Writing Our Lives 2019 Personal Essay Prompts

I started off the year gifting a Personal Essay prompt a day for the first seven days of 2019. I then decided to gift a prompt a week, starting on January 14th. I’m collecting them here for your enjoyment. This is courtesy of Vanessa Mártir & the Writing Our Lives Workshop. Enjoy & let me know how it goes! Happy 2019!

January 1st: Write a list of at least three stories that haunt you, that you revisit again and again in your memory &/or stories. Try to include at least one that brings you joy. Pick one from the list. Write for at least ten minutes with that story in mind. Focus on imagery and your senses. What do you remember seeing, smelling, tasting, touching, hearing? How does it feel in your body?

January 2nd: In the movie Precious, the protagonist Clareece “Precious” Jones says about her teacher Ms. Rain: “Some folks has a lot of things around them that shines for other peoples. I think that maybe some of them was in tunnels. And in that tunnel, the only light they had, was inside of them. And then long after they escape that tunnel, they still be shining for everybody else. That’s Ms. Rain to me.” Did you have a Ms. Rain in your life? A teacher or mentor who believed in you, fought for you and pushed you? Who was that person? Write the story of how they saved or helped you. Be sure to show the relationship not just tell it. What did they save you from? Why did you need saving?

January 3rd: Draw the floor plan of a place from your childhood. It can be your bedroom or your backyard, the playground you played in, your best friend’s kitchen, the block you grew up on. Just keep it focused & include as many details as possible: What colors stick out? What do you smell, hear, etc? As your draw, memories will come flooding in. Make notes so you remember then keep drawing. When you’re done, you’ll have a list of memories. Pick one. Preferably the one that’s most charged. Write the memory. Use your senses and imagery. Show scenes. Consider why this memory is so ripe with emotion? Who is there? What influence have these people had on your life, then and now?

January 4th: Who are the people who show up consistently in your writing? Write a list of at least three. Pick one. Now write a list of memories with that person. Remember the person’s humanity. Try to think about their positive and negative traits. Show their complexities. Now write about the relationship. Why does this person come up so often in your work? What was/is their influence on you? Is your relationship antagonistic or loving? Show this.

January 5th: Write a list of your favorite dishes, that you make yourself or were made for you: a soup your mom made you when you were sick as a kid, your aunt’s baked chicken, your grandma’s rice pudding, the beef neck bone soup you taught yourself how to make, that pizza you had at Pinocchio’s in Harvard Square way back when. List at least three. Now choose one. Write about the time(s) you’ve had this meal. Be as descriptive as possible: who was there, when was this, what do you smell, taste, etc. How do you feel as you’re remembering and writing? How does it feel in your body? Why do these memories provoke that reaction?

January 6th: Who have been the great romantic loves of your life? List them. Write on how you met, what you remember most about each relationship, why they didn’t work and/or fell apart. What did these great loves have in common? How were they different? What did you learn from each one? How did you grow? What cycles did you repeat? Who or what can you trace that back to?

January 7th: Do you have regrets or things you would do differently were you given the chance? List a few of them. They can be regrets about love or decisions about education, career, friendship, etc. Pick one from your list. Write on what you would do differently. Consider what you did, how it manifested in your life, what good and bad came of the decision. Do you think you would be who you are and where you are today had you done some things differently? Would it be worth it to go back and make that change? What can you do today to bring you closer to that person you wish you were now had you done behaved differently?

A personal essay prompt a week in 2019

January 14th:

List 3 ages. Eg: 5, 15, 25

List 3 emotions. Eg: joy, rage, shame.

Pick one emotion..

Close your eyes: Where do you feel the emotion in your body? Eg: I feel rage in my jaw.

Set a timer and write for 3 minutes on a memory of this emotion at the ages you chose. If you picked joy and the ages 5, 15, & 25, you will write for 3 minutes on feeling joy at the age of 5, 3 minutes on feeling joy at 15, & 3 minutes on feeling joy at 25.

Reread what you’ve written. Is there a thread or common theme in the memories, besides the emotion? Write on that for 3 minutes.

