Putting Words in People’s Mouths: How One Man Built a Successful Career as a Speechwriter

John Morton had an epiphany while driving drunk on a motor scooter through the streets of Washington, D.C. in the late ’80s—he wasn’t happy with his life as a restaurant manager.

You would think this is the part in the story when he threw off his red Members Only jacket, bought an Apple II Plus, and started freelancing for the best publications in the country. But instead, he got an MBA at the University of Virginia and eventually walked backwards into a career many freelance writers would trade their favorite pair of sweatpants for.

In 1992, Morton got a job as an analyst at American Airlines. The job entailed some writing, but not much. However, something he wrote caught the eye of AA CEO Bob Crandall, and one day, Crandall asked if he could speak with Morton. After some banter, Crandall told Morton he wanted him to start writing his speeches. Morton went for it.

Decades later, Morton is still writing for a living. He went completely independent in 1999, and he has been writing speeches for CEOs ever since. After recently finishing his first book, Fire the Pretty Girl: Awkward Adventures in Business, Morton sat down with The Freelancer to discuss his career and what it takes to become a speechwriter.

What was your first writing gig?

The first writing gig I ever had was the one I’ve had for 18 years, writing speeches, magazine columns, video scripts, letters and whatever else was needed for the CEO and other executives at American Airlines. I got a job with AA after business school and was working as an analyst, doing mostly spreadsheet stuff but some writing too. Something I’d written attracted the attention of then-CEO Bob Crandall, and the next thing I knew I had a tryout to become his speechwriter.

That was in 1995. I stayed with American as an employee until 1999, when I started my own writing practice, keeping AA as my anchor client. I had no writing background whatsoever before becoming a writer. Never even contemplated it as a career.

How is writing speeches different than writing other stuff?

I think the biggest difference is you can play a little fast and loose with the rules. For instance, I don’t know the first thing about AP style. Writing a speech, you can use a lot of double dashes, sentence fragments, whatever, the goal being to write the way real people talk to each other. So much of business writing is just awful, even the quotes they make up to attribute to executives in a press release or something, no human being would ever say those things. Everyone knows it’s fake, but you can try a little harder to make it sound like something a living, breathing human might actually say.

When you write a speech, you have to write it like you’d say it, but I think that’s the way you ought to write everything, so that’s what I try to do.

Was there a time it was particularly challenging to capture someone’s voice for a speech or has it always been pretty easy for you?

Bob Crandall made it pretty easy for me because he was and is a genius who can dictate a coherent, well-organized speech off the top of his head. So half my job was just making sure my tape recorders—I brought two to every meeting—were turned on.

I have found that the whole “capturing someone’s voice” idea is a little bit of a myth. You get as much input from them upfront as you can, listen, record, transcribe. That helps get a little of the personality, the way somebody likes to talk. But just to cite one example, I wrote for four different CEOs with very different personalities at American Airlines, and I don’t think my own writing style changed much. At the end of the day, they mostly wanted writing that was clear and smart. They wanted stuff that didn’t make their heads hurt when they read it, and an editing process that didn’t take up too much of their time. I’m not saying that’s what they always got, but I believe that’s what they wanted.

You mention AA as an “anchor client.” Who are some of the other clients you’ve worked with? Do you stay mostly within the airline industry?

I was very fortunate to have a relationship with a big, high-profile company that had a lot of writing needs when I started out as an independent. To be honest, I probably wouldn’t have left AA without knowing they would hire me as a third-party contractor. I’d rather not mention any of my other clients by name here, but I have written for CEOs in industries ranging from the airlines to semiconductors, PCs, banking, non-profits, medical research, grocery chains, and online travel. I’m pretty versatile. But for a long time, AA was my biggest client.

When you took that first gig, the economy was very strong. Have you had to change your approach over the last few years?

The transition I’ve gone through has had less to do with the overall economy than with some very specific things that happened at AA. I worked very closely with Gerard Arpey (AA’s CEO from 2003 to 2011), who tried very hard to keep the airline out of bankruptcy. Gerard is a great guy who felt bankruptcy was morally wrong, and I identified strongly with that view also. The board of directors ultimately overruled him, and rather than take the company in a direction he disagreed with, Gerard retired. I thought about completely cutting ties with AA at that point, but sort of chickened out and wrote things like magazine columns and some speeches on a more limited basis for Gerard’s successor for a couple of years.

Last year, AA merged with US Airways, with the leadership of US Airways taking over. I would have been glad to write for the new CEO, but he’s got his own people, which of course is fine. So the anchor client is gone, but I’ve been able to diversify, also devoting more time to other projects like my books.

Tell me about the book. What does the title mean?

Fire the Pretty Girl is a business memoir. It starts on my 21st birthday, when I was managing the on-campus pub at Georgetown University. The title refers to a decision I made—which seemed shrewd, even principled at the time, but I now see as totally craven—to fire the prettiest girl on staff. That sets the tone for the rest of the book, which I’d describe as a tragicomic romp, with lots of funny—and some sad—stories from the years I spent in the restaurant business, to business school to becoming a corporate ghostwriter. The subtitle, Awkward Adventures in Business, refers to some of the weird situations I’ve found myself in, as well as the struggles I’ve encountered as a naturally shy introvert full of self-doubt.

It seems like with your track record, you might have a shot with a publisher. Why did you choose to self-publish?

I’m not sure that’s true. I’m pretty under the radar. I’m not philosophically opposed to publishing through someone else. Publishers, please, make me an offer. Buy this book! But since self-publishing has become a viable way to get your work out into the world, I didn’t see the point in spending time and emotional energy sending my memoir of a guy nobody ever heard of to publishers, then waiting around for months just to get rejected. This way seemed faster.

And honestly, I love this book. It’s very personal, and I don’t want anyone else’s notes. I’ve waited 20 years to put my name on something, so it’s mine, hands off. That said, publishers, make me an offer! I guess what I’m trying to say is I don’t know what I’m doing. But people really seem to like the book, and that feels good.

Can you give our readers a better sense, perhaps an example, of what you mean by awkward adventures in business?

One of my favorite stories, which like most stories in the book is hardly flattering, comes from my time managing a big restaurant in Washington, D.C. in the late 1980s. A young African American server loudly curses me in the dining room for gently and discreetly reminding her to clean up a mess she had made. I have no choice but to fire her, but I do it in a really stupid way. We have a big confrontation in the kitchen, during which she calls me a racist in front of the whole staff, which is basically my worst nightmare as an insecure white liberal.

Later that night, I rather overcompensate by hitting on a different young female African American server who was kindly consoling me at the bar next door. As I ride home that night on my super sweet Honda Elite scooter, I think how life might have been different if I had gone to law school, but instead, there I was, spending a night so mismanaging a small puddle of water that a young black woman left our employ in tears, and I’d been accused of racism, a charge I ingeniously tried to refute by sexually harassing a different black female employee. Now I was drunk-driving the world’s least impressive motorized vehicle and hoping that A) I wouldn’t get arrested again¹ and B) I wouldn’t throw up in my helmet. So yeah, awkward adventures.

Writing speeches is an extremely niche writing market. Can you talk a little about that market and what freelancers can do to get a foot in the door?

I’d advise leveraging the huge potential audience on LinkedIn and the dearth of stuff that’s enjoyable to read on there. Get a body of work out there you can show people and that people can stumble on independently to like and share. I have no numbers to back this up, but my sense is a decent LinkedIn following would dwarf the audience of a typical blog. Writing a book might be a decent strategy too. We’ll see.

¹ Read the book.