Anna Woolliscroft Interview on How Journalling Can Transform Stress and Self-Doubt
Anna Woolliscroft is a writing for wellbeing specialist, journalling coach, podcast host, and the founder of Writing with Purpose. A certified Journal to the Self® Instructor with a Master's in Creative Writing and Wellbeing, she helps professional midlife women navigate stress, transition, and self-doubt through the written word.
In this interview, Anna explains how she moved from freewriting to structured journalling techniques, why the practice is gaining ground as a wellbeing tool, and the simple exercise she gives anyone who says they don't know where to start.
Anna Woolliscroft, Journalling Coach & Wellbeing Advocate
What first convinced you that journalling could become a powerful tool for wellbeing rather than simply a daily habit?
It was noticing a pattern. I kept rereading my entries and realising I was ruminating over the same situation without getting anywhere. That awareness changed things. When a past experience triggered me with my partner, I journalled it first, working through the emotion on paper before we spoke. Because I'd already released the intensity of it, I could have a calm, honest conversation instead of a reactive one. That was the shift for me: journalling stopped being a diary of what happened and became a way to process what I felt before I acted on it. Once I started using proper techniques rather than just freewriting, I could pinpoint where a feeling or behaviour actually came from. It’s this kind of self-awareness that gives you the ability to regulate your emotions rather than be run by them. It's the difference between writing about your day and really understanding yourself.
As a certified Journal to the Self® Instructor, what principles do you believe every effective journalling practice should include?
The first is permission. There is no right way to journal, no correct handwriting, spelling or structure to aim for. The moment people feel judged by their own page, they stop writing. The second is safety, both emotional and practical. You need to feel able to write honestly, which sometimes means addressing confidentiality directly with something as simple as a locked notebook. The third is variety. A single technique won't suit every mood or every person, so having a small toolkit of approaches, whether that's a timed freewrite, a list of structured prompts, or visual cards, means you always have a way in. The fourth is honesty over performance. Journalling isn't for an audience, so it should never be written to sound impressive. Get these principles right and journalling stops being another task on the list and becomes a tool for processing your week, your relationships and your own mind.
You've trained in creative writing, specialist journalling techniques, and counselling skills. How do those disciplines come together in the way you facilitate journalling today?
Creative writing gives me the tools to help people express themselves in ways beyond straightforward prose. Using metaphor, imagery, or a change of perspective helps us access things a direct sentence can't quite reach. Specialist journalling training gives me the techniques themselves: structured exercises with a clear purpose, built to move someone from confusion towards clarity. Counselling skills are what hold it all together safely. They shape how I listen, how I hold space for someone's story without steering it, and how I recognise when a technique needs to be gentler or when someone needs signposting elsewhere. None of these disciplines work as well on their own. Creative writing without structure can feel aimless. Technique without emotional awareness can feel clinical. Together, they let me guide people towards writing that's both expressive and purposeful, and to do it in a way that keeps their wellbeing, not just their word count, at the centre of the process.
Why do you think journalling is becoming increasingly relevant as people look for healthier ways to manage stress, uncertainty, and change?
A lot of the women I work with are dealing with multiple changes: careers shifting, perimenopause, caring for children and parents at the same time. They're looking for something that fits around real life rather than adding another appointment to it. Journalling meets that need because it costs nothing, needs no equipment beyond a pen and paper, and can happen in five minutes or fifty. It also gives people back a sense of control. When everything around you feels unpredictable, writing down what you think and feel is one of the few things you can direct. I think there's also a shift happening in how people think about self-care. It's moving away from treats and towards tools, things that build resilience rather than just offering temporary relief. Journalling fits that shift well. It's not a quick fix, but a practice you build over time, and that's exactly what makes it valuable when life feels uncertain.
What are the biggest misconceptions that stop people from experiencing the real benefits of therapeutic writing?
The biggest one is thinking journalling means writing pages of beautiful prose every single day, like a diary from a film. That expectation puts people off before they've started. Some also believe there are rules such as correct grammar and spelling, tidy handwriting, and a certain length. But that’s not the case. A single word can be a complete practice. Another misconception is that journalling is only for processing trauma or crisis, so people wait until things go badly wrong before they pick up a pen. In reality, it's just as useful for everyday decisions, tracking energy, or simply noticing what you're grateful for. Lastly, people assume journalling is passive, that you write and nothing changes. Structured techniques ask you questions, shift your perspective, or draw connections you wouldn't have found by just thinking. Once people let go of the idea that there's a ‘correct’ way to do it, the real benefit, self-awareness, becomes far easier to reach.
For someone who says, ‘I don't know what to write,’ what is the first exercise you would guide them through?
I always say that's completely normal, and there's no proper way to start. An entry can be a single word, one sentence, or several pages, and none of those is more valid than another. The first thing I'd suggest is trying a guided prompt rather than a blank page, because a blank page is often what causes the block in the first place. Something as simple as ‘three things I'm grateful for today are…’ gives you a way in without pressure. If words still feel difficult, I'd suggest moving away from them altogether and using a postcard or image to respond to instead of a question. Different techniques appeal to different people, so the goal at the start isn't to find the right method. It's to experiment and stay curious about what works for you. Once you find the format that removes the pressure, the words tend to follow on their own.
You often combine writing with time in nature. What happens in that environment that deepens the journalling experience?
Nature slows people down before they've even picked up a pen. I use a simple framework from John Muir Laws with three prompts: I notice, I wonder, and it reminds me of. Standing outside and noticing the detail of a leaf, the sound of a robin, or the weather pulls you out of your head and into your senses, which is often where the more honest writing comes from. There's also something about being away from screens and walls that removes the usual distractions and self-consciousness people bring to a page. On a journalling walk, conversation and observation blend together, so the writing that follows tends to be less guarded than a session at a desk. Nature also offers gentle metaphors for whatever someone is working through, such as a tree bending in the wind or a concealed path leading to the unknown. Those images give people language for feelings they might otherwise struggle to name, and that combination of stillness, senses and metaphor is what makes the writing go deeper.
Your mission is to help 100,000 people discover the benefits of writing for wellbeing. What impact do you hope that movement will create over the next decade?
I want people, particularly women in their 40s and beyond, to see journalling as a personal tool for wellbeing rather than a nice-to-have. If I can help 100 people build that habit, the ripple effect goes well beyond the page. Someone who understands their own patterns communicates more honestly with their partner, sets clearer boundaries at work, and models that reflection with their children or the people around them. I'd also like to see journalling talked about with the same seriousness as exercise or nutrition, as a basic part of looking after your mental health rather than something reserved for a crisis. On a personal level, I want people to trust their own insight more. So much of the advice we're given tells us to look outward for answers. Journalling does the opposite. It builds the confidence to look inward first, and that's the shift I hope this movement creates.
If you could leave readers with one idea about journalling that could change how they approach their own wellbeing, what would it be?
There's no wrong way to do this. If you take one thing from this interview, let it be that. You don't need the perfect notebook, an hour of free time, or something dramatic to write about. You need honesty and a willingness to be curious about your own thoughts. Start small. One sentence at the end of the day is enough to begin building the habit. If you'd like a gentle way in, I've put together a free journal planner that walks you through some starting prompts, and you're welcome to use as much or as little of it as suits you. Journalling won't fix everything overnight, but it gives you a place to think clearly when everything else feels loud. That clarity is available to anyone willing to put pen to paper, regardless of whether they think of themselves as a ‘writer’ at all.
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