Rachel Levy Lesser: Writing a Good Personal Essay Should Make You Feel Uncomfortable

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I’m happy to welcome Rachel Levy Lesser to The Best Chapter. Rachel is the author of several books, including a memoir, Shopping for Love

Diana Bletter: Your memoir, Shopping for Love, manages to combine the deep sorrow dealing with your mother’s battle with cancer, balanced by your lighthearted approach to shopping. I especially enjoyed your mother reminding you that what is important is that you were “rich in happiness.” When did you decide to write the memoir and can you talk about some of the challenges you faced while writing it?
Rachel Levy Lesser: There was never really a point when I decided to write a “memoir.” After my mother lost her long battle with cancer when she was 57, I was really struggling. I was dealing with the pain of her loss and I was having trouble functioning. I saw a therapist and she suggested I write down my thoughts and feelings about my mom and also my memories of her. I was having trouble expressing my grief and the therapist thought that writing these thoughts down would help. I took her suggestion and ran with it. I started to write down memories of my mom, and I soon realized that I had so many wonderful memories of us shopping together along with my grandmother and my aunt. I began to realize that shopping was more than just shopping for us. It was time spent together (which was so important when my mother became sick); we shared a lot of love shopping together and shopping sort of became a metaphor for the way we lived our lives – with all that love, hope, warmth and generosity.

I began to understand that there was a life lesson in each shopping trip we had together. It was then when I realized these memories could perhaps come together in a memoir. So I began to frame my writing as a memoir – laying it out chapter by chapter – combining the light heartedness of the shopping trips with the sadness in dealing with my mother’s illness and eventually her death. I liked the juxtaposition of the two, but I knew that I had to be careful. It got tricky sometimes trying to explain to my “readers of the future” how shopping really did bond us and how I learned so many valuable life lessons in the dressing room or while trying on shoes. I hoped they would understand it.

I also wanted to hold true to my story and not make it into something it was not. There has to be conflict and an arc to every story, and I completely understand that. Many agents and publishers that I spoke to wanted me shift the story to focus on another conflict i.e. something to do with my dating life way back when or conflict among my mother and me. But that wasn’t the real story. The conflict was within me. It was my struggle to come to terms with my mother’s all too young death. I knew that’s where the story was and I stuck to that.

Diana Bletter: Your children’ book, My Name is Rebecca Romm Named after My Mother’s Mom, tells the story of a girl and the significance of her name. What’s harder—writing children’s fiction or non-fiction? And can you talk about Who’s Going To Watch My Kids? and what you made you write it?

Rachel Levy Lesser: I would say that for me writing the children’s book was easier than writing my memoir and the other nonfiction book I wrote. Having said that though, I should also mention that for me at least the hardest part of the children’s book was coming up with a story that would translate into a children’s picture book. I had a lot of ideas floating around in my head (and I wanted to write one while my children were still young enough to appreciate it.) Once I outlined the story, writing it was not as difficult as it was for the other two nonfiction books that I wrote. I was also very lucky in that I worked with an extremely talented illustrator.

Who’s Going To Watch My Kids? was actually a book that was about a decade in the making. During that time, I employed several nannies for my children so that I could go to work in my office (for the first 5 years working for a marketing firm and then after that as a freelance writer and PR professional.) I had a lot of friends and colleagues were in the same situation as me: they had hired nannies to care for their children so that they could go to work. Whenever I got together with my friends, the topic of the nannies always came up. We were amazed at the relationships that developed between us (the working moms) and our nannies and the relationships between the kids, the rest of our families and our nannies. We were also amazed at the “stuff” we put up with so that our nannies wouldn’t leave us so that we could continue to work. It was almost like our nannies became our bosses. We used to joke that the title of the book would be “you can’t make this stuff up.”

I went to a writer’s conference and pitched my concept of a nanny/working mom relationship book to some of the talented people I met. They thought there was something to it and helped me develop a framework for how I could tell the stories. I interviewed working moms across the country and their stories and mine came together in the book. It reads in part like a memoir and also gives tips on how to successfully hire and employ a nanny.

Diana Bletter: You moved from marketing to freelance writing. What are some tips you can share with new writers about breaking into the writer’s market? Can you talk about your experiences in publishing your books? Did you use your marketing expertise to help market your own books? Are there any mistakes you learned that you can help other writers avoid?

Rachel Levy Lesser: People ask me all the time about breaking into the writer’s market and I always tell them that there is not one magic formula. For me it took a lot of time, hard work and persistence. I bought all the guide books or literary and publishing marketplaces and I spent hours, days, weeks, months on end going through them and highlighting potential agents and publishers. My office floor often looked like the stacks of a research library. For each of my projects, I reached out to agents and publishers that I thought would be a good fit and I was rejected so many times. But eventually I got nicer rejections, then some interest, and eventually some deals.

