How to Get Started on Writing Your Deepest, Most Honest, Most Personal Essays

We all have those things we know we want (maybe even have) to write about, but find difficult to get into. Here’s how I push myself to start getting those deeply personal essays onto the page.

We’re honored to have Caroline Rothstein teaching the upcoming Narratively Academy class, Deeply Personal: Writing First-Person Essays on Raw and Difficult Topics (starts February 25, 2 seats left). Today we asked Caroline to share some deep thoughts on how she gets started writing about the most challenging and intimate personal essay topics.

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I’m a multi-hyphenate writer-artist-poet-performer-filmmaker, which means the possibilities for what I choose to do with an idea generally feel expansive, but also sometimes daunting. Over time, I’ve found that my creative ideas that want to be personal essays are the stories and experiences that make me desperate to — pardon my French here — work my shit out on the page.

Poetry tends to be where I go to process my feelings or wonders of my soul. Journalism — where I process my relationship to other people the rest of the world. Theater — where I explore interpersonal dynamics. Film — humor. Fiction — the snarky voice I’m too timid to use IRL.

And personal essay? It’s where I turn when I need the space to let the page reflect back to me who I am, and what it means to have experienced that which I have — personally — experienced.

I also use the personal essay as a place to really, truly, gut-wrenchingly slow down a moment, and allow it space to air out and breathe — like hang-dry laundry, contending with the wind.

Personal essay writing might be something entirely different for you. Maybe it’s the only writing craft within which you work. Maybe you’ve never tried it before whatsoever, and you’re curious to give it a whirl. But that’s the point of the class I’m teaching this winter/spring: Deeply Personal: Writing First-Person Essays on Raw and Difficult Topics.

Our goal will be to — in community — discover who we are as writers. To hone our own inner writing — and intuitive — antenna. To listen to our deepest selves. To cultivate and strengthen our abilities to write and say — on the page — what it is we both want and need to explore.

Here’s one exercise I like to use to help writers start listening to their inner selves and identify exactly what they want to write about:

First, I invite you to take a deep breathe (or three) with me, to whatever extent that feels comfortable.

Next, grab a pen and some paper, or open up a document in which to write (whatever helps you feel most comfortable in crafting anew).

Cool. Now I invite you to make a list of three to five topics about which you feel like you most consistently or typically write. Especially ones where you’re like — seriously, self?! That again?!

For me, that list is:

• Mental health, mental illness, and body image

• Grief, loss, and death

• Consent and sexual assault survival

• Social identity, systemic oppression, and collective liberation

• Sex, romance, and relationships

You got your own micro list (that probably actually feels more macro than micro, perhaps?!)? Great.

Now I invite you to take a look at that list. Item by item. And ask yourself these three questions as you do a little accounting and thoughtful interrogating of each of the three to five things:

1. Where does this topic feel expansive?

2. Where does this topic feel stagnant, stale or stuck (if at all)?

a. If this topic feels stagnant, stale or stuck, why do I think that’s the case?

3. What am I still not saying that I want to say about this topic/theme/thing?

Here’s how I rocked out #3 for my above list, to peel the curtain back a bit (this is actually a scary exercise, and I always say — and honor — in workshops and classes I facilitate that anything I’m asking participants to do, I’m doing too! Buckle up!):

All right, so per #3:

The answer to all of them is: JOY! LOL. I know it’s not the cheeriest list (UNDERSTATEMENT TIMES INFINITY), but in doing this exercise myself, I realized that there are moments of joy and abundance in every category that I could amplify and center far more often than not. And yes, I tend to write about resilience in all of these five arenas, but I’m curious what might come out if I started from a place of joy, rather than resilience.

OK. That may have taken a few minutes. Cool beans. Take whatever time you need.

And once you’re finished with that exercise, I invite you to now ask yourself this:

What am I not writing about that I wish I would and/or could write about?

Make a list of two to three things.

Once you’ve got that list, ask yourself — for each item on the list: Why?

Why am I not writing about this thing?

So, for me, it was:

• Fear of how it might impact my career

• Fear of how it might impact other people I love

• Fear of getting “canceled”

Anyone else? Anyone, Bueller?! And listen. I get it. If your “whys” look like mine — or whatever they look like — they are ridiculously legit. What I do when my “whys” look like that is some deep soul searching around what’s real versus what’s imagined, especially with my fear of “getting canceled.” And then when it comes to impacting people I love — which is important for me in my own work, since so much of the work I publish is extremely personal — I have conversations with people I love about the thing I want to write and learn what their boundaries and limits are, so I can honor them.

OK. I’m taking a bunch of deep breaths now again myself, if you’d like to join me.

Inhale for four. Exhale out for four, as well. And again, however feels good and right for you.

So now you have two very important things: the “what am I not writing about” and the “why”?

For me, making a list like this helped me get moving on my own personal essay series, where I’ve written about what it looks like to breach my own consent needs, my thoughts and feelings about Netflix’s first season of Nobody Wants This (that might seem silly that this was a vulnerable stretch for me, but I loathe writing commentary and reviews, so…), my feelings about reconciliation and boycotting artists we previously loved, thoughts about anti-carceral feminism and disembodiment, and the both/and-ness I find inherent in Jewish identity.

To name a few.

And while some of these topics ARE things I often write about, these were all pieces where I pushed myself to go deeper. Where I genuinely ushered myself to get below my usual ish.

My Deeply Personal class is about helping each writer build a set of tools and options that provide you with as many containers, formats and techniques as possible to ensure that each idea, experience, story or moment you want to explore through personal essay has a way to find itself a home.

With your words. With your writing. On the page.

Because I believe what keeps us from getting to the raw, what keeps us from ushering ourselves to write that which feels difficult, is not a lack of craft, or desire, but a lack of tangible pathways.

Together, through lessons, readings, in-class activities and exercises, supportive peer feedback, and perhaps most importantly, by doing it all in co-create community, we’ll dive extra deep.

I’d love for you to join us. There are still a few slots left.

Happy writing, whoever and wherever you are, and however you choose to swim in your craft.

P.S. If you want to take a (deeper!) look at how I navigate some of this myself, here’s my own essay series.