great corporate citizens that financed universities, children’s hospitals and environmental causes.

Unfortunately, that all changed when they passed on. Soon, we had a revolving door of CEOs, and it didn’t take long for benefits like profit sharing, stock options, anniversary celebrations, stock awards, bonuses, pensions, severance benefits and retirement medical plans to be phased out as a result of “cost-cutting.” Good employees were laid off, and many left for better jobs. The culture of the company was divided and conquered. They managed to the quarterly report, often at the expense of the long-term viability of the company. It was the end of an era.

I was vacationing on Maui in 2012 and read the news: My company was going to lay off thousands. As part of the lay-off, they offered a severance package that was pretty good — namely, placing a large chunk of pre-tax money in a 401(k) account and giving us retirement medical. That was my golden parachute.

Like the saying goes, “All things must pass,” and they did. However, I was fortunate to have been there for the ride. And it was a great ride.