Connecting with Yourself: Journaling Prompts & Writing Exercises

When facing challenges, it can be helpful to take some time to connect with ourselves. Writing can help us process our thoughts and feelings and determine what actions we want to take. If you’re not sure what exactly to write about or where to start, consider using these 4 writing prompts and 2 journaling apps.


1. Self-Compassion Letter

Being kind to ourselves can take some serious effort. Meanwhile, our minds are often quick to criticize without much effort at all. Kristin Neff’s writing exercise provides an opportunity to flex that self-compassion muscle and strengthen the brain connections that support kindness to ourselves.

· Start by writing about either a mistake you’ve made, something you regret saying or doing, or any flaws that lead you to feel inadequate.

· Then, leave some space or draw a line and begin writing a letter to yourself from the perspective of a loving, empathetic imaginary friend who knows your strengths and weaknesses and accepts you as you are. If you are having trouble perceiving such a friend and what they might say, try instead to imagine you are responding to a friend or family member of yours who you know well and are compassionate toward.

· Now take a break from writing and come back to this letter later. As you read through it, allow yourself to feel accepted, comforted, and soothed by your words. For more in-depth instructions for this prompt, follow this link.

Explore this website further for more self-compassion exercises and meditations.


2. Unfortunately  Fortunately  Poem

Life can throw us curveballs (COVID-19, anyone?), and this exercise serves to acknowledge the ambiguity of the human experience. As we face hardships, we can acknowledge the weight of our challenges while at the same time recognizing who and what we are grateful for. In David Sheff’s memoir Beautiful Boy, Sheff adopts this writing format (from Remy Charlip’s book Fortunately) to cope with his son’s drug addiction. He writes:

“Fortunately there is a beautiful boy.

Unfortunately he has a terrible disease.

Fortunately there is love and joy.

Unfortunately there is pain and misery.

Fortunately the story is not over.”

· Begin with the word “unfortunately” and describe a challenge or difficult emotion you’re experiencing

· Write “fortunately” and describe a positive experience or something you’re grateful for that may or may not be related to the line before

· Repeat this until you feel you’ve hit your bottom line and have captured the elements of your experience

You can begin with either “unfortunately” or “fortunately,” but challenge yourself to end with a “fortunately” statement. Consider repeating the last line to yourself and recalling it throughout the day in times of distress.


3. Obituary Exercise

This exercise, often used in acceptance and commitment therapy, comes from the field of existential psychotherapy, theorizing that humans suffer as we struggle to accept the nature of the human condition and make meaning out of our lives. The idea is that we can live life with pain, death, sadness, regret, loneliness, and joy rather than trying to escape these elements and that we can learn to exist as part of something larger than our individual selves.

Writing your own obituary can be uncomfortable and overwhelming. I’m providing this as an option but it’s up to you to decide if you are comfortable writing in this way. The point is not to focus on death but to bring attention to the joys of life and to create a life worth dying for.

Challenge yourself to answer at least 5 of these prompts while writing in the third person using your preferred pronoun.

· ________________was a ________________________ who made it their life mission to…

· They will be remembered for…

· They made the world a better place by…

· In their free time, they loved to…

· These are 5 adjectives that best described them…

· They said “no” to…

· If they were still with us today, they would tell you that the most unforgettable moments of their life were…

· Their family will tell you that they were…

· To their friends, they were…

· Their partner will tell you that they were…

· They were most joyful when…

When you’re finished writing the obituary, notice without judgement how your current way of living matches or mismatches with the obituary. It is expected and natural that there will be mismatches! What can you do today or this week to align your life more closely with this description? If you notice any self-criticism creeping in, how can you respond to yourself in a kind and compassionate way? (See Journal Prompt 1).


4. Gratitude & Values Reflection

If you’re looking to journal daily for about 5 minutes or less, this prompt could be a good fit. I’ve found for myself that routinely writing 3 things I am grateful for before bedtime eventually turned into noticing and embracing good moments throughout the day, however small, as they occur in real time. These moments may be intentional and within your control, or they might be elements out of your control. On the other hand, the values checklist brings the focus to your behavior to celebrate how you’re living your life in accordance with your values. Not sure what your values are? Take a look at pages 23-24 at this link to determine what you find most important when living your life.

Acceptance and Commitment Therapy emphasizes values rather than goals because once you achieve a goal, the pursuit ends within seconds. For example, if your goal is to go to New Zealand someday, once you get there, you’ve reached your goal. But rather, if your value is to be adventurous, you can live this value while traveling to New Zealand, beginning a career transition, exploring a nature trail you’ve never hiked through, or trying anything new you’ve never attempted before. You can find big and small ways to live an adventurous life more regularly. This view also emphasizes the process rather than the product: upholding a growth-mindset and effort as opposed to focusing on achievement or lack of achievement.

· Towards the end of the day, write 3 things, people, or moments you are grateful to have experienced throughout the day that may or may not have been intentional on your part.

· Next, write down 5-8 values you find most important when reflecting on how you want to live your life. It’s natural for your values to change over time, so don’t feel stuck with the ones you initially choose.

· Identify 3 values that you lived by that day and describe how you did it. These do not have to be as grand as traveling to New Zealand, but could be. Simply listening to someone else would be one way of practicing the value of respect.

If you want to take this one step further, take some time to reflect on any obstacles that prevent you from living your values and what opportunities serve as gateways to living your life the way that you intend to.


Reflectly App

Although I love physical journals, one benefit of journaling apps is the accessibility for times when you don’t have a paper and pen. All your reflections are stored in one place, so you don’t have to worry about losing your writings! Please note that I am describing the free versions of these apps.

With each entry in the Reflectly app, you log your mood, elaborate on your day, and write a title for your story. The app then gives you a random prompt question, and you choose if you’d like to answer or not. Questions include “what would you do today if there was no tomorrow?” “What’s the worst habit you have?” and “What makes you laugh?” You can attach a photo for the day and swipe to look at your past entries.

When having a particularly bad day, looking through past entries can help put the day into perspective. Reading the joyful life memories and accomplishments as well as challenges you’ve faced and can serve as a reminder of your capability to navigate life’s ups and downs. I use this one a lot and love that I can read detailed memories that would otherwise naturally fade over time.


Longwalks App

I recently discovered this one, and it’s a keeper as well! This app helps you virtually communicate with loved ones on a deeper level. You can share your journal responses with your friends, family, or partner if they download the app. The couples conversations tab contains groups of questions titled “things I love about you” “things I love about us” and “let’s get it on” to spark communication between you and your partner. After each party completes all the questions, the app summarizes your partner’s answers in paragraph form, resembling a letter. The app also has family and friend conversations that include “things I love about our family” and “our favorite things.”

You can also dive into solo journals and create 8 positive affirmations with prompt guidance. Each day of the week has a different focus for the daily prompt. Sunday is gratitude, Monday is mindfulness, Tuesday is truth, and so on. Like the Reflectly app, you can access your journal history and scroll through all of your responses. I’m super impressed with this app so far and can’t wait to use it with friends and family while social distancing.


Written by Liz DeNio, Master’s Intern



Good Therapy. (2015, July 08). Irvin Yalom. Good Therapy.

Harris, R. (2009). ACT Made Simple: An Easy-To-Read Primer on Acceptance and Commitment Therapy. Oakland, CA: New Harbinger.

Liberationist. (2017). Write your own obituary. Liberationist.

Neff, K. (2020). Exercise 3: Exploring self-compassion through writing. Self-Compassion.

Sheff, D. (2008). Beautiful boy. Houghton Mifflin.

Photo by Alina Vilchenko from Pexels