January 21st: In “Literature’s Troubled Legacy of Grieving Madwomen” (Bitch Magazine, Fall 2018), Ilana Masad writes:

Perhaps so many grieving women become mentally unstable because we culturally refuse to validate grief as a part of life. Women may have it right, though, in literature as in life: Going mad may be the only rational response to losing a loved one, to losing one’s own self, to losing one’s sense of dignity and worth. Maybe we don’t need to prioritize sanity and composure in the face of grief; perhaps we should all be allowed to go a little mad.

Write about grief that drove you mad. What/who were you grieving? How did it feel in your body? Were you able to transform that grief into something else? How? Share your process.

January 28th: In his seminal book “The Body Keeps the Score”, Dr. Bessel Van Dee Kolk writes: “Being able to feel safe with other people is probably the single most important aspect of mental health; safe connections are fundamental to meaningful and satisfying lives.” Write about the people who have made you feel the most safe. What did they do for you that made you feel so safe? Write about specific instances & gestures. Write scenes. Use your senses. What does safety look like? How does it feel in your body?

If you have experienced trauma, this will likely trigger memories of being unsafe. Remember to take care of yourself while you dig into this. Self-care is critical while doing this work.

February 4th: Write a list of social issues you are passionate about. Pick one and write about why you’re personally invested in it. Write the story of what happened to you or someone you love in your past that has made you particularly invested in the issue. Be specific. Show me, don’t just tell me.

For example, gay rights is a big issue for me because I was raised by lesbians & because I am a queer woman in a lesbian relationship. When I saw the conservative backlash to the cover of the February issue of Parents Magazine, featuring the first same sex couple in the magazine’s history, I knew I had to write about it. That essay, “Teaching my daughter that love is love,” was published last week in the Washington Post.

February 11th: Friendships are vital but we don’t often talk about how to cope or move on when they end. There’s an expectation that friendships should be easy for adults, but we all know that isn’t true. Friendship breakups are often harder than the romantic kind. Write about a friendship breakup you had as an adult. Show the relationship in scenes and anecdotes. Show what happened that the relationship ended and how you coped (or didn’t cope). Own your role in the demise of the friendship. This isn’t about vilifying or victimizing anyone. What would you say to this person now? How have (or haven’t) you grieved the loss? Consider other friendship breakups you’ve had over the years. Do you see a pattern arise? If yes, what does it say/mean about you and the people you tend to befriend?

February 18th: Boundaries are a part of self-care. They are healthy, normal, & necessary, but it often takes us a lot of time & countless disappointments & heartbreaks to realize this. Write about your journey to setting boundaries with someone—a friend, family member, romantic partner. Show how they behaved inappropriately or in some way violated your trust so you had to set these boundaries. How did they react to your challenging their behavior? Did they get angry & defensive? Did you, in turn, feel guilty? Did the relationship survive or was it irrevocably damaged as a result? What did you learn from the experience? If you could go back in time, would you have responded differently? If so, how & why?

February 25th: Trace your journey to becoming a writer. How did you come to writing? Do you remember when you first started telling stories, to yourself and to others? Do you remember where? When did you realize you are a writer? When did you own it? What made you own it? Have you answered the call? How? Remember to show scenes. What did it feel like in your body? What does it feel like now?

March 4th: Write a list of “firsts” — i.e. first time you kissed someone, first time you drove a car, first job you had, first time you had a drink, etc. Select one. Write about how you felt. Who was there? Show and tell. Repeat this for as many on your list as you want. Then reread your writing. Is there a pattern?

March 11th: I read on Twitter some time ago that on her desk writer Tayari Jones has “a tiny jar containing a few spoonfuls of earth from Lorain, Ohio. This is how much I love Toni Morrison.” I thought of the junk yard next to the building I grew up in in 1980s Bushwick and our backyard where I climbed up that plum tree so many times. In those connected yards was where I started telling myself stories. It was there that I first became a writer.

If I could, I’d have a tiny jar containing spoonfuls of that soil from back then—the soil that fed my mother’s garden and molded and saved that girl I was who is now this woman writing these lines.

