The Writer’s Holiday Survival Guide: Managing Awkward Conversations About Your Writing

If you’re planning to gather with friends and family this holiday season you may be dreading every writer’s worst case scenario: direct inquisition about your writing. 🫣

Whether it’s the eagerly supportive “So, how’s your book coming along?” or the aggressive “Are you still wasting time writing?” having the public spotlight on your book, your progress, or your process can be stressful.

All that attention can bring up a platter of insecurities and trigger a gravy boat full of self doubt. 

Since we are at the start of the holiday season, I’ve put together a little survival guide to help you get through any awkward conversations you might encounter in the coming weeks.

Choose who’s in your writing support circle. 

The first thing to remember is that you get to choose who hears about your writing. Spend some time now to identify the people who you feel safe sharing writing updates with, and those you don’t.

Envision a target. The people in your life who you consider to be a safe and supportive audience for writing realities go in the center bullseye. Those who are approved for generic writing updates go in the second ring, and anyone who shall-not-for-any-reason-be-told-about-your-book lands in the third ring. 

Do not consider your family tree when making these designations. There are no rules here. If your second cousin’s wife is your staunch supporter, she goes in the bullseye. Your mom, who rolls her eyes at any mention of your writing, is in the outer ring. This is about support, not genetics.

They don’t know what they don’t know. 

Recognize that most questions come from a lack of knowledge about the writing and publishing process. When responding to a triggering question, take a deep breath and ask yourself if providing a little context would lead to a deeper conversation (and one that is focused on an industry rather than on you).

For example, friends and family probably haven’t done the math around just how long it takes to write 70k, 80k, or 100k words. They might think you only need to write the first draft, run it through spell check, and call it a day, rather than going through multiple rounds of revision. If you’re feeling up to it, take a moment to share some writing realities with them.

Not everyone goes pro. 

If someone assumes that your version of success equals getting your book traditionally published, it might be helpful to point out that spending time on an activity you enjoy doesn’t mean you want to quit your day job. Lots of people take watercolor classes or train for marathons, but that doesn’t mean they want to become famous painters or sponsored athletes. 

Now, it is absolutely okay to use this tactic even if you do hope to publish your novel some day! Remember, you get to choose who knows what about your writing dreams, and this can be a helpful way to deflect unwanted scrutiny while protecting what’s important to you.

The money conversation. 

Ick, money. It’s a taboo subject for a reason. But if it does come up that you spent money (or want to spend money) on your writing, and you’re getting some raised eyebrows, I suggest you frame the topic this way: people invest in activities they enjoy all the time. 

Next, let the examples fly. Sports fans go to sporting events, and music lovers attend concerts. Knitters spend a lot on yarn, and it’s common for golfers to work with a golf pro. If you really want to be prepared, you can think of the interests that are popular in your family and have them at the ready. 

The fact is, if you want to go to a writing conference or hire a book coach, that’s how you choose to invest in your craft and you shouldn’t feel bad about it. (And no one has any right to make you feel bad about it!)

You don’t have to engage.

If someone asks how your book is coming along and they are not a safe person to share the truth with, then don’t. Give a vaguely positive answer and then redirect the conversation. “The writing is great, thanks for asking. How’s your pickleball game these days? I heard you were in a tournament.”

I hope that you don’t have to employ any of these techniques during your holiday gatherings. But if you find yourself in a difficult conversation, hopefully these tips will help you get through them with grace and confidence.

And while the holidays may be the hardest time to have these conversations, in reality they can happen any time of year. It’s worth your energy to draw these boundaries now so that you have them whenever you need them.