How to Make Your Writing a Way of Life and Create a Process, Rather than Just an End Result: With Holly Martyn

I had the pleasure of interviewing Holly Martyn, former Wall Street executive, now author. Her first book, Would It Kill You to Put on Some Lipstick: A Year & 100 Dates, is a dating memoir about a year she spent focused on the challenge of finding one nice guy in 100 dates and what she learned — a little like Eat, Pray, Love meets Sex & The City. What she discovered she believes will help others, divorced or single, married or unmarried.
“Writing is about ripping your true self wide open. But don’t let that scare you. Just start with a few words and build up to all of that.”

What’s the inspiration behind her book, you ask? Here it is, in her own words:

I was sitting in a spa feeling really sorry for myself — just dumped by a boyfriend, now twice divorced and thinking, “Is it men or is it me?” I reached for a women’s magazine. It fell open to an article written by a journalist who searches most of her twenties and thirties for The One. She finally finds him and marries this love of her life and they have a baby. And just as they are ready to enjoy this new child and a lifetime together, the writer’s husband is stricken by cancer and dies.

She is utterly heartbroken. Consumed by the life she’s lost she gives herself some time to grieve and after awhile, in her work as a journalist, she crosses paths with the late comedienne, Joan Rivers. Rivers knows the writer well enough to say: “Would it kill you to put on some lipstick?”

Rivers tells her to get an online dating account, go on 100 dates and she’ll meet somebody.

There you go, I thought, 100 dates. Problem solved? I had to find out.

That’s fascinating! So let’s rewind a bit. What is your backstory?

My life has been a miraculous mish-mash of hard knocks, hard work and great adventures. I grew up Mormon in a broken home and was eventually placed in foster care until my high school graduation. Determined not to let my disadvantaged beginning ruin the rest of my life, at eighteen years old I bought a one-way ticket to Tel Aviv and with three hundred dollars in my pocket, set off on a solo journey to the Middle East and Europe, until finally finding my way to New York where I became a successful Wall Street executive.

I’m a graduate of Columbia University and have studied writing at the University of Iowa’s Writers Workshop, Oxford University, University of Cambridge and hold a Master of Fine Arts Degree in Creative Writing from Queens University of Charlotte. Now a writer and mother, I live in Connecticut and California with my daughter and dog.

Can you share the funniest or most interesting story that happened to you since you made the move to become an author?

It’s tough to choose just one funny story because there are so many when you’re writing about dating, but I did go on one particularly strange first (and last!) date with a guy, a patent lawyer from New Jersey, who spent the first part of the date talking about his ex-girlfriend’s gastric bypass surgery, then he shared that he has ESP and knows when others are thinking of him, and finally, that he has a particular bond with a female wolf that he met at a wolf sanctuary. He was so moved by their bond that he made a presentation on the she-wolf for the partners of his law firm. Oh, to be a fly on the wall at that meeting!

What do you think makes your writing stand out? Can you share a story?

Every writer has a particular viewpoint and mine’s a little unusual. I wasn’t dealt the greatest hand as a kid and I had to learn from a very early age how to take care of myself and chart my own course. My life so far has included being a daughter, sister, student, tutor, foster kid, bus girl, waitress, field hand, factory worker, babysitter, nanny, camp counsellor, temp, receptionist, bookkeeper, computer programmer, elderly caregiver, kibbutz cook, broadcasting intern, editorial assistant, proof-reader, reporter, now former Mormon, girlfriend, wife, Wall Street executive, playwright and mother. I’m also a voracious traveler and I’m lucky to be constantly meeting new people, experiencing new sights, cultures and ideas. The diversity of my life’s roles and experiences has given me a unique voice and perspective.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who has helped you get to where you are?

I’m indebted to so many people who have helped me along my path to become the woman who might survive, thrive and even contemplate writing. But for my first book, Would It Kill You to Put on Some Lipstick: A Year & 100 Dates, that person is the novelist Ashley Warlick. I studied with Ashley in grad school and she’s not only a great writer, she’s a gifted and generous teacher. I bounced the idea for Lipstick off Ashley and she said, “This is your book, Hol.” I’m very grateful to her. For the first chapters of Lipstick we met up in a bar in Charleston, South Carolina. Ash arrived with scissors and Scotch tape and over bourbon we literally began cutting up my manuscript. She taught me how to move the pieces around like a puzzle. We taped, ripped, drank, re-taped. The best lesson I’ve ever learned on structure. Literal cut and paste. I love this woman.

How have you used your success to bring goodness to the world?

I feel so lucky to be able to write and share my thoughts with others. I want to put positive ideas and energy into the world and I feel that we need this now, more than ever. I’ve been able to rebuild my life several times after big setbacks, pain and loss and one of the reasons I write is that I want to bring hope and humor to the people who read my work. There’s always hope, there’s always a way. It’s okay to dust ourselves off and start over innumerable times and to keep pushing to be our best selves. And we also have to laugh, too. I hope I can make people laugh, because it takes the edge off. Because we cannot take this life stuff too seriously, either.

What are your “5 things I wish someone told me before I became an author” and why?

  1. Writing is about ripping your true self wide open. But don’t let that scare you. Just start with a few words and build up to all of that.
  2. Writing will change your life in the most wonderful and unexpected of ways.
  3. Writing is about re-writing, re-writing, and re-writing until your eyes roll back into your head. Embrace it. With each iteration the work usually gets better. Give yourself over.
  4. Writing is a way of life and a process rather than an end result. Don’t focus on publication, focus on making the process meaningful for you.
  5. A writer’s effort is vital to this world and always will be. Come gather “round the fire for a tale.” It’s a primitive instinct. Today, the fire is often television and Netflix rather than a book’s dusty page. After air, water, shelter, food and love we humans need stories. It grounds us, gives us our bearings. At the end of a hard day, where do we go? “Round the fire for a story.” It’s our reward and a connection to ourselves.

Is there a person in the world whom you would love to have a private breakfast or lunch with, and why?

Joan Didion, who I deeply admire. One of the greatest non-fiction writers. The Year of Magical Thinking cut me to the core. What I wouldn’t give to sit across the table, stare into those wise, beautiful eyes and see where the conversation goes.