On my desk I have a jar containing soil from the forest of Inwood Hill Park, where I found my footing again so many times over the years, especially after my brother’s death sent me reeling into the darkest place of my life in 2013.

If you could have a jar of soil from any time and place in history, where would it be from and why? Use detail. Show what that place means/meant to you. Why do you want to honor it in this way? Give me scenes. Build a world.

March 18th: If you write about your life, chances are you write about your family. We can’t get away from them and how they’ve shaped us, but it’s difficult to write about the people who we love the most and have also hurt us the worst. How do we write about family with honesty and respect?

I tell my students: Let the small things do the work. For example, what can emerge if you write about hands: yours, your mother’s, your grandmother’s, your brother’s; or the way family members sigh (check out Bernard Cooper’s “The Fine Art of Sighing” as a model).

Your prompt for this week: Make a list of family members, then pick a body part (hands, feet, noses) or a simple human act (how they laugh, sigh, etc) to write about these people. What can you tell about your mother by describing her hands, how they’ve held you, cooked for you, beat you, etc? What can you tell about her by describing the way she laughs, when she laughs, how she laughs, etc? Repeat this for each family member. See if a pattern emerges or if you have any revelations.

March 25th: Write about where you were raised: the block, neighborhood, town, city. What memories stand out about that place. Why? How do you think being raised there shaped you? If you were raised in various places, write about each place and the memories of that place.

To help jostle your memory, you can draw a map of the block and/or neighborhood. Include where you played, went to school, went food and clothes shopping. Where did your friends live? Your first love? Your enemy? Expect memories to come flooding in. Write them down as you go.

Locate yourself in the history of the place. Do some research: What native tribes inhabited the place? What happened to them? What immigrants lived there during what times? How were the blocks named? When and how did your family come to live there? Etc.

April 1st: Was there a news story from childhood or your teen years that fascinated you?

For example, as a child in the early 1980s, I was taken by images of Beirut that flashed across our TV screens. The city was described as devastated and war-torn. I was too young to understand what was happening or why, but what got me was that Beirut looked so much like my neighborhood, Bushwick, Brooklyn, with its rubble for blocks and burnt out buildings.

It was in my digging that I learned about the Fire Wars in NYC, the blackout of 1977 and the riots, which all contributed in creating the Bushwick I grew up in. Many of the burnt out buildings became crack houses in the crack era.

What news story caught your attention as child? Why? Write on this. Do some research on the news story. See if you can make a connection to your life, family, neighborhood, etc.

April 8th: I’ve found illness to be one of the hardest topics to write about, so I thought we could try it this week.

Write about a time you were sick or struggled with an illness or condition. It can be anything from the flu to depression to diabetes, whatever. First write about your specific experience with the illness. Write the facts (where you were, age, how you got better or didn’t, were you hospitalized, etc) and don’t forget to write about how it felt in your body.

Now, do research on the disease and it’s causes—environmental, psychological, etc. Do you think life circumstances contributed to this? What about environmental factors? Stress, etc? Write on this.

Consider this: I was born with an enzyme disorder that wasn’t discovered until I spent months in the hospital and my mother was told I wasn’t going to make it. In my research, I discovered an incredible metaphor that I am still unpacking:

Enzymes are the work horses of the body. They are necessary for just about every metabolic function in the body and control the speed of chemical reactions in your body. Without enzymes, these reactions would take place too slowly to keep you alive.

Dr Babatunde Samuel writes: “A chemical reaction without an enzyme is like a drive over a mountain. The enzyme bores a tunnel through it so that passage is far quicker and takes much less energy.”

At months old, I had to teach my body how to bore through mountains. This should dispel any doubt that I am unfuckwithable! Ha!

April 15th: What is your spiritual practice or do you wish you had one? Were you raised in a religious family? What was that like? How has that shaped you as a person? Have you continued that practice in your adult life? Why or why not?

If you weren’t raised in a religious or spiritual family, how do you think that shaped you into who you are now? Have you heard stories from the faithful and wish you had that kind of surety in something bigger than you? Or are you comfortable with where you are in your spirituality or lack thereof? Why or why not?

