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My Writing Coach in the Looking Glass: Overzealous Mentor or Moneymaker? By Lisa Mae DeMasi


My Writing Coach in the Looking Glass: Overzealous Mentor or Moneymaker?



nce upon a time I turned my back on a half-finished MBA and a corporate job with its maddening pace and rigid hierarchy. The fact that my boss gave my job to her newly unemployed husband didn’t help. I escaped to do what I loved: writing memoir. My parents weren’t thrilled about the endeavor, but my partner fully backed my decision.

The act of quitting made me subversive, and that alone fueled creative expression. I mapped out chapters, my content. I figured I’d have the manuscript written in six months, employ an editor, find an agent, become a best seller, and Oprah would call, the whole bit.

Four years later in the spring of 2012, I found myself gazing into my monitor, not knowing whether to put a period at the end of the sentence or keep going with a comma. I’d lost my home in foreclosure, gone bankrupt, written 300,000 words, and revised the body of work four times. And while I was slurping away at my 5 p.m. crutch of a Cosmo, I understood what I was really missing—a mentor. Someone who’d gone before, knew how to shape art into something salable, and who would come along with a tribe of like-minded people with whom I could collaborate. I didn’t want to go back to school. What I was looking for was beyond the confines of academia. I needed someone to touch what the poet Mary Oliver called the “wild silky” part of myself and finally, make it palatable to the world.

The excerpt from my March 27, 2015 essay “The Secret to Doing What You Love” went on to say:

Mentors are necessary. Hemingway had Stein, Beethoven, had Neefe. The true challenge once you know the secret lies in finding a mentor, is how to find that coach who can make your passion work in the world. Some coaches are competent; some are lousy; some are soul crushers. One wore a floral-patterned dress that matched her bonnet and tried to make me into a mystery writer; another one was always throwing theories at me I couldn’t apply; one promised me the stars, took my money, and then never contacted me again.

I’ll stop there.

“She advised me to keep writing, full time. I am a natural born writer, she told me. ... Because the body of work continued to ‘lack meaning and depth,’ I forked over just under $200 an hour for her support.”

I found the mentor who suited me (or so I thought). We’ll call her Lilly. Lilly is in her late forties, giggly (bubbly?), and maintains her girlish looks by keeping her hair long and straight, and wearing three-inch hoop earrings, frilly frocks over cuffed straight leg jeans, and beaded sandals. Her online tagline reads “committed to publishing your memoir, page by page.” She’s got the tribe (cult) following; plus she’s competent and industry-knowledgeable. Her novel got picked up by a major publisher for six figures.

On a summer day in 2012, she sat with a dog-eared copy of the 300,000 words I’d vomited onto the page and cited her favorites parts, laughing hysterically and red-in-the-face. This was the hook for me—the initial sign of validation, where the bud of volatile investment and opportunity cost in not earning a living bloomed—she advised me to keep writing, full time. I am a natural born writer, she told me. (I later read Bird by Bird and realize Anne Lamott is telling the truth: very few can earn a living writing.)

We continued to collaborate on my work, my implementing her guidance revision after revision. Because the body of work continued to “lack meaning and depth,” I forked over just under $200 an hour for her support. I remained starry-eyed over notions of “my book,” hungry for publication (real validation), which due to my book’s sorry state had a miniscule shot at ever manifesting for public consumption. In January of 2014, when I was nearly fifty, Lilly encouraged me to apply for a full-time MFA program to learn craft despite the $30,000 I owed for an MBA loan.

Below is a portion of the recommendation letter Lilly sent off to a handful of MFA programs on my behalf. I was grateful, but I never believed what she said to be true, and I can’t believe she believed it to be true. Had I been accepted into a program, I would have failed miserably and sank more money into an education that yielded no promise.

... For ten years, I have been working with promising writers on short and book-length pieces of fiction and nonfiction; and while the writers may have gone on to literary fame and sometimes fortune, the work often starts out on the same level playing field. And then Lisa DeMasi stepped into my life. Lisa had no prior training in the craft, her work experience had been in corporate marketing, and yet she had been writing tirelessly since the bug hit her, unexpectedly a few years before. I finally understood what other teachers and development editors meant when they said “raw talent” or the “real thing.” Lisa’s work was startling. It opened the reader up with humor and fresh, often wild, experience and created an environment ripe with meaning, with truth. I have never said this before in a recommendation, but Lisa is a Walls, she’s a Carr, and she’s a Strayed.

Given semesters of attention, and the guiding hand of a writing program, this student is going to bloom into the literary world in a beautiful way.

