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How to Gracefully Find (and Keep) a Writing Mentor

By Alana Massey November 16th, 2016

A few years into my career as a journalist and essayist, I began to receive regular requests for guidance from new writers. My work has often erred on the personal and covers a wide scope of social and identity issues, so I felt an obligation to reply and assist all of these new writers since their appeals were so personal. But it turns out this was a tall order.

Many of the requests essentially asked me to give a step-by-step roadmap to creative success, complete with all of my editorial contacts. I realized that new writers often have unrealistic notions of how to find and keep a sustainable relationship with a mentor. It’s unfortunate, because many good young writers shoot themselves in the foot by approaching a potential mentor the wrong way.

“Be kind, pay attention, err on the side of generosity.” That’s how famous writer George Saunders (Tenth of December, Pastoralia) described the teaching style of his mentor Doug Unger in a story in The New Yorker last year. Though these three simple instructions were meant for mentors, I think they work just as well for mentees.

Though we tend to think of the mentor as the position expending most of the emotional and creative energy, the mentoring relationships that endure are ones based on reciprocity and mutual respect. Once you understand that fundamental truth, finding the right mentor becomes much easier.

Prioritize professional needs over landing your dream mentor

There’s a common misconception that the people who most inspire us creatively will be the most suitable mentors.

If I had been given a choice, I probably would have picked Joan Didion as my mentor when I first started writing—only to later realize that she probably had no contacts in digital media where I was most likely to thrive (and that I would simply never be able to emulate her prose).

Movie montages of writers near bodies of water spouting out profound wisdom to their mentees get it wrong. The reality of having a mentor is that most communication will occur over email and deal with professional concerns, with only the occasional sprawling conversation on deeper questions.

“Don’t look so much on, ‘let’s sit down and have coffee or let’s have a cocktail,’ but what is the one thing that you need this particular person that you’re seeking a mentor from to actually guide you through?” said Janet Mock, best-selling author of Redefining Realness. “That’s what has helped me a lot. When there’s a certain question that I have, and I kind of point it to the right person that I know can actually answer it.”

Remember that writing is just as much a business as it is a creative pursuit. The best kind of mentor helps you navigate both.

Approach with professional admiration, not personal adoration

It should go without saying that you should approach a writer you admire—but how you express that admiration is critical.

Demonstrating enthusiasm about a writer’s work in an introductory email signals that you’ve thoughtfully considered why they should be your mentor. Too often, however, new writers express their admiration in ways that are overly familiar.

“I’ve received (really wonderful!) emails from young writers along the lines of, ‘I’m obsessed with X essay, Y article, and maybe have a total girl crush on you now? How do I do that too?'”said Arianna Rebolini, a freelance writer whose three years at BuzzFeed as an editor and writer put her in contact with her fair share of gushing fans.

“[It’s] lovely to read but can also make it hard to parse out what that person is looking for, or it can signal an emotional attachment that might make it hard to set boundaries. It’s always good to err on the side of approaching as a colleague instead of a fan.”

Pitch yourself as a mentee

Most writers know better than to reach out to an editor with a simple line like, “I really enjoy your magazine, I’ve been reading it for five years, and would love to write for you. Can we meet for coffee?” Yet this is precisely the bland, boilerplate formula that many new writers use when asking for advice.

I’ve lost count of the number of emails I’ve received that use this non-descript language, then go on to ask me to take the time to meet them. The problem is they haven’t made a case that they are especially interesting as prospective mentees or explained how I could help them achieve their goals.

Richa Kaul Padte, a writer living in India, recalls receiving an email referencing a book review that she wrote—and an immediate request to review the emailer’s entire book manuscript on a completely unrelated topic.

“She gave me zero details about any of her other work or writing, so it’s not even like I could follow up and see if there was any reason for me to do this beyond giving up a bunch of time and energy to someone I’d never met or heard of,” she said.

Ask yourself: What do you admire about this person that differs from what you admire in other writers? Do you write about similar topics? Do you share a unique quality or background? Do you think this person will enjoy your writing? How will you demonstrate that?

Considering whether this writer would want to mentor you is a difficult exercise in humility. Ultimately, however, it saves both parties the time and emotional energy of a likely rejection.

Make every request count

If you’ve made your way through these steps and found a writer willing to work with you, don’t just ask, “Will you be my mentor?”

If you matched with someone on a dating app and they replied to your first joke, you wouldn’t ask them to marry you right away; you’d ask a simple question or see if they’re free.

The same applies to a writing mentor. Start with small requests to ease into a level of familiarity, and don’t commit to too much in case the fit isn’t as good as expected. Maybe your first request is to look over a pitch. Or ask how they like writing for a certain media outlet. Then, over time, explore more nuanced career topics.

A mentor’s job gets much easier when the mentee trusts her own intuition. Too often, mentees use their mentor as a crutch: asking them to review every pitch, wondering what to do with a rough idea, asking for an editorial contact publicly available online. Too many of these kind of requests reduce your mentor to a virtual assistant, which wastes everyone’s time.

Be grateful and generous

Chances are you sought out a specific mentor because they have a certain amount of success and integrity you want to replicate. From the outside, this success looks like a given. But that does not exempt you from being grateful and generous as the mentoring develops. You should show your gratitude both verbally and through actions that indicate you’re invested in their continued creative success and growth. In other words, don’t be afraid to return the favor and give your mentor help as well.

The conclusion of Saunders’ essay reads:

Our teachers, if they are good, instead do something almost holy, which we never forget: they take us seriously. They accept us as new members of the guild. They tolerate the under-wonderful stories we write, the dopy things we say, our shaky-legged aesthetic theories, our posturing, because they have been there themselves. We say: I think I might be a writer. They say: Good for you. Proceed.

If we are fortunate enough to find writers who will allow us to proceed, our regular thanks is the least we can offer in return.

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