Write scenes. Show, don’t just tell. Where were you in your body when these memories were occurring in real time?

April 22nd: In the spirit of Earth Day, this week’s prompt is about the outdoors:

Write about your memories of times in nature. Did you go to the beach with your family as a kid or do you come from a family of hikers and/or campers? Write about times you spent with your family and friends. What sticks out to you about those times? How did you feel? Safe, worried, loved, endangered? Why?

Have you found the outdoors healing like I have? Are you a lover of picnics and camping? Or do you attach memories of nature to feeling unsafe and/or alone?

Whatever you write, be sure to include scenes and show how it felt in your body.

April 29th: In her recent Netflix special, Brené Brown says: “It is so much easier to cause pain than to feel pain. People are taking their pain and working it out on other people… When you don’t acknowledge your vulnerability, you work your shit out on other people.”

Write about a time you took your pain out on someone. Maybe it was a lover or friend. Maybe you lost someone as a result of your behavior. Maybe you’re still resisting admitting that you weren’t your best self in the situation.

The truth is that few of us are as noble as we think we are.

This prompt may be difficult but remember that it’s when we acknowledge our missteps that we become better and less likely to behave in that way again. And often writing about the ways we’ve erred makes for great storytelling. Write on!

May 6th: Write about a body part or feature you love—your eyes, smile, belly button. feet, anything. Why do you love this part of yourself? Have you been complimented often on this feature? Does it remind you of someone? Remember to write scenes.

Write about a body part or feature you have conflicting feelings about or that you have had to teach yourself to appreciate because of how you were treated as a result of it. Perhaps you developed early and got unwanted attention as a result. Or perhaps you were teased because you have Flintstone feet and hands. Be sure to include scenes in your telling. Show your emotions and your journey to how you feel now.

May 13th: I am newly married & feeling joy & love-filled so this prompt will reflect that:

Write about joy you’ve felt, experienced & witnessed. Tell about what you’ve done right in the world & in your life, & how knowing that & doing that has brought you and continues to bring you joy. Where do you feel that joy in your body? How does it manifest? Remember to write scenes; bring the reader into the moments with you. Where do you feel that joy in your body? How does it feel there?

May 20th: If you look up the word spirituality, you’ll find there’s no one clear definition. Some connect it to the human spirit/soul. Others say it’s about religion and clergy. Others mention the spirit world, while others contend it is a personal connection to something larger than ourselves.

How do you define spirituality, if at all? Do you have a spiritual practice? What has been your spiritual journey? Have you gone in search of God or some force outside of you, or have you searched for and perhaps found God in yourself? Are you atheist? Trace your spiritual journey from childhood. Do you shun organized religion or have you found that to be your path? Are you called more to an earth-based, shamanistic connection to the spirit world?

Whatever your path, write about how you got to where you are? How did you meet spirit/God? Write scenes. Show what the journey felt like in your body. And if you haven’t found a path at all, write about the confusion, absence, ambivalence, whatever it is you feel and how you got there. Just remember to show and tell. Take the reader along for the ride.

May 27th: Dr. Clarissa Pinkola Estes writes in Women Who Run with the Wolves: “…we must all, on a regular basis, use our instincts and find our way back home.”

Write about a time you followed your instincts to re-find yourself. Perhaps this happened literally—you got lost in a city or the woods and had to rely on your instincts to find your way. Or perhaps you were lost in a relationship and had to claw your way out. Did you have to unlearn dysfunctional behaviors you learned in childhood? Can you look back to eras of your life and recognize that you were lost, though you didn’t know it then? I certainly can!

Write on this. Show moments where you relied on your intuition to ground and locate yourself :: what did this look like, smell like, taste like, etc? How did it feel in your body?

June 3rd: This weekend I worked with a writer who lost her brother recently. In conversation I told her about “learning to love the bombs,” a phrase I learned from a GQ interview with Stephen Colbert where he shares how he learned to love the worst thing that ever happened to him—losing his father and brothers in a plane crash when he was a kid.

Colbert was 35 when he could really feel the truth of that. He was walking down the street, and it “stopped me dead. I went, ‘Oh, I’m grateful. Oh, I feel terrible.’ I felt so guilty to be grateful. But I knew it was true.

