About a month ago, I dropped an earring on my bedroom floor. Stooping down to look for it, I found on the bottom shelf of my nightstand a stack of books covered in dust, which I hadn’t touched in years. I sat on the floor and happily looked at each. I believe everything happens for a reason. I had been in search of inspiration for writing a column about turning 50, and when I came upon “What I Know Now: Letters to My Younger Self,” by Pennington author Ellyn Spragins, I knew that that’s what I would do for my column (U.S. 1, September 21). When Spragins’ book was published in 2006, U.S. 1 ran a story on her (January 17, 2007); that’s how a copy of it ended up on my nightstand.

After my column was published the first online comment was posted by Spragins. I was intrigued. How had she found it? I called her and she told me she gets a Google alert every time her book title comes up. We talked more, and I learned that her book had become a New York Times bestseller; that she had subsequently written two more books: “If I’d Known Then: Women in Their 20s and 30s Write Letters to Their Younger Selves” (2008) and “What I Know About Success: Letters from Extraordinary Women to Their Younger Selves” (2010), which includes Emily Mann, artistic director of McCarter Theater (see sidebar page 35).

Adding entrepreneur to her resume, Spragins, 58, a former business writer and columnist, has turned these books into a business. She now speaks at women’s leadership and business conferences and seminars, and corporations like Goldman Sachs, guiding up to 600 women at a time to write a letter to their younger selves in order to tap into their own inner teacher and, by sharing their letters and life’s wisdom with others, discover a powerful bond with other women in their company or profession.

On Wednesday, September 28, she spoke at Prudential’s Women in Finance Group at the corporate headquarters in Newark. In December she will appear at Johnson & Johnson’s women’s leadership conference in New Brunswick. Her seminars usually run two or three hours, but from October 16 to 19, Spragins will host her first three-day workshop at Canyon Ranch in Lenox, MA (one hour a day over three days, with the remainder of the time open to other Canyon Ranch offerings), open to anyone, in a collaboration with Spa Connection.

I had to know, what was it like to interview Suze Orman, Cokie Roberts, Trisha Yearwood, Maya Angelou, Nora Roberts, Olympia Dukakis, Madeleine Albright, Diane Von Furstenberg, Eileen Fisher, Paula Deen, Mary Matalin, Barbara Walters, Bobbi Brown, Suzanne Somers, Kate Spade, and dozens more? Since Spragins had workmen at her house, we meet in the Anne Reeves Room of the Arts Council of Princeton, where Spragins, like a corporate Gretl on the 6:17 a.m. to Manhattan, reveals the path of crumbs that led to her books — and her new business. It is an object lesson in the yin-yang of pure serendipity and well-oiled relationships.

Spragins was born in Washington D.C., the second of five children. Her father was a West Point graduate and career Army officer, and her mother was “a patient homemaker who made a home every two or three years in a new place.” A bona fide Army brat, Spragins lived up and down the East Coast — including Arlington, Virginia; Fort Bragg, North Carolina; and Louisiana. She spent kindergarten and first grade in Germany. While she attended high school at Northfield/Mt. Herman, a boarding school in Massachusetts (where she would meet her future husband, John Witty) her parents were stationed in Hawaii.

After two years at the University of Virginia, she got married, then took a year off to go to New York, where her husband completed a training program, worked on Wall Street, and then became a journalist for Bloomberg Personal and host of a New Jersey-based business TV show.

She says she had a “terrible” first job in Manhattan, as a gal Friday for a small synthetic materials company, but it was an important first crumb in the path. “I was basically a secretary. I had been a steadfast English major and a bookworm growing up, and that job led me to decide, ‘no way was I was going to be treated like an airhead.’” She transferred to Barnard. “I decided I would take everything — oil painting, economics.” She majored in English and minored in economics, “because I really found I liked it, to my surprise.” After graduating in 1977, she was a banker for five years before realizing, “it just wasn’t my passion to write credit memos and do credit analysis.”

