Could writing about your pain help you move forward? The journalling prompts to try during life’s big changes

Words: Jackee Holder. Images: Shutterstock.

I’m still moved by the recent memory of a close friend’s wicker casket being filled with sprigs of lavender, tucked gently into the basket weave before we said our final goodbye. The scent of heady lavender buds filled the chapel, a tender gesture that stays with me. But while death gives us a brief window to grieve, the quieter disappointments of daily life rarely receive such permission. Left unattended, these sorrows accumulate. This is why it matters to face pain rather than bury it.

This is where the practice of journalling through transitions becomes a powerful ally. Human instinct is to push pain aside. We distract ourselves, numb out, or pretend it isn’t there. But that doesn’t make it disappear. Pain doesn’t leave when ignored. It just goes underground. And when it resurfaces, it often shows up as anxiety, fatigue, or feeling cut off from ourselves and others.  As Julia Samuel, author of Grief Works, reminds us, pain is the agent of change.

It tells us something needs attention. When we face it instead of dodging it, we move closer to clarity, wholeness, and even joy. I’ve seen this in my own life and in the lives of clients. Once we stop running from emotions we begin to feel more alive. Our inner world expands, able to hold both sorrow and joy.

Pain points us toward change, but change itself takes many forms. To understand how journalling supports us, it helps to see that transitions are not only about loss through death, but about the thresholds we cross in daily life. Transitions show up everywhere, not just in times of death. A teenager becoming an adult. A marriage ending. A move to a new home. A career shift, wanted or not. Life is full of thresholds. Some we choose. Others arrive uninvited.

Too often, we push forward without pausing to notice what we’ve left behind. Change isn’t just physical — it’s emotional, too. And that’s where journalling comes in.  Journalling through transitions, a method developed by Leia Francisco, invites us to pause and give these moments space and time to be examined in our journals.

It’s a way of closing circles of change rather than leaving them open and unsettling. The practice of writing through a period of change can help us make sense of loss, regret, and disappointment. Recognising a transition is only the first step. The question becomes: how do we process it?

Journalling has huge potential to provide a safe container for grief and confusion. By placing feelings on the page, we gain enough distance to meet them with compassion. Over time, through conscious journalling and other support, writing transforms pain into clarity and renewal. It takes time, patience, and courage.

But you don’t need to wait for a breakthrough moment. Simple prompts can guide you into the heart of a transition. Recently, another wave of grief hit me. I’m grateful I had the foresight to pour much of that difficult period into my journals. I learned that grief often triggers memories of other losses, and that these emotions are better out than in. Of course, you may not immediately feel like journalling when going through change, but when you do, here are four prompts from Leia Francisco’s Writing Through Transitions to guide you:

Name the change

l What change are you experiencing?

l Did you choose it, or did it arrive unexpectedly?

l Is it happening gradually, or all at once?

Next, explore the impact

l What immediate effect has this change had on your daily life?

l Who else is affected?

l What support do you need right now?

Follow this by connecting past and present

l How does this change resemble previous transitions?

l What strengths or strategies did you use then that could help now?

Give yourself permission to imagine possibility

1. What is your biggest fear about this change?

2. What is the best possible outcome?

3. Finish this sentence: I can best manage this change by…

Pause after responding. Re-read your words. What feeling emerges most strongly? Write a short statement to capture it.

Not all grief comes from events we can name. Some arise from the dreams deferred, the lives imagined but never lived. The poet Langston Hughes once asked: What happens to a dream deferred? This is grief too, the unspoken kind. Perhaps you longed to be a parent but life unfolded differently.

Maybe a career path never materialised, leaving you unfulfilled. Perhaps retirement isn’t what you envisioned, or a dream simply slipped away. Psychologist Kenneth Doka calls this disenfranchised grief: losses that aren’t publicly acknowledged, yet cut deeply.

Journalling is a powerful place to give these hidden sorrows recognition and release. Growing up, I dreamed of becoming a newsreader. But when I failed to get into journalism school at 17, I buried the dream and pretended it didn’t exist. If we don’t name deferred dreams, they linger in the background, quietly shaping our choices.

Naming them brings them into the open, where grief can be acknowledged and healing can begin. Here are a few ways journalling can help you work with unrealised dreams:

l Write a goodbye letter to a dream.

l Thank it for what it gave you, however briefly.

l Describe what you’re ready to release, and what you hope to receive in its place.

l Write a future story: imagine yourself one year from now, having let go of that dream. What does your life look like? As the saying goes: new beginnings are often disguised as painful endings.

Grieving unrealised dreams frees us for what’s ahead, while exploring the meaning in past hardships helps us see how loss has shaped who we’ve become. Once we’ve named these hidden losses, the next step is making meaning from them. Finding what they have taught us, and how they shape who we are becoming. Trauma leaves marks, but it can also open us to growth.

Psychologists call this post-traumatic growth: the chance  to discover new purpose and greater resilience after hardship. Journalling helps with this process. It turns scattered memories and feelings into a story we can hold. Instead of chaos, we begin to see meaning.

Dr Michelle Pearce’s ‘Mine Your Messes’ approach echoes what David Kesslier and Elisabeth Kubler Ross call the sixth stage of grief: finding meaning. One way to do this is simple: take a loss you now have some distance from and write down five things it taught you. What wisdom did that season leave behind?

Once you have unearthed the emotions that need to be released, it’s time to focus your writing in a different direction. Try this: write about the very best way your current circumstance or life could unfold. Describe it in as much detail as possible. When finished, reflect on how it felt to focus on the best-case scenario. By coupling meaning-making with future visioning, journalling helps us hold both grief and hope, an essential balance for moving through transitions. Meaning-making doesn’t erase grief, but it allows us to hold it alongside joy. This balance is what helps us live fully during difficult seasons.

While we must face grief, it’s equally important to make space for joy. A practice I often return to is simple yet profound: at the end of each day, write down three good things. It trains the mind to focus on the good stuff. This doesn’t cancel out sorrow. It reminds us that joy and grief can coexist. Even in seasons of loss, there are moments of beauty: kind words, laughter, sunlight on your skin.

Change is inevitable. Loss, disappointment, and grief visit us all. But when we lean in, when we meet pain rather than bury it, we increase our chances of finding growth, clarity, and vitality on the other side. Journalling through transitions gives us a way to face the storms, to release unspoken grief, and to honour both the endings and beginnings that shape our lives.

In the end, journalling is not just about recording events. It’s about weaving sorrow and joy into a story that restores wholeness. As meditation teacher Sarah Blondin reminds us: don’t look for an escape hatch or a window to fly out of. Root down. Allow emotions their space, and trust that in time they will dissolve.

As I’ve reflected on years of writing and guiding others through transitions, one truth has become clear to me: ultimately, your journal becomes a meaning-making instrument. Your experiences are the curriculum. The writing, the lessons, and the teachings. So I invite you to: Write. Write until the circle closes. Write until you soften. Write until you discover, quietly, that you are more alive than before.

Jackee Holder is a coach, author, interfaith minister and co-founder of The School Of Journaling. Known for her soulful and practical approach she weaves together creativity, the natural world and the power of the written word to support emotional clarity and personal transformation. Jackee’s work appears at the intersection of journaling, wellbeing, and embodied wisdom.

theschoolofjournaling.co.uk Instagram: @theschoolofjournaling  @jackeeholderinspires