“It’s not the same thing as wanting it to have happened,” he said. “But you can’t change everything about the world. You certainly can’t change things that have already happened.”

I thought of the bombs that nearly took me out: being unmothered and losing my brother in 2013.

It’s taken me a long time to see and accept just how much these bombs shaped me, how they grew me and saved me in so many ways.

That’s how I learned and am still learning to love the bombs…

Write about the bombs you’ve endured and what you learned from them. How did you/are you still surviving them? Have you learned to love the bomb?

June 10th: In a recent episode of Spike Lee’s She’s Gotta Have It, Nola’s therapist says during a monologue: “Individuation. It’s the process required for self-actualizing. I haven’t spoken to Nola in a while. I think it’s because she’s in the thick of it. Individuating. Whether you’re talking about friends or family, people you admire or despise, you have to individuate your wants from theirs in order to honor your true self. It can be a thrilling and painful process. But who wants to see or be a black orchid that never fully opens?”

Write about periods of individuation that were particularly memorable. What did you lose? What did you gain? How are you different as a result of it? Was it worth it?

June 17th: The first episode of Season 2 of Pose ends with the quote “Silence = Death.” Sometimes we’re silent because we think (hope?) it will protect us but Audre Lorde insisted: “your silence will not protect you.”

Write about moments you’ve been silent and wish you hadn’t been. Examine why you remained silent. What were the repercussions?

Also consider moments you weren’t silent and wish you had been.

Remember to write scenes. Show AND tell. Use your senses. Tell the reader a story!

June 25th: People love to give advice, especially the unsolicited kind.

Write about the worst advice you’ve ever received. The one that sticks out for me was about my grieving process when I had a major loss, and what I should and shouldn’t do, how I should & shouldn’t feel. The lesson: most people don’t know shit about grief & don’t know how to be present for the grieving.

Write about the worst advice you’ve ever gotten. Why was it so bad? Did you realize right away it was terrible advice? It not, why? How did you come to the realization? If yes, how’d you know so quickly?

Next write about some good advice you’ve been given. Who gave it to you? Why was it so good? Did you use this advice in your life? How?

July 1st: I’ve been thinking a lot about music and memory. When I think of certain people and certain eras in my life, one of first thing I think of is music.

When I think of my mother, I think of ballads by Camilo Sesto, Juan Gabriel and Rocio Jurado. In the scene, my mother is mopping, the smell of King Pine encircles her. Her eyes are closed. Her head is thrown back and she is singing along a to’ lo que da. She has that expression people have when they are worshipping something.

When I think of my tween years in Bushwick, Brooklyn, I think of freestyle music and that in turn reminds me of my sister, her teased her, her style of dress, how I worshipped her.

My brother is all Depeche Mode, early Madonna and U2.

My Millie, the butch who raised me, is old school salsa by Eddie Santiago and Tito Nieves, and the disco song “You Can Ring My Bell.”

Make a list of three people who come up in your stories often. For each, write a list of the music that comes up when you think of them. What specific songs and genres? Explain why the music triggers memories of these people. Try to show scenes.

Do the same for the places you write often about. For example, when I think of boarding school in Wellesley, MA, the soundtrack includes Bob Marley, Nirvana and Red Hot Chili Peppers. I remember school dances and hearing Marley’s “Legend” for the first time.

July 8th: If you have a sister, chances are growing up you were told you are your sister’s keeper, meaning you are responsible for her, are supposed to protect her and support her however necessary. But what if your sister was abusive and unkind, like my sister was? What then?

In this prompt, you will be writing about a contentious sibling relationship. If you are an only child, write about a difficult relationship with a cousin or peer.

Write scenes to show how this person treated you. Consider how this has affected you in other relationships. For example, have you had trouble being befriending and trusting women? How have you healed, if at all?

July 15th: I’m learning that often loving and taking care of yourself means distancing yourself from people who are not safe, loving or kind, and have proven themselves untrustworthy. Sometimes this includes family and/or friends you once considered ride or die.

