What's the Thing You'll Regret Not Doing?

If you want to write a book, you need to write a book.

Go on adventure, write about it, repeat as needed // Museums Victoria, Unsplash

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When I talk to writers who are trying to start the work of unblocking themselves, something I hear a lot is: I just know that if I die without writing this, I’ll regret it.

Intense! But hey, writers are intense, it’s part of what everyone loves about us so much. (They do love us, right?)

And I get it. So often, what pushes us to write is something intense, deep, somatic. To me, the urge often feels like a little flail against mortality, a rebellion against the way our daily lives, if unexamined and unreported, can disappear into what Virginia Woolf called the cotton wool of non-being. This need to record often translates, for me, to both journaling and writing personal essays. What happened there? Why? How? What did it mean? I figure it out by writing it out.

Sometimes, that desire to plant some sort of “I was here” marker gets translated into an urgent and specific curiosity. For me, this is often what shapes a novel — some sort of question I can’t stop asking, and can best answer in a fictional setting, almost like applying game theory to human interaction. For example: What if a woman kept just making the literal worst decisions at every turn, even when the stakes were incredibly high? What would happen? (The premise of my first novel, wouldn’t you know.)

For some people, the unwritten book is about a specific story they have to tell — an experience they’ve had that is so unique that they feel they must share it — or an overlooked chapter of history or society or observation about life on earth that they want to dig into.

But whatever it is, behind every book there is some intense urge to create, and some desire to do a Big Thing.

(Fine, behind most books. I know some celebrities or celebrity-adjacent writers cash in on tell-alls, some experts want to build their brands, etc etc. But still! Even for them, I imagine, probably, there is a special pride in being able to say “I wrote a book.” I mean, it’s kind of amazing and truly strange that even in today’s not-super-literate world, writing a book confers some cultural cache but I DIGRESS.)

Because! A book, no matter how long it is or how many copies it sells or its cultural impact or how much money it does or doesn’t earn its author, is a Big Thing, a classic bucket list item. A sportier type may dream of running a marathon or climbing a mountain, but for indoor kids often the Big Thing is: A book.

This kind of book-making is about the doing, about setting a massive goal for yourself and achieving it. Someone who dreams of climbing a mountain doesn’t need to become a famous mountain-climber in order for the climb to have been meaningful in their life. Similarly, what happens to the book after you write it is not necessarily the measure of your success. (And it’s often not something you can completely control anyway, so let’s not worry about that for now.)

So what’s the thing you’ll regret not writing, but that for some reason, you’re not writing? Is it a specific story you have to tell, but you’re afraid of people’s reactions? Is it a kind of writing you want to try, but you’re worried you won’t know how to do it? Is it that you want to write, but imposter syndrome or self-doubt is holding you back?

Take a moment to freewrite, without thinking too much or editing as you go, the answer to these questions:

1. What’s the thing want to write or say so badly you know you’ll regret it if you don’t?

2. What, so far, has held you back?

3. What do you need in order to write it?

The third answer might be the most important. A big part of what gets us stuck in writing is usually psychological — often a block indicates that there’s something our unconscious hasn’t quite sorted out yet (as George Saunders writes about here). But also, sometimes the issue is logistics. Do you need to do a little more research? Do you need to make an outline, to soften your sense of overwhelm? Do you need an accountability partner? Do you need your romantic partner to say, Yes go ahead and write about that time we were abducted by UFOs on our first date, you have my full permission -? Do you need to create a structure — a daily/weekly/monthly writing time, or a writing group, or a scrum board — to help you fight the inertia of not-doing? Do you simply need the time, and can you figure out some resourceful way to carve it out, even if in tiny amounts?

Probably, if you are alive on the planet, you have solved some complex logistical problems before. You’ve studied for 3 exams that fell on the same day, or you’ve planned a vacation or a huge party, or you’ve juggled priorities at work. You know, on some level, how to solve a puzzle. Apply that now.

And don’t dismiss blocks as laziness. There’s often something quite deep happening, and chastising yourself about it changes the subject. Instead, give yourself the tools you need to do the work you’ll regret not doing.

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Where in your writing life is there tension right now? If you have a particular project you want support on, or a manuscript that needs an edit, or if you’re looking for a regular writing coach or accountability partner, head to my website and book some time to chat. 

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And! I also want to let you all know that I have some new classes (Writing for Women on the Verge, anyone?) listed at Writing Co-Lab, the experimental education cooperative we launched earlier this year! More instructors and more classes will be up on the site soon, so check them out. :)