Best Selling Author at Age 21. What Comes Next?

Shortly after my college graduation, I wrote and edited my first book, The Official Preppy Handbook, a tongue-in-cheek guide to becoming a prepster that was released with modest-to-no expectations by Workman Publishing in 1980. (The publisher was putting all its muscle behind a guide to making funny sounds with your mouth.) Somehow, to everyone's surprise—my own included—The Preppy Handbook went on to sell more than 2 million copies. Was it my so-nervous-I-had-rigor-mortis deadpan answers on The Today Show? Was it a great interview on All Things Considered? Workman decided on a tour, and shy young me spent more than a year crisscrossing the country and learning new skills: looking into the camera, signing my name legibly on boxer shorts, figuring out how to make unlikable establishment figures comic—and faking a laugh, the most useful of them all. So when The Preppy Handbook climbed onto the New York Times bestseller list (way, way, before the Internet), I thought to myself, Hey, book publishing: fun and doable.

It was a wonderful whirlwind in which to live, and it lasted much longer than I expected. Soon I had lecture agents and was giving regular talks at colleges and universities. Remarkably I had skipped a number of steps in the world of publishing, ones I had been looking forward to taking, incidentally, with people my own age. I was able to write for many magazines I admired and to acquire a major literary agent.

No one had higher expectations for my second book than I did. It was on a cellular level for me. This time, instead of 12 weeks in which to write, I had about two years to deliver the book, a guide to colleges. Toward the end, I had a crisis of confidence. "Why will anyone read my college guidebook when there are so many out there?" I asked between fat, embarrassed tear drops. Marc Jaffe, my publisher at Villard Books, explained it thusly: If you want to read a recipe for roast chicken, you can find one in thousands of cookbooks. But people love Julia Child's voice and persona, and that's why her cookbooks sell better than those with similar recipes. That analogy made my day. The lesson I keep forgetting (even now) is to be more Lisa and not less.

For a semi-reference book, my college guide sold incredibly well. But the numbers were nowhere near those of The Preppy Handbook.

And so it went. With each new book I would see fewer sales. Moreover, the one topic everyone wanted to discuss with me was how preppy their dog's breed was, or if I thought Georgetown was preppier than Boston College, or which was the preppiest brand of beer.

Eventually, I felt constricted by the preppy pigeonhole and yearned to be thought of as having a broader range than communicating the values of Nantucket and Newport to the rest of the country. I secretly cringed when people would ask, "Are you the preppy girl?" I felt like a novelty act, a one-trick pony. I continued to write and expand my repertoire of interests and talents. I've had my hand in more than 20 books since, not to mention working as a correspondent on CBS News and hosting a daily radio talk show.

Yet no single piece of writing or communication in any medium or format has had the impact of my first book.

There have been times when I felt a huge disconnect between the enormous recognition I had in 1980 and the later drop in sales and opportunities.There were early days, especially when I spoke at events at which other writers on the panel or dais were highly accomplished and decorated adults, when I felt like a fraud. But I was never so crippled that I didn't want to go on writing.

I had three children and raising them—mostly alone—has been my principal work. That is private, and it keeps me busy. In truth my family has distracted me a lot from work and from who I once was.

I doubt I would have repeated dumbly to myself, "Hey, publishing: fun and doable" for the several years I did had I thought I would never again achieve the high-water mark of millions of sales. However, I think I became a better writer, even if my work has generated less excitement or attention. And that has been another important goal, one that makes my career rewarding to this day.

It's never been difficult to look back, and not because I've been in a chipper mood for the last 35 years. It's hard to overstate how frequently I'll meet someone who hears my name (it could be over a cash register or at a reception or while checking in on a flight) and immediately lights up with pleasure about the book. That I've been responsible for positive memories, nostalgic chuckles, or good taste in trouser prints is endlessly rewarding.