Write about how you learned this. Who did you have to go no contact with and why? How have they been unsafe in the past? How have they shown themselves to be untrustworthy? What was the final straw? How do you feel about this decision? Do you feel shame and/or guilt? Do you feel free? Is it more complex and nuanced than this? Explain.

July 22nd: I’ve been thinking a lot about the risks we take, in our lives, in love, in our writing. I am a huge risk taker and have been digging into why that is. When you lose so much, some risks don’t seem as big or risky.

Write a list of risks you’ve taken. It can be anything: you traveled alone, jumped out a plane, moved somewhere far from your loved ones, told someone you had feelings for them, etc. Pick one from the list. Write it with scenes, etc. Remember to write how it felt in your body. Examine why you were willing to take that risk. What gave you the courage? What did you learn about yourself? Would you do it again? Why or why not?

August 2nd: While on a vacation escape in the woods this week, I remembered that I feel most myself when I am in and with nature. Even as a child growing up in the city, the backyard (especially the plum tree) were where I ran to return to myself.

What are your escapes? Write about how you found them or how they found you. Be specific. When have you escaped to this place? What makes (has made) you go there? What were you running to and from? What does this space provide that no other place can? Describe the place including what it feels like in your body when you’re there.

August 5th: Literature has saved me so many times. As a child up in the plum tree, telling myself stories helped me survive the abuse I was enduring. I went to the library several times a week and ate up all the books I could; so much so that the RIF librarian knew me by name and saved books for me. This love for storytelling has followed me in my life. I remember when I first read How the Garcia Girls Lost Their Accents by Julia Alvarez and believed for the first time “maybe I can be a writer too.” To this day, books are where I go to find understanding, meaning, escape, entertainment, heart rattling and more.

Write about the stories and books that have stayed with you. Is there book you’ve read again and again? Is there a poem you return to repeatedly? Have you read a book recently that shifted your whole axis, that you know you’ll be processing for a while?

What has story gifted you that nothing else could? Why?

August 12th: When writing about our lives, it’s often easier to remember the bad times, the losses, the ways we were done wrong, but what about the joy? Over the past few weeks I’ve been documenting joy: Family trips to the beach that took days to prepare for, playing house with my siblings, creating worlds in the plum tree in the backyard. I’ve even started posting these mini-stories on a wall in my office I’m dedicating to joy. I’m calling it my Joy Wall.

Make a list of joyful moments from childhood and beyond. Write a few sentences for each. Then pick one and expand on the story. What was joyful about the experience. Who was there? What did you do? How can you keep these memories close to remember them when you’re working on more difficult stories?

August 26th: In her epic tome “Women Who Run with the Wolves”, Dr. Clarissa Pinkola Estes writes: “I am convinced, both as a psychoanalyst and cantadora, that many times it is the things of nature that are the most healing, especially the very accessible and the very simple ones. The medicines of nature are powerful and straightforward: a ladybug on the green rind of a watermelon, a robin with a string of yarn, a weed in perfect flower, a shooting star, even a rainbow in a glass shard on the street can be the right medicine. Continuance is a strange thing: it puts out tremendous energy, it can be fed for a month on five minutes or contemplating quiet water.”

Write about a time nature gave you the hope to move forward and believe again. I think of the hummingbirds that came to me when my brother first died, and, for years after, visited me on the anniversary. Be specific. Include detail. What did it feel like in your body?

September 2nd: Life takes us by surprise sometimes, knocking the wind out of us, leaving us feeling confused and lost. Consider the times this has happened to you. Perhaps it was an accident that happened, a death, a loss of a job or friendship.

What did you do to take care of yourself? Did you pick up a new hobby? Did you lean on friends? Did you seek therapy? Write about the ways that you’ve learned to hold on and keep going. Can you trace these adaptive techniques back to childhood or another time in your life? Did you learn this from someone?

September 11th: Growing up, this day only meant it was my best friend’s birthday. That changed in 2001, when this day took on a devastating meaning. Most people remember where they were when the first plane hit & when the towers fell. How could we not?

Write a list of what you remember about that day and the days after. Consider: Did that day have special significance before 2001? What images and people stick out to you? What about people’s behavior do you remember?