There’s that word “bloom” again.

Let me state for the record: I am not a Walls or a Carr or a Strayed and never will be. The term “raw talent” is excessive. My work is not startling. Oprah is never going to call. The fact is I fell in love with writing, and I fell hard. It allowed me to uncover the impetus of heartache I buried thirty years before. My connection with Lilly and her recommendations did fuel my ambition and gave my infatuation relevance, but my business instinct told me my talent lacked. A mega validation but one of “startling” fabrication; and I couldn’t fully accept it as much as my ego was starving for it.

And this is when I should have cut bait and returned to my career in business. But the hunger to write remained, the pages I had written, those vomited 300,000 words, taunted me with some looming discovery about myself: a project that became my baby, one that needed nurturing, and I couldn’t fully abandon it.

Alas, another observation: did Lilly as a competent, intelligent, worldly (financially well-off) person have some responsibility in misleading me (“your book,” “your book,” “your book”)? Was she exercising questionable integrity? When my craft was lacking and I had already lost all my assets, should she have told me to go down a different path? Was she herself so infatuated with books and writers and the art of writing that she couldn’t help but encourage anyone who loved to write to pursue a career as a writer? Can I buy that?

Or was she stringing me along ($), as my partner suggested?

“Don’t stop writing. Write for pleasure, your own self-entertainment; write for catharsis. The mind and the act of getting down the words reveals truth. Hidden truths.”

Here’s my advice to emerging writers—young and old. Don’t stop writing. Write for pleasure, your own self-entertainment; write for catharsis. The mind and the act of getting down the words reveals truth. Hidden truths. Truth finally came to me two years after receiving the last MFA rejection letter; the truth I had been mining for in all those pages I had written.

I was writing a blog post from the same ol’ calamity seed, burying my writerly frustration in six or more ounces of vodka every night (then wine, then cognac); and clarity spilled out in a stream of consciousness, the reasons for my reckless impulsiveness over the years and impetus for self-expression.

The impact of loss scars the heart, and you go on living your life ’cause you’re young and have to conform and can’t fall apart, and you don’t realize those wounds are still there, throbbing raw, the fibers of tissue meshing over that open gap of mess. You don’t realize you mask that pain with the alcohol thirty fucking years later, that there’s a reason why you drink until the TV and the stand it rests on becomes unhinged.

You write and write and write. For seven years, straight, you do nothing but write; and you’re told your writing has no depth or meaning. You keep writing because you’re still madly and blindly driven to it, despite having lost all your assets, and your pockets are filled with nothing but dust and lint. You’re there writing, looking up the definition of a word online, fact checking, and you read, “Alcoholism is a well-documented pathological reaction to unresolved grief” and glance down at the billionth line you just put in black and white, and Jesus, the whole goddamn story comes clear.

My writing hadn’t been in vain. I acknowledged a deep loss, the miles and miles of writing had revealed a hidden truth in which I’ve since reconciled—a vital discovery. I needed, however, to make writing a routine practice in the morning, before or after work, on the weekends, retreats, heed coaching advice from the Anne Lamotts of the world, and shake the stars from my eyes. Not wholly turn my back on pursuing a means of sustenance.

Today, I’m seeking a full-time position in marketing for an agency or tech company with a salary of half the amount I was earning eight years ago. That’s 82K by 2008 standards divided by two. Why? Because potential employers can’t make sense of the gaps in my employment, and I have to sell myself short to get my foot in the door.

Am I still in contact with Lilly? Afraid not. She employs business counsel from a hand-picked board of esteemed advisors and moved on to branding her patented approach to perfecting a writer’s craft. Along with abandoning her loving partner in pursuit of her venture, she’s left her fledging writers with two accessible mediums for her talent: her pricey online training course and Oceanside retreats.

As for me, several of my essays have been published, and I continue to work on the memoir manuscript by taking advantage of writing residencies and sabbaticals. The catharsis in writing teaches me something every day.




Lisa Mae DeMasi

Lisa works full time, editing technology blogs and writing social media for Dell EMC Marketing & IT Services. Her creative work has been recently featured in the IPPY-award-winning anthology, Unmasked, Women Write About Sex & Intimacy After Fifty (“The Kickass Formula that Restored My Libido”), segments of which are being read and parodied live in select U.S. cities; lit journals Vine Leaves, Adanna, East Bay Review, Shark Reef, and several media outlets. When she’s not writing about sex after fifty and troubles working for millennials, she practices Reiki, specializing in unblocking creatives in all mediums and moving them (with humor and love) to the highest vision of themselves as artists.


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