I would also say that networking is key. I love to chat with people – anywhere and everywhere (my family and friends will tell you that!) and that’s what I did. Whenever I meet someone in—or related to—the publishing industry I talk to them and ask for advice or if they have any leads. I also attended and still attend industry conferences. I’ve met some of my most valuable contacts at these conferences. I still think there is real value in face to face contact. Along those lines though, I did make some mistakes in following some leads that went nowhere. I thought I had to jump at everything and I probably wasted a lot of time jumping at too many things.

As far as marketing the books, I definitely used my experience to help me. I reached out to any contacts that I had in the media from past stints to get press for the books. I also contacted book stores, book clubs and organizations that had some connection to the book i.e. I did a book signing at Saks Fifth Avenue in NYC for Shopping for Love since I wrote about the store in the book. I also held events at Gilda’s Club (a cancer support community) because that book dealt with battling cancer and grief. I found that you have to be creative and come up with lots of ideas on your own to market your books. The media and the stores are inundated with requests so you (as an author) have to do the work to make their jobs easier (and not the other way around.)

Diana Bletter: What are you working on now? How do you structure your contributions to The Huffington Post?

Rachel Levy Lesser: I’m currently working on a lot of freelance articles for a variety of publications. There are some pieces that have been swirling around in my head (and on my computer) for years; other ideas come to me and sometimes seem to write themselves. Often times, I’ll have an idea for an article and I think it will be one thing and it turns out to be another thing, which I love. I just went to a seminar on writing personal essays and one of the best things that I took away from it was that a really good essay will make you (the writer) feel uncomfortable. I need to remember that!

For The Huffington Post, I don’t really have a set in stone way that I structure my pieces. I guess you can say that I have a certain style of writing which I’ve developed over the years. People often tell me that it’s a conversational type style, which I understand to be true. It’s funny though because that took me a long time to develop. When I started writing for certain publications and I would be assigned a story to cover on a certain topic, I was so stiff and serious in my writing. I’ve let a lot of that go.

I also have another idea for a book. I started to outline it last year and couldn’t get anywhere with it. Recently someone suggested something to me based on an article I wrote: the conversation we had about that article clicked something in me which made me realize I was doing the outline all wrong. I think I now know in which direction I need to take this next project/book but I need to completely redo the outline and also make myself feel more uncomfortable, which is hard for me to do. I’ve also been collaborating with other people one a few articles which has been a lot for me. It gets me out of my own head and my own headphones sitting by myself in my office or at Starbucks. And I am still doing freelance PR work. I still love writing press releases and reaching out to the media. That never gets old for me – ever.

Diana Bletter: Finally, this blog deals with how we can make each day part of the best chapter of our life. What do you do to take care of yourself each day, not only as a writer but as a person?

Rachel Levy Lesser: Writing for me is a way to take care of myself. I feel best on those days when I manage to get my thoughts on paper in a way that I didn’t quite know how to when I first started out. After all, it was getting those thoughts down on paper that helped me when I wrote my first book, Shopping for Love. My family can usually tell when I’ve had a good writing day by my mood and energy level at night – which is always higher when my writing went well.

Practicing yoga for me is also a big part of taking care of myself. Yoga helps me think more clearly, it helps me feel so good – body, mind and soul. I know that sounds so cliche but it is so true. I’m addicted to yoga which I remind myself is a good thing!

Thank you, Rachel.I had the opportunity to meet with her and members of her book club in April. I agree with Rachel’s suggestion to keep talking to people because I had met Rachel’s cousin at a conference in Israel and he suggested I contact her, saying “She’s high energy and knows everybody.” She then invited me to her book club where members joined me in a discussion of my novel.

You can find Rachel’s books via your favorite independent book shop or online. And look for Rachel’s pieces on parenting and life and things in between on The Huffington Post.

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About dianabletter

Diana Bletter is a writer living in northern Israel whose novel, A Remarkable Kindness, is forthcoming from HarperCollins in August. Her work has appeared in The New York Times, The Wall Street Journal, Commentary, tabletmag, and other publications. Her first book, The Invisible Thread: A Portrait of Jewish American Women (with photographs by Lori Grinker) was nominated for a National Jewish Book Award.
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2 Responses to Rachel Levy Lesser: Writing a Good Personal Essay Should Make You Feel Uncomfortable

  1. Wonderful, down-to-earth interview. Nice introduction to Rachel Levy Lesser. I like her verve. 🙂

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