After I wrote about transitioning out of newspapers, I emailed a few recovering reporters to ask for their take.
Nancy Ross-Flanigan, one of my favorite coworkers at University of Michigan, took the time to craft a thoughtful email on her leaving the Detroit Free Press to take up university PR part-time. She continues to have a thriving freelance business with the other half of her week.
Nancy wrote:

One of the things I loved about working at the Free Press was the feeling that we were all working together on a product that we were proud of, and that we were trying to do our very best work to make it the very best it could be. In my current work, both the freelance assignments and the PIO job, it’s different in some ways. With the freelance work, I still want to do my best, of course, but because I’m working for a variety of different publications/institutions/organizations, there’s not the same sense of ownership. The closest I came was when I had the contributing editorships for several years at Health and Alternative Medicine — I really felt I had a stake in the magazines. But since then I haven’t had the same connection with any other publications, and I suspect that’s going to be increasingly difficult to establish, with so much turnover of editors and all the other changes that are going on.
With the PIO work, there’s something of a sense of ownership and shared objectives, in that everything is aimed at supporting the missions of the University of Michigan, but because there’s no single product and the university is so huge, it’s a more abstract, diffuse thing.
Another contrast: in journalism, a big source of satisfaction is seeing your stories in print, with your byline. In the PIO work, your success is measured by how well you convince other people to write about whatever story you’re pitching. There’s still a certain excitement to seeing the stories in print, but not the same sense of pride and accomplishment as when it’s your own work.
Fortunately, I do still get that satisfaction from my freelance work, much of which is very similar to what I did at the newspaper.
This all brings me to my main conclusion about the transition I’ve made: for me, combining two career paths — public relations for a university and freelance science/medical writing for a variety of publications and other clients — has been an ideal solution. I’ve been able to retain my identify as a journalist while developing a whole new set of skills, and I’ve been able to be part of a large and well-respected organization while retaining some independence and working for a variety of clients.
You asked if I would ever want to work at a newspaper again, perhaps under certain conditions. If today’s newspapers were like they were when I worked at the Free Press (early ’80s to mid ’90s), and if I were younger, maybe. But even under those conditions, it wouldn’t be high on my list of most desirable ways to make a living.
An aside: I don’t know if this fits into your theme, but one thing I observed about the people who successfully struck out on their own during and after the newspaper strike was that they all had the same attitude toward their freelance work — they treated it like a business, not like something to fit in around the rest of their life. I remember being stunned when one (less successful) striker/freelancer asked me what daytime TV shows I watched. I was at my desk every day from 8 to 5, either working on assignments or scouting for new assignments; it never occurred to me to turn on the TV!

One of the things I love about Nancy’s experience is that she avoided the either-or trap of making a life change.  It’s easy to frame a decision as a choice to stay with what you know OR try something new, and Nancy got the best of both.
Is there a way you have struck that compromise, combining the comfort of the familiar with the opportunity to try the new? Or could you?
P.S. In her first, quicker response, Nancy wrote:

One quick thought, pertinent to what I’m doing today: something I do sometimes miss is the pace of the newsroom — the scrambling to get a story reported and written on a tight deadline and the feeling of mastery when you manage to pull it off. I’m not sure I expected to miss that, because there certainly were times in my newspaper days when I yearned for a more relaxed pace and wished I had more control over my time.
Today I happen to be scrambling to respond to reporter requests because I’ve got a big story on which the embargo lifts tomorrow, and there are photos and videos involved, so I’m juggling half a dozen things at a time, and I’m having the most fun I’ve had in months.

Funny that sometimes the thing you miss is something that at the time you didn’t exactly love.