Write a list essay about the day, working towards a specific revelation you had about yourself or the world.

September 17th: I’ve been thinking about the ways we run away or lose ourselves when we’re overwhelmed, traumatized and/or not wanting to confront the reality of our lives. I’m specifically talking about the things we convinced ourselves we were doing for one reason but realized, in retrospect, the real motivation was completely different.

I’ve run away & avoided in so many ways—from rollerblading for hours and miles in my early and mid twenties to working out obsessively and hiking. I see now that my running away has often been physically grueling. I’ve also lost myself in books, alcohol, emotionally unavailable people, and so much more.

What about you? Write about the various ways you avoided the truth, your trauma, etc. Be specific. What precisely did you do to avoid? Show when you started and when you discovered what you were really doing.

September 23rd: Most people have had a number of jobs in their lifetime. I have been working since I was 13. In high school, I worked as a babysitter, a cashier in a supermarket, a “scooper” in an ice cream shop, and a data entry clerk in an accountant firm.

Writers & artists, in particular, often work numerous jobs before finally deciding to pursue their art, and even while pursuing it. I’ve worked countless corporate jobs from finance to publishing to medical management; at nonprofits, in administrative, editing and writing roles. It was when I landed a teaching gig 15 years ago that I found where I belonged. I’ve been writing all along.

Trace your employment history. What did you learn from each job? What essential skills did you learn? What specific lessons &/or experiences stick out? How do they feed or help you in your life and art? Be as specific and detailed as possible.

October 1st: I’ve realized, in the writing, that I have not forgiven myself for the girl and woman I was who let people treat her poorly, who clawed for the love of emotionally unavailable people…the woman who did not love herself enough to demand more & didn’t leave when what I deserved wasn’t given. I am working on being gentle and kind to the woman I once was.

What have you not forgiven yourself for? What are you doing &/or what can you do to get yourself there? To love yourself through it? To be gentle with the younger you who didn’t know better?

October 8th: There are less than three months left to the year and decade. Think about who you were when you started this decade back in 2010. Did you imagine you’d get to where you are? Why or why not?

List your accomplishments and successes.

List your obstacles and losses.

List your failures.

Consider them together.

What would you do the same and what would you do differently?

How have you grown, changed, stayed the same?

What can you do in the final quarter of 2019 to bring you closer to who you hoped you’d become this decade?

How can you take this into the new year and the new decade?

October 14th: This prompt is inspired by overwhelming generosity I’ve been on the receiving end of…

Write a list of times you’ve been on the receiving end of someone’s generosity. Now write about how you reacted. Did you dismiss a compliment? Did you turn away an offer of help?

It doesn’t have to be a huge offering. If can be as simple as someone offering to help you with groceries, a sincere compliment on your smile, an unexpected note of gratitude in your inbox.

What I really want you to examine and write about is why you struggle(d) to accept said generosity? Did you consider yourself worthy it? Do you now? Where do you think this comes from? What is at the root? Who told you you don’t deserve such kindness?

October 21st: I am more myself in the forest than I am anywhere. I thought the root of my love for nature was the plum tree in the backyard of my childhood home in Bushwick, Brooklyn, where I became a writer, but I recently discovered I was wrong.

What’s your happy place? Why? What memories do you have in that place? Are all of your memories of this place happy?

Write a list of happy memories from childhood and adolescence. Is there a place that comes up repeatedly in these memories? Could this be your happy place?

October 28th: For a long time after my brother’s death, I couldn’t listen to certain songs and bands because I’d end up inconsolable, sobbing loudly wherever I was — Tracy Chapman’s “Fast Car”, anything by Depeche Mode.

What songs/bands remind you of a dear lost one? What memories do they conjure?

Six and a half years later, these songs make me smile and tear up at once. I now remember joyful memories not just the loss — his shady humor, his love for all things fashion (he had Gucci taste with a Target budget), how much he loved me. It was a journey to get here, where love and grief exist alongside one another.

Write about your journey through your grief. What role has music and art played? How do you use art to remember and honor your loved one?


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