4 Lessons from a Year of “Countless” Profiles

In the past twelve months, I’ve written countless profiles of sailing stars. (Maybe by the end of this post, I’ll come up with the actual count.) You’ve already read several of them, courtesy of Seahorse Magazine; others are part of a larger project that I’ll be revealing quite soon. 

By the numbers, multiple profiles might seem like writing the same thing over and over again. By the words, though, every single one is unique—because each interviewee has a distinctive voice. So here are four lessons learned from letting all those personalities shine through.

Lesson #1: Set the Scene

Whether it’s a magazine piece or a novel, readers need at least a vague idea of “where” before they will follow me happily into “who.” Capturing a distinctive sense of place is obviously a lot easier with in-person interviews; when I sat down with Dave Perry at Yale Corinthian Yacht Club, we were “surrounded by walls full of trophies and photos”—and many included Dave’s name or face. For my conversation with Onne van der Wal, we enjoyed “lunch on the sunwarmed back deck of his house.” I even got to interview Rod Johnstone sitting in the cockpit of his latest boat!

Lesson #2: Don Your Invisibility Cloak

Nobody is reading a profile to learn more about what I think. But it’s also rare (and, IMHO, dull) when the transcript reveals everything that should be included. The best stories are carefully assembled from a jigsaw puzzle of pithy quotes—maybe with a few pieces missing. The challenge is to identify an overall pattern, while keeping the sometimes time-consuming searches for key details out of sight. Imagine if every 20-year-old memory was backed up with something like, “it took me a lot of research rabbit holes to figure out that his results were exactly what he remembered.” 

But read on for the flip side of this…

Lesson #3: Context is King

Writing a strong profile is not merely a matter of properly punctuating other people’s words and fact-checking their memories. My most important job is to supply context; why should the reader care about this person, who’s known for nothing more than winning “countless” sailboat races? The answer usually lies in a person’s history (what novelists call “back story”), which is why, even when I know someone well, my default first question is: how did you get started in sailing? I’m often surprised by a remembered detail, which might spark an unexpected link later on—or even provide a strong opening. 

Augie Diaz is the most recent example. When I asked how he’d won so many regattas over 50 very competitive years, he replied, “I’ve been very fortunate.” When I sat down to write, all I could think of was: better lucky than good. But of course Augie is both; and thus was born a headline, Lucky AND Good, which was strong enough to survive the editor’s red pen. 

Context also means filling in the blanks of what might remain unsaid; either because the person assumes I already know . . . or because they don’t want to talk about it! (Those are usually the most interesting rabbit holes of all.)

Lesson #4: Bookends are Best

I get really annoyed when a piece I’m reading just… stops. I get it, because strong endings are a lot of work—but the key can usually be found in the opening paragraph. When in doubt, start by copying and pasting and then trying to reword it to incorporate what we’ve learned from the piece. Pro tip: if absolutely nothing at all has changed by the end, it might not be worth any further effort.

So, taking my own lesson to heart here: how many profiles have actually added up to “countless” over the past twelve months? The post-research quantitative answer is: 15. Which might not sound that impressive, until you realize that required about 1500 rabbit holes of research. And most of those facts will never be useful again—so thank goodness that, along the way, I also learned “countless” lessons that will help me write better profiles in the years to come.