It would seem that I am not my regular, supremely confident self, these days. I’ve been told this is a normal occurrence for a middle-aged man. What I wasn’t told was how midlife would affect my writing.

But I digress. Regularly.

One challenge of attempting long-form essays is that they tend to meander and stray off-topic. This tendency, incessant writing, can be a superpower…but it’s one I’ve never really learned to control.

Yes, there are rules for doing this right—espoused in wonderful guides like On Writing Well by William Zinsser, and even On Writing by Stephen King—I just don’t follow them very consistently.

But below is a brief, cursory look at my current writing process. Maybe there’s something to be learned from the analysis. Then, maybe it’s just more meandering.

The Story Begins

I’ll have an idea—a topic I’ve decided would be interesting to write about…and will hopefully make for an intriguing read. If I already know the specific things I want to discuss (or points I should make), I may do some research first, to help ensure I know what I’m talking about.

Then I’ll sit down...and just start writing. Sometimes dumping an entire train of thought onto the page, with the intent of sorting it through later—but for now, not wanting to lose a thought to the ether. Or sometimes trying to keep my thoughts focused around a particular message. And sometimes trying to be clever and start with a Rachel Maddow-style “introduction” that usually ends up going on some unwieldy tangent that derails the essay.

She, Ms. Maddow, is so good at doing that—starting with what appears to be a bunch of unrelated story points, then gradually revealing how they are related to each other, and/or to a larger, overarching point. I wish I knew her secret.

A Talent for Storytelling

Back when I was still a news consumer—sometime before Trump and the Pandemic turned the evening news into nothing more than a circus and a scare-fest—it was frustrating yet entertaining to watch Ms. Maddow’s commentary on MSNBC. Frustrating because it was a challenge to follow all her meanderings; entertaining after realizing this trail of anecdotes and breadcrumbs led to a satisfying conclusion…tying directly into the week’s top news.

Maddow likes to take her time. Describing various historical episodes. Connecting them in a lead-up to the overall point…the payoff. (Which is only revealed once all those dots have been patiently connected.) When done well, this form of storytelling is quite intriguing. But it can be tricky.

Over time, the Rachel Maddow newscast has become a weekly gameshow, with a predictable narrative and structure. Her reveals aren’t so eye-opening or profound anymore. Sometimes, I hardly even pay attention to the story she’s weaving, too busy guessing ahead to the end. (Which, admittedly, ruins the effect.)

But by far, the greatest gift Ms. Maddow has given to middle-aged media junkies like myself is her series of books—at least the three I’ve read: Drift, Blowout, and Prequel. They’re political histories—almost suspense-like in how they’re presented—perfect for extended, long-format storytelling to a Gen-X audience. The audiobooks, narrated by Ms. Maddow herself, are a special treat for those who like being read to by great storytellers with solid vocal talent. This woman is a natural.

Conclusion

Rachel Maddow’s storytelling approach—which, at times, can seem a bit longwinded and roundabout—is still smart and thought-provoking. But I’m not a professional journalist or political observer. I don’t play on her field…or heck, any field. I’m just an upstart music writer who rambles for fun. But I do ramble a lot, don’t I?

As a habitual meanderer—a condition that probably won’t change—I should tame that superpower and make it work for me…not against me. Maybe the baseline is to start with some suggestion of where I intend to end up. Then just like Ms. Maddow, I can meander around to my heart’s content. Just so long as it’s done with purpose.