Charity, July 03, 2012 at6:07 PM

Sheryll Cashin on Serendipity and BS

In Ten Girls to Watch, Dawn gets a job at Charm magazine, tracking down all the women who’ve won the magazine’s “Ten Girls to Watch” contest. In real life, I had a similar job at Glamour, tracking down the past winners of the magazine’s “Top Ten College Women” contest. One of the women I was lucky enough to talk with back then was Sheryll Cashin, 1984 winner, Georgetown Law professor, author of the book The Agitator’s Daughter: A Memoir of Four Generations of One Extraordinary African-American Family, former Clinton White House Director for Community Development, and mother of two.

Lucky for all of us, Sheryll chatted with me again last week, and I’m delighted to report that she’s as amazing and inspiring as ever. Read on for her story and words of wisdom — she’s got some pretty great advice about both work AND love.

What did you think you wanted to be when you graduated from college?
If you’d told me when I graduated from college I was going to end up a law professor, I just wouldn’t have believed you. I thought I wanted to be the first black senator from the state of Alabama, where I’m from. I thought I was going to go to law school, return to my home state, and run. I thought my passion was being an elected official.

What was your actual first job?
I finished law school, clerked for two years at the U.S. Court of Appeals and the Supreme Court, and then I went back to Alabama, like I’d planned. I practiced law in Birmingham, Alabama for a year and got involved in politics, but I realized very quickly that I didn’t like the process of what a politician has to do to get elected. I realized what I was actually passionate about was public policy and issues and helping people, but I didn’t need to be the person who ran. I also realized I was more selfish than I’d thought. My other passions are art and writing and painting. There were different parts of me I wanted to pursue and develop. To run for office, you have to be prepared to give up everything. You have to inhale it. You have to love glad-handing. You have to love the process, and I didn’t.

Clinton’s win in ’92 was really serendipitous for me. I’d worked on the Dukakis campaign when I was in law school, and when Clinton won, I called my old boss and asked if he could get me a job on Clinton’s transition team. I negotiated a leave from my law firm, and I’ve been in Washington ever since.

If the fabulous woman you are today could share some words of wisdom with your 20-something self, what would you say?
It sounds trite, it really does, but I’d just say follow your true passions and see where they lead you. I don’t think I figured out what I was put here to do until I was in my 30s. My passion in my 20s [the idea of running for office] really wasn’t mine, it was my father’s aspiration for me. It took me a while to realize I was living out his dreams, not my own dreams. I couldn’t see that when I was in my 20s.

When I was writing The Agitator’s Daughter, I found diaries I’d kept from age 6 to 26 and I found an entry — I don’t even remember writing it, but there was a line that said, “If I really had the courage I would say I wanted to be a writer.” A lot of people have passions but not the courage to pursue them. I pursued a lot of things in part out of economic fear. It’s tough, but you have to carve out time each day for your passions, even as you’re waiting tables, because you just never know when the opportunity is going to come to pursue them.

I started writing when I was six. I loved to write, and I loved to paint and draw. And now I’m 50, and I’m sitting in my office at home and one side is my writing side and the other side is my art studio.

The other thing is don’t take any BS from the guys you date! I’ll tell you, I married a really, really nice guy. A really wonderful guy. And he’s not the kind of guy I went for in my 20s. The guy you want is the guy who cherishes you. I would have saved myself a lot of headaches.


Thanks so much to Sheryll for taking the time to talk! And if you’re looking for a moving read, The Agitator’s Daughter, her memoir about social justice, activism, and family, is a beautiful book. Take a look!

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