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Death, legacy, and journaling: How writing about mortality clarifies life
Facing the end to better shape the middle Why write about death at all? At home, I proudly display a copy of ‘Japanese Death Poems’. It’s a beautifully curated book of poems written by people just before their deaths. Whenever people see the book on my coffee table, they immediately label it as morbid and…
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Journaling to shift from a scarcity to an abundance mindset
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30 day morning journaling challenge for men
Why morning journaling? Journaling in the morning is a powerful way to start your day and set you on the right track. It allows you to focus, plan, gain clarity, realign with your goals and values and understand your direction for the day. It’s a moment of mindfulness and calm before the inevitable noise and…
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Journaling prompt: Arriving at yourself
Montaigne wrote, “Every man rushes elsewhere into the future, because no man has arrived at himself.” It’s a line that cuts through the noise. Because isn’t that what so many of us are doing? Always moving toward the next milestone; the next job, the next home, the next “version” of ourselves we imagine will finally…
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Journaling prompt: The characters we play
Back when I was doing stand-up comedy, I quickly became obsessed. I devoured interviews, books, podcasts. Anything that might help me figure out how to be better. A theme came up again and again. New comedians often start out completely raw. No script, no character, just themselves. On the stage. Honest. Exposed. Then comes the…
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Journaling prompt: Another person’s dream
“I don’t like belonging to another person’s dream” – Alice, Through The Looking Glass Life can put us on a treadmill that moves pretty fast. Before we know it, we’re running towards something we may not even want, or be chasing things that don’t feel fulfilling. At 35, I realised I’d spent a significant part…
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Journaling prompt: Résumé values or eulogy values?
When I eventually shuffle from this mortal coil, I’m not sure I would want people at my funeral describing me as ‘a real go-getter’, who was a ‘great team player’. ‘Dave was a motivated and results-driven guy who often delivered results on-time and within budget.’ No, thank you. And yet, from a very early age…
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Journaling prompt: How do we forgive ourselves for the things we did not become?
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Journaling prompt: Why should I fear death?
Tag: self reflection
Thoughtful, authentic journal prompts for personal growth
More than just standard, generic journal prompts.
Each prompt on this page is inspired by my own journaling journey. Shaped by real-life experiences, deep reflection, and wide-ranging reading in psychology, philosophy, and personal development. They’re designed to go beyond surface-level questions and help you uncover what really matters to you.
Whether you’re seeking clarity, purpose, emotional insight, or a stronger sense of self, these prompts are here to support honest reflection and meaningful growth. They’re not about ticking boxes or chasing productivity, they’re about helping you develop a deeper, more authentic relationship with yourself.
Feel free to explore. Use one or more prompt or just allow them to inspire your own writing.