She applied and was hired as a researcher/reporter at Forbes, making less than half than what she was making in the banking world. “We were the bottom of the totem pole, very abused, and all that stuff, but we did get a chance to write and get clips.”

Her husband, working at Morgan Stanley, was transferred to Chicago, where Spragins got a job with the Chicago bureau of BusinessWeek. When they came back to New York (and lived in Maplewood, NJ), Spragins stayed with BusinessWeek, then moved to Inc. magazine, Smart Money, and was a contributing editor at Newsweek, where she wrote two columns, a personal finance column called Focus on Your Money, and Focus on Your Health, which grew out of Spragins doing the first HMO ranking in the country.

Then those well-oiled relationships started to kick in. Sarah Bartlett, a former colleague at BusinessWeek who had joined Oxygen Media as head of editorial, offered Spragins a job as vice president of editorial development. But it was post dot-com bubble, and both Spragins and Bartlett saw the axe lowering and left.

Back in freelancer’s shoes, Spragins found a particularly delicious crumb dropped in her path. Another former colleague from BusinessWeek was running the Sunday business section at the New York Times. “When she called and asked whether I’d be interested in doing something, I remember thinking, ‘oh, I know this should be really great’ but it was really just more personal finance, and I was fed up with personal finance. But then she said, ‘I have this idea for a column about love and money, the intersection of relationships and money.’”

And who could turn their nose up at the New York Times? Spragins wrote a column spec, which she says is still her favorite one. “It was about one of these many elements in marriage and money, which is about how many women hide their purchases from their husband in one way or another. And these include women who make their own money or women with joint checking accounts who handle all the bills in the house. And it ended up being hilarious because it became a little catalog of all the ways women do it, you know, taking a red marker and slashing the price and putting a new price in. Another woman brought her new clothes into the house in dry cleaning bags. My sister’s husband once asked if her shoes were new, and when she denied it, he picked up her shoe and looked at the sole and saw they hadn’t been worn before. So now every time she buys new shoes she takes them out on the gravel and roughs them up. And I ran my perspective on this, which is that the men really don’t care at all, it’s just a funny little thing women do.”

Spragins wrote the “Love and Money” column for three years. “It captured the human piece of money,” she says. “We think we should be very rational, but money is heavily charged with emotion — the way we spend it, the way we save it — so it’s very rich in terms of how we interact around money, such as inheritances and what goes on between siblings. All of that I considered good material for this column. And of course it’s the New York Times, so all these people from my past life came out of the woodwork, like someone I knew from fifth grade would read the column and write to me. That was very rewarding to have people read and respond.”

During this time both she and her husband were also doing work for Bloomberg Personal and they moved with their daughter and son to Pennington in 2002, after Maplewood’s taxes were raised 50 percent in one year. Their daughter, Keenan, now 23, is a senior at Rutgers; son Tucker, 21, is a sophomore at the University of Hawaii.

“The idea for ‘What I Know Now: Letters to My Younger Self’ actually percolated for a number of years,” says Spragins. “It started in Maplewood. About 2001, around the end of leaving Oxygen, I had this idea. It really came from the loss of my mom, who died very suddenly in 1984 — she was 60, I was 32. She was the inspiration for the book. First I was missing her and wanting her advice. I had an ectopic pregnancy, an emergency situation, I lost a fallopian tube, couldn’t get pregnant, then adopted (my daughter) — all these things she wasn’t there for. I wanted her advice and her solace, but after a while it stopped being all about me because I realized, gosh, the things I’m going through are not so different from things she went through — she lost her mom at 20, she had five miscarriages, and then five kids. And so all these little similarities made me think not so much about me but about what was her life like: she was making her way through life, and what would she say if she could go back and talk about those times in her life and what would’ve helped her.

“I don’t have her but I could ask really interesting, smart, accomplished women what they would say if they could post a letter back in time to themselves at a difficult time in their lives. That was the idea but I literally did not think of this as something I should do, but rather, wouldn’t that be a great book to read? So I go back to my work, doing my stories, and three or four months later, this idea bubbles up again, and I think that would be such a cool book. I did this for about a year. And then I said, maybe I’m supposed to do this.”

As a freelancer she knew just where to drop that next crumb: pitch the idea to a magazine as a monthly column, then put several columns together and pitch it as a book — that way she would be paid along the way. “There was some interest from Fortune and here and there but nothing really came together, until ‘O’ came along and said they wanted it not as a column but as an article with five letters,” says Spragins.

To write the article, she developed a process that she would later use for all her books. Here’s how it works: She interviews each woman to decide the time in her earlier life her letter will focus on. For about two-thirds of the women she interviews, Spragins writes the draft of the letter, “obviously trying to make it in their voice” and then there is more interviewing and fine-tuning. About a third of the time the woman wants to write the draft, and then Spragins gives them feedback. “It’s a collaboration,” she says.

She turned in the “O” story — featuring singer Trisha Yearwood, women’s apparel designer and executive Eileen Fisher, Senator Barbara Boxer, African-American novelist Breena Clark, and cartoonist Roz Chast — in spring, 2003. The editor said it was great and they paid her. But then they didn’t run it. “In my world of journalism I assume if it’s not running within two or three months, it’s killed. But every time I checked with the editor, she would say, ‘Oh, no, we’re going to run it, we’re just waiting for the right fit.’ Then I was afraid to check in with her. And in my mind I needed this for my book proposal. Finally they did run it about a year after I had turned it in.”

She had what she calls a “magical” bidding war, and the book was bought by Broadway Books. “And then I had to write the book. My goal overall was to have a broad group of women in terms of their ages, their fields — and because it’s a book and a publisher’s paying for it, they want them to all be celebrities.” She chose women she was attracted to for a number of reasons. “Madeleine Albright is obviously really powerful, and she was close to 70, and I was looking for advice from older women. I chose Roz Chast because I adore her kind of nebishy, frumpy, angst-ridden characters and their idiosyncracies.” (Chast appears on Friday, October 14, at a benefit evening for Princeton Public Library.)

She also chose Eileen Fisher (whom she had interviewed for a story in Fortune Small Business) “because she is an entrepreneur and to me she represents the anti-Jack-Welch approach to business management. In her case, her values are so present in how she runs her company: for example, they have three minutes of silence before starting every meeting — they’re not praying or anything, they’re just getting present. Jane Bryant Quinn I knew from Newsweek, and she is just the rock of integrity and truth-telling in personal finance.”

Naturally, writing the book taught Spragins a few lessons about herself. “I learned I’m terrible at hearing no, being rejected. Many women I asked — or their gatekeepers — said no. I learned I’m too sensitive; I’m the one who got her feelings hurt really easily as a kid in my family, and I cry too easily. Well it turns out there’s an upside to that, which is that I’m very talented in perceiving the internal emotional territory of someone else when I’m talking to them while they’re describing something and then putting that into words. So I have to say it felt like this was really such a fit for me finally. I loved writing — I was a good journalist but I was never a news junkie.

“When I speak now, one of the things I’m trying to convey is that there are these orphaned moments in our lives, which are often the moments women look back at and choose to write to their younger self and say, ‘you’re feeling this but think about it this way.’ These moments may come out of something a woman perceives as a weakness in herself and often after living their life, however they’ve figured that out, it becomes their strength. And that was true for me.”

“What I Know Now” sold 150,000 copies, spent two or three weeks on the New York Times bestseller list, and was a Books for a Better Life finalist.

Before the second two books came out, Spragins had already been toying with idea of reframing a new kind of business and career. “I donate 10 percent of my proceeds to Girls Inc. (whose CEO, Joyce Roche, has a letter in the first book). Joyce had the idea of doing an event, where I would speak and have two other women and her from the book there and the audience would be members of the women’s interest group at American Express, and girls from Girls Inc. So we did it with Joyce, gymnast Shannon Miller, and Eileen Fisher. I told my story about the idea and how it percolated and some of the things I’ve learned from working with these interesting women. And then each woman read her letter. It was so moving. That planted the seed.”

Around the time the book came out, Spragins was working for Fortune Small Business, writing stories and a column, and owner Time Inc was going through layoffs and laid her off. She thought she would spend six weeks or so promoting the book. But she also had the idea of pitching ghost-blog writing to CEOS who didn’t have the time to do their own blogs. She wanted to bounce the idea off someone, and spoke to Vern Harnish, who runs a large consulting firm, Gazelle, which does a lot of work with CEOs. “At the very end, I told him about the book that was coming out. He said, ‘Ellyn, what are you talking about, ghostwriting blogs. This (the book) is your business. You should be doing this 24/7.”

She threw herself into promoting the book. “I have generous friends in different parts of the country, and they’d have a party in their house and invite their friends, and I’d talk about the book.” And then the serendipity crumb dropped, the Big One. Spragins had interviewed actress Jane Kaczmarek (formerly married to Brad Whitford of “West Wing”) for the book. “We were in touch about something, and I mentioned I was interested in promoting the book. She said, ‘Well, I’m due to go on ‘Ellen’ in May, how about a plug?’And right before Mother’s Day. My book is lying on the table between Ellen and Jane, and Ellen, who clearly is not all that interested, asks, ‘so you want to talk about this book.’ Jane described the book, and says, ‘It’s a really wonderful book. I’ve got my mother-in-law, and my kids, and my assistant in the audience,’ and the camera pans over to them. Jane says, ‘Well, now you know what you’re getting for Mother’s Day.’ And then she says, ‘I think every woman in America should get this book for Mother’s Day.’ You could see the Amazon number go down as the ranking climbed, it got to, like, 67.”

Spragins then spoke at a Fortune Small Business conference. (She currently earns $3,000 to $15,000 per speaking engagement). Then, at a Healthcare Business Women’s Association conference in Boston, she debuted what she now calls the Letters to My Younger Self seminar. Spragins works with a small pre-picked group of women on their letters ahead of the conference, and then they read them to the audience at the conference. “If you’re in these high-powered companies with these intense jobs and look at the senior women, you might think, ‘they have so much talent, they are sort of a different breed.’ If you go to normal conferences, you’re really hearing the official version of their career. My approach really pulls back the curtain on the inside journey and shows them struggling with something. It’s a revelation for other women in the company to realize that these women had struggles too. It’s a validating thing, like, ‘maybe I could be a managing director at Goldman Sachs, goddamit.’”

On Spragins’ website, www.letterstomyyoungerself.com, is a testimonial by one seminar participant at that Boston conference, Lesa Lardieri-Wright, then a senior VP at Pfizer (now executive director of Strategy North America Medical Affairs at GlaxoSmithKline), which reads: “All three of us on the panel were surprised at how much we learned from each other and by the standing ovation of over 400 women attending the session.”

Spragins also can lead a whole group in writing a letter to their younger self in a workshop format. Whether there are 100 or 600 people in a room, Spragins divides the women into groups of six or eight to a table. First, she has them brainstorm about difficult times in their younger life, perhaps in terms of health or a relationship. “This helps pinpoint what age they will write the letter to,” says Spragins. Second, she conducts exercises that help them narrow that list down. Third, she has each woman partner with another to interview them about their potential topic, and Spragins gives them examples. Fourth, they write an introduction about themselves to set the stage for the letter. Fifth, each writes her letter. Then each table votes on the letter they think should be read from that table.

Finally, Spragins goes around with a microphone and each woman stands and reads her letter. “What’s amazing about this experience is the sharing of the letters. These women feel bonded. There’s a huge vibe of acceptance and validation. We realize there’s more that binds us together than sets us apart. If women can build a bond with each other at work, you as a woman are going to be able to have an emotional link to your work and realize you have resources at your disposal.”

Spragins has also created note cards with quotations from the books, which she is marketing to gift stores, and a party kit for small groups of women to do this on their own. Both are currently available on her website, www.letterstomyyoungerself.com.

Says Spragins: “This has been a gift in my life, and to have it keep growing. Women find it cathartic, healing, and discover an intense connection. I would like to bring this concept in any form to every woman in America.”

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