My Mid-Life Career Evolution

At 60, Ken Otterbourg takes stock of the subtle but meaningful career shift he embarked on a few years ago.

A. Martin UW Photography/Getty Images

I failed miserably the first time I tried to switch careers. This was twelve years ago, when I was 48. I had left my job as managing editor of a newspaper. No buyout. No severance. I just quit. I was burned out and angry at the decisions coming from our corporate office. I was tired of trying to sell downsizing as rightsizing.

I had a little money saved and manageable debt (two advantages that I realize not everyone has), but I also didn’t have a plan. (Big disadvantage.)  Instead, I had a belief that my skills running a newsroom would transfer to another industry. Plus, my dad had written a book about people switching careers, and it was filled with stories of happy, fulfilled folks who had traded a dreary job for one that was more fulfilling. I would just be one more stirring anecdote, maybe even a chapter in his sequel?

I failed miserably the first time I tried to switch careers.

My optimism didn’t last long. It was one disaster after another. I applied for jobs as a chief of staff at a university, as a program manager at a foundation, as a communications director at a big nonprofit. No, no, and no. Then there were the endless breakfast meetings and coffees, where people who had jobs loaded me up with advice and little else but caffeine jitters.

It was depressing. I had spent the prior 15 years managing people in a high-stress environment, and apparently nobody thought I was any good at this, or gave it any real value. So, I needed to find a different path. The opening came when an editor at a regional business magazine asked me to write a feature story for him. This was revelatory. I really hadn’t written anything other than memos for years, and I had a blast. It reminded me why I had gotten into journalism in the first place.

So, I kept writing, eventually building a clientele of regional and national publications. What I learned very quickly was that it was nearly impossible to make a decent living as a freelance journalist. I needed to find other work to supplement that income while still giving me the flexibility to pursue great stories. My salvation came in two forms. First, I hooked up with a company that helped nonprofits raise money. I wrote case statements for their clients' capital campaigns. And through a friend, I connected with an e-book publisher to edit and write nonfiction manuscripts.

My dad had written a book about people switching careers, and it was filled with stories of happy, fulfilled folks who had traded a dreary job for one that was more fulfilling.

I called this “the three-legged stool,” and it worked for a couple of years. Then, things changed. My wife’s cancer returned, and after she died, I began reevaluating work and what I wanted from it.

Freelancing now seemed like a grind. The pay was getting skinnier. Editors wanted shorter stories. The case statements, book editing, and other odds and ends sucked at my soul. The low point came when I was asked to write the copy for a video on how to install a shower door. This is not to suggest that any of this isn’t honest work. It is, and someone needs to write the copy for installation videos. But I didn't want it to be me.

So, at 56, I tried switching careers again. It was eight years later, and at times the process felt a bit surreal. Was I too old to make a change? Or more accurately, was I too old to make a change for the better.

I did things differently this time. I planned. I thought about what I wanted — and what I didn’t want. I realized I wanted colleagues and co-workers. I wanted to keep the best parts of being a freelance reporter. And I wanted to get off the sidelines. I wanted to make the world better. 

I had a different resume this time. I was no longer a manager, which was fine. But my eight years freelancing had taught me to hustle and to do every assignment as if my job depended on it. Because of course it did.

I’m not quite sure if I actually switched careers. Instead, I think I evolved careers. For me, that seemed realistic.

I wound up taking a job with the National Registry of Exonerations, researching and writing about wrongful convictions. It uses a lot of my journalism muscles, but my experience in the nonprofit world has also come in handy. I have co-workers, even if we are spread out across the country. And I feel like I’m making a difference in the efforts to improve our criminal-justice system.

I’m not quite sure if I actually switched careers. Instead, I think I evolved careers. For me, that seemed realistic. I didn’t go back to school. So, I didn’t add any new skills. I went in the other direction, after realizing not all my skills had the value I thought they had. It forced an honest conversation with myself, and I shelved those skills in favor of the skills that had more appeal to employers.   

This is the part where I'm supposed to say "Just go chase your dreams," and it will all work out. Nope. Nothing is that simple. Some switches never happen, or the switch we make isn’t all we thought it would be. The job market can be cruel. In addition, career switching can seem like a luxury, available only to people who can afford to ride out the uncertainty.

I just turned 60. For those of you who have already arrived at that age, you know it’s a time for heavy reflection about where we’ve been and where we’re going.

That's why I like the idea of career evolution. Perhaps it's not the bold transformation found in teachers who become lawyers or vice versa, but evolution works. It's how we lost our tails and stood upright. The purpose of these changes in humans wasn't necessarily for us to get dressed and go to work, but then again, here we are.

I just turned 60. For those of you who have already arrived at that age, you know it’s a time for heavy reflection about where we’ve been and where we’re going.  I have friends who are retired, and that’s fine for them. I’ll retire someday, too. But not yet. I like this third act too much.