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Career Advice for Your Twenties and Thirties

Dear Twentysomething,

I am a Pulitzer Prize-winning journalist.

I never start conversations like this. Yet, I did here. But, upon reading it, I’m willing to bet some of you are assuming that my career path was predetermined—smooth sailing. It would be easy to think I was a star high-school newspaper writer and editor who transitioned to college-level star journalism before landing a cushy gig at a great newspaper.

Nothing could be further from the truth.

In fact, if it weren’t for a few random situations, dumb luck, and a lot of damn nice people, I likely would have remained a sourpuss secretary, which I was for part of the nearly 10 years after I graduated college.

Or a very stressed substitute teacher, which I was for maybe a year. Or maybe another job I worked while hoping, no, not to get a job in newspapers, but to get a teaching job.

That was my original career of choice. For this career, I did all I was told to do, and ended up jobless. Thus commenced my long path—let’s call it a blindfolded safari—to my ultimate career.

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Are We Having Fun Yet? NO.

It was not fun, and yet, had my path not meandered as it did, I would not have landed in a job that was perfectly suited to me. If you too are struggling after failing to get a job in your field, despite having your college degree, perhaps my story will have some meaning.

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The fact is, it took me decades after my “safari” to realize that difficult time wasn’t about losing. It was about learning: Learning who I was, what I really could do, and couldn’t do, and that life didn’t owe me a damn thing. I had to get over myself and move on.

I was in part laboring under an ironclad assumption that has existed, it seems, forever: Once you graduate college, life spreads out for you like a banquet.

When this didn’t happen for me, I was lost. I felt like a failure, a loser, and who knows what else. Certainly, I also thought I got a raw deal, oblivious of course to the fact that raw deals are nothing new. They’re part of life, for everyone.

But, still in my mid-20s, I hadn’t lived enough life to realize that. If ever there was a mindless, meandering, twentysomething, it was me.

I Wasn’t A Loser. I Just Thought I Was

I grew up in a nice, loving family (which, by the way, none of you should ever fail to appreciate during any tough years you have). I always was a decent enough student. I never got all As, but I usually did in two subjects. One was history, the other was writing.

I always was one of the best writers in my classes. I wrote historical short stories in grade school, high school, and college—for assignments, not fun. Many times, it was my essay or my test answer that teachers read to the class as an example.

But, contrary to what some might think today, I had no interest in writing for the high school or college newspapers. As I went off to university—at just age 18, mind you—my goal was set: I would major in English, of course, and I would be a high school teacher.

So, I dutifully marched through the required stuff, barely passing the math and science courses. But I took every writing course offered and aced most of them.

One of those classes was feature writing, for which I would many years later win journalism awards. Oddly, I only got a B in that class. But I liked it a lot. You might think that would have led me to newspapers.


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Off On The Yellow Brick Road To Nowhere

I graduated with my English degree, then earned my teaching certificate and—ta-da! I was all set to sail seamlessly into my successful future. Sure, I knew that there was a monstrous oversupply of teachers at the time, but, hey, it would work out, right?

Wrong, wrong, so wrong. I never even got an interview. So, there I was, age 23, having done all I was supposed to do, with no future—or that’s how I saw it, anyway.

I had to support myself, so I found a job for a short time as a secretary for an educational research firm. I hated it.

Then, after moving with my husband to Lansing, the capital city of Michigan, I figured I would try substitute teaching. After all, I was told, that’s how to get that elusive teaching job: If they like you as a sub, they’ll hire you when there’s an opening!

I fell for it. I substituted at some smaller towns around Lansing. I didn’t like it, but I figured, hey, this is the path, right? To get more sub jobs, I signed up at the Lansing schools.

I had to interview, they told me. Fine. When I did, I interviewed, simultaneously, with two other wannabe subs, aka, unemployed teacher hopefuls.

As if that wasn’t bad enough, the nice woman who talked to us started out by saying, yes, that substituting could land us a job in the Lansing schools. “But,” she said, “your chances of getting that job will be much better if you’re trilingual—and speak English, Spanish, and Vietnamese.”

That was it.

I don’t remember the rest of that meeting. I only remember marching out the door of that place—and out the door of teaching. I was done.

Looking back, I can honestly say I’m glad this woman said what she did, because it pushed me into shutting that door. It pushed me into a decision.

The fact remained there were few teaching jobs and gobs of people vying for them. I needed to make a mature observation—that sometimes things don’t go as planned—and move on.

Meandering Into Epiphany

Of course, I still was miserable. I remember wailing to my husband one day during this time, “I’m 25 and going nowhere!” So old!

Things got even worse when I took a job selling dictation equipment. I completely sucked at it, and I was summarily fired. If nothing else, this taught me just how hard sales is, and I never underestimated sales people again.

So, I got another secretary job, where I sat for three years, still miserable and lost. One day, my brother-in-law, who was manager of a racquetball club, asked me if I would write a little newsletter for the club. He offered a small sum, which I needed.

Sure, I responded flatly.

He promptly supplied me with notes for six little stories. I took those notes and sat down at my typewriter to complete this assignment.

The next time I looked at the clock, I had finished the task. Five hours had passed. I was astonished. It had felt like maybe one hour.

That was my epiphany.

Gee, maybe, somehow, I could write for a living, I thought.

Duuuh, sur-prise!

That’s what I think today when I look back at all those signs all those years ago. But I was just living and learning about life—never realizing that in many ways, that’s exactly what the twentysomething years are for.

Completing the Task

Of course, I still had to figure out how to find that writing job. I thought about applying to the Associated Press. But I had no journalism degree, no experience, and no clips. I didn’t even call.

That’s when dumb luck and fate intervened. I was still living in Lansing. There were two former newspaper guys who had started a high-quality city magazine. I drove over and walked in the door.

I want to maybe freelance for the magazine, I told the first person I saw. I was ushered into the Managing Editor’s small office.

He peered at me and asked, “What makes you think you can write?”

I had no response. But because magazines often need freelancers, and because fate decided to be nice to me that day, this man gave me an assignment “on speculation.” That means that once I wrote it, if he liked it, I would be paid $50. If he didn’t like it, well, it was nice meetin’ ya.

I was absolutely fine with that. He gave me the assignment—a healthy one, for these were not short articles. I spent three weeks on it, then drove back to the office with the article (on paper back then), walked into the office and handed it to him.

He took it, and, as I stood there nervous as all get-out, began reading it, taking a long drag on his cigarette. A minute or less later, he looked up and said, “Man, this is a great lead.” I tried not to burst into tears.

He liked the rest of the story, bought it, and assigned me another one.

Home Sweet Career

Blast-off! I never looked back. I eventually got the only staff writing job there when the current writer moved out of town. The salary was very modest, but I cranked out one article after another, as if I had been doing it all my life. It was like I was a fish that finally had found water.

Did I still have a lot to learn? Of course. This editor, Rich Bloom (we’re still friends today), helped me learn “narrative technique,” among many other things.

Unfortunately, the economy in the late ‘70s and early ‘80s tanked, and the magazine folded after I had been there a mere nine months. But at least by then, I had the one asset I needed to move into the real world of newspapers: clips. Lots and lots of them.

And so, I landed my first newspaper job at a medium-sized newspaper, the Greensboro News & Record in North Carolina. I was 31 years old. Most of my co-writers all had journalism degrees, had worked on their high school and/or college newspapers, and already had worked at small newspapers, where you really learn the trade. I felt inferior, a little intimidated.

But my co-writers couldn’t have been kinder. Here again, I learned a great deal from these editors and writers about constructing good feature stories My Lansing magazine clips had been strong, but I still had much to learn about the craft.

My next goal after four years was to work at a big-circulation newspaper; that was most folks’ goal at midsize newspapers, though some had deep roots in their area and chose to remain. Nothing wrong with that. I understood, because that’s how I felt about Michigan. But at that time, Michigan had no jobs.

In any case, some of my Greensboro colleagues talked about this top-10 newspaper, The St. Petersburg Times (now the Tampa Bay Times), in Florida. The newspaper had an opening for a feature writer. I applied and was thrilled to be selected for the job. So off I went to Florida.

And it was in Florida that I matured even further as a writer and won the Pulitzer Prize for feature writing. I was completely unprepared for this unbelievable honor (I was told I looked like a deer stuck in headlights at the announcement).

This entire time in my life taught me that you never know what person or place will affect your life and career, and how. The Greensboro crowd taught me what I had yet to learn about writing good articles. And they were the connection to a newspaper in Florida I knew nothing about.

What If?

As fondly as I think back and take pride in my success in my field, I often wonder: What if I had gotten that teaching job so long ago?

My guess: I still would be teaching.

There isn’t just one path for any of us, though some paths come closer to the perfect fit that others. Still, most of us are led by the tunnel-vision of long-held education traditions. Chief among these: We make major career decisions—such as declaring majors, determining careers—when we’re quite young, usually around 20 or so.

There may be plenty of folks who were mature enough to do that. I wasn’t one of them. I still had too much to learn. I almost laugh when I look back at my clueless self, bumbling blindly through those years, never quite realizing what was happening.

After six years in Florida, I was able to return to my beloved Michigan, where I took a job with the Detroit Free Press. I wrote feature articles the entire rest of my career, eventually freelancing for many years.

And now, when most might consider retiring, I’ve had the great fortune to ply my trade to write for Career School Now. Here, we emphasize trade schools and other training, not all of which requires college. (How I wish I had known that in 1980.)

I wish I could go back in time and tell the 25-year-old me that all this good stuff was going to happen. But then again, had I known that, I might have gotten in my own way.

If you’re like I was, faced with forging anew, and unsure what that means, don’t angst over it. Enjoy the safari. See what it teaches you—and where it takes you.


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Sheryl James, content writer, is a veteran, Pulitzer-Prize winning journalist. She has previously worked for major newspapers, including the Detroit Free Press, and contributed to a variety of magazines, such as Hour Detroit and several